dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b17219fcebd74ae7ac99426fccd85e3c | Nc1ccc(Cl)c(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(Cl)c(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)c(Cl)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.ClC=1C=C(N)C=CC1Cl>>ClC=1C=C(C=CC1Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)Cl)Cl)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]1.[O:1]=[C:2]([c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](=[O:27])[Cl:33])[Cl:35]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18... | Nc1ccc(Cl)c(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(Cl)c(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)c(Cl)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2f235573ea2831a0bfc0ca6a7a1d25e86fe9750de044d017cedf9966e87994b8 | 152f5a74588b671b90d31333a44ad79a10117acd8e5ede06fca5e8c644a4e2e7 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | [Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[Cl;H0;D1;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[Cl;H0;D1;+0:1]-[c:17](:[c:18]):[c:19](-[Cl;H0;D1;+0:7]):[c:20]:[c:21]-[#7:22]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[O;D1;H0:9]=[C;H0;D3... | 10.2 | [{"value": 10.2, "product": "ClC=1C=C(C=CC1Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)Cl)Cl)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (1.04 g, 3.03 mmol) in 25 mL of dichloromethane and 3,4-dichloroaniline (0.982 g, 6.06 mmol) in 8 mL of pyridine. The crude product was recrystallized from ethyl acetate-hexanes to yield 0.184 g of the title co... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Aromatic halide.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(Cl)c(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(Cl)c(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a52bb8c1753c453fa00de43f77a5ce8a | Nc1ccc(Cl)cc1Cl.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(Cl)cc1Cl)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)cc1Cl | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.ClC1=C(N)C=CC(=C1)Cl>>ClC1=C(C=CC(=C1)Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=C(C=C2)Cl)Cl)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:34][c:35]1[Cl:36].[O:1]=[C:2]([Cl:11])[c:12]1[cH:13][cH:14][cH:9][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](=[O:27])[Cl:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:... | Nc1ccc(Cl)cc1Cl.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(Cl)cc1Cl)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)cc1Cl | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 08f6fd1cc318cdb2fa23c9eb29a97032bbce3d4ed3ae3fdc6be78ee7a60521f7 | ff709637114d139dc59366a7fc358c91f087a54b59bfe5b228e07ff4c733add3 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | [#16:1]-[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c:7]:1-[C;H0;D3;+0:8](-[Cl;H0;D1;+0:9])=[O;D1;H0:10].[Cl;H0;D1;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:16].[Cl;D1;H0:17]-[c;H0;D3;+0:18]1:[cH;D2;+0:19]:[c;H0;D3;+0:20](-[Cl;D1;H0:21]):[c:22]:[c:23]:[c;H0;D3;+0:24]:1-[NH2;D1;+0:25]>>[#16:1]-[c... | 18.5 | [{"value": 18.5, "product": "ClC1=C(C=CC(=C1)Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=C(C=C2)Cl)Cl)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2,4-dichloroaniline (1.89 g, 11.7 mmol) in 15 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate, ethanol and methanol (1:1:... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Secondary amide.Secondary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(Cl)cc1Cl.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(Cl)cc1Cl)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c9e1e702e704b5496cf56b75362d6ea | Cc1ccc(N)cc1C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C)c(C)c2)cc1C | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.CC=1C=C(N)C=CC1C>>CC=1C=C(C=CC1C)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)C)C)C=CC=C1)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:34][c:35]1[CH3:36].Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[S:15][S:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[C:23](Cl)=[O:24]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[S:15][S:16][c:17]2[cH:18][cH:19][cH:2... | Cc1ccc(N)cc1C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C)c(C)c2)cc1C | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 5e7dfe57baccae2b9f8237d28bb05b03f973be38ed0d1e13108e5b3f0bc6e511 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 16.8 | [{"value": 16.8, "product": "CC=1C=C(C=CC1C)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=C(C=C2)C)C)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (1.12 g, 3.26 mmol) in 25 mL of dichloromethane and 3,4-dimethylaniline (0.79 g, 6.52 mmol) in 8 mL of pyridine. The crude product was triturated with ethyl ether and filtered to yield 0.28 g of the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Cc1ccc(N)cc1C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C)c(C)c2)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-577baf93dbe446b29bfcb8fc756ce4c3 | Nc1cc(Cl)cc(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cc(Cl)cc(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)cc(Cl)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.ClC=1C=C(N)C=C(C1)Cl>>ClC=1C=C(C=C(C1)Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC(=C2)Cl)Cl)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][c:6]([Cl:7])[cH:33][c:34]([Cl:35])[cH:11]1.[O:1]=[C:2]([Cl:10])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:22][cH:8][cH:24][c:25]1[C:26](=[O:27])[Cl:32]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:1... | Nc1cc(Cl)cc(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cc(Cl)cc(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)cc(Cl)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 08f6fd1cc318cdb2fa23c9eb29a97032bbce3d4ed3ae3fdc6be78ee7a60521f7 | ff709637114d139dc59366a7fc358c91f087a54b59bfe5b228e07ff4c733add3 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[NH2;D1;+0:5]):[c:6]:[c;H0;D3;+0:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1.[Cl;H0;D1;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15].[Cl;H0;D1;+0:16]-[C;H0;D3;+0:17](=[O;D1;H0:18])-[c:19]1:[c:20]:[c:21]:[cH;D2;+0:22]:[cH;D2;+0:23]:[cH;D2;+0:24]:1>>[Cl;D1;H0:1]-[c;H0;... | 22.5 | [{"value": 22.5, "product": "ClC=1C=C(C=C(C1)Cl)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC(=C2)Cl)Cl)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 3,5-dichloroaniline (1.87 g, 11.7 mmol) in 15 mL of pyridine. The crude product was recrystallized from ethanol, then ethyl ether to yield 0.78 g of the title... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Secondary amide.Secondary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl.N1=CC=CC=C1 | null | null | Nc1cc(Cl)cc(Cl)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cc(Cl)cc(Cl)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)cc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e404142def44ea88cbeeff7e6caace1 | Nc1ccc(F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(F)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.FC1=CC=C(N)C=C1>>FC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)F)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](Cl)=[O:26]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21]... | Nc1ccc(F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(F)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 0b7f4098d290755c90a886d0c252e496f0da36f344c58467b3815e0aa364cb08 | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 9.7 | [{"value": 9.7, "product": "FC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)F)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (1.00 g, 2.92 mmol) in 20 mL of dichloromethane and 4-fluoroaniline (0.657 g, 5.91 mmol) in 5 mL of pyridine. The crude product was triturated with hot ethanol-ethyl acetate mixture, filtered, and recrystallize... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2ee1555109fc4f4f898ac529b39d3c5b | Nc1cccc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cccc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(C(F)(F)F)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC=1C=C(C=CC1)C(F)(F)F>>FC(C=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=CC=C1)=O)(F)F | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:12])[F:37])[cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[S:20][S:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28](Cl)=[O:29]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH... | Nc1cccc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cccc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(C(F)(F)F)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | ba094faccfda206d55221a88b09dbf39cf5aec45419b40567010e90901b5e999 | 9b195be506a1a77c1e22fa83b6e1bae8eb184b6ad68b5c3e4c30319262990215 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[F;D1;H0:11]-[C;H0;D4;+0:12](-[F;D1;H0:13])(-[F;H0;D1;+0:14])-[c:15](:[c:16]):[c:17]:[c:18](-[NH2;D1;+0:19]):[c:20]>>[F;D1;H0:11]-[C;H0;D4;+0:12](-[F;D1;H0:21])(-[F;D1;H0:13])-[c:15](:[c:16]):[c:17]:[c:18](-[NH;D2;+... | 15.1 | [{"value": 15.1, "product": "FC(C=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=CC=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 3-aminobenzotrifluoride (1.87 g, 11.6 mmol) in 15 mL of pyridine. The crude product was recrystallized from ethanol, then ethyl ether to yield 0.519 g of the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Trifluoro group.Primary amine | Trifluoro group.Trifluoro group.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cccc(C(F)(F)F)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cccc(C(F)(F)F)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(C(F)(F)F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6450132c7d642aaab511c2f2ec3bcb7 | COc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>COc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1OC | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.COC=1C(=CC=CC1)N>>COC1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)OC)C=CC=C1)=O | [cH:7]1[c:8]([NH2:9])[c:34]([O:35][CH3:36])[cH:33][cH:32][cH:31]1.Cl[C:10](=[O:2])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:1][cH:23][cH:24][c:25]1[C:26](Cl)=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][... | COc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | COc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1OC | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 7a899fabf59db6681ca9e7bd4f2b39435b8652ebf37db403cb4d9ebcff19ad6c | 1a6275414974c3f596ec292776f90484d83a560cecc1ad2212064aa4086df0c7 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:1-[#16:9].Cl-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14].[C;D1;H3:15]-[#8:16]-[c;H0;D3;+0:17]1:[c:18]:[c:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:[c;H0;D3;+0:22]:1-[NH2;D1;+0:23]>>[#16:9]-[c:8]1:[cH;D2;+0:7]:[c:24]:[cH;D2;+0:5... | 21.3 | [{"value": 21.3, "product": "COC1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)OC)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and o-anisidine (1.42 g, 11.5 mmol) in 10 mL of pyridine. The crude product was recrystallized from ethanol-ethyl acetate, then again from acetonitrile-DMF to yie... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Ether.Primary amine | Ether.Ether.Secondary amide.Secondary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | COc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>COc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b718485e058f488da242388c9e90b503 | COC(=O)c1sccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>COC(=O)c1sccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccsc1C(=O)OC | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=C(SC=C1)C(=O)OC>>C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)NC1=C(SC=C1)C(=O)OC)C(=O)NC1=C(SC=C1)C(=O)OC | [NH2:10][c:30]1[cH:31][cH:32][s:33][c:34]1[C:35](=[O:36])[O:37][CH3:38].Cl[C:11](=[O:2])[c:13]1[cH:14][cH:15][cH:1][cH:17][c:18]1[S:19][S:6][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[C:27](Cl)=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[... | COC(=O)c1sccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | COC(=O)c1sccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccsc1C(=O)OC | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 1abaa488e786db809080c2263cc57980c9cf7fb2cca818a69953e9baf68adb70 | 4a74bb4b1a11a78c14e69605ccf0912bf413a242d2df7d70e86626954e018c66 | O=C(Nc1ccsc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccsc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:1-[S;H0;D2;+0:9]-[S;H0;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[C;H0;D3;+0:15](-Cl)=[O;D1;H0:16]):[c:17].[C;D1;H3:18]-[#8:19]-[C:20](=[O;D1;H0:21])-[c:22]1:[#16;a:23]:[c:24]:[c:25]:[c;H0;D3;+0:26]:1-[NH2;D1;+0:27]>>[C... | 59 | [{"value": 59.0, "product": "C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)NC1=C(SC=C1)C(=O)OC)C(=O)NC1=C(SC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 18 | HOUR | A solution of 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane was added to a solution of methyl 3-amino-2-thiophenecarboxylate (1.82 g, 11.6 mmol) in 14 mL of pyridine at 23° C. The reaction mixture was stirred for 18 hours at 23° C. under nitrogen atmosphere. The precipitate formed was c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine.Disulfide | Ester.Secondary amide.Secondary amide.Disulfide | c1ccsc1.c1ccccc1.c1ccccc1 | c1ccsc1.c1ccccc1.c1ccccc1.c1ccsc1 | c1ccsc1.c1ccccc1.c1ccccc1.c1ccsc1 | null | ClCCl.N1=CC=CC=C1 | 23 | 18 | COC(=O)c1sccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>COC(=O)c1sccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccsc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f7687fce75f4342a1006eb952201a30 | Nc1ccc(C(F)(F)F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(C(F)(F)F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(C(F)(F)F)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=CC=C(C=C1)C(F)(F)F>>FC(C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C(F)(F)F)C=CC=C1)=O)(F)F | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:11])[F:36])[cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[S:20][S:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28](Cl)=[O:29]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH... | Nc1ccc(C(F)(F)F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(C(F)(F)F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(C(F)(F)F)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | ba094faccfda206d55221a88b09dbf39cf5aec45419b40567010e90901b5e999 | 9b195be506a1a77c1e22fa83b6e1bae8eb184b6ad68b5c3e4c30319262990215 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[F;D1;H0:11]-[C;H0;D4;+0:12](-[F;D1;H0:13])(-[F;H0;D1;+0:14])-[c:15]1:[c:16]:[c:17]:[c:18](-[NH2;D1;+0:19]):[c:20]:[c:21]:1>>[F;D1;H0:22]-[C;H0;D4;+0:12](-[F;D1;H0:11])(-[F;D1;H0:13])-[c:15]1:[c:16]:[c:17]:[c:18](-[... | 24.3 | [{"value": 24.3, "product": "FC(C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C(F)(F)F)C=CC=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (1.12 g, 3.26 mmol) in 25 mL of dichloromethane and 4-aminobenzotrifluoride (1.05 g, 6.53 mmol) in 8 mL of pyridine. The crude product was recrystallized from water-DMF to yield 0.47 g of the title compound, mp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Trifluoro group.Primary amine | Trifluoro group.Trifluoro group.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(C(F)(F)F)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(C(F)(F)F)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(C(F)(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95cacae25c9e40e49862ee7c1efd578d | Nc1ncc(Br)cn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ncc(Br)cn1)c1ccccc1SSc1ccccc1C(=O)Nc1ncc(Br)cn1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=NC=C(C=N1)Br>>BrC=1C=NC(=NC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=C(C=N2)Br)C=CC=C1)=O | [NH2:3][c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][n:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](Cl)=[O:26]>>[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][c... | Nc1ncc(Br)cn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ncc(Br)cn1)c1ccccc1SSc1ccccc1C(=O)Nc1ncc(Br)cn1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 7f949b0f98d34899cd267e5eb2d06cf009ba7b2d60e613c9cd2591b03bc754fa | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ncccn1)c1ccccc1SSc1ccccc1C(=O)Nc1ncccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]:[c:16]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:17]-[c:18])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]:[c:16])-[c:8](... | 11.1 | [{"value": 11.1, "product": "BrC=1C=NC(=NC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=C(C=N2)Br)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-amino-5-bromopyrimidine (2.03 g, 11.7 mmol) in 16 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol, filtered... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | null | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ncc(Br)cn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ncc(Br)cn1)c1ccccc1SSc1ccccc1C(=O)Nc1ncc(Br)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-11fa6b61f94248b8980e3d5948aa63fb | N#Cc1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>N#Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C#N)cc2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=CC=C(C#N)C=C1>>C(#N)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C#N)C=CC=C1)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:35][cH:36]1.Cl[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24](Cl)=[O:25]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[S:16][S:17][c:18]2[cH:19][cH:20][c... | N#Cc1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | N#Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C#N)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | b6e30462973aab3da6f9362b407a7f6f56fd4f435d03bfe5f7b9cfc2aa626e56 | c813481c121cec3c4d3841e0937d4ead02e5bd769a2a0f81aa76e63905a965b9 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 12.5 | [{"value": 12.5, "product": "C(#N)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)C#N)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-aminobenzonitrile (1.38 g, 11.7 mmol) in 11 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol (1:1), filtered... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Nitrile.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | N#Cc1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>N#Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C#N)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7da54477b90c42788a92fc7c0bf018be | CS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(C)(=O)=O)cc2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.CS(=O)(=O)C1=CC=C(C=C1)N>>CS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)C)C=CC=C1)=O | [O:3]=[S:33]([c:32]1[cH:6][cH:7][c:8]([NH2:9])[cH:39][cH:40]1)([CH3:34])=[O:35].Cl[C:10](=[O:11])[c:12]1[cH:13][cH:1][cH:15][cH:16][c:17]1[S:18][S:2][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](Cl)=[O:27]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c... | CS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(C)(=O)=O)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 17aa62473bb616012597b840da7270c9d08a47da314ff3e256453ed1ac09f2b3 | d3e4c27a17571d4b1804b7920121c68df73b33d6aa2a2f9ae2a99691a8d61071 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1-[S;H0;D2;+0:9]-[S;H0;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[C;H0;D3;+0:15](-Cl)=[O;D1;H0:16]):[c:17].