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-c34472859da14a81bfe0f74e60f15c43 | ord-d90b8545ce624e38851dac4a9f3f4f7e | C=C(Cl)C#N.CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl]>>CC(=O)N[C@@H]1CCC[C@H]1CC(Cl)C#N | C(C)(=O)N[C@H]1[C@@H](CCC1)[Hg]Cl.ClC(C#N)=C.[BH4-].[Na+]>>C(C)(=O)N[C@H]1[C@@H](CCC1)CC(C#N)Cl | [CH2:10]=[C:11]([Cl:12])[C:13]#[N:14].[Cl][Hg][C@H:9]1[C@H:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][CH2:7][CH2:8]1>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:10][CH:11]([Cl:12])[C:13]#[N:14] | C=C(Cl)C#N.CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl] | CC(=O)N[C@@H]1CCC[C@H]1CC(Cl)C#N | null | null | C(C)O | C-C Coupling | OtherReaction | 813c883b37d223e954814d49496c21b60c618eb7559fd40099bdb9a8228830b8 | 6e201f253d299cba9dce11df416351b338d329a97929620e1451b17f0c1815ea | C1CCCC1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[C@H;D3;+0:9]-1-[Hg]-[Cl].[CH2;D1;+0:10]=[C;H0;D3;+0:11](-[Cl;D1;H0:12])-[C:13]#[N;D1;H0:14]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[C@H;D3;+0:9]-1-[CH2;D2;+0:10]-[CH;D3;+0:11](-[Cl;D1;H0:12])-[C:13]#[N;D1;H0:14] | null | [] | null | null | 1 | HOUR | 16.1 g of trans-1-acetamido-2-chloromercuriocyclopentane are suspended in 200 ml of ethanol. 10.7 ml of 2-chloroacrylonitrile are added, followed by 1.7 g of sodium borohydride in 40 ml of ethanol as rapidly as possible while cooling in ice. After 1 hour at room temperature, the mixture is filtered with suction through... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Vinyl | Secondary halide | C1CCCC1 | C1CCCC1 | C1CCCC1 | Other | C(C)O | null | 1 | C=C(Cl)C#N.CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl]>C(C)O>CC(=O)N[C@@H]1CCC[C@H]1CC(Cl)C#N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-97229f5d221e4003a7da36fedb95fb89 | BrCCCc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>>COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1 | C1COCCOCCOCCOCCOCCO1.COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCCBr>>COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CCCC1=CC=CC=C1 | Br[CH2:25][CH2:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[CH3:1][O:2][C:3]1=[N:4][CH:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]2)[C:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])=[C:22]([CH3:23])[NH:24]1>>[CH3:1][O:2][C:3]1=[N:4][C:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:1... | BrCCCc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1 | COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1 | null | null | CCOCC.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 69bd184bd50d5f8030cbcd013a55654dd34a76502f9c7e73150d5666f6af2c6d | 79f91905cac93931d90e647e5870a720684802114bcbb1f1276120120f789420 | C1=NC(c2ccccc2)=CCN1CCCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5]1=[#7:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])=[C;H0;D3;+0:16](-[C;D1;H3:17])-[NH;D2;+0:18]-1>>[#8:4]-[C:5]1=[#7:6]-[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])=[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[CH;D3;+0:16](-[C... | 60.7 | [{"value": 60.7, "product": "COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (4.0 g, 12.0 mmol) in dry dimethylformamide (10 ml) under argon was treated with finely ground potassium carbonate (4.97 g, 36.0 mmoles), 3-phenylpropyl bromide (2.19 ml, 14.4 mmoles) and a catalytic amount o... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Ester | Ester.Tertiary amine | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1.c1ccccc1 | HBr | CCOCC.CN(C=O)C | null | 72 | BrCCCc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>CCOCC.CN(C=O)C>COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4b02aacf4a8944cd8a856d38eed02d31 | COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1>>CC1=C(C(=O)OC(C)C)C(c2cccc([N+](=O)[O-])c2)N(CCCc2ccccc2)C(=O)N1 | COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CCCC1=CC=CC=C1.Cl>>CC1=C(C(N(C(N1)=O)CCCC1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C | C[O:31][C:30]1=[N:32][C:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)=[C:3]([C:4](=[O:5])[O:6][CH:7]([CH3:8])[CH3:9])[CH:2]([CH3:1])[N:20]1[CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][C:2]1=[C:3]([C:4](=[O:5])[O:6][CH:7]([CH3:8])[CH3:9])[CH:10]([c:11]2[cH:12][c... | COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1 | CC1=C(C(=O)OC(C)C)C(c2cccc([N+](=O)[O-])c2)N(CCCc2ccccc2)C(=O)N1 | null | null | CO | Miscellaneous | OtherReaction | d538af1adbc15be2de60ad1e905730d779fc523cf32febd61d9d4602374832b0 | fd1bed75df609a723368d936508c74e6b719ae806e80d6fe44cafd400786f4c4 | O=C1NC=CC(c2ccccc2)N1CCCc1ccccc1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:3]-[C;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])-[CH;D3;+0:13](-[C;D1;H3:14])-[N;H0;D3;+0:15]-1-[C:16]-[C:17]>>[C:17]-[C:16]-[N;H0;D3;+0:15]1-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[NH;D2;+0:3]-[C;H0;D3;+0:13](-[C;D1;H3:14])=[C;H0;D3;+0:8... | 169.6 | [{"value": 169.6, "product": "CC1=C(C(N(C(N1)=O)CCCC1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1,6-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (1.96 g. 4.34 mmoles) in methanol (20 ml) was treated with 2.5 N hydrochloric acid (5 ml) and the resulting mixture was allowed to stir at room temperature overnight. A colorless solid prec... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Tertiary amine | Enamine.Ester.Urea | C1=CN=C[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1.c1ccccc1 | Other | CO | null | 8 | COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCc1ccccc1>CO>CC1=C(C(=O)OC(C)C)C(c2cccc([N+](=O)[O-])c2)N(CCCc2ccccc2)C(=O)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-149ebce89605495e8a96c6b0c1e5b343 | C=CCBr.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>>C=CCN1C(OC)=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C1C | COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CC=C | Br[CH2:3][CH:2]=[CH2:1].[NH:4]1[C:5]([O:6][CH3:7])=[N:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[C:19]([C:20](=[O:21])[O:22][CH:23]([CH3:24])[CH3:25])=[C:26]1[CH3:27]>>[CH2:1]=[CH:2][CH2:3][N:4]1[C:5]([O:6][CH3:7])=[N:8][C:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])... | C=CCBr.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1 | C=CCN1C(OC)=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C1C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | eead7f143e10bd3d3fa729cd1133dbc68f4a42e9e5f83d11674551b45e00250e | 053e47696b6258b5976a7f5c88bd667d518c6a89339edb8d9a46e06a01e12534 | C1=NC(c2ccccc2)=CCN1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[#8:4]-[C:5]1=[#7:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])=[C;H0;D3;+0:16](-[C;D1;H3:17])-[NH;D2;+0:18]-1>>[#8:4]-[C:5]1=[#7:6]-[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])=[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[CH;D3;+0:1... | 58.9 | [{"value": 58.9, "product": "COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (4.0 g, 12.0 mmol; see Example 1A) in dry dimethylformamide (10 ml) was treated with finely ground potassium carbonate (6.6 g, 48.0 mmoles) and allyl bromide (1.7 ml, 20.0 mmole). The resulting suspension was... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Ester.Allyl | Ester.Tertiary amine.Allyl | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 10 | C=CCBr.