[C;D1;H3:18]-[S;H0;D4;+0:19](=[O;D1;H0:20])(=[O;H0;D1;+0:21])-[c;H0;D3;+0:22]1:[cH;D2;+0:23]:[c:24]:[c:25](-[NH2;D1... | 56 | [{"value": 56.0, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)C)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-aminophenyl methyl sulfone (2.00 g, 11.7 mmol) in 16 mL of pyridine. The crude product was recrystallized from acetonitrile-DMF to yield 2.0 g of the title ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine.Disulfide.Sulfone | Secondary amide.Secondary amide.Disulfide.Sulfone.Sulfone | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | CS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(C)(=O)=O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-433c355fb94b481c9dee297890a544bc | Nc1cc(Cl)ncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cc(Cl)ncn1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)ncn1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=NC=NC(=C1)Cl>>ClC1=CC(=NC=N1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=NC(=C2)Cl)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][n:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:29]1[C:30](=[O:26])[Cl:31]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:... | Nc1cc(Cl)ncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cc(Cl)ncn1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)ncn1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 884eacce4242e627a95d5a5d354ec6923c10e46aa2cb7578ac5a93f339d94e94 | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ccncn1)c1ccccc1SSc1ccccc1C(=O)Nc1ccncn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#16:6]-[#16:7]-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[C;H0;D3;+0:14](-[Cl;D1;H0:15])=[O;H0;D1;+0:16].[NH2;D1;+0:17]-[c:18]1:[#7;a:19]:[c:20]:[#7;a:21]:[c:22]:[c:23]:1>>[Cl;D1;H0:15]-[c;H0;D3;+0:14]1:[#7;a:24]:[c:25]:[#7;a:26]:[c:27](-[#7... | 12.3 | [{"value": 12.3, "product": "ClC1=CC(=NC=N1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=NC(=C2)Cl)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 90 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-amino-6-chloropyrimidine (1.51 g, 11.7 mmol) in 12 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol, filtere... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1.c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cc(Cl)ncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cc(Cl)ncn1)c1ccccc1SSc1ccccc1C(=O)Nc1cc(Cl)ncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7c194310fbba4e8fa2c9c67981d2dbf3 | Nc1ccc(I)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccc(I)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(I)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.IC1=CC=C(N)C=C1>>IC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)I)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][cH:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](Cl)=[O:26]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21]... | Nc1ccc(I)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccc(I)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(I)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 0b7f4098d290755c90a886d0c252e496f0da36f344c58467b3815e0aa364cb08 | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 36 | [{"value": 36.0, "product": "IC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)I)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-iodoaniline (2.54 g, 11.6 mmol) in 20 mL of pyridine. The crude product was recrystallized from water-DMF to yield 1.48 g of the title compound, mp 268°-271... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccc(I)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccc(I)cc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(I)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d989fed42294e84a3366f42f847f891 | CCc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CCc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1CC | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.C(C)C1=C(N)C=CC=C1>>C(C)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)CC)C=CC=C1)=O | [cH:5]1[cH:6][cH:7][c:8]([NH2:9])[c:34]([CH2:35][CH3:36])[cH:33]1.Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:19][c:20]1[cH:21][cH:1][cH:23][cH:24][c:25]1[C:26](Cl)=[O:27]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[S:18][S:1... | CCc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CCc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1CC | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 49c984089c3266fdc90fd3e269b10a04d794c54780f8560852f5efac400661a8 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:1-[#16:14].[C;D1;H3:15]-[C:16]-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[cH;D2;+0:19]:[c:20]:[c:21]:[c;H0;D3;+0:22]:1-[NH2;D1;+0:23]>>[#16:14]-[c:13]1:[cH;D2;+0:12]:[c:24]:[cH;D2;+0:10... | 33.6 | [{"value": 33.6, "product": "C(C)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)CC)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 90 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-ethylaniline (1.40 g, 11.6 mmol) in 12 mL of pyridine. The crude product was recrystallized from acetonitrile-DMF to yield 1.0 g of the title compound, mp 2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | CCc1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CCc1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b9c2430e1724400a4c74be58252de98 | Nc1ccncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1ccncn1)c1ccccc1SSc1ccccc1C(=O)Nc1ccncn1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=NC=NC=C1>>N1=CN=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=NC=C2)C=CC=C1)=O | [n:3]1[cH:29][cH:28][c:27]([NH2:26])[n:32][cH:31]1.Cl[C:2](=[O:1])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:4][cH:22][c:23]1[C:24](Cl)=[O:25]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][n:7][cH:8][n:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:... | Nc1ccncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1ccncn1)c1ccccc1SSc1ccccc1C(=O)Nc1ccncn1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | f30f048d4d94488d1eed9939ac47c3f1423d2e6839e26f5bac1b9200646d6546 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccncn1)c1ccccc1SSc1ccccc1C(=O)Nc1ccncn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[NH2;D1;+0:14]-[c:15]1:[#7;a:16]:[cH;D2;+0:17]:[n;H0;D2;+0:18]:[cH;D2;+0:19]:[c:20]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:18]-[c;H0;D3;+0:12](:[#7;a:21]:[c:22]):[c:23]:[... | 2 | [{"value": 2.0, "product": "N1=CN=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=NC=NC=C2)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 90 using 2,2'-dithiobisbenzoyl chloride (3.00 g, 8.74 mmol) in 75 mL of dichloromethane and 4-aminopyrimidine (1.66 g, 17.5 mmol) in 14 mL of pyridine. The crude product was triturated with a hot mixture of acetonitrile and DMF, filtered, and recryst... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1ccncn1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1ccncn1)c1ccccc1SSc1ccccc1C(=O)Nc1ccncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a7cf2ad202e4c1397b6b815cf8ebc70 | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cccc([N+](=O)[O-])c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc([N+](=O)[O-])c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.[N+](=O)([O-])C=1C=C(N)C=CC1>>[N+](=O)([O-])C=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1.Cl[C:2](=[O:1])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[S:19][S:20][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[C:27](Cl)=[O:28]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]... | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cccc([N+](=O)[O-])c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc([N+](=O)[O-])c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 4472955bfa88478abba07a4cc7154c307fb81084178d69a517c77e496ac53b12 | ad52e94667c28774f72157b153acd6400c4e6e1d52c0236ded1aefe4a3462786 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 24.9 | [{"value": 24.9, "product": "[N+](=O)([O-])C=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 3-nitroaniline (1.60 g, 11.6 mmol) in 13 mL of pyridine. The crude product was recrystallized once from ethanol-ether, then twice from acetonitrile-DMF-water ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Nitro group.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cccc([N+](=O)[O-])c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8758a287794b4b4db01fbda93c571355 | Nc1ccccc1S(N)(=O)=O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>NS(=O)(=O)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1S(N)(=O)=O | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=C(C=CC=C1)S(=O)(=O)N>>NS(=O)(=O)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)S(=O)(=O)N)C=CC=C1)=O | [NH2:1][c:31]1[cH:32][cH:33][cH:34][cH:35][c:36]1[S:37](=[O:3])(=[O:4])[NH2:38].Cl[C:12](=[O:13])[c:14]1[cH:5][cH:16][cH:17][cH:18][c:19]1[S:2][S:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28](Cl)=[O:29]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c... | Nc1ccccc1S(N)(=O)=O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | NS(=O)(=O)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1S(N)(=O)=O | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 7ac7bc0cc5662ec00f4922bec048a5b26d4576545016181297e777317cc514df | 237c94f9bfeb760408a4fe8675c80a8ef696736e818eb00c99939b94b6dc2129 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[S;H0;D2;+0:9]-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13](-[C;H0;D3;+0:14](-Cl)=[O;D1;H0:15]):[c:16].[N;D1;H2:17]-[S;H0;D4;+0:18](=[O;H0;D1;+0:19])(=[O;H0;D1;+0:20])-[c:21](:[c:22]):[c;H0;D3;+0:23](-[NH2;D1;+0:24]):[c:25]... | 19.6 | [{"value": 19.6, "product": "NS(=O)(=O)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)S(=O)(=O)N)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 6 | DAY | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-aminobenzenesulfonamide (2.00 g, 11.6 mmol) in 16 mL of pyridine. The reaction mixture was stirred for 6 days at 23° C. under nitrogen atmosphere. The crude... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Sulfonamide.Primary amine.Disulfide | Sulfonamide.Sulfonamide.Secondary amide.Secondary amide.Disulfide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | 23 | 144 | Nc1ccccc1S(N)(=O)=O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>NS(=O)(=O)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1S(N)(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d887acf58894cdeab531ebdbbaba9ed | CC(C)c1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CC(C)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1C(C)C | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.C(C)(C)C1=C(N)C=CC=C1>>CC(C)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)C(C)C)C=CC=C1)=O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH2:10].Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[S:19][S:20][c:21]1[cH:22][cH:23][cH:33][cH:34][c:35]1[C:36](Cl)=[O:28]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]... | CC(C)c1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CC(C)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1C(C)C | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | ad35fcc7b8c9e958b6441183e4e1bf74ea30caaf297bb377d3d908c17c91c784 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#16:6]-[#16:7]-[c;H0;D3;+0:8]1:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c;H0;D3;+0:13]:1-[C;H0;D3;+0:14](-Cl)=[O;H0;D1;+0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[C;D1;H3:20]-[CH;D3;+0:14](-[C;D1;H3:21])-[c;H0;D3;+0:13]1:[c:12]:[cH;D2;+0:11]:[c:22]:[c:23]:[c:24]:... | 14.3 | [{"value": 14.3, "product": "CC(C)C1=C(C=CC=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=C(C=CC=C2)C(C)C)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 90 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-isopropylaniline (1.60 g, 11.6 mmol) in 13 mL of pyridine. The crude product was recrystallized twice from acetonitrile-DMF to yield 0.45 g of the title com... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | CC(C)c1ccccc1N.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CC(C)c1ccccc1NC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1C(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-820622bd6d264f8c8a3784a27744ca1b | Nc1cccc(I)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(Nc1cccc(I)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(I)c1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.IC=1C=C(N)C=CC1>>IC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)I)C=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([I:9])[cH:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25](Cl)=[O:26]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([I:9])[cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[S:17][S:18][c:19]1[cH:20][cH:21]... | Nc1cccc(I)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(Nc1cccc(I)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(I)c1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 0b7f4098d290755c90a886d0c252e496f0da36f344c58467b3815e0aa364cb08 | c921e1c0b5b9c51b320d433f7de9030371670d372e19746642da538aefef62d9 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:15]-[c:16])-[c:3](:[c:4]):[c:5].[O;D1;H0:7]=[C;H0;D3;+0:6](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | 7.3 | [{"value": 7.3, "product": "IC=1C=C(C=CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC(=CC=C2)I)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (3.00 g, 8.74 mmol) in 75 mL of dichloromethane and 3-iodoaniline (3.82 g, 17.5 mmol) in 17 mL of pyridine. The crude product was triturated with hot ethanol, filtered, and recrystallized first from water-DMF, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Aromatic halide.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | Nc1cccc(I)c1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>O=C(Nc1cccc(I)c1)c1ccccc1SSc1ccccc1C(=O)Nc1cccc(I)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9d750e19d8b4a39925f795da813a080 | CCOP(=O)(Cc1ccc(N)cc1)OCC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CCOP(=O)(Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(CP(=O)(OCC)OCC)cc2)cc1)OCC | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.NC1=CC=C(CP(OCC)(OCC)=O)C=C1>>C(C)OP(OCC)(=O)CC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(NC1=CC=C(C=C1)CP(=O)(OCC)OCC)=O)=O | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:46][cH:47]1)[O:48][CH2:49][CH3:31].Cl[C:12]([c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[S:20][S:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28](Cl)=[O:29])=[O:37]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:... | CCOP(=O)(Cc1ccc(N)cc1)OCC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CCOP(=O)(Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(CP(=O)(OCC)OCC)cc2)cc1)OCC | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 5e7dfe57baccae2b9f8237d28bb05b03f973be38ed0d1e13108e5b3f0bc6e511 | 71b0db43b87ed77f957cef6da658499ea92707aa5812cfa83af28fea1b8a9f46 | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10].[#15:11]-[#8:12]-[CH2;D2;+0:13]-[CH3;D1;+0:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[#15:11]-[#8:12]-[CH2;D2;+0:13]-[C;D1;H3:19].[#8:20]-[#15:21](-[#8:22])(-[C:23])=[O;H0;D1;+0:7].[O;D1;H0:2]=[C;H0;D3;+0:1](-[#... | 59.2 | [{"value": 59.2, "product": "C(C)OP(OCC)(=O)CC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(NC1=CC=C(C=C1)CP(=O)(OCC)OCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 3 | DAY | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and diethyl 4-aminobenzylphosphonate (2.90 g, 11.6 mmol) in 23 mL of pyridine. The reaction mixture was stirred for 3 days at 23° C. under nitrogen atmosphere. Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | 23 | 72 | CCOP(=O)(Cc1ccc(N)cc1)OCC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CCOP(=O)(Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(CP(=O)(OCC)OCC)cc2)cc1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3891158d65564d66834bcdc1c2f37155 | CCN(CC)CC.NC1CC1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(NC1CC1)c1ccccc1SSc1ccccc1C(=O)NC1CC1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.C1(CC1)N.C(C)N(CC)CC.ClCCl.ClCCl>>C1(CC1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2CC2)C=CC=C1)=O | CC[N:3]([CH2:4]C)[CH2:6][CH3:5].[NH2:23][CH:24]1[CH2:25][CH2:26]1.Cl[C:2](=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[S:13][S:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[C:21](Cl)=[O:22]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[S:13][S:14][c:15]1[cH:16][cH:17][cH:18][cH:19]... | CCN(CC)CC.NC1CC1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(NC1CC1)c1ccccc1SSc1ccccc1C(=O)NC1CC1 | null | null | null | Acylation | OtherReaction | 406c1d410511822e2c32fadbc4b9d0e0b66c76e5428cd1d7ed0d65ddb3d4516e | 6bae7498e135285c9d695c8eebe8b4e8c6f211037b0a32e9828a1cf0341cfdf0 | O=C(NC1CC1)c1ccccc1SSc1ccccc1C(=O)NC1CC1 | C-C-[N;H0;D3;+0:1](-[CH2;D2;+0:2]-C)-[CH2;D2;+0:3]-[CH3;D1;+0:4].Cl-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9].Cl-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14].[NH2;D1;+0:15]-[C:16]1-[C:17]-[C:18]-1>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:4]-[CH2;D2;+0:3]-1)-[c:12](:[c:13]):[c... | null | [] | null | null | 3 | HOUR | A solution of 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 20 mL of dichloromethane was added dropwise to a solution of cyclopropylamine (0.52 mL, 7.5 mmol) and triethylamine (1.2 mL, 9.0 mmol) in 20 mL of dichloromethane. A solid formed immediately, the mixture was stirred for 3 hours and then filtered. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine.Tertiary amine | Secondary amide.Secondary amide | null | C1CC1 | C1CC1.c1ccccc1.c1ccccc1.C1CC1 | HCl | null | null | 3 | CCN(CC)CC.NC1CC1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(NC1CC1)c1ccccc1SSc1ccccc1C(=O)NC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce2fac42f05a4292a71802d2a5aa59d9 | C1CCNC1.CCN(CC)CC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(c1ccccc1SSc1ccccc1C(=O)N1CCCC1)N1CCCC1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.N1CCCC1.C(C)N(CC)CC>>N1(CCCC1)C(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N1CCCC1 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.CC[N:24]([CH2:25][CH3:26])[CH2:28][CH3:27].Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][S:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](Cl)=[O:18]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][S:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](=[O:... | C1CCNC1.CCN(CC)CC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(c1ccccc1SSc1ccccc1C(=O)N1CCCC1)N1CCCC1 | null | null | ClCCl | Acylation | OtherReaction | ea8ca56c36032f7821db62c41ccbf83211b61d9406fd5204e4c894ae1cb14783 | 53ffcfd2622b76ac9a654abbf10337346a70bce028c9c648756066334eefd291 | O=C(c1ccccc1SSc1ccccc1C(=O)N1CCCC1)N1CCCC1 | C-C-[N;H0;D3;+0:1](-[C:2]-[CH3;D1;+0:3])-[C:4]-[CH3;D1;+0:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].Cl-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15].[C:16]1-[C:17]-[C:18]-[C:19]-[NH;D2;+0:20]-1>>[O;D1;H0:12]=[C;H0;D3;+0:11](-[N;H0;D3;+0:1]1-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:5]-[C:4]-1)-[c:13](:[c:14]... | 60.6 | [{"value": 60.6, "product": "N1(CCCC1)C(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 112 using 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 15 mL of dichloromethane and pyrrolidine (0.63 mL, 7.5 mmol) and triethylamine (1.2 mL, 9 mmol) in 20 mL of dichloromethane, to give 0.75 g of the title compound as a foam, mp 62°-63° C.;
... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary amine.Tertiary amine | Tertiary amide.Tertiary amide | C1CCNC1 | C1CC[NH]C1.C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.C1CC[NH]C1 | HCl | ClCCl | null | null | C1CCNC1.CCN(CC)CC.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl>O=C(c1ccccc1SSc1ccccc1C(=O)N1CCCC1)N1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90022719d27c459586f6b49166817b5d | CC(=O)N(C)[Si](C)(C)C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl.O=C(O)C1CCNCC1>>O=C(O)C1CCN(C(=O)c2ccccc2SSc2ccccc2C(=O)N2CCC(C(=O)O)CC2)CC1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.N1CCC(C(=O)O)CC1.CN(C(C)=O)[Si](C)(C)C>>C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N1CCC(CC1)C(=O)O)C(=O)N1CCC(CC1)C(=O)O | [Si]([N:26]([CH3:27])[C:30]([CH3:29])=[O:31])([CH3:28])([CH3:33])[CH3:34].Cl[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24](Cl)=[O:25].[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][NH:7][CH2:35][CH2:36]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([C:8](... | CC(=O)N(C)[Si](C)(C)C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl.O=C(O)C1CCNCC1 | O=C(O)C1CCN(C(=O)c2ccccc2SSc2ccccc2C(=O)N2CCC(C(=O)O)CC2)CC1 | null | N1=CC=CC=C1 | ClCCl | C-C Coupling | OtherReaction | bdfeab0ac9bf070110ff45deb052163efdc5c171b8bd808dd3b12b5bf4f50f9d | 5986769fffda6caef634a288ef2bd834f11c82f4530b102cbf566cd6049b565e | O=C(c1ccccc1SSc1ccccc1C(=O)N1CCCCC1)N1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[CH3;D1;+0:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:13](-[CH3;D1;+0:14])=[O;D1;H0:15])-[Si](-[CH3;D1;+0:16])(-[CH3;D1;+0:17])-[CH3;D1;+0:18].[C:19]-[C:20]-[NH;D2;+0:21]-[C:22]-[C:23]>>[C:19]-[C:20]-[N;H0;D3;+0:21](-[C;H0;D3... | null | [] | null | null | 24 | HOUR | Isonipecotic acid (4-piperidinecarboxylic acid) (0.76 g, 6 mmol), N-methyl-N-trimethylsilylacetamide and 3 drops of pyridine were stirred at room temperature for 2 hours. This suspension was added to a filtered solution of 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 15 mL of dichloromethane. The solvent was rem... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Tertiary amide.Secondary amine.Silyl protective group | Carboxylic acid.Tertiary amide.Tertiary amide | C1CCNCC1 | C1CC[NH]CC1.C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HCl | N1=CC=CC=C1.ClCCl | null | 24 | CC(=O)N(C)[Si](C)(C)C.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl.O=C(O)C1CCNCC1>N1=CC=CC=C1.ClCCl>O=C(O)C1CCN(C(=O)c2ccccc2SSc2ccccc2C(=O)N2CCC(C(=O)O)CC2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4f02f7260614e1283e973c416bc0d8e | CC(C)(C)OC(=O)[C@H](CCCNC(=N)N)NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)OC(C)(C)C>>N=C(N)NCCC[C@H](NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(=O)O | CC(C)(C)OC([C@@H](NC(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)OC(C)(C)C)CCCNC(N)=N)=O>>C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)O | CC(C)(C)[O:39][C:37]([C@@H:29]([NH:28][C:26]([c:25]1[c:20]([S:19][S:18][c:17]2[c:12]([C:10]([NH:9][C@@H:8]([CH2:7][CH2:6][CH2:5][NH:4][C:2](=[NH:1])[NH2:3])[C:40](=[O:41])[O:42]C(C)(C)C)=[O:11])[cH:13][cH:14][cH:15][cH:16]2)[cH:21][cH:22][cH:23][cH:24]1)=[O:27])[CH2:30][CH2:31][CH2:32][NH:33][C:34](=[NH:35])[NH2:36])=[... | CC(C)(C)OC(=O)[C@H](CCCNC(=N)N)NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)OC(C)(C)C | N=C(N)NCCC[C@H](NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(=O)O | null | null | ClCCl.FC(C(=O)O)(F)F | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 59.8 | [{"value": 59.8, "product": "C1(=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the general method of Example 122 using N,N'-[Dithiobis (2,1-phenylenecarbonyl)bis-L-arginine-bis(1,1-dimethylethyl) ester, (1.31 g, 2.0 mmol) from Example 127 in 15 mL of dichloromethane and 15 mL of trifluoroacetic acid. The residue was triturated with ethanol and 1N HCl to yie... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl.FC(C(=O)O)(F)F | null | null | CC(C)(C)OC(=O)[C@H](CCCNC(=N)N)NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)OC(C)(C)C>ClCCl.FC(C(=O)O)(F)F>N=C(N)NCCC[C@H](NC(=O)c1ccccc1SSc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-85957d48a087410d9c293b7d5c14f82e | CC(=O)N[C@@H](CS)C(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>>CC(=O)NC(CSSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)O | O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)S(=O)(=O)N.C(C)(=O)N[C@@H](CS)C(=O)O>>C(C)(=O)NC(C(=O)O)CSSC1=C(C=CC=C1)C(NC1=CC=C(C=C1)S(N)(=O)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][C@@H:5]([CH2:6][SH:7])[C:28](=[O:29])[OH:30].[s:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15](=[O:16])[n:17]1-[c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]([CH2:6][S:7][S:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[... | CC(=O)N[C@@H](CS)C(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1 | CC(=O)NC(CSSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)O | null | null | null | Miscellaneous | OtherReaction | b009af05d472ccdcc7c275cf7d538d0fec35d7c49529303a2e355b9dd8798d3e | e8a16c39a4da768b069d0811166d9dd2e9252bf47af9bd7cebb79eb4280a5696 | O=C(Nc1ccccc1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[SH;D1;+0:6].[O;D1;H0:7]=[c;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:12]):[s;H0;D2;+0:13]:[n;H0;D3;+0:14]:1-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:14]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19])-[c:9](:[c:10]):[c:11](-[S;H0;D2;+0... | 81.6 | [{"value": 81.6, "product": "C(C)(=O)NC(C(=O)O)CSSC1=C(C=CC=C1)C(NC1=CC=C(C=C1)S(N)(=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the method of Example 132 using 0.8 g (2.4 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzenesulfonamide and 0.39 g (2.4 mmol) of N-acetyl-L-cysteine. The product was washed with ether and dried in vacuo to give 0.92 g of the title compound, mp 218°-220° C.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aliphatic thiol | Secondary amide.Disulfide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | CC(=O)N[C@@H](CS)C(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>>CC(=O)NC(CSSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e6baa83df414e8490e7a223e4d371a6 | CC(S)C(=O)NCC(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>>CC(SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)NCC(=O)O | O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)S(=O)(=O)N.SC(C(=O)NCC(=O)O)C>>S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC(C(=O)NCC(=O)O)C | [CH3:1][CH:2]([SH:3])[C:24](=[O:25])[NH:26][CH2:27][C:28](=[O:29])[OH:30].[s:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11](=[O:12])[n:13]1-[c:14]1[cH:15][cH:16][c:17]([S:18]([NH2:19])(=[O:20])=[O:21])[cH:22][cH:23]1>>[CH3:1][CH:2]([S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[NH:13][c:14]1[cH:15][cH:1... | CC(S)C(=O)NCC(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1 | CC(SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)NCC(=O)O | null | null | null | Miscellaneous | OtherReaction | b009af05d472ccdcc7c275cf7d538d0fec35d7c49529303a2e355b9dd8798d3e | e8a16c39a4da768b069d0811166d9dd2e9252bf47af9bd7cebb79eb4280a5696 | O=C(Nc1ccccc1)c1ccccc1 | [C;D1;H3:1]-[C:2](-[SH;D1;+0:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[O;D1;H0:11]=[c;H0;D3;+0:12]1:[c:13](:[c:14]):[c:15](:[c:16]):[s;H0;D2;+0:17]:[n;H0;D3;+0:18]:1-[c;H0;D3;+0:19](:[c:20]:[c:21]):[c:22]:[c:23]>>[C;D1;H3:1]-[C:2](-[S;H0;D2;+0:3]-[S;H0;D2;+0:17]-[c:15](:[c:16]):[c:13](-[C;H... | 92.3 | [{"value": 92.3, "product": "S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC(C(=O)NCC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the method of Example 132 using 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzenesulfonamide and 0.25 g (1.5 mmol) of 2-mercapto-propionylglycine. The product was washed with ether and dried in vacuo to give 0.65 g of the title compound, mp 254°-256° C.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Aliphatic thiol | Secondary amide.Disulfide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | CC(S)C(=O)NCC(=O)O.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>>CC(SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1)C(=O)NCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40ccfc0f214f4effb36ca78515638c20 | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.O=C(O)c1ccccc1S>>NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)O)cc1 | O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)S(=O)(=O)N.C(C=1C(S)=CC=CC1)(=O)O>>S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)O)C=CC=C1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[n:9]2[c:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[s:18]2)[cH:29][cH:30]1.[SH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26](=[O:27])[OH:28]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16... | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.O=C(O)c1ccccc1S | NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)O)cc1 | null | null | CO.O1CCCC1 | Miscellaneous | OtherReaction | 7156f34f0b223a21fe8e63830f3aca92fa983f2819e149259ffa96be70b7d466 | 2c5b5782f2989be8587a871e910ab32ac50067c6617ca6fd58b9c99c5fcadb6f | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c:4]:[c:5](-[SH;D1;+0:6]):[c:7].[O;D1;H0:8]=[c;H0;D3;+0:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[s;H0;D2;+0:14]:[n;H0;D3;+0:15]:1-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20])-[c:10](:[c:11]):[c:12](-[... | 95.5 | [{"value": 95.5, "product": "S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the method of Example 132 using a suspension of 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzene sulfonamide in a mixture of 15 mL of methanol and 15 mL of tetrahydrofuran, and 0.23 g (1.5 mmol) of thiosalicylic acid. The product was washed with ether and dried in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Secondary amide.Disulfide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | CO.O1CCCC1 | null | null | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.O=C(O)c1ccccc1S>CO.O1CCCC1>NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-52d9d3961073476a8fa59d53b9462e89 | COC(=O)c1ccccc1S.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>>COC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1 | O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)S(=O)(=O)N.C(C=1C(S)=CC=CC1)(=O)OC>>S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)OC)C=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[SH:11].[s:12]1[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[c:19](=[O:20])[n:21]1-[c:22]1[cH:23][cH:24][c:25]([S:26]([NH2:27])(=[O:28])=[O:29])[cH:30][cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11][S:12][c:13]1[cH:14][cH:15][cH:1... | COC(=O)c1ccccc1S.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1 | COC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1 | null | null | CO.O1CCCC1 | Miscellaneous | OtherReaction | 7156f34f0b223a21fe8e63830f3aca92fa983f2819e149259ffa96be70b7d466 | 2c5b5782f2989be8587a871e910ab32ac50067c6617ca6fd58b9c99c5fcadb6f | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[SH;D1;+0:6]):[c:7].[O;D1;H0:8]=[c;H0;D3;+0:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[s;H0;D2;+0:14]:[n;H0;D3;+0:15]:1-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[S;H0;D2;+0:6]-[S;H0;D2;+0:14]-[c:12](:[c:13]):[c:10](-[C;H0;D3;+0:9](=[O;D1;H0... | 92.7 | [{"value": 92.7, "product": "S(N)(=O)(=O)C1=CC=C(C=C1)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared according to the method of Example 132 using a suspension of 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzene sulfonamide in a mixture of 15 mL of methanol and 15 mL of tetrahydrofuran, and 0.27 g (1.6 mmol) of methyl thiosalicylate. The product was triturated with ether, filt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Secondary amide.Disulfide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | CO.O1CCCC1 | null | null | COC(=O)c1ccccc1S.NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1>CO.O1CCCC1>COC(=O)c1ccccc1SSc1ccccc1C(=O)Nc1ccc(S(N)(=O)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-039c45d2d6ad447186631f36b49d7ebe | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.OCC(O)CS>>NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSCC(O)CO)cc1 | O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)S(=O)(=O)N.O1CCCC1.OC(CS)CO>>OC(CSSC1=C(C(=O)NC2=CC=C(C=C2)S(N)(=O)=O)C=CC=C1)CO | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[n:9]2[c:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[s:18]2)[cH:25][cH:26]1.[SH:19][CH2:20][CH:21]([OH:22])[CH2:23][OH:24]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[S:18][S:19][CH2:... | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.OCC(O)CS | NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSCC(O)CO)cc1 | null | null | CO | Miscellaneous | OtherReaction | b009af05d472ccdcc7c275cf7d538d0fec35d7c49529303a2e355b9dd8798d3e | e8a16c39a4da768b069d0811166d9dd2e9252bf47af9bd7cebb79eb4280a5696 | O=C(Nc1ccccc1)c1ccccc1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;D1;H0:4]=[c;H0;D3;+0:5]1:[c:6](:[c:7]):[c:8](:[c:9]):[s;H0;D2;+0:10]:[n;H0;D3;+0:11]:1-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:1]-[C:2]-[S;H0;D2;+0:3]-[S;H0;D2;+0:10]-[c:8](:[c:9]):[c:6](-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:7... | null | [] | null | null | null | null | This compound was prepared according to the method of Example 132 using a suspension of 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl) benzenesulfonamide in a mixture of 15 mL of methanol, and 15 mL of tetrahydrofuran and 2,3-dihydroxy-1-propanethiol. The product was washed with ether and dried in vacuo to g... | 10.6084/m9.figshare.5104873.v1 | null | Aliphatic thiol | Secondary amide.Disulfide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | CO | null | null | NS(=O)(=O)c1ccc(-n2sc3ccccc3c2=O)cc1.OCC(O)CS>CO>NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSCC(O)CO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b264e10282d462783a148a83796833e | CC(=O)N[C@@H](CS)C(=O)O.CCC(C)C(C(=O)O)n1sc2ccccc2c1=O>>CCC(C)C(NC(=O)c1ccccc1S[SH](CCC(=O)O)NC(C)=O)C(=O)O | CC(C(C(=O)O)N1SC2=C(C1=O)C=CC=C2)CC.C(C)(=O)N[C@@H](CS)C(=O)O>>C(C)(=O)NS(SC1=C(C(=O)NC(C(=O)O)C(CC)C)C=CC=C1)CCC(=O)O | [SH:16][CH2:17][C@@H:18]([C:19](=[O:20])[OH:21])[NH:22][C:23]([CH3:24])=[O:25].[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]([n:6]1[c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[s:15]1)[C:26](=[O:27])[OH:28]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[S:15][SH:16]([CH... | CC(=O)N[C@@H](CS)C(=O)O.CCC(C)C(C(=O)O)n1sc2ccccc2c1=O | CCC(C)C(NC(=O)c1ccccc1S[SH](CCC(=O)O)NC(C)=O)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | af210ac592073827101a713c86f606364ea86b0e185a54e240864af93e67c70c | f1560323bad9af1dc55279d6e8cf7e6a1314dd20a0b0e11e3d2fbbb83e4fd24d | c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[C@@H;D3;+0:5](-[C:6]-[SH;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[C:11]-[C:12](-[C:13](=[O;D1;H0:14])-[O;D1;H1:15])-[n;H0;D3;+0:16]1:[s;H0;D2;+0:17]:[c:18](:[c:19]):[c:20](:[c:21]):[c;H0;D3;+0:22]:1=[O;D1;H0:23]>>[C:11]-[C:12](-[NH;D2;+0:16]-[C;H0;D3;+0:22](=[O;D1;H0:23]... | null | [] | null | null | 18 | HOUR | A solution of 0.58 g (2.2 mmol) of [S-(R*,R*)]-3-methyl-2-(3-oxo-3H-benzo[d]isothiazol-2-yl)pentanoic acid in 20 mL of methanol was treated with 0.36 g (2.2 mmol) of N-acetyl-L-cysteine and the reaction was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was triturated with 10... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aliphatic thiol | Secondary amide.Secondary amide | c1ccc2sncc2c1 | c1ccccc1 | c1ccccc1 | null | CO | null | 18 | CC(=O)N[C@@H](CS)C(=O)O.CCC(C)C(C(=O)O)n1sc2ccccc2c1=O>CO>CCC(C)C(NC(=O)c1ccccc1S[SH](CCC(=O)O)NC(C)=O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-950cfed0e8884a9ab3f2f0fdcbee3869 | CCOC(=O)N=NC(=O)OCC.O=C(c1ccccc1)c1ccccc1S>>O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 | SC1=C(C(=O)C2=CC=CC=C2)C=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>C(C1=CC=CC=C1)(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1 | O=[C:3](N=N[C:2](O[CH2:8][CH3:7])=[O:1])O[CH2:21][CH3:20].[c:9]1([C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:10][cH:11][cH:12][cH:13][c:14]1[SH:15]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[S:15][S:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[C:23](... | CCOC(=O)N=NC(=O)OCC.O=C(c1ccccc1)c1ccccc1S | O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 | null | null | C1=CC=CC=C1.C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | ae531ed1d67e6f3eff4e1aecb1c565f4851e348294c3b629df76efe8dc4172ca | 50231886f82502b0a0a5c3927d4f2befa588a6f1d904da84171fca8b4ef3048c | O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 | O=[C;H0;D3;+0:1](-N=N-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[CH2;D2;+0:4]-[CH3;D1;+0:5])-O-[CH2;D2;+0:6]-[CH3;D1;+0:7].[O;D1;H0:8]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[SH;D1;+0:17]):[c:18]>>[O;D1;H0:3]=[C;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[c:19]:[c:20]:[c:21]:[cH;D2;+0:5]:[cH;D2;+0:4]:1)... | 50.7 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "C(C1=CC=CC=C1)(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 2-mercaptobenzophenone (2.3 g, 7.4 mmol) in diethyl ether (10 mL) was added dropwise diethyl azodicarboxylate (0.65 g, 3.7 mmol). The solution was stirred for 5 minutes at room temperature, then diluted with benzene (40 mL) and refluxed for 16 hours. The solution was cooled and concentrated in vacuo le... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Diazene.Aromatic thiol | Ketone.Ketone.Disulfide | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1=CC=CC=C1.C(C)OCC | null | 0.083333 | CCOC(=O)N=NC(=O)OCC.O=C(c1ccccc1)c1ccccc1S>C1=CC=CC=C1.C(C)OCC>O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-169cfd162f7a4903b732bbd90fedb229 | NO.O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1>>O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=NO)c1ccccc1 | C(C)(=O)OCC.C(C1=CC=CC=C1)(=O)C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1.Cl.NO.Cl>>ON=C(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1)C1=CC=CC=C1 | [NH2:24][OH:25].O=[C:23]([c:22]1[c:17]([S:16][S:15][c:14]2[c:9]([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][cH:8]3)[cH:10][cH:11][cH:12][cH:13]2)[cH:18][cH:19][cH:20][cH:21]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[S:15][S:... | NO.O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 | O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=NO)c1ccccc1 | null | null | C(C)O.