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>CN(C=O)C.C(C)(=O)OCC>C=CCN1C(OC)=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-580a557c2ed64af0a505c01de0c132cc | CN(CCCCl)Cc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>>COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCN(C)Cc1ccccc1 | C1COCCOCCOCCOCCOCCO1.COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N(C)CCCCl>>COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CCCN(CC1=CC=CC=C1)C | Cl[CH2:25][CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1.[CH3:1][O:2][C:3]1=[N:4][CH:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]2)[C:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])=[C:22]([CH3:23])[NH:24]1>>[CH3:1][O:2][C:3]1=[N:4][C:5]([c:6]2[cH:7][cH:8][c... | CN(CCCCl)Cc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1 | COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCN(C)Cc1ccccc1 | null | null | CCOCC.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 69bd184bd50d5f8030cbcd013a55654dd34a76502f9c7e73150d5666f6af2c6d | 79f91905cac93931d90e647e5870a720684802114bcbb1f1276120120f789420 | C1=NC(c2ccccc2)=CCN1CCCNCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5]1=[#7:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])=[C;H0;D3;+0:16](-[C;D1;H3:17])-[NH;D2;+0:18]-1>>[#8:4]-[C:5]1=[#7:6]-[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])=[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[CH;D3;+0:16](-[C... | 50.9 | [{"value": 50.9, "product": "COC=1N(C(C(=C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC(C)C)C)CCCN(CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester (2.0 g, 6.0 mmol) in dimethylformamide (7.0 ml) was treated with finely ground potassium carbonate (1.7 g, 12.0 mmoles), N-benzyl-3-chloro-N-methylpropylamine (2.37 g, 12.0 mmol) and a catalytic amount of 18-c... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Ester | Ester.Tertiary amine | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1.c1ccccc1 | HCl | CCOCC.CN(C=O)C | null | null | CN(CCCCl)Cc1ccccc1.COC1=NC(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C(C)N1>CCOCC.CN(C=O)C>COC1=NC(c2cccc([N+](=O)[O-])c2)=C(C(=O)OC(C)C)C(C)N1CCCN(C)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f2cd4b96968d4d249dc0ff9ac8165438 | COc1ccc(CCl)cc1.NC(N)=S>>COc1ccc(CSC(=N)N)cc1.Cl | NC(=S)N.COC1=CC=C(CCl)C=C1>>Cl.COC1=CC=C(CSC(N)=N)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:14])[cH:12][cH:13]1.[S:8]=[C:9]([NH2:10])[NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C:9](=[NH:10])[NH2:11])[cH:12][cH:13]1.[ClH:14] | COc1ccc(CCl)cc1.NC(N)=S | COc1ccc(CSC(=N)N)cc1.Cl | null | null | O1CCCC1.CCOCC | Protection | OtherReaction | dae623ec10e42086cc0292009bc19d7d58877ce2428714b92cfbbb5102c39de2 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | c1ccccc1 | [Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]>>[ClH;D0;+0:1].[N;D1;H2:6]-[C;H0;D3;+0:7](=[NH;D1;+0:8])-[S;H0;D2;+0:9]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93.8 | [{"value": 93.8, "product": "Cl.COC1=CC=C(CSC(N)=N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A suspension of thiourea (38 g, 50.0 mmole) in dry tetrahydrofuran (40 ml) was cooled to 0° C. under argon and was treated dropwise with 4-methoxybenzylchloride (8.0 g, 50.0 mmole). After the addition was completed, the cooling bath was removed and the reaction was allowed to stir at room temperature for 2 hours. It wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | null | null | c1ccccc1 | null | O1CCCC1.CCOCC | 0 | 2 | COc1ccc(CCl)cc1.NC(N)=S>O1CCCC1.CCOCC>COc1ccc(CSC(=N)N)cc1.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d76b34220cb74d5c9ef8c5b1ac5cef9c | C=CCBr.COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1>>C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | [H-].[Na+].COC1=CC=C(C=C1)CSC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C.C(C=C)Br>>COC1=CC=C(C=C1)CSC=1N(C(C(=C(N1)C)C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])CC=C | Br[CH2:3][CH:2]=[CH2:1].