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[O;D1;H1:9]-[N;H0;D2;+0:8]=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | 35.9 | [{"value": 32.0, "product": "ON=C(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.9, "product": "ON=C(C1=C(C=CC=C1)SSC1=C(C=CC=C1)C(=O)C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The [2-(2-benzoyl-phenyldisulfanyl)-phenyl]phenyl-methanone (0.55 g, 1.2 mmol) was diluted with ethanol (5 mL) and anhydrous pyridine (5 mL). Hydroxylamine hydrochloride (1 g, 14 mmol) was added and the solution was refluxed for 90 minutes. The solution was cooled and poured into cold aqueous HCl (1N). Ethyl acetate wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)O.N1=CC=CC=C1 | null | null | NO.O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=O)c1ccccc1>C(C)O.N1=CC=CC=C1>O=C(c1ccccc1)c1ccccc1SSc1ccccc1C(=NO)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f05182efc7494917864a6ea459070b88 | O=P(O)(O)O.O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=S(=O)(O)O>>O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | N.[O-]P(=O)([O-])[O-].[O-]P(=O)([O-])[O-].[O-]P(=O)([O-])[O-].[F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].P(O)(O)(O)=O.S(O)(O)(=O)=O>>O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | [O:1]=[P:2]([OH:3])([OH:9])[OH:13].[O-][P:4]([O-])([O-])=[O:5].[O-][P:7]([O-])(=[O:6])[O-:8].[O-][P:11]([O-])([O-])=[O:12].O=S(=O)([OH:10])[OH:14]>>[O:1]=[P:2]12[O:3][P:4]3(=[O:5])[O:6][P:7](=[O:8])([O:9]1)[O:10][P:11](=[O:12])([O:13]2)[O:14]3 | O=P(O)(O)O.O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=S(=O)(O)O | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | null | null | null | Miscellaneous | OtherReaction | bbf733c5cb49dcf8bae08bd465b7cb92c6362632f86a8f05af9849a1d176f723 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | O=S(=O)(-[OH;D1;+0:1])-[OH;D1;+0:2].[O-;H0;D1:3]-[P;H0;D4;+0:4](-[O-])(-[O-])=[O;H0;D1;+0:5].[O-]-[P;H0;D4;+0:6](-[O-])(-[O-])=[O;D1;H0:7].[O-]-[P;H0;D4;+0:8](-[O-])(-[O-])=[O;D1;H0:9].[O;D1;H0:10]=[#15:11](-[OH;D1;+0:12])(-[OH;D1;+0:13])-[OH;D1;+0:14]>>[O;D1;H0:9]=[P;H0;D4;+0:8]12-[O;H0;D2;+0:1]-[P;H0;D4;+0:4]3(=[O;H0... | null | [] | null | null | null | null | In 1970, Richmond et al ('641 supra) reacted phosphate rock with phosphoric acid and then with sulfuric acid. The resulting acidulate was subsequently neutralized with anhydrous ammonia to produce a 7-21-0 (N--P2O5 --K2O) grade slurrey fertilizer. In later investigations Pottgiesser et al ('162 supra) produced a 13.5-6... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | O1P2OP3OP1OP(O2)O3 | O1P2OP3OP1OP(O2)O3 | HO- | null | null | null | O=P(O)(O)O.O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].O=S(=O)(O)O>>O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-97bc304407514ba8bc93cfbe5770416a | CC(=O)OO.CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1ccccn1>>CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1cccc[n+]1[O-] | CN(S(=O)(=O)C1=NC=CC=C1)C1=C(C(=CC=C1)Cl)Cl.C(C)(=O)OO>>CN(S(=O)(=O)C=1[N+](=CC=CC1)[O-])C1=C(C(=CC=C1)Cl)Cl | CC(=O)O[OH:20].[CH3:1][N:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1[Cl:10])[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1[Cl:10])[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n+:19]1[O-:20] | CC(=O)OO.CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1ccccn1 | CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1cccc[n+]1[O-] | null | null | null | Miscellaneous | OtherReaction | a6e542b06734899af4300a4d264aed7eb1e13d986216fa692ade3c6e81fedca9 | c3ab83b3edcbc4bfd42c0a952aa2c988db0a3f4c3e00c1396c2ecfcd2e6940e6 | O=S(=O)(Nc1ccccc1)c1cccc[nH+]1 | C-C(=O)-O-[OH;D1;+0:1].[#16:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[#16:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | null | [] | null | null | null | null | N-methyl-N-(2,3-dichlorophenyl)-2-pyridinesulfonamide (1.7 g, 5.3 mmol) is treated with 40% peracetic acid (approx. 12 ml) at 35°-45° under N2 for 14 hours. The excess peracetic acid is removed under vacuum, and the residue is diluted with methylene chloride, poured into water, neutralized with aq. sodium bicarbonate, ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | HO- | null | null | null | CC(=O)OO.CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1ccccn1>>CN(c1cccc(Cl)c1Cl)S(=O)(=O)c1cccc[n+]1[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-032d77276ec347c0b8611cfd56e26b51 | C=CCBr.O=S(=O)(Nc1ccccc1C(F)(F)F)c1cccc[n+]1[O-]>>C=CCN(c1ccccc1C(F)(F)F)S(=O)(=O)c1cccc[n+]1[O-] | C(C=C)Br.FC(C1=C(C=CC=C1)NS(=O)(=O)C=1[N+](=CC=CC1)[O-])(F)F.[H-].[Na+]>>C(C=C)N(S(=O)(=O)C=1[N+](=CC=CC1)[O-])C1=C(C=CC=C1)C(F)(F)F | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14])[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][n+:23]1[O-:24]>>[CH2:1]=[CH:2][CH2:3][N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14])[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][c... | C=CCBr.O=S(=O)(Nc1ccccc1C(F)(F)F)c1cccc[n+]1[O-] | C=CCN(c1ccccc1C(F)(F)F)S(=O)(=O)c1cccc[n+]1[O-] | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 4b716d2054b81e5a5a6e7964bd25a3d424d12bd268f271f58b49ac0e4ed91ee6 | 90c7a3d73a4d167431bb3c161f6525d0660b6b51ccf160c8c2113b2fb8ab28eb | O=S(=O)(Nc1ccccc1)c1cccc[nH+]1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[#7;a;+:4]:[c:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a;+:4]:[c:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 30 | MINUTE | To N-(2-trifluoromethylphenyl)-2-pyridinesulfonamide 1-oxide (compound 129, Table A) (1.0 g, 3.0 mmol) in 10 ml of DMF is added NaH (0.30 g, 6.2 mmol) under N2, and the mixture is stirred at RT for 30 minutes. Allyl bromide (0.82 g, 0.59 ml, 6.8 mmol) is added dropwise, and the mixture is stirred at RT for 48 hours. It... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine.Allyl | null | null | c1ccccc1.C1=CC=[NH+]C=C1 | HBr | CN(C)C=O | null | 0.5 | C=CCBr.O=S(=O)(Nc1ccccc1C(F)(F)F)c1cccc[n+]1[O-]>CN(C)C=O>C=CCN(c1ccccc1C(F)(F)F)S(=O)(=O)c1cccc[n+]1[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6da5e6fc912a4f39abb42807db3359a7 | CC(=O)OO.CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1ccccn1>>CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1cccc[n+]1[O-] | CN(S(=O)(=O)C1=NC=CC=C1)C1=NC=C(C=C1Cl)Cl.C(C)(=O)OO>>CN(S(=O)(=O)C=1[N+](=CC=CC1)[O-])C1=NC=C(C=C1Cl)Cl | CC(=O)O[OH:20].[CH3:1][N:2]([c:3]1[n:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[Cl:10])[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1>>[CH3:1][N:2]([c:3]1[n:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[Cl:10])[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n+:19]1[O-:20] | CC(=O)OO.CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1ccccn1 | CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1cccc[n+]1[O-] | null | null | null | Miscellaneous | OtherReaction | a6e542b06734899af4300a4d264aed7eb1e13d986216fa692ade3c6e81fedca9 | c3ab83b3edcbc4bfd42c0a952aa2c988db0a3f4c3e00c1396c2ecfcd2e6940e6 | O=S(=O)(Nc1ccccn1)c1cccc[nH+]1 | C-C(=O)-O-[OH;D1;+0:1].[#16:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[#16:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | null | [] | null | null | null | null | Following the procedures of Example 1, N-methyl-N-(3,5-dichloro-2-pyridyl)-2-pyridinesulfonamide is oxidized with 40% peracetic acid to give the title compound, MS m/e 334.00 (M+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | c1ccncc1.C1=CC=[NH+]C=C1 | HO- | null | null | null | CC(=O)OO.CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1ccccn1>>CN(c1ncc(Cl)cc1Cl)S(=O)(=O)c1cccc[n+]1[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a21c399ab50c44979c3f814313d13bd3 | CI.O=S(=O)(Nc1cccnc1Cl)c1cccc[n+]1[O-]>>CN(c1cccnc1Cl)S(=O)(=O)c1cccc[n+]1[O-] | ClC1=NC=CC=C1NS(=O)(=O)C=1[N+](=CC=CC1)[O-].CI>>CN(S(=O)(=O)C=1[N+](=CC=CC1)[O-])C=1C(=NC=CC1)Cl | I[CH3:1].[NH:2]([c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Cl:9])[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][n+:18]1[O-:19]>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Cl:9])[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][n+:18]1[O-:19] | CI.O=S(=O)(Nc1cccnc1Cl)c1cccc[n+]1[O-] | CN(c1cccnc1Cl)S(=O)(=O)c1cccc[n+]1[O-] | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=S(=O)(Nc1cccnc1)c1cccc[nH+]1 | I-[CH3;D1;+0:1].[#7;a;+:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[Cl;D1;H0:11]):[#7;a:12]:[c:13]>>[#7;a;+:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[c:8](:[c:9]):[c:10](-[Cl;D1;H0:11]):[#7;a:12]:[c:13] | null | [] | null | null | null | null | The title compound of Example 5 above is reacted with methyl iodide (0.6 g, 0.26 ml, 4.2 mmol) to give N-methyl-N-(2-chloro-3-pyridyl)-2-pyridinesulfonamide 1-oxide, MS m/e 300.00 (M+ +1).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccncc1.C1=CC=[NH+]C=C1 | HI | null | null | null | CI.O=S(=O)(Nc1cccnc1Cl)c1cccc[n+]1[O-]>>CN(c1cccnc1Cl)S(=O)(=O)c1cccc[n+]1[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-acc451c6d71348d3baa782dc1cdfbe6d | C1CO1.CC(C)(C)CCCCC(=O)O>>CC(C)(C)CCCCC(=O)OCCO | C1CO1.C1CO1.C1CO1.C=C.C1CO1.C1CO1.C(CCCCC(C)(C)C)(=O)O.C1CO1.C1CO1.C1CO1>>C(CCCCC(C)(C)C)(=O)OCCO | [CH2:12]1[CH2:13][O:14]1.[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[O:11][CH2:12][CH2:13][OH:14] | C1CO1.CC(C)(C)CCCCC(=O)O | CC(C)(C)CCCCC(=O)OCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 465f35bbfde0d5babd162017ed09f5142d87aedf8ed0abe047dfea06e57e4673 | def7b1b7f2b04b0f2ff5ecfc0b043d7990825ab8ad8f99ebaf633c8077c610aa | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:6]-[C:5]-[OH;D1;+0:7] | null | [] | 100 | CELSIUS | 20 | MINUTE | To a one liter stainless steel autoclave, equipped with a mechanical stirrer, heater, cooling coils, automatic temperature controller, and a tared ethylene oxide cylinder, in a series of runs is added 500 grams neononanoic acid and 2.0 g of the selected catalyst. The reactor is heated to approximately 100° C. and a gas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester.Primary alcohol | C1CO1 | null | null | null | null | 100 | 0.333333 | C1CO1.CC(C)(C)CCCCC(=O)O>>CC(C)(C)CCCCC(=O)OCCO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d50e6d173a8247479425da3781712173 | C1CO1.CC(C)(C)CCCCCC(=O)O>>CC(C)(C)CCCCCC(=O)OCCO | C1CO1.C(CCCCCC(C)(C)C)(=O)O>>C(CCCCCC(C)(C)C)(=O)OCCO | [CH2:13]1[CH2:14][O:15]1.[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[OH:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH2:14][OH:15] | C1CO1.CC(C)(C)CCCCCC(=O)O | CC(C)(C)CCCCCC(=O)OCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 465f35bbfde0d5babd162017ed09f5142d87aedf8ed0abe047dfea06e57e4673 | def7b1b7f2b04b0f2ff5ecfc0b043d7990825ab8ad8f99ebaf633c8077c610aa | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:6]-[C:5]-[OH;D1;+0:7] | null | [] | 100 | CELSIUS | 20 | MINUTE | To a one liter stainless steel autoclave, equipped with a mechanical stirrer, heater, cooling coils, automatic temperature controller, and a tared ethylene oxide cylinder, in a series of runs is added 500 grams neodecanoic acid and 2.0 g of the selected catalyst. The reactor is heated to approximately 100° C. and a gas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester.Primary alcohol | C1CO1 | null | null | null | null | 100 | 0.333333 | C1CO1.CC(C)(C)CCCCCC(=O)O>>CC(C)(C)CCCCCC(=O)OCCO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8fea9f03fff34b1c8f6436c578cdb536 | CCOC(=O)CCNC(=O)C(CSC(C)=O)Cc1ccccc1>>O=C(O)CCNC(=O)C(CS)Cc1ccccc1 | [OH-].[Na+].C1(=CC=CC=C1)C.C(C)(=O)O.C(C)(=O)SCC(C(=O)NCCC(=O)OCC)CC1=CC=CC=C1.[OH-].[Na+]>>SCC(C(=O)NCCC(=O)O)CC1=CC=CC=C1 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[CH:9]([CH2:10][S:11]C(C)=O)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[CH:9]([CH2:10][SH:11])[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CCOC(=O)CCNC(=O)C(CSC(C)=O)Cc1ccccc1 | O=C(O)CCNC(=O)C(CS)Cc1ccccc1 | null | null | CO | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | c1ccccc1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].C-C-[O;H0;D2;+0:7]-[C:8](-[C:9])=[O;D1;H0:10]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[SH;D1;+0:1].[C:9]-[C:8](=[O;D1;H0:10])-[OH;D1;+0:7] | null | [] | null | null | 3 | HOUR | A solution of the product from part (a) (1.02 g., 3.02 mmole) in methanol (6 ml.) is chilled (ice/methanol) and to it, under nitrogen, is added 1N sodium hydroxide (6.35 ml.) over 15 minutes. The mixture is stirred for 3 hours while warming to room temperature (TLC indicates incomplete reaction), and additional 1N sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | c1ccccc1 | HO- | CO | null | 3 | CCOC(=O)CCNC(=O)C(CSC(C)=O)Cc1ccccc1>CO>O=C(O)CCNC(=O)C(CS)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f14fe96832c846f8acc6375afbb7a901 | CC(=O)SCC(Cc1ccccc1)C(=O)O.COC(=O)CCCN>>COC(=O)CCCNC(=O)C(CSC(C)=O)Cc1ccccc1 | C(C(=O)Cl)(=O)Cl.C(C)(=O)SCC(C(=O)O)CC1=CC=CC=C1.Cl.NCCCC(=O)OC.C(C)(C)N(CC)C(C)C>>C(C)(=O)SCC(C(=O)NCCCC(=O)OC)CC1=CC=CC=C1 | O[C:9](=[O:10])[CH:11]([CH2:12][S:13][C:14]([CH3:15])=[O:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][NH2:8]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[CH:11]([CH2:12][S:13][C:14]([CH3:15])=[O:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:... | CC(=O)SCC(Cc1ccccc1)C(=O)O.COC(=O)CCCN | COC(=O)CCCNC(=O)C(CSC(C)=O)Cc1ccccc1 | null | CN(C=O)C | C(Cl)Cl.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | 1 | HOUR | Oxalyl chloride (0.37 ml., 4.2 mmole) is added, under nitrogen, to a solution of (±)-2-[(acetylthio)methyl]-3-phenylpropanoic acid (0.95 g., 4.0 mmole) in ethyl ether (8 ml.). This mixture is cautiously treated with a catalytic amont of dimethylformamide (3 drops), and then stirred for one hour at room temperature. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C.C(Cl)Cl.C(C)OCC | null | 1 | CC(=O)SCC(Cc1ccccc1)C(=O)O.COC(=O)CCCN>CN(C=O)C.C(Cl)Cl.C(C)OCC>COC(=O)CCCNC(=O)C(CSC(C)=O)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-769057d21a9f49c2a23e796d958b008c | COC(=O)CCCCNC(=O)C(CSC(C)=O)Cc1ccccc1>>O=C(O)CCCCNC(=O)C(CS)Cc1ccccc1 | [OH-].[Na+].C(C)(=O)SCC(C(=O)NCCCCC(=O)OC)CC1=CC=CC=C1>>SCC(C(=O)NCCCCC(=O)O)CC1=CC=CC=C1 | CC(=O)[S:13][CH2:12][CH:11]([C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[O:3]C)=[O:10])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[CH:11]([CH2:12][SH:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)CCCCNC(=O)C(CSC(C)=O)Cc1ccccc1 | O=C(O)CCCCNC(=O)C(CS)Cc1ccccc1 | null | null | CO.C(C)(=O)OCC | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | c1ccccc1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].C-[O;H0;D2;+0:7]-[C:8](-[C:9])=[O;D1;H0:10]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[SH;D1;+0:1].[C:9]-[C:8](=[O;D1;H0:10])-[OH;D1;+0:7] | null | [] | null | null | 10 | MINUTE | 1N Sodium hydroxide (12.9 ml., 3.8 equiv.) is added dropwise over 10 minutes to a chilled solution (ice bath) of the product from part (b) (1.20 g., 3.41 mmole) dissolved in methanol (13 ml.) under a nitrogen atmosphere. The mixture is stirred at 0° for 10 minutes and then allowed to warm to room temperature and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | c1ccccc1 | HO- | CO.C(C)(=O)OCC | null | 0.166667 | COC(=O)CCCCNC(=O)C(CSC(C)=O)Cc1ccccc1>CO.C(C)(=O)OCC>O=C(O)CCCCNC(=O)C(CS)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-878353b2e518459d97d4c3e89c51a6f3 | COC(=O)CCCCCCNC(=O)C(CSC(C)=O)Cc1ccccc1>>COC(=O)CCCCCCNC(=O)C(CS)Cc1ccccc1 | O.Cl.[OH-].[Na+].C(C)(=O)SCC(C(=O)NCCCCCCC(=O)OC)CC1=CC=CC=C1>>SCC(C(=O)NCCCCCCC(=O)OC)CC1=CC=CC=C1 | CC(=O)[S:16][CH2:15][CH:14]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:13])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH:14]([CH2:15][SH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:2... | COC(=O)CCCCCCNC(=O)C(CSC(C)=O)Cc1ccccc1 | COC(=O)CCCCCCNC(=O)C(CS)Cc1ccccc1 | null | [Zn] | CO | Reduction | OtherReaction | 7702cd666d5d9a9f1bdea3600e3b84cc62dd11d3f2cea261702317a39db4e581 | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | c1ccccc1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[SH;D1;+0:1] | null | [] | null | null | null | null | (±)-7-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]heptanoic acid, methyl ester (1.43 g., 3.77 mmole) is dissolved in methanol (30 ml.) by warming, and then chilled in an ice bath under nitrogen. 1N Sodium hydroxide (3.77 ml., 1.0 eq.) is added dropwise over 10 minutes to this solution. The mixture is stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | null | null | c1ccccc1 | HO- | [Zn].CO | null | null | COC(=O)CCCCCCNC(=O)C(CSC(C)=O)Cc1ccccc1>[Zn].CO>COC(=O)CCCCCCNC(=O)C(CS)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cd6c544d691047e28572b2af8207df9c | CC(C)(N)CNCCN.CCC(C)=O>>CCC(C)NCCNCC(C)(C)N | [H][H].NC(CNCCN)(C)C.CC(CC)=O>>CC(CC)NCCNCC(C)(C)N | [NH2:5][CH2:6][CH2:7][NH:8][CH2:9][C:10]([CH3:11])([CH3:12])[NH2:13].O=[C:3]([CH2:2][CH3:1])[CH3:4]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH2:6][CH2:7][NH:8][CH2:9][C:10]([CH3:11])([CH3:12])[NH2:13] | CC(C)(N)CNCCN.CCC(C)=O | CCC(C)NCCNCC(C)(C)N | null | [Pt] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | null | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C;D1;H3:4] | 69.5 | [{"value": 69.5, "product": "CC(CC)NCCNCC(C)(C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 146 g (1.1 moles) of N-(2-amino-2-methylpropyl)-1,2-ethanediamine, 84.4 (1.17 moles) of 2-butanone, 300 ml methanol, and 3.0 g of 10% platinum on carbon were reacted in a 1 liter autoclave at 80° C. under 800 pounds per square inch (psi) hydrogen pressure. After two hours the reaction mixture was cooled, t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | null | Other | [Pt].CO | null | null | CC(C)(N)CNCCN.CCC(C)=O>[Pt].CO>CCC(C)NCCNCC(C)(C)N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b296aa432e43463e8f3c1a0d26a6db83 | CCC(C)NCCN1CC(C)(C)NC(C)(C)C1=O.Clc1nc(Cl)nc(Cl)n1>>CCC(C)N(CCN1CC(C)(C)NC(C)(C)C1=O)c1nc(Cl)nc(Cl)n1 | C([O-])([O-])=O.[Na+].[Na+].N1=C(Cl)N=C(Cl)N=C1Cl.CC(CC)NCCN1C(C(NC(C1)(C)C)(C)C)=O>>ClC1=NC(=NC(=N1)Cl)N(CCN1C(C(NC(C1)(C)C)(C)C)=O)C(CC)C | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH2:6][CH2:7][N:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[NH:13][C:14]([CH3:15])([CH3:16])[C:17]1=[O:18].Cl[c:19]1[n:20][c:21]([Cl:22])[n:23][c:24]([Cl:25])[n:26]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]([CH2:6][CH2:7][N:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[NH:13][C:14]([CH3:15])([CH3:16])[C:... | CCC(C)NCCN1CC(C)(C)NC(C)(C)C1=O.Clc1nc(Cl)nc(Cl)n1 | CCC(C)N(CCN1CC(C)(C)NC(C)(C)C1=O)c1nc(Cl)nc(Cl)n1 | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1e1e3c2fd5a9e68e6b66ceb7f38ba57529dd1cfdb540b7a418aa13a9f2f6d698 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CNCCN1CCNc1ncncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[#7;a:7]:1.[C:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:8]-[C:9](-[C;D1;H3:10])-[N;H0;D3;+0:11](-[C:12]-[C:13])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[#7;a:7]:1 | null | [] | null | null | 30 | MINUTE | In a 1 liter three-necked flask were placed 300 ml of water which was cooled to 1° C. 46.1 g (0.25 mole) of cyanuric chloride was dissolved in 240 ml acetone and added to the water in the flask. A white slurry formed which was stirred while adding to it dropwise, 63.9 g (0.25 mole) of 1-[2-(2-butylamino)ethyl]-3,3,5,5-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncncn1 | c1ncncn1 | C1C[NH]CCN1.c1ncncn1 | HCl | O.CC(=O)C | null | 0.5 | CCC(C)NCCN1CC(C)(C)NC(C)(C)C1=O.Clc1nc(Cl)nc(Cl)n1>O.CC(=O)C>CCC(C)N(CCN1CC(C)(C)NC(C)(C)C1=O)c1nc(Cl)nc(Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-217b10af343044bfa5761f4da10eaeb8 | COc1ccc(C(=O)Cl)c(OC)c1.NC1CN2CCC1CC2>>COc1ccc(C(=O)NC2CN3CCC2CC3)c(OC)c1 | Cl.Cl.NC1CN2CCC1CC2.COC1=C(C(=O)Cl)C=CC(=C1)OC.C([O-])([O-])=O.[Na+].[Na+].O>>Cl.N12CC(C(CC1)CC2)NC(C2=C(C=C(C=C2)OC)OC)=O | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:18]1[O:19][CH3:20])=[O:8].[NH2:9][CH:10]1[CH2:11][N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH:10]2[CH2:11][N:12]3[CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17]3)[c:18]([O:19][CH3:20])[cH:21]1 | COc1ccc(C(=O)Cl)c(OC)c1.NC1CN2CCC1CC2 | COc1ccc(C(=O)NC2CN3CCC2CC3)c(OC)c1 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NC1CN2CCC1CC2)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | 23.7 | [{"value": 23.7, "product": "Cl.N12CC(C(CC1)CC2)NC(C2=C(C=C(C=C2)OC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-aminoquinuclidine dihydrochloride, 6.95 g, (0.349), 2,4-dimethoxybenzoyl chloride, 700 g, (0.0349 mole), anhydrous sodium carbonate, 36.99 g, (0.349 mole), 175 ml water, and 175 ml chloroform was stirred rapidly to achieve good mixing of the 2 layers for 20 hrs. The chloroform layer was then separated, w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CN2CCC1CC2 | HCl | C(Cl)(Cl)Cl | null | null | COc1ccc(C(=O)Cl)c(OC)c1.NC1CN2CCC1CC2>C(Cl)(Cl)Cl>COc1ccc(C(=O)NC2CN3CCC2CC3)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-03d1b8f05e4141739d0b6c4cac54a2f6 | CCCOc1ccccc1C(=O)Cl.NC1CN2CCC1CC2>>CCCOc1ccccc1C(=O)NC1CN2CCC1CC2 | C(CC)OC1=C(C(=O)Cl)C=CC=C1.Cl.Cl.NC1CN2CCC1CC2.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>>Cl.N12CC(C(CC1)CC2)NC(C2=C(C=CC=C2)OCCC)=O | Cl[C:11]([c:10]1[c:5]([O:4][CH2:3][CH2:2][CH3:1])[cH:6][cH:7][cH:8][cH:9]1)=[O:12].[NH2:13][CH:14]1[CH2:15][N:16]2[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]2>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[NH:13][CH:14]1[CH2:15][N:16]2[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]2 | CCCOc1ccccc1C(=O)Cl.NC1CN2CCC1CC2 | CCCOc1ccccc1C(=O)NC1CN2CCC1CC2 | null | null | C(=O)=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NC1CN2CCC1CC2)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | null | [] | null | null | null | null | To a solution of 3.82 g (0.0192 mole) of 3-amino quinuclidine dihydrochloride in about 25 ml of carbon dioxide-free water was added 8 g (0.025 mole) of barium hydroxide octahydrate. The mixture was warmed for 5 minutes and then dried to a powder on a rotary evaporator. While protecting from contamination with carbon di... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CN2CCC1CC2 | HCl | C(=O)=O.C(Cl)Cl | null | null | CCCOc1ccccc1C(=O)Cl.NC1CN2CCC1CC2>C(=O)=O.C(Cl)Cl>CCCOc1ccccc1C(=O)NC1CN2CCC1CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bc32b8c0b4ec4edd970f899e38ffb207 | CNc1cc(OC)c(C(=O)NC2CN3CCC2CC3)cc1Cl.O=C([O-])/C=C/C(=O)[O-]>>CNc1cc(OC)c(C(=O)[NH+]([O-])C2CN3CCC2CC3)cc1Cl.Cl | N12CC(C(CC1)CC2)NC(C2=C(C=C(C(=C2)Cl)NC)OC)=O.C(\C=C\C(=O)[O-])(=O)[O-]>>Cl.N12CC(C(CC1)CC2)[NH+](C(C2=C(C=C(C(=C2)Cl)NC)OC)=O)[O-] | [CH3:1][NH:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9](=[O:10])[NH:11][CH:13]2[CH2:14][N:15]3[CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20]3)[cH:21][c:22]1[Cl:23].O=C([O-])/C=C/C([O-])=[O:12]>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9](=[O:10])[NH+:11]([O-:12])[CH:13]2[CH2:14][N:15]3[CH2:16][CH2:17][CH:18]2[CH2... | CNc1cc(OC)c(C(=O)NC2CN3CCC2CC3)cc1Cl.O=C([O-])/C=C/C(=O)[O-] | CNc1cc(OC)c(C(=O)[NH+]([O-])C2CN3CCC2CC3)cc1Cl.Cl | null | null | null | Miscellaneous | OtherReaction | 258aaf9b783ac766ef04674a8049683ffe8fe0219b73c2d32e0bb4ecd173400f | a267a1d067671b1e552868d2a160d189ea3d111697964c07c12357f5fdb70c13 | O=C([NH2+]C1CN2CCC1CC2)c1ccccc1 | O=C(-[O-])/C=C/C(-[O-])=[O;H0;D1;+0:1].[#7:2]-[C:3]-[C:4](-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8])-[C:9]>>[#7:2]-[C:3]-[C:4](-[NH+;D3:5](-[O-;H0;D1:1])-[C:6](=[O;D1;H0:7])-[c:8])-[C:9] | null | [] | null | null | null | null | N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide, fumarate [1:1] is converted to the free base by partitioning with aqueous sodium hydroxide and methylene chloride. Using the procedure of Example 1, the free base is reacted with peracetic acid to obtain the N-oxide and finally with hydrogen chl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.C1CN2CCC1CC2 | HO- | null | null | null | CNc1cc(OC)c(C(=O)NC2CN3CCC2CC3)cc1Cl.O=C([O-])/C=C/C(=O)[O-]>>CNc1cc(OC)c(C(=O)[NH+]([O-])C2CN3CCC2CC3)cc1Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d08bf726ee614cf79e621b0c1f4b7772 | CC/C=C\C=C/CCCCCCCCCC=O>>C=CCCCCCCCCC/C=C\C=C/CC | C([O-])([O-])=O.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.C(CCCCCCCCC\C=C/C=C\CC)=O>>C=CCCCCCCCCC\C=C/C=C\CC | O=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH:14]=[CH:15]/[CH2:16][CH3:17]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH:14]=[CH:15]/[CH2:16][CH3:17] | CC/C=C\C=C/CCCCCCCCCC=O | C=CCCCCCCCCC/C=C\C=C/CC | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O | Functional Group Interconversion | OtherReaction | 7702fabf33730b36d4194facf6bd167de8537ce3feabb6e16a2ab5a7eed012b1 | 327d0a428f3694bfca03537421df2e7fd8c75afd031319c50b8fe23cc3ad9de2 | null | O=[CH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH;D2;+0:1]=[C;D1;H2:4] | null | [] | null | null | null | null | (Z,Z)-1,12,14-heptadecatriene (TRIENE) was synthesized conveniently from Wittig Salt and aldehyde in aqueous dioxidepotassium carbonate heterogeneous medium (Lechat 1982). A mixture of 3.57 g (0.01 mol) of methyl triphenylphosphonium bromide (Alfa Inorganics), 1.7 g (0.14 mol) of potassium carbonate, 10 ml of 1,4-dioxa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Allyl | null | null | null | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O | null | null | CC/C=C\C=C/CCCCCCCCCC=O>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O>C=CCCCCCCCCC/C=C\C=C/CC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-844bfa4964764092a84084123ac463f1 | COCC(=O)c1ccccc1.[N-]=[N+]=Nc1ccc(C=O)cc1>>COc1ccccc1C(=O)C=Cc1ccc(N=[N+]=[N-])cc1 | [OH-].[Na+].COCC(=O)C1=CC=CC=C1.N(=[N+]=[N-])C1=CC=C(C=O)C=C1.CO>>N(=[N+]=[N-])C1=CC=C(C=C1)C=CC(=O)C1=C(C=CC=C1)OC | [CH3:1][O:2][CH2:11][C:9]([c:8]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)=[O:10].O=[CH:12][c:13]1[cH:14][cH:15][c:16]([N:17]=[N+:18]=[N-:19])[cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[CH:11]=[CH:12][c:13]1[cH:14][cH:15][c:16]([N:17]=[N+:18]=[N-:19])[cH:20][cH:21]1 | COCC(=O)c1ccccc1.[N-]=[N+]=Nc1ccc(C=O)cc1 | COc1ccccc1C(=O)C=Cc1ccc(N=[N+]=[N-])cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cd8e70743afbaf8cc3e1648c822b76750ea4c274097b1fe30a5c4f36c14db898 | 1902fedd2f6f28e542a9d6629d43010d6b353c17fbfbb909c81a69c2aae0d321 | O=C(C=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](-[C:8](=[O;D1;H0:9])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | null | [] | 25 | CELSIUS | 24 | HOUR | In a 500-ml flask were placed 15 g of 2-methoxyacetophenone (made by Aldrich Co., 99% purity), 15 g of p-azidobenzaldehyde (manufactured by Kanto Chemical Co., Ltd.), 50 g of 10% aqueous solution of NaOH, and 50 g of methanol. The mixture was stirred in a yellow light at 25° C. for 24 hours. After completion of the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ether | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | 25 | 24 | COCC(=O)c1ccccc1.[N-]=[N+]=Nc1ccc(C=O)cc1>>COc1ccccc1C(=O)C=Cc1ccc(N=[N+]=[N-])cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-735299a0ef624d81b9ed5d77439bde1a | COc1ccc2occc(=O)c2c1>>COc1ccc2c(c1)C(O)CCO2 | COC=1C=CC2=C(C(C=CO2)=O)C1.C(C)N(CC)CC>>COC=1C=CC2=C(C(CCO2)O)C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9](=[O:10])[cH:11][cH:12][o:13]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12][O:13]2 | COc1ccc2occc(=O)c2c1 | COc1ccc2c(c1)C(O)CCO2 | null | [Pd] | C(C)O | Reduction | OtherReaction | e1dfc477dd91c2adbdb4bc7db294c9d008cf28766629c0b98080643a9de74bfe | 0034de6654eff673c4919a40321b83463404d852b0929d3401429300290e8760 | c1ccc2c(c1)CCCO2 | [O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[o;H0;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9] | null | [] | null | null | null | null | A solution of 6-methoxy-4-benzopyranone (31.6 g), triethylamine (4.9 ml) and 10% palladium on carbon (3.16 g) in absolute ethanol (1.7 l) is stirred under an atmosphere of hydrogen for 19 hours. The reaction mixture is filtered and evaporated in vacuo yielding the desired hydrogenated product as a pale yellow liquid.
C... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Secondary alcohol | c1ccc2occcc2c1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | null | [Pd].C(C)O | null | null | COc1ccc2occc(=O)c2c1>[Pd].C(C)O>COc1ccc2c(c1)C(O)CCO2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-649ea945dd7e4b54ae14924d504966d6 | C1CCNCC1.COc1ccc2c(c1)C(O)CCO2>>COc1ccc2c(c1)C(N1CCCCC1)CCO2 | N1CCCCC1.CS(=O)(=O)Cl.COC=1C=CC2=C(C(CCO2)O)C1.C([O-])(O)=O.[Na+]>>COC=1C=CC2=C(C(CCO2)N2CCCCC2)C1 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.O[CH:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[O:18][CH2:17][CH2:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:16][CH2:17][O:18]2 | C1CCNCC1.COc1ccc2c(c1)C(O)CCO2 | COc1ccc2c(c1)C(N1CCCCC1)CCO2 | null | null | C(Cl)Cl.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | f191075d01d8ca635ca442f38e41e9ed3fd1376be4d1b8e4347a724a27f399d5 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCCC2N1CCCCC1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7])-[C:11]-[C:12] | null | [] | null | null | 2 | HOUR | Methane sulfonyl chloride (14.9 ml) is added dropwise to a stirred solution of the product obtained in Step 1. (31.6 g) and triethylamine (29.3 ml) in methylene chloride (750 ml) cooled to 0° C. under nitrogen. The reaction mixture is stirred at RT for 21/2 hours and cooled to 0° C. Piperidine (175 ml) is added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2c(c1)CCCO2 | C1CC[NH]CC1.c1ccc2c(c1)CCCO2 | C1CC[NH]CC1.c1ccc2c(c1)CCCO2 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 2 | C1CCNCC1.COc1ccc2c(c1)C(O)CCO2>C(Cl)Cl.C(C)N(CC)CC>COc1ccc2c(c1)C(N1CCCCC1)CCO2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-000cebf4787344f1bf7d418a9168b1b4 | BrCCCBr.Oc1ccc2c(c1)C(N1CCCCC1)CCO2>>BrCCCOc1ccc2c(c1)C(N1CCCCC1)CCO2 | [OH-].[K+].OC=1C=CC2=C(C(CCO2)N2CCCCC2)C1.BrCCCBr>>BrCCCOC=1C=CC2=C(C(CCO2)N2CCCCC2)C1 | Br[CH2:4][CH2:3][CH2:2][Br:1].[OH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH:12]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:19][CH2:20][O:21]2>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH:12]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:19][CH2:20][O:21]2 | BrCCCBr.Oc1ccc2c(c1)C(N1CCCCC1)CCO2 | BrCCCOc1ccc2c(c1)C(N1CCCCC1)CCO2 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | CCOCC.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)OCCC2N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 48 | HOUR | Crushed potassium hydroxide (1.15 g) and tetrabutyl ammonium chloride (0.61 g) are added to a solution of the product obtained in Step 3. (4.8 g) in 1,3-dibromopropane (21 ml). The reaction mixture is stirred under nitrogen at RT for 48 hours, diluted with diethyl ether, washed with water and extracted into 5% aq. HCl.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1CC[NH]CC1.c1ccc2c(c1)CCCO2 | HBr | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC.C(C)OCC | null | 48 | BrCCCBr.Oc1ccc2c(c1)C(N1CCCCC1)CCO2>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC.C(C)OCC>BrCCCOc1ccc2c(c1)C(N1CCCCC1)CCO2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2956eb50cd4a4f1bb50c59a5120211de | COc1cccc2c(=O)ccoc12>>COc1cccc2c1OCCC2O | COC1=CC=CC=2C(C=COC21)=O.C(C)N(CC)CC>>OC1CCOC2=C1C=CC=C2OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[o:9][cH:10][cH:11][c:12]2=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][CH2:10][CH2:11][CH:12]2[OH:13] | COc1cccc2c(=O)ccoc12 | COc1cccc2c1OCCC2O | null | [Pd] | C(C)O | Reduction | OtherReaction | 75e7adcdbf2c81d6a6b8c6e0ffad15bb1e3e6ab17dc1e935c9e35b034caefa6e | 0034de6654eff673c4919a40321b83463404d852b0929d3401429300290e8760 | c1ccc2c(c1)CCCO2 | [O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[o;H0;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9] | null | [] | null | null | null | null | A solution of 8-methoxy-4-benzopyranone (31.6 g), triethylamine (4.9 ml) and 10% palladium on carbon (3.1 g) in absolute ethanol (1.7 l) is stirred under an atmosphere of hydrogen (P=52 lbs.) overnight. The resulting solid is filtered, washed with diethyl ether and evaporated in vacuo yielding the desired product as a ... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Secondary alcohol | c1ccoc2ccccc12 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | null | [Pd].C(C)O | null | null | COc1cccc2c(=O)ccoc12>[Pd].C(C)O>COc1cccc2c1OCCC2O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-badde64ec33c4001be5240ae6f4f35f0 | C1CCNCC1.COc1cccc2c1OCCC2O>>COc1cccc2c1OCCC2N1CCCCC1 | CS(=O)(=O)Cl.OC1CCOC2=C1C=CC=C2OC.C(C)N(CC)CC.N1CCCCC1>>COC1=CC=CC=2C(CCOC21)N2CCCCC2 | [NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.O[CH:12]1[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]2[O:9][CH2:10][CH2:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][CH2:10][CH2:11][CH:12]2[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | C1CCNCC1.COc1cccc2c1OCCC2O | COc1cccc2c1OCCC2N1CCCCC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f191075d01d8ca635ca442f38e41e9ed3fd1376be4d1b8e4347a724a27f399d5 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCCC2N1CCCCC1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7])-[C:11]-[C:12] | null | [] | null | null | 2 | HOUR | Methane sulfonyl chloride (14.9 ml) is added dropwise to a solution of the product obtained in Step 1. (31.6 g) and triethylamine (29.3 ml) in methylene chloride (750 ml) cooled to 0° C. under nitrogen. The reaction mixture is stirred for 11/2 hours; piperidine (175 ml) is added and the reaction mixture is stirred unde... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.C1CC[NH]CC1 | c1ccc2c(c1)CCCO2.C1CC[NH]CC1 | HO- | C(Cl)Cl | null | 2 | C1CCNCC1.COc1cccc2c1OCCC2O>C(Cl)Cl>COc1cccc2c1OCCC2N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-11041e93a6764496b437ae0e8552152e | BrCCCBr.Oc1cccc2c1OCCC2N1CCCCC1>>BrCCCOc1cccc2c1OCCC2N1CCCCC1 | BrCCCBr.OC1=CC=CC=2C(CCOC21)N2CCCCC2.[OH-].[K+].O>>BrCCCOC1=CC=CC=2C(CCOC21)N2CCCCC2 | Br[CH2:4][CH2:3][CH2:2][Br:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[O:12][CH2:13][CH2:14][CH:15]2[N:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[O:12][CH2:13][CH2:14][CH:15]2[N:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | BrCCCBr.Oc1cccc2c1OCCC2N1CCCCC1 | BrCCCOc1cccc2c1OCCC2N1CCCCC1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)OCCC2N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:4]-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:8] | null | [] | null | null | 8 | HOUR | Crushed potassium hydroxide (4.1 g) and tetrabutyl ammonium chloride (2.2 g) and H2O (5 ml) are added to a stirred mixture of the product obtained in Step 3. (17.2 g) and 1,3-dibromopropane (74.8 ml). The reaction mixture is stirred under nitrogen overnight, diluted with diethyl ether, and extracted with 5% aq. HCl. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCO2.C1CC[NH]CC1 | HBr | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)OCC | null | 8 | BrCCCBr.Oc1cccc2c1OCCC2N1CCCCC1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)OCC>BrCCCOc1cccc2c1OCCC2N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5b26df7fe2534bf0910c119f65b7be7d | COc1cccc2c1OC(C)(C)C2=O>>COc1cccc2c1OC(C)(C)C2O | [BH4-].[Na+].COC1=CC=CC=2C(C(OC21)(C)C)=O>>COC1=CC=CC=2C(C(OC21)(C)C)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][C:10]([CH3:11])([CH3:12])[C:13]2=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][C:10]([CH3:11])([CH3:12])[CH:13]2[OH:14] | COc1cccc2c1OC(C)(C)C2=O | COc1cccc2c1OC(C)(C)C2O | null | null | C(C)O.C(Cl)Cl | Reduction | Reduction of ketone to secondary alcohol | 755c7bdda3ccaa9e2a097b82c386f43f2881f1d49e6c3707dce72c3ac00b51db | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCO2 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | null | null | null | null | An aqueous solution of sodium borohydride (8.2 g, 50 ml) is added to a stirred solution of the product obtained in Step 3. (41.8 g) in ethanol (1 l) and the mixture refluxed for 3 hours and evaporated in vacuo. The residue is taken up in water and toluene, the layers are separated and the organic phase washed, dried an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | C(C)O.C(Cl)Cl | null | null | COc1cccc2c1OC(C)(C)C2=O>C(C)O.C(Cl)Cl>COc1cccc2c1OC(C)(C)C2O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29d226711096432384d0866c11b1dd4d | C1CCNCC1.COc1cccc2c1OC(C)(C)C2O>>COc1cccc2c1OC(C)(C)C2N1CCCCC1 | N1CCCCC1.COC1=CC=CC=2C(C(OC21)(C)C)O.C([O-])(O)=O.[Na+].CS(=O)(=O)Cl>>COC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2 | [NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.O[CH:13]1[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]2[O:9][C:10]1([CH3:11])[CH3:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[O:9][C:10]([CH3:11])([CH3:12])[CH:13]2[N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1 | C1CCNCC1.COc1cccc2c1OC(C)(C)C2O | COc1cccc2c1OC(C)(C)C2N1CCCCC1 | null | null | C(Cl)Cl.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | ff764035e14a0e265d5118c5ee8287c96fc78766bbde588c108e1e9046e67926 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCC2N1CCCCC1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8])-[C:12]-[C:13] | null | [] | 0 | CELSIUS | 3 | HOUR | Triethylamine (29 ml) is added to a stirred solution of the product obtained in Step 4. (25.4 g) in methylene chloride (560 ml) at RT under nitrogen. Methanesulfonyl chloride (11.1 ml) is added dropwise to the mixture which is cooled to 0° C. The mixture is stirred for 3 hours at RT, cooled to 0° C., piperidine (128 ml... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.C1CC[NH]CC1 | c1ccc2c(c1)CCO2.C1CC[NH]CC1 | HO- | C(Cl)Cl.C(C)N(CC)CC | 0 | 3 | C1CCNCC1.COc1cccc2c1OC(C)(C)C2O>C(Cl)Cl.C(C)N(CC)CC>COc1cccc2c1OC(C)(C)C2N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-62c89f061fa24da181f2e8c2e39d52b5 | COc1cccc2c1OC(C)(C)C2N1CCCCC1>>CC1(C)Oc2c(O)cccc2C1N1CCCCC1 | COC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2.Br>>OC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2 | C[O:7][c:6]1[c:5]2[c:11]([cH:10][cH:9][cH:8]1)[CH:12]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[C:2]([CH3:1])([CH3:3])[O:4]2>>[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]2[CH:12]1[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | COc1cccc2c1OC(C)(C)C2N1CCCCC1 | CC1(C)Oc2c(O)cccc2C1N1CCCCC1 | null | null | C(C)(=O)O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)OCC2N1CCCCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5]>>[#8:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | 7-Methoxy-3-piperidino-2,2-dimethylbenzofuran (65.1 g) is added to a stirred mixture of glacial acetic acid (340 ml) and 48% HBr (340 ml) and the solution refluxed for 3 hours. The reaction mixture is poured into crushed ice/H2O and brought to a pH=8-10. The alkaline reaction mixture is extracted with methylene chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCO2.C1CC[NH]CC1 | Other | C(C)(=O)O | null | null | COc1cccc2c1OC(C)(C)C2N1CCCCC1>C(C)(=O)O>CC1(C)Oc2c(O)cccc2C1N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f0acfd39ea7a462683b5b3c43269d05e | BrCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1>>CC1(C)Oc2c(OCCCBr)cccc2C1N1CCCCC1 | BrCCCBr.[OH-].[K+].O.OC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2>>BrCCCOC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2 | Br[CH2:8][CH2:9][CH2:10][Br:11].[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([OH:7])[cH:12][cH:13][cH:14][c:15]2[CH:16]1[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13][cH:14][c:15]2[CH:16]1[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22... | BrCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1 | CC1(C)Oc2c(OCCCBr)cccc2C1N1CCCCC1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | CCOCC.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)OCC2N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:4]-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:8] | null | [] | null | null | 20 | HOUR | Potassium hydroxide (1.47 g), tetrabutyl ammonium chloride (0.77 g) and H2O (1 ml) are added to a solution of the product obtained in Step 6. (6.6 g) in 1,3-dibromopropane (27 ml). The reaction mixture is stirred for 20 hours and diluted with diethyl ether and washed with 5% aq. HCl. The acidic solution is washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCO2.C1CC[NH]CC1 | HBr | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC.C(C)OCC | null | 20 | BrCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC.C(C)OCC>CC1(C)Oc2c(OCCCBr)cccc2C1N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e1cc7aae472c4f0e89601c6881976e37 | BrCCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1>>CC1(C)Oc2c(OCCCCBr)cccc2C1N1CCCCC1 | [OH-].[K+].OC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2.BrCCCCBr>>BrCCCCOC1=CC=CC=2C(C(OC21)(C)C)N2CCCCC2 | Br[CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([OH:7])[cH:13][cH:14][cH:15][c:16]2[CH:17]1[N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12])[cH:13][cH:14][cH:15][c:16]2[CH:17]1[N:18]1[CH2:19][CH2:20][CH2:21... | BrCCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1 | CC1(C)Oc2c(OCCCCBr)cccc2C1N1CCCCC1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | CCOCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)OCC2N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:4]-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:8] | null | [] | null | null | 5 | HOUR | Crushed potassium hydroxide (19.6 g) and tetrabutyl ammonium chloride (1.7 g) are added to a solution of 7-hydroxy-3-piperidino-2,2-dimethylbenzofuran (14.4 g) in 1,4-dibromobutane (69.4 ml) and the mixture stirred at RT under nitrogen for 5 hours. The reaction mixture is diluted with ether, washed with water, extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCO2.C1CC[NH]CC1 | HBr | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC | null | 5 | BrCCCCBr.CC1(C)Oc2c(O)cccc2C1N1CCCCC1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCOCC>CC1(C)Oc2c(OCCCCBr)cccc2C1N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d9fe4eea0d14c78998610d953418f18 | COc1ccc(COC(=O)N[C@H](CO)C(=O)OCc2ccccc2)cc1>>COC[C@@H](NC(=O)OCc1ccc(OC)cc1)C(=O)OCc1ccccc1 | [N+](=[N-])=C.C(=O)=O.CC(=O)C.C(C1=CC=CC=C1)OC([C@H](NC(=O)OCC1=CC=C(C=C1)OC)CO)=O.B(F)(F)F.CCOCC>>C(C1=CC=CC=C1)OC([C@H](NC(=O)OCC1=CC=C(C=C1)OC)COC)=O | [OH:2][CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]1)[C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]1)[C:18](=[O:19])[... | COc1ccc(COC(=O)N[C@H](CO)C(=O)OCc2ccccc2)cc1 | COC[C@@H](NC(=O)OCc1ccc(OC)cc1)C(=O)OCc1ccccc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 70208f2708ef916b87826db62bd559464d026f06571e7efe1ab0d84891b316f6 | e85669534439e6064e577a50279050476a21ceb3b9ce2038de4518b5b972fb94 | O=C(CNC(=O)OCc1ccccc1)OCc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[OH;D1;+0:6]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;D1;H3:7] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)OC([C@H](NC(=O)OCC1=CC=C(C=C1)OC)COC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester (720 mg, 2.00 mmol) is dissolved in dry dichloromethane (20 ml) and the solution cooled to dry ice/acetone. Boron trifluoride etherate (100 μl) is added followed by the portionwise addition of diazomethane (30 mmol in 20 ml CH2Cl2). After about 30 minutes the solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | COc1ccc(COC(=O)N[C@H](CO)C(=O)OCc2ccccc2)cc1>ClCCl>COC[C@@H](NC(=O)OCc1ccc(OC)cc1)C(=O)OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c71b9f3cdcad49d1b3a53a42a03aed7c | Nc1cccc2c1OC(F)(F)O2.O=[N+]([O-])c1cc([N+](=O)[O-])c(Cl)c(C(F)(F)F)c1>>O=[N+]([O-])c1cc([N+](=O)[O-])c(Nc2cccc3c2OC(F)(F)O3)c(C(F)(F)F)c1 | Cl.O[Li].O.FC1(OC2=C(O1)C=CC=C2N)F.[N+](=O)([O-])C1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)Cl>>FC1(OC2=C(O1)C=CC=C2NC2=C(C=C(C=C2C(F)(F)F)[N+](=O)[O-])[N+](=O)[O-])F | [NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[O:18][C:19]([F:20])([F:21])[O:22]2.Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:28][c:23]1[C:24]([F:25])([F:26])[F:27]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[c:17]2[O:18]... | Nc1cccc2c1OC(F)(F)O2.O=[N+]([O-])c1cc([N+](=O)[O-])c(Cl)c(C(F)(F)F)c1 | O=[N+]([O-])c1cc([N+](=O)[O-])c(Nc2cccc3c2OC(F)(F)O3)c(C(F)(F)F)c1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccc3c2OCO3)cc1 | Cl-[c;H0;D3;+0:1](:[c:2](-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6]):[c:7]):[c:8](-[#7;+:9]):[c:10].[#8:11]-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7;+:9]-[c:8](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:13](:[c:15]):[c:12]-[#8:11]):[c:2](-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6]):[c:7] | null | [] | null | null | 20 | MINUTE | 20.8 g of LiOH.H2O are added at 0° C. to a solution of 24.5 g of 2,2-difluoro-4-amino-1,3-benzodioxole in 70 ml of dimethyl sulfoxide. The mixture is then stirred for 20 minutes. Subsequently, a solution of 38.3 g of 2,4-dinitro-6-trifluoromethylchlorobenzene in 70 ml of dimethyl sulfoxide is added, and the resultant r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)OCO2 | HCl | CS(=O)C.O | null | 0.333333 | Nc1cccc2c1OC(F)(F)O2.O=[N+]([O-])c1cc([N+](=O)[O-])c(Cl)c(C(F)(F)F)c1>CS(=O)C.O>O=[N+]([O-])c1cc([N+](=O)[O-])c(Nc2cccc3c2OC(F)(F)O3)c(C(F)(F)F)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-38fb1d06294f4f07968ae0a46176877a | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2)cc1>>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(Cl)cc3)cc2)s1 | C(C)OC(NNC(C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)Cl)=O)=S>>C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)Cl | O=[C:7]([NH:6][NH:5][C:4]([O:3][CH2:2][CH3:1])=[S:25])[CH:8]([CH3:9])[O:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][n:6][c:7]([CH:8]([CH3:9])[O:10][c:11]2[cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH... | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2)cc1 | CCOc1nnc(C(C)Oc2ccc(Oc3ccc(Cl)cc3)cc2)s1 | null | null | S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | ff34a009045b5c9adf9fb943f11b38be8f1350c0755ea4ec5e2842f930b046f9 | 5caf0fd195797c78f794bcf8d12286f6659d5c73f87eedb48b36b62a76260df7 | c1ccc(Oc2ccc(OCc3nncs3)cc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;H0;D1;+0:5])-[#8:6]-[C:7])-[C:8](-[#8:9])-[C;D1;H3:10]>>[#8:9]-[C:8](-[C;D1;H3:10])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[#8:6]-[C:7]):[s;H0;D2;+0:5]:1 | 52.4 | [{"value": 52.4, "product": "C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 10 ml of concentrated sulfuric acid cooled to -5° C. was added, with stirring, 2.0 g of 3-[2-[4-(4-chlorophenoxy)phenoxy]-propionyl]-thiocarbazic acid-O-ethyl ester gradually. After stirring at the same temperature for 10 minutes, the reaction mixture was poured over 100 g of ice followed by extracting with ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Thioamide | Ether | null | c1nncs1 | c1nncs1.c1ccccc1.c1ccccc1 | HO- | S(O)(O)(=O)=O | null | null | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2)cc1>S(O)(O)(=O)=O>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(Cl)cc3)cc2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dedcc622a9794abe8181ef0f7412474d | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cc2)cc1>>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C(F)(F)F)cc3)cc2)s1 | C(C)OC(NNC(C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)C(F)(F)F)=O)=S>>C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)C(F)(F)F | O=[C:7]([NH:6][NH:5][C:4]([O:3][CH2:2][CH3:1])=[S:28])[CH:8]([CH3:9])[O:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][n:6][c:7]([CH:8]([CH3:9])[O:10][c:11]2[cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][c:1... | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cc2)cc1 | CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C(F)(F)F)cc3)cc2)s1 | null | null | S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | ff34a009045b5c9adf9fb943f11b38be8f1350c0755ea4ec5e2842f930b046f9 | 5caf0fd195797c78f794bcf8d12286f6659d5c73f87eedb48b36b62a76260df7 | c1ccc(Oc2ccc(OCc3nncs3)cc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;H0;D1;+0:5])-[#8:6]-[C:7])-[C:8](-[#8:9])-[C;D1;H3:10]>>[#8:9]-[C:8](-[C;D1;H3:10])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[#8:6]-[C:7]):[s;H0;D2;+0:5]:1 | 57.4 | [{"value": 57.4, "product": "C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 10 ml of concentrated sulfuric acid cooled to -5° C. was added, with stirring, 2.0 g of 3-[2-[4-(4-trifluoromethylphenoxy)phenoxy]-propionyl]-thiocarbazic acid-O-ethyl ester gradually. After stirring at the same temperature for 10 minutes, the reaction mixture was poured over 100 g of ice followed by extracting with... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether.Thioamide | Ether | null | c1nncs1 | c1nncs1.c1ccccc1.c1ccccc1 | HO- | S(O)(O)(=O)=O | null | null | CCOC(=S)NNC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cc2)cc1>S(O)(O)(=O)=O>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C(F)(F)F)cc3)cc2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f72db97d8ce54dbba8cafdb5ed72d91d | CCOc1nnc(CBr)s1.Oc1ccc(Oc2ccccc2)cc1>>CCOC1=NN=C(Oc2ccc(Oc3ccccc3)cc2)[SH]1C | C(C)(=O)OCC.C([O-])([O-])=O.[K+].[K+].BrCC=1SC(=NN1)OCC.O(C1=CC=CC=C1)C1=CC=C(C=C1)O>>C(C)OC=1S(C(=NN1)OC1=CC=C(C=C1)OC1=CC=CC=C1)C | Br[CH2:23][c:7]1[n:6][n:5][c:4]([O:3][CH2:2][CH3:1])[s:22]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4]1=[N:5][N:6]=[C:7]([O:8][c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[SH:22]1[CH3:23] | CCOc1nnc(CBr)s1.Oc1ccc(Oc2ccccc2)cc1 | CCOC1=NN=C(Oc2ccc(Oc3ccccc3)cc2)[SH]1C | null | null | CC(=O)C | Acylation | OtherReaction | 8f406dc626aae18297683d0b62d3d601ac9366fdba7a91cf80dd60f751fe5c84 | 54efcbe8e120567f454985a52b84b5c2743f8a3bfcd524048dd0be68629ab022 | C1=NN=C(Oc2ccc(Oc3ccccc3)cc2)S1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[#8:6]-[C:7]):[s;H0;D2;+0:8]:1.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:7]-[#8:6]-[C;H0;D3;+0:5]1=[N;H0;D2;+0:4]-[N;H0;D2;+0:3]=[C;H0;D3;+0:2](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[SH;D3;+0:8]-1-[CH3;D1;+0:1] | 74.2 | [{"value": 74.2, "product": "C(C)OC=1S(C(=NN1)OC1=CC=C(C=C1)OC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.76 g of 4-phenoxy phenol was dissolved in 10 ml of acetone followed by adding 0.6 g of anhydrous potassium carbonate and 1.0 g of 2-bromomethyl-5-ethoxy-1,3,4-thiadiazole. The resulting mixture was refluxed with stirring and heated for 2 hours. After cooling, 100 ml of ethyl acetate was added followed by washing with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | c1nncs1 | C1=NN=C[SH]1 | C1=NN=C[SH]1.c1ccccc1.c1ccccc1 | Br- | CC(=O)C | null | null | CCOc1nnc(CBr)s1.Oc1ccc(Oc2ccccc2)cc1>CC(=O)C>CCOC1=NN=C(Oc2ccc(Oc3ccccc3)cc2)[SH]1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-08f23e697a564844a42b9eee52f2f3d1 | CCOc1nnc(C(C)Br)s1.Cc1ccc(Oc2ccc(O)cc2)cc1>>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C)cc3)cc2)s1 | CC1=CC=C(OC2=CC=C(C=C2)O)C=C1.C([O-])([O-])=O.[K+].[K+].BrC(C)C=1SC(=NN1)OCC>>C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)C | Br[CH:8]([c:7]1[n:6][n:5][c:4]([O:3][CH2:2][CH3:1])[s:25]1)[CH3:9].[OH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([CH3:20])[cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][n:6][c:7]([CH:8]([CH3:9])[O:10][c:11]2[cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][c:19]([CH3:20])[cH:21][c... | CCOc1nnc(C(C)Br)s1.Cc1ccc(Oc2ccc(O)cc2)cc1 | CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C)cc3)cc2)s1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(Oc2ccc(OCc3nncs3)cc2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[#7;a:7]:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[CH;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[#7;a:7]:1 | 73.6 | [{"value": 73.6, "product": "C(C)OC=1SC(=NN1)C(C)OC1=CC=C(C=C1)OC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.84 g of 4-(4-methylphenoxy)phenol was dissolved in 5 ml of acetone followed by adding 0.87 g of anhydrous potassium carbonate and 1.0 g of 2-(1-bromoethyl)-5-ethoxy-1,3,4-thiadiazole. The resulting mixture was refluxed with stirring and heating for 2 hours. After cooling, insoluble salts were filtered off, and aceton... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1nncs1.c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | null | CCOc1nnc(C(C)Br)s1.Cc1ccc(Oc2ccc(O)cc2)cc1>CC(=O)C>CCOc1nnc(C(C)Oc2ccc(Oc3ccc(C)cc3)cc2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-35eabf0f8e394ae3b362808c91e10ea1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.COC(=O)CCCCN>>COC(=O)CCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | CN1CCOCC1.C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.CN1CCOCC1.Cl.NCCCCC(=O)OC.C(C(C)C)OC(=O)Cl>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCC(=O)OC | O[C:10](=[O:11])[C@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[C@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.COC(=O)CCCCN | COC(=O)CCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14]-[NH2;D1;+0:15]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:15]-[C:14]-[C:13] | 96.2 | [{"value": 96.2, "product": "C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a cold (ca -30° ), stirred solution of 26.5 g (0.1 mole) of t-butoxycarbonylphenylalanine (BOC-Phe) and 11.2 g (0.1 mole) of N-methylmorpholine in 150 ml of dimethylformamide (DMF) was added dropwise 13.2 ml (0.1 mole) of isobutylchloroformate. After warming and then holding the temperature at ca. -15° for about ten... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | null | 8 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.COC(=O)CCCCN>CN(C=O)C>COC(=O)CCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dfc940d1027e4824b71c811ac0ae7fe4 | COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C>>COC(=O)CCCCCNC(=O)[C@@H](N)Cc1ccccc1 | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(=O)OC.Cl.O1CCOCC1>>Cl.COC(CCCCCNC([C@@H](N)CC1=CC=CC=C1)=O)=O | CC(C)(C)OC(=O)[NH:14][C@H:13]([C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:12])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[C@@H:13]([NH2:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | COC(=O)CCCCCNC(=O)[C@@H](N)Cc1ccccc1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | null | [] | null | null | null | null | To a solution of the title compound of Example 2 (43.1 g, 0.11 mole) in 100 ml of dioxane was added 100 ml of 6M hydrogen chloride/dioxane. After about 30 min. the solution was concentrated in vacuo to dryness and the residue triturated thoroughly with diethyl ether. The solid was collected and washed well with diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | null | COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C>O1CCOCC1>COC(=O)CCCCCNC(=O)[C@@H](N)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-df3ebfe50c8c461e85592be41123da00 | COC(=O)CN.CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)O>>COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](CCSC)C(=O)O.Cl.COC(CN)=O>>COC(CNC([C@H](NC(=O)OC(C)(C)C)CCSC)=O)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][NH2:6].O[C:7](=[O:8])[C@@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[C@@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | COC(=O)CN.CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)O | COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[NH2;D1;+0:18]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-... | null | [] | null | null | null | null | The title compound was prepared by the general method of Example 1 using 24.9 g (0.1 mole) of t-butoxycarbonyl-D-methionine (BOC-D-Met) and 13.8 g (0.11 mole) of glycine methyl ester hydrochloride. The crude product was recrystallized from ethyl acetate/Skellysolve B to give the title compound, which was used in subseq... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | null | HO- | null | null | null | COC(=O)CN.CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)O>>COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-37b5bfcf3c62463e96183b6c7a43b894 | COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C>>CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O | COC(CNC([C@H](NC(=O)OC(C)(C)C)CCSC)=O)=O.[OH-].[K+]>>C(C)(C)(C)OC(=O)N[C@H](CCSC)C(=O)NCC(=O)O | C[O:20][C:18]([CH2:17][NH:16][C:14]([C@@H:5]([CH2:4][CH2:3][S:2][CH3:1])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15])=[O:19]>>[CH3:1][S:2][CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[NH:16][CH2:17][C:18](=[O:19])[OH:20] | COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C | CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound of Example 8 (32.0 g, 0.1 mole) was dissolved in 200 ml of methanol to which was added 200 ml of 2M potassium hydroxide. After ca. 5 min. at room temperature the solution was concentrated to about half volume and diluted with ethyl acetate. The solution was neutralized by washing with two portions of... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | null | null | COC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C>CO>CSCC[C@@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5cde0d6b47b04ae18f76dd684a697a17 | C1COCCO1.