[N:4]1=[C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]2)[NH:16][C:17]([CH3:18])=[C:19]([C:20](=[O:21])[O:22][CH3:23])[CH:24]1[c:25]1[cH:26][cH:27][cH:28][c:29]([N+:30](=[O:31])[O-:32])[cH:33]1>>[CH2:1]=[CH:2][CH2:3][N:4]1[C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12... | C=CCBr.COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1 | C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f03f094e921b267e82057738c56ab464b4b57b7d8df30d00ca3f068584045edc | 420901d0309b6d43f9fb54f735a3fdb3c597eba34e73c20212594aadd4810bda | C1=CC(c2ccccc2)NC(SCc2ccccc2)=N1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]1=[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[C;H0;D3;+0:11](-[#16:12]-[C:13])=[N;H0;D2;+0:14]-[C:15]-1-[c:16]>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]1=[C:8](-[C;D1;H3:9])-[N;H0;D2;+0:10]=[C;H0;D3;+0:11](-[#16:12]-[C:13])-[N;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:... | null | [] | null | null | 10 | MINUTE | A slurry of sodium hydride (168 mg, 4.2 mmole, 60% in mineral oil dispersion) in 5 ml of dry tetrahydrofuran at 0° C. under argon was treated dropwise with 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, methyl ester in 15 ml of dry tetrahydrofuran. After an additio... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Monosulfide.Allyl | Tertiary amine.Monosulfide.Allyl | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | 0.166667 | C=CCBr.COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1>O1CCCC1>C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ebc0f98a75d5489382dc12d3f1ffea4a | C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1>>C=CCN1C(=S)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | COC1=CC=C(C=C1)CSC=1N(C(C(=C(N1)C)C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])CC=C.FC(C(=O)O)(F)F.C(C)S>>CC1=C(C(N(C(N1)=S)CC=C)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC | COc1ccc(C[S:6][C:5]2=[N:7][C:8]([CH3:9])=[C:10]([C:11](=[O:12])[O:13][CH3:14])[CH:15]([c:16]3[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]3)[N:4]2[CH2:3][CH:2]=[CH2:1])cc1>>[CH2:1]=[CH:2][CH2:3][N:4]1[C:5](=[S:6])[NH:7][C:8]([CH3:9])=[C:10]([C:11](=[O:12])[O:13][CH3:14])[CH:15]1[c:16]1[cH:17][cH:18][cH:19... | C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | C=CCN1C(=S)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Miscellaneous | OtherReaction | 1981159823e39300360aee1006beb0d9a9f179e23d79282fd80a02bf8fef051f | 4615674a4902b93d1abcb6db311cc613ae24f07687969fb173863070d67c3b66 | S=C1NC=CC(c2ccccc2)N1 | C-O-c1:c:c:c(-C-[S;H0;D2;+0:1]-[C;H0;D3;+0:2]2=[N;H0;D2;+0:3]-[C:4](-[C;D1;H3:5])=[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-[#7:11]-2-[C:12]-[C:13]=[C;D1;H2:14]):c:c:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]1=[C:4](-[C;D1;H3:5])-[NH;D2;+0:3]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:11](-[C:12]-[C:13]=[C;D1;H2:14])-[C:10]-1 | null | [] | null | null | 2 | HOUR | 1,6-Dihydro-2-[[(4-methoxyphenyl)methyl]thio]-4-methyl-6-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid, methyl ester (1.0 g, 2.14 mmol) in 15 ml of dichloromethane under argon at room temperature was treated with trifluoroacetic acid (0.6 ml, 0.85 g, 7.7 mmole) and ethanethiol (0.4 ml, 0.33 g, 5.4 mmole). ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Monosulfide | Enamine.Thiourea | c1ccccc1.C1=CN=C[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HO- | ClCCl | null | 2 | C=CCN1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1>ClCCl>C=CCN1C(=S)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f73f852b61ff4be4a5f6a8930b465af7 | COC(=O)[C@@H](C)NC(=O)[C@@H]1CCCN1C(=O)C(C)CSC(C)=O>>CC(CS)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)O | COC([C@H](NC([C@H]1N(CCC1)C(C(CSC(C)=O)C)=O)=O)C)=O.