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C>>COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.Cl.O | C(C)(C)(C)OC(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(=O)OC.Cl.O1CCOCC1>>O.Cl.N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(=O)OC.N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(OC)=O.Cl | [CH2:6]1[CH2:7][O:60][CH2:9][CH2:55][O:56]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44](=[O:45])[C@@H:46]([NH:21][C:22](=[O:23])[CH2:24][NH:25][C:26](=[O:27])[C@H:28]([NH:10][C:11](=[O:12])[O:35][C:20]([CH3:8])([CH3:19])[CH3:64])[CH2:30][CH2:31][S:32][CH3:33])[CH2:47][c:48]1[cH:49][cH:... | C1COCCO1.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C | COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.Cl.O | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 1eb9f9bad8df2ed4a5013c42562dfad69178cfdd17cf7123774db00e33167a9a | 83bb2cfddad31ecdb1957349ae1a47c1f8a1d56fcdea61bfe359f575971cab76 | c1ccccc1.c1ccccc1 | [CH2;D2;+0:1]1-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-1.[C:7]-[C:8]-[C@@H;D3;+0:9](-[NH;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-[C;H0;D4;+0:14](-[CH3;D1;+0:15])(-[CH3;D1;+0:16])-[CH3;D1;+0:17])-[C:18](=[O;D1;H0:19])-[#7:20]-[C:21]-[C:22](=[O;D1;H0:23])-[NH;D2;+0:24]-[C@... | null | [] | null | null | 1 | HOUR | The title compound of Example 10 (12.0 g) was dissolved in 50 ml of dioxane to which was added 50 ml of 6M hydrogen chloride/dioxane. After about one hour, the volatiles were removed in vacuo and the residue triturated thoroughly with diethyl ether. The title compound (10.9 g) was collected as an analytically pure hydr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Ether.Ether.Secondary amide.Boc | Ester.Ester.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Primary amine.Primary amine.Monosulfide | C1COCCO1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O1CCOCC1 | null | 1 | C1COCCO1.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](CCSC)NC(=O)OC(C)(C)C>O1CCOCC1>COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.COC(=O)CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](N)CCSC.Cl.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7110aa93414d4664b7879c9e173b8a54 | CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(OC(=O)OCC(C)C)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.ClCCl.O=C([O-])[O-].O=S(=O)([O-])O>>CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O)N... | ClCCl.S([O-])(O)(=O)=O.[K+].C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=C(C=C1)OC(=O)OCC(C)C)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(=O)OC)CC.C([O-])([O-])=O.[K+].[K+]>>O.Cl.C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCCCCCC(=O)OC)CC.C(C)(C)(C)OC(=O)N([C@@... | [CH3:1][CH2:2][N:3]([C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:56])[CH3:66])[C@@H:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][C:51](=[O:52])[O:53][CH2:31][CH:32]([CH3:48])[CH3:50])[cH:18][cH:19]1)[C:20](=[O:21])[NH:22][C@H:23]([CH2:24][CH2:25][S:26][CH3:27])[C:82](=[O:83])[NH:84][CH2:85][C:86](=[O:87])[NH:88][C@@H:89]([C... | CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(OC(=O)OCC(C)C)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.ClCCl.O=C([O-])[O-].O=S(=O)([O-])O | CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.Cl.Cl.O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 9cb59a237f03cec0f6065f95c0bce58d49ea6ca2e2e826e2b3188b08090421b5 | 2654ea69a5122c8288d135ec1f252cd8535ebaf6d52bf1338c76182c65f32e29 | O=C(CCc1ccccc1)NCC(=O)NCC(=O)NCCc1ccccc1.O=C(CCc1ccccc1)NCC(=O)NCC(=O)NCCc1ccccc1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[C:13]-[CH2;D2;+0:14]-[NH;D2;+0:15]-[C;H0;D3;+0:16](=[O;D1;H0:17])-[C:18](-[C:19])-[#7:20]-[C:21](=[O;D1;H0:22])-[C:23]-[#7:24]-[C;H0;D3;+0:25](=[O;D1;H0:26])-[C@H;D3;+0:27](-... | null | [] | null | null | null | null | To a stirred mixture of 1.7 g (1.9 mmole) of the title product of Example 52 in 40 ml of methanol was added 10 ml of 10% aqueous potassium carbonate. After about 75 minutes the resultant solution was poured into a mixture of 150 ml of dichloromethane and 100 ml of 0.5M potassium bisulfate. The organic phase (containing... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether.Ether.Secondary amide.Secondary amide.Boc | Carbamic ester.Ester.Ether.Ether.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Aromatic alcohol.Aromatic alcohol.Monosulfide.Boc.Boc | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CO | null | null | CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(OC(=O)OCC(C)C)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.ClCCl.O=C([O-])[O-].O=S(=O)([O-])O>CO>CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCCCCCC(=O)OC.CCN(C(=O)OC(C)(C)C)[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCSC)C(=O... |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93fa51c8f7084cf4905f1b5a5619a265 | ClCCCBr.c1ccc(CN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(Cc2ccccc2)CC1 | BrCCCCl.C(C1=CC=CC=C1)N1CCNCC1.CS(=O)C.[OH-].[K+]>>Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCCl | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | ClCCCBr.c1ccc(CN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(Cc2ccccc2)CC1 | null | null | O | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 163.9 | [{"value": 55.0, "product": "Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 163.9, "product": "Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 31.5 g of 1-bromo-3-chloropropane were added to a mixture of 35 g of 1-benzylpiperazine, 150 ml of dimethyl sulfoxide and 25 g of potassium hydroxide. The resulting mixture was stirred at room temperature for 3 hours. Water was added to the resulting solution, the reaction product was extracted with ether, dried (magne... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | O | null | 3 | ClCCCBr.c1ccc(CN2CCNCC2)cc1>O>Cl.Cl.ClCCCN1CCN(Cc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4a99484645cc4c6ca8fde2874eaff9ec | Cl.ClCCCN1CCN(Cc2ccccc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(Cc2ccccc2)CC1 | NC(=S)N.Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCCl.C(C)N(CC)CC.[OH-].[Na+]>>Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCS | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | Cl.ClCCCN1CCN(Cc2ccccc2)CC1.NC(N)=S | Cl.SCCCN1CCN(Cc2ccccc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 78 | [{"value": 78.0, "product": "Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 15 g of thiourea were added to a solution of 35 g of -benzyl-4-(3-chloropropyl)piperazine dihydrochloride, 20 g of triethylamine and 250 ml of reagent ethanol, and the mixture was refluxed for 8 hours. After the addition of a solution of 10 g of sodium hydroxide in 50 ml of water, the resulting mixture was refluxed for... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(Cc2ccccc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(Cc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e0666140f18d4bf7be07a753ad3f837c | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccccc2)CC1>>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | C1(=CC=CC=C1)N=C=O.Cl.Cl.C(C1=CC=CC=C1)N1CCN(CC1)CCCS.C(C)N(CC)CC>>O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=CC=C1 | [ClH:2].[O:3]=[C:5]=[N:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>>[ClH:2].[OH2:3].[OH:4][C:5]([NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18]... | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccccc2)CC1 | Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 3bf647ffd3af34283e2312f784edbca620c93d73a88c64f1c90f0c5841a13287 | c6ec1d581e09757064752f97a5c83429292625d25a23d379af2b6feb108d2455 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[O;D1;H1:10])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH2;D0;+0:4] | 41.9 | [{"value": 20.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.6 g of phenyl isocyanate were added to a solution of 4.0 g of 3-(4-benzylpiperazin-1-yl)propanethiol dihydrochloride and 2.6 g of triethylamine in 50 ml of methylene chloride. The mixture was refluxed for four hours, washed with water and dried (sodium sulfate). Precipitation of the salt with ethereal hydrochloric ac... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccccc2)CC1>C(Cl)Cl>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2696e8dc20db40a1b56b86bc942054c8 | ClCCCBr.Clc1ccc(CN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | ClC1=CC=C(CN2CCNCC2)C=C1.[OH-].[K+].BrCCCCl>>Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCCl)C=C1 | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | ClCCCBr.Clc1ccc(CN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 74 | [{"value": 74.0, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Utilizing the procedure described in Example 1(a), 20.0 g of 1-(4-chlorobenzyl)piperazine, 100 ml of dimethyl sulfoxide, 15.0 g of potassium hydroxide and 15.0 of 1-bromo-3-chloropropane yielded 25.1 g (74% of theory) of 1-(4-chlorobenzyl)-4-(3-chloropropyl)piperazine dihydrochloride as a white crystalline solid.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.Clc1ccc(CN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dd78e8a69cf04d3fa6ac7e292bbcdfdd | Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCCl)C=C1.C(C)N(CC)CC.[OH-].[Na+].NC(=S)N>>Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1 | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S | Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 75 | [{"value": 75.0, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Utilizing the procedure described in Example 1(b), 6.0 g of thiourea, was reacted with 25.2 g of 1-(4-chlorobenzyl-4-(3-chloropropyl)piperazine dihydrochloride and 8.7 g of triethylamine in 200 ml of reagent ethanol. The hydrolysis was effected with 5.0 g of sodium hydroxide in 50 ml of water. Work-up as described abov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d2e024e70544f24ae5de4bfff5d6753 | CN=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl | CN=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.CNC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][N:2]=[C:3]=[O:4].[ClH:24].[SH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][NH:2][C:3]([OH:4])=[SH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21]... | CN=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | c1ccc(CN2CCNCC2)cc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;H0;D1;+0:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[SH;D2;+0:7]=[C;H0;D3;+0:3](-[OH;D1;+0:4])-[NH;D2;+0:2]-[C;D1;H3:1] | 64.4 | [{"value": 32.0, "product": "Cl.Cl.CNC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "Cl.Cl.CNC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 0.4 g of methyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.75 g (32% of theory) of N-methyl-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}thiocarbamate d... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CN=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a06c362448a46898ee87d972b4b0e1c | CC(C)N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CC(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl | C(C)(C)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.C(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[ClH:26].[SH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5]([OH:6])=[SH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][c:19... | CC(C)N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CC(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | c1ccc(CN2CCNCC2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;H0;D1;+0:6].[C:7]-[C:8]-[SH;D1;+0:9]>>[C:7]-[C:8]-[SH;D2;+0:9]=[C;H0;D3;+0:5](-[OH;D1;+0:6])-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 56.3 | [{"value": 28.0, "product": "Cl.Cl.C(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "Cl.Cl.C(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 0.5 g of isopropyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.7 g (28% of theory) of N-isopropyl-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}thiocarbam... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CC(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d1937c896e54cb4b8977e4368ead391 | O=C=NC1CCCCC1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | C1(CCCCC1)N=C=O.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1>>Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [O:3]=[C:4]=[N:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.[Cl:1][c:24]1[cH:23][cH:22][c:21]([CH2:20][N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][SH:12])[CH2:29][CH2:28]2)[cH:27][cH:26]1>>[ClH:1].[ClH:2].[OH:3][C:4]([NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[SH:12][CH2:13][CH2:14][CH2:15][N:16]... | O=C=NC1CCCCC1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9ddf29a0add694314a86de0a39264129a9713962546a4ec140d50667e08753fd | 126df213390631efc30fe64ae8364e595ba3d5d450128f642d2c5ebbd6a2ca21 | C(NC1CCCCC1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5])-[C:6].[C:7]-[C:8]-[SH;D1;+0:9].[Cl;H0;D1;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[OH;D1;+0:5])=[SH;D2;+0:9]-[C:8]-[C:7])-[C:6].[Cl;D1;H0:16]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[ClH;D0;+0:10] | 100.7 | [{"value": 30.0, "product": "Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.7, "product": "Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 1.0 g of cyclohexyl isocyanate, 2.1 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol and 10 ml of methylene chloride was stirred at room temperature overnight and then concentrated in vacuo. The residue crystallized upon standing. The product was recrystallized from aqueous ethanol, dissolved in ether... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Aliphatic thiol | Aromatic halide.Secondary amine | c1ccccc1 | c1ccccc1 | C1CCCCC1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | 8 | O=C=NC1CCCCC1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1915446d4e914e9ba2cead88cca852e5 | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | C1(=CC=CC=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [ClH:2].[O:3]=[C:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[CH2:28][CH2:29]1>>[ClH:2].[OH:3][C:4]([NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][C... | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 107.1 | [{"value": 53.0, "product": "Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.1, "product": "Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 4.3 g of phenyl isocyanate, 12.7 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 7.3 g of triethylamine and 100 ml of methylene chloride, to give 9.1 g (53% of theory) of N-phenyl-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}thiocarbamate ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccccc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fcb401d798df4579a0d7b003226aee98 | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl | C(CCC)C1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N:9]=[C:10]=[O:11])[cH:30][cH:31]1.[ClH:33].[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[CH2:28][CH2:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10]([OH:11])=[SH:12][C... | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CCCCc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 56.8 | [{"value": 28.0, "product": "Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.0 g of 4-n-butylphenyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.85 g (28% of theory) of N-(4-n-butylphenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-191ac2eaae9442b6b59ea19756714b3f | Cl.O=C=Nc1ccc(F)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.OC(Nc1ccc(F)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | FC1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.FC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [ClH:2].[O:3]=[C:4]=[N:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[ClH:2].[OH:3][C:4]([NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)=[SH:13][CH2:14][CH2:15][CH2:16][N:... | Cl.O=C=Nc1ccc(F)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.OC(Nc1ccc(F)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 92.3 | [{"value": 47.0, "product": "Cl.Cl.FC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "Cl.Cl.FC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 0.8 g of 4-fluorophenyl isocyanate, 2.2 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.6 g of triethylamine and 25 ml of methylene chloride, to give 1.41 g (47% of theory) of N-(4-fluorophenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]prop... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccc(F)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.OC(Nc1ccc(F)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d33367d8f1b54a0ba584c0599674b958 | Cl.O=C=Nc1ccc(Cl)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.O.OC(Nc1ccc(Cl)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | ClC1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.CCl>>O.Cl.Cl.ClC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [ClH:2].[O:3]=[C:5]=[N:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1.[SH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH2:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[CH2:30][CH2:31]1>>[ClH:2].[OH2:3].[OH:4][C:5]([NH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)=[SH:14][CH2:15][CH2:16... | Cl.O=C=Nc1ccc(Cl)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.O.OC(Nc1ccc(Cl)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(C)N(CC)CC | Acylation | OtherReaction | 3bf647ffd3af34283e2312f784edbca620c93d73a88c64f1c90f0c5841a13287 | c6ec1d581e09757064752f97a5c83429292625d25a23d379af2b6feb108d2455 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[O;D1;H1:10])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH2;D0;+0:4] | 42.4 | [{"value": 21.0, "product": "O.Cl.Cl.ClC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "O.Cl.Cl.ClC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.5 g of 4-chlorophenyl isocyanate, 3.5 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 1.2 g of triethylamine and 50 ml of methyl chloride, to give 1.1 g (21% of theory) of N-(4-chlorophenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)N(CC)CC | null | null | Cl.O=C=Nc1ccc(Cl)cc1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(C)N(CC)CC>Cl.O.OC(Nc1ccc(Cl)cc1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-326edc7cd8db46ef8ec72874e2c49ab5 | Cl.O=C=Nc1ccc(Cl)c(Cl)c1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.OC(Nc1ccc(Cl)c(Cl)c1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | ClC=1C=C(C=CC1Cl)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.ClC=1C=C(C=CC1Cl)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [ClH:2].[O:3]=[C:4]=[N:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1.[SH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH2:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[CH2:30][CH2:31]1>>[ClH:2].[OH:3][C:4]([NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1)=[SH:14][CH2:15][... | Cl.O=C=Nc1ccc(Cl)c(Cl)c1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.OC(Nc1ccc(Cl)c(Cl)c1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 52.2 | [{"value": 26.0, "product": "Cl.Cl.ClC=1C=C(C=CC1Cl)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "Cl.Cl.ClC=1C=C(C=CC1Cl)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.6 g of 3,4-dichlorophenyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.9 g of triethylamine and 50 ml of methylene chloride, to give 1.2 g (26% of theory) of N-(3,4-dichlorophenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccc(Cl)c(Cl)c1.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.OC(Nc1ccc(Cl)c(Cl)c1)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cf45e59bdef54089b629c31b7412880d | CCN(CC)CC.COc1ccccc1N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.Cl.Cl.Cl.O.O.O | COC1=C(C=CC=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.COC1=C(C=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C1=CC=CC=C1)Cl.O.O.COC1=C(C=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C1=CC=CC=C1)Cl.Cl.Cl | [CH2:18]([N:19]([CH2:20][CH3:22])[CH2:44][CH3:43])[CH3:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]=[C:10]=[O:11].[ClH:61].[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:47][N:48]([CH2:49][c:51]2[cH:27][cH:26][c:54]([Cl:21])[cH:53][cH:52]2)[CH2:57][CH2:58]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c... | CCN(CC)CC.COc1ccccc1N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.Cl.Cl.Cl.O.O.O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 28033e2d67866b16340c76bc9501d8fe873ef33747a77835ac25a8f39fd65bd5 | 4749bac01e6e887a02951c249ccae0b96f7479ff629d0210328fb7b10470049c | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1.C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH2;D2;+0:6]-[CH3;D1;+0:7].[Cl;H0;D1;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[#7:14]2-[C:15]-[CH2;D2;+0:16]-[N;H0;D3;+0:17](-[C:18]-[C:19]-[C:20]-[SH;D1;+0:21])-[CH2;D2;+0:22]-[CH2;D2;+0:23]-2):[cH;D2;+0:24]:[cH;D2;+0:... | 48.2 | [{"value": 20.0, "product": "O.Cl.Cl.COC1=C(C=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C1=CC=CC=C1)Cl.O.O.COC1=C(C=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C1=CC=CC=C1)Cl.Cl.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "O.Cl.Cl.COC1=C(C=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C1=CC=CC=C1)Cl.O.O.COC1=C(C=CC=C1)NC(O)=SCCCN... | null | null | null | null | The procedure described in Example 2 was followed, using 1.3 g of 2-methoxyphenyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)piperazin--yl]propanethiol dihydrochloride, 0.9 g of triethylamine and 50 ml of methylene chloride, to give 0.9 g (20% of theory) of N-(2-methoxyphenyl)-S-{3-[4-(chlorobenzyl)piperazin-1-yl]propyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Tertiary amine.Tertiary amine.Aliphatic thiol | Secondary halide.Secondary halide.Ether.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCN(CC)CC.COc1ccccc1N=C=O.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.COc1ccccc1NC(O)=[SH]CCCN1CCN(C(Cl)c2ccccc2)CC1.Cl.Cl.Cl.O.O.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c50c30503cc343a3939f9f57a5d8d133 | COc1cccc(N=C=O)c1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>COc1cccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)c1.Cl | COC=1C=C(C=CC1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.COC=1C=C(C=CC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]=[C:9]=[O:10])[cH:29]1.[ClH:31].[SH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9]([OH:10])=[SH:11][CH2:12][CH2:13][CH2:14][N:15]2... | COc1cccc(N=C=O)c1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | COc1cccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)c1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 63.3 | [{"value": 32.0, "product": "Cl.Cl.COC=1C=C(C=CC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "Cl.Cl.COC=1C=C(C=CC1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.3 g of 3-methoxyphenyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.9 g of triethylamine and 50 ml of methylene chloride, to give 1.35 g (32% of theory) of N-(3-methoxyphenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1cccc(N=C=O)c1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>COc1cccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)c1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7f2d634825de4fb38e53460cd8c87fba | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>COc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O | COC1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:28][cH:29]1.[ClH:31].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15... | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | COc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | d8c9c1a89d54a4cd76e63eccb394ecc0c920cdad853402e3a087dd7621e6fd3e | bc4576d342715dde5eb26e659c67b11b56a595de68edf5b187c45e442919e403 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 48.9 | [{"value": 25.0, "product": "O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.9, "product": "O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 0.9 g of 4-methoxyphenyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.72 g (25% of theory) of N-(4-methoxyphenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>COc1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cc89c78e3c7641519d60f0df07730851 | CC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O | C(C)(=O)C1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.C(C)(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([N:8]=[C:9]=[O:10])[cH:29][cH:30]1.[ClH:32].[SH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][C:9]([OH:10])=[SH:11][CH2:12][CH2:13][CH2... | CC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | d8c9c1a89d54a4cd76e63eccb394ecc0c920cdad853402e3a087dd7621e6fd3e | bc4576d342715dde5eb26e659c67b11b56a595de68edf5b187c45e442919e403 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 55.1 | [{"value": 29.0, "product": "O.Cl.Cl.C(C)(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.1, "product": "O.Cl.Cl.C(C)(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.0 g of 4-acetylphenyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.83 g (29% of theory) of N-(4-acetylphenyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]prop... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ca1b8ca8d82f487c9acd52ad82720fa7 | CCOC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CCOC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl | C(C)OC(=O)C1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.C(C)OC(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[C:11]=[O:12])[cH:31][cH:32]1.[ClH:34].[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11]([OH:12])... | CCOC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CCOC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 55.2 | [{"value": 28.0, "product": "Cl.Cl.C(C)OC(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "Cl.Cl.C(C)OC(=O)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.1 g of 4-ethoxycarbonylphenyl isocyanate, 2.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 0.7 g of triethylamine and 50 ml of methylene chloride, to give 0.85 g (28% of theory) of N-(4-ethoxycarbonylphenyl)-S-{3-[4-(4-chlorobenzyl)pip... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCOC(=O)c1ccc(N=C=O)cc1.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCOC(=O)c1ccc(NC(O)=[SH]CCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-077a49be5a59401b8abfc287ca092333 | Cc1ccc(CN2CCNCC2)cc1.ClCCCBr>>Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.Cl | BrCCCCl.CC1=CC=C(CN2CCNCC2)C=C1.[OH-].[K+].CS(=O)C>>Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCCl)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][NH:10][CH2:15][CH2:16]2)[cH:17][cH:18]1.Br[CH2:11][CH2:12][CH2:13][Cl:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1.[ClH:19].[ClH:20] | Cc1ccc(CN2CCNCC2)cc1.ClCCCBr | Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.Cl | null | null | O | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | ace038913084fcdf81b35aa8057c48e144f1d774d55e84580611fa34db8b1552 | da87afc172ebd302d462893afe878066c210a24130312f3acba00f6d41a889fd | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 274.5 | [{"value": 94.0, "product": "Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 274.5, "product": "Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A mixture of 14.0 g of 1-(4-methylbenzyl)piperazine, 8.0 g of potassium hydroxide and 125 ml of dimethyl sulfoxide was stirred for 45 minutes. 11.8 g of 1-bromo-3-chloropropane were then added, and the mixture was stirred for an additional hour. Water was added, and the product was extracted with ether, and the extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | Br- | O | null | 0.75 | Cc1ccc(CN2CCNCC2)cc1.ClCCCBr>O>Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-76581291372d4210a560be5a42ab7838 | Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.NC(N)=S>>Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCCl)C=C1>>Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCS)C=C1 | Cl[CH2:13][CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][N:7]([CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[CH2:16][CH2:15]1.[ClH:20].NC(N)=[S:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][SH:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1.[ClH:20] | Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.NC(N)=S | Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 72 | [{"value": 72.0, "product": "Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCS)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCS)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 7.7 g of thiourea, 23.0 g of 1-(4-methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride, 6.5 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 6.0 g of sodium hydroxide in 40 ml of water. Work-up, as described above, gave ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | c1ccccc1.C1C[NH]CC[NH]1 | HCl | C(C)O.O | null | null | Cc1ccc(CN2CCN(CCCCl)CC2)cc1.Cl.NC(N)=S>C(C)O.O>Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1a29534138cf42879b452e139d3dd015 | CCN(CC)CC.Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl.O=C=Nc1ccccc1>>Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cl.Cl.Cl.O.O.O | C1(=CC=CC=C1)N=C=O.Cl.Cl.CC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)C.O.O.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)C.Cl.Cl | [CH3:1][CH2:8][N:7]([CH2:6][CH3:5])[CH2:38][CH3:39].[CH2:9]1[N:10]([CH2:11][CH2:12][CH2:13][SH:14])[CH2:24][CH2:25][N:34]([CH2:33][c:32]2[cH:31][cH:30][c:29]([CH3:28])[cH:54][cH:53]2)[CH2:35]1.[ClH:58].[C:15](=[O:16])=[N:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8]... | CCN(CC)CC.Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl.O=C=Nc1ccccc1 | Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cl.Cl.Cl.O.O.O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 8101f5def4764d3a464ace49dcd811a6b5a64aaa086c4febacde1faa81e5ff91 | 6c59d446178fa8326efe9e6fcc7fe762e06c74f526449b4f57ac008c79818102 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1.C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[C:4]-[CH3;D1;+0:5])-[CH2;D2;+0:6]-[CH3;D1;+0:7].[O;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13].[SH;D1;+0:14]-[C:15]-[C:16]-[C:17]-[#7:18]1-[C:19]-[CH2;D2;+0:20]-[N;H0;D3;+0:21](-[C:22]-[c:23])-[CH2;D2;+0:24]-[CH2;D2;+0:25]-1>>[#16:26]-[C:27]-[CH2;D2;+0:... | 48.2 | [{"value": 20.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)C.O.O.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)C.Cl.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)C.O.O.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CC... | null | null | null | null | The procedure described in Example 2 was followed, using 1.4 g of phenyl isocyanate, 4.0 g of 3-[4-(4-methylbenzyl)piperazin-1-yl]propanethiol dihydrochloride, 1.2 g of triethylamine and 50 ml of methylene chloride, to give 1.1 g (20% of theory) of N-phenyl-S-{3-[4-(4-methylbenzyl)piperazin-1-yl]propyl}thiocarbamate di... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Tertiary amine.Tertiary amine.Aliphatic thiol | Secondary amine.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCN(CC)CC.Cc1ccc(CN2CCN(CCCS)CC2)cc1.Cl.O=C=Nc1ccccc1>C(Cl)Cl>Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cc1ccc(CN2CCN(CCC[SH]=C(O)Nc3ccccc3)CC2)cc1.Cl.Cl.Cl.O.O.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-73dfc2a4ed354bdeacc95510bbfc783d | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1.ClCCCBr>>CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl | BrCCCCl.ClC1=CC=C(CN2C(CNC(C2)C)C)C=C1.[OH-].[K+].CS(=O)C>>ClC1=CC=C(CN2C(CN(C(C2)C)CCCCl)C)C=C1 | [CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH:13]([CH3:14])[CH2:15][NH:16]1.Br[CH2:17][CH2:18][CH2:19][Cl:20]>>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH:13]([CH3:14])[CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][Cl:20] | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1.ClCCCBr | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5]1-[C:6]-[#7:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:6]-[C:5]-1-[C;D1;H3:4] | 58 | [{"value": 58.0, "product": "ClC1=CC=C(CN2C(CN(C(C2)C)CCCCl)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 22.0 g g of 1-bromo-3-chloropropane were added to a mixture of 33.0 g of 4-chlorobenzyl-2,5-dimethylpiperazine, 25.0 g of potassium hydroxide and 125 ml of dimethyl sulfoxide. After stirring the solution for 3 hours at room temperature, water was added, the product was extracted with ether, and the extract was dried (m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | O | null | 3 | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1.ClCCCBr>O>CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ac25165bc3e44b80977c05d9becefbc7 | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl.NC(N)=S>>CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCS.Cl.Cl | [OH-].[Na+].NC(=S)N.ClC1=CC=C(CN2C(CN(C(C2)C)CCCCl)C)C=C1.C(C)O>>Cl.Cl.ClC1=CC=C(CN2CC(N(CC2C)CCCS)C)C=C1 | [CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH:13]([CH3:14])[CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][Cl:21].NC(N)=[S:20]>>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH:13]([CH3:14])[CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][SH:20].[ClH:21].[ClH:... | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl.NC(N)=S | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCS.Cl.Cl | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | N-C(-N)=[S;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5]>>[C:2]-[C:3]-[CH2;D2;+0:4]-[SH;D1;+0:1].[ClH;D0;+0:5] | 249.9 | [{"value": 83.0, "product": "Cl.Cl.ClC1=CC=C(CN2CC(N(CC2C)CCCS)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 249.9, "product": "Cl.Cl.ClC1=CC=C(CN2CC(N(CC2C)CCCS)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 12.7 g of thiourea and 26.0 g of 1-(4-chlorobenzyl)-2,5-dimethyl-4-(3-chloropropyl)piperazine in 250 ml of reagent ethanol. The hydrolysis was effected with 10.0 g of sodium hydroxide in 50 ml of water. Work-up, as described above, gave 26.5 g (83% of theory) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | O | null | null | CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCCl.NC(N)=S>O>CC1CN(Cc2ccc(Cl)cc2)C(C)CN1CCCS.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93cf949e00b544a7b8fbd151bc44a719 | CC(c1ccccc1)N1CCNCC1.ClCCCBr>>CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.Cl | C1(=CC=CC=C1)C(C)N1CCNCC1.[OH-].[K+].BrCCCCl>>Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCCl | [CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][NH:12][CH2:17][CH2:18]1.Br[CH2:13][CH2:14][CH2:15][Cl:16]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18]1.[ClH:19].[ClH:20] | CC(c1ccccc1)N1CCNCC1.ClCCCBr | CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.Cl | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | ace038913084fcdf81b35aa8057c48e144f1d774d55e84580611fa34db8b1552 | da87afc172ebd302d462893afe878066c210a24130312f3acba00f6d41a889fd | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 409.8 | [{"value": 96.0, "product": "Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 409.8, "product": "Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 17(a) was followed, using 16.5 g of 1-(1-phenylethyl)piperazine, 8.0 g of potassium hydroxide, 125 ml of dimethyl sulfoxide and 9.5 g of 1-bromo-3-chloropropane. Work-up, as described above, gave 28.0 g (96% of theory) of 1-(1-phenylethyl)-4-(3-chloropropyl)piperazine dihydrochloride ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | Br- | CS(=O)C | null | null | CC(c1ccccc1)N1CCNCC1.ClCCCBr>CS(=O)C>CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d017d716638549a595ea280009b45216 | CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.NC(N)=S>>CC(c1ccccc1)N1CCN(CCCS)CC1.Cl | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCCl>>Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCS | Cl[CH2:15][CH2:14][CH2:13][N:12]1[CH2:11][CH2:10][N:9]([CH:2]([CH3:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:18][CH2:17]1.[ClH:20].NC(N)=[S:16]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][SH:16])[CH2:17][CH2:18]1.[ClH:20] | CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.NC(N)=S | CC(c1ccccc1)N1CCN(CCCS)CC1.Cl | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 51 | [{"value": 51.0, "product": "Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.4, "product": "Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 9.8 g of thiourea, 29.0 g of 1-(1-phenylethyl)-4-(3-chloropropyl)piperazine dihydrochloride, 8.3 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 6.0 g of sodium hydroxide in 40 ml of water. Work-up, as above, gave 14.5 g (51%... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | c1ccccc1.C1C[NH]CC[NH]1 | HCl | C(C)O.O | null | null | CC(c1ccccc1)N1CCN(CCCCl)CC1.Cl.NC(N)=S>C(C)O.O>CC(c1ccccc1)N1CCN(CCCS)CC1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d4976450c77348398a9bbdba85a55e9b | CC(c1ccccc1)N1CCN(CCCS)CC1.Cl.O=C=Nc1ccccc1>>CC(c1ccccc1)N1CCN(CCC[SH]=C(O)Nc2ccccc2)CC1.Cl.O.O | C1(=CC=CC=C1)N=C=O.Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCS.C(C)N(CC)CC>>O.O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C)C1=CC=CC=C1 | [CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][SH:16])[CH2:26][CH2:27]1.[ClH:29].[C:17](=[O:18])=[N:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][SH:16]=... | CC(c1ccccc1)N1CCN(CCCS)CC1.Cl.O=C=Nc1ccccc1 | CC(c1ccccc1)N1CCN(CCC[SH]=C(O)Nc2ccccc2)CC1.Cl.O.O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 94.8 | [{"value": 38.0, "product": "O.O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "O.O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)C(C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.6 g of phenyl isocyanate, 4.5 g of 3-[4-(1-phenylethyl)piperazin-1-yl]propanethiol dihydrochloride, 1.3 g of triethylamine and 50 ml of methylene chloride, to give 2.1 g (38% of theory) of N-phenyl-S-{3-[4-(1-phenylethyl)piperazin-1-yl]propyl}thiocarbamate dihy... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(c1ccccc1)N1CCN(CCCS)CC1.Cl.O=C=Nc1ccccc1>C(Cl)Cl>CC(c1ccccc1)N1CCN(CCC[SH]=C(O)Nc2ccccc2)CC1.Cl.O.O |
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