[OH-].[K+]>>SCC(C(=O)N1[C@H](C(=O)N[C@H](C)C(=O)O)CCC1)C | CC(=O)[S:4][CH2:3][CH:2]([CH3:1])[C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]1[C:12](=[O:13])[NH:14][C@H:15]([CH3:16])[C:17](=[O:18])[O:19]C>>[CH3:1][CH:2]([CH2:3][SH:4])[C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]1[C:12](=[O:13])[NH:14][C@H:15]([CH3:16])[C:17](=[O:18])[OH:19] | COC(=O)[C@@H](C)NC(=O)[C@@H]1CCCN1C(=O)C(C)CSC(C)=O | CC(CS)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)O | null | null | null | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | C1CCNC1 | 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] | 62.7 | [{"value": 62.7, "product": "SCC(C(=O)N1[C@H](C(=O)N[C@H](C)C(=O)O)CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (S)-[3-(Acetylthio)-2-methyl 1-oxopropyl]-L-prolyl-D-alanine methyl ester (4 g) is taken into potassium hydroxide/aqueous methanol (3 g of potassium hydroxide in 14 ml of water and 70 ml of methanol) and the solution is kept at room temperature for 2 hours. The product (2.1 g) is isolated using the procedure described ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | C1CC[NH]C1 | HO- | null | null | 2 | COC(=O)[C@@H](C)NC(=O)[C@@H]1CCCN1C(=O)C(C)CSC(C)=O>>CC(CS)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-94d50d7044474d4f8c6033ec795dc15c | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CSC2>>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 | N1=CC(=CC=C1)C1=CC(=C2N1CSC2)C(=O)O.CN(C=O)C.ClCCCl>>Cl.ClC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2 | C(C[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][S:17][CH2:18]2>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][S:17][CH2:18]2 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CSC2 | Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 | null | null | C1CCCCC1.S(=O)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | cf8f2baf4bb848035eb10b6a611e1a1957d0ca765a4605f66fc3dd62ac8bf212 | d17829d7867afbdc103a0b2c7f35d7a0a76eb305fe44b655f945b9584718a72c | c1cncc(-c2ccc3n2CSC3)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[Cl;H0;D1;+0:11]-C-C-[Cl;H0;D1;+0:12]>>[Cl;H0;D1;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[ClH;D0;+0:11] | null | [] | 20 | CELSIUS | 30 | MINUTE | A suspension of 5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid (8.8 g) in a mixture of thionyl chloride (6.25 cc), dimethylformamide (0.05 cc) and 1,2dichloroethane (100 cc) is heated under reflux with stirring for 2 hours and 30 minutes. The reaction mixture is cooled to a temperature of about 20° C. and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1cc2n(c1)CSC2 | HO- | C1CCCCC1.S(=O)(Cl)Cl | 20 | 0.5 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CSC2>C1CCCCC1.S(=O)(Cl)Cl>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-47cc5b7ec62c400e8d9aa5bf0052b74e | O=C(Cl)c1cccnc1.O=C(O)C1CSCN1>>O=C(O)C1CSCN1C(=O)c1cccnc1 | Cl.C(C1=CN=CC=C1)(=O)Cl.S1CNC(C1)C(=O)O.C(C)N(CC)CC>>C(C1=CN=CC=C1)(=O)N1CSCC1C(=O)O | Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1.[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][S:6][CH2:7][NH:8]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][S:6][CH2:7][N:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1 | O=C(Cl)c1cccnc1.O=C(O)C1CSCN1 | O=C(O)C1CSCN1C(=O)c1cccnc1 | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 54f36c76161a8ed9c718bf3b5609daa0d109fa9e172dfbee46708dc908b72e36 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cccnc1)N1CCSC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[C:11]1-[C:12]-[#16:13]-[C:14]-[NH;D2;+0:15]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:15]1-[C:14]-[#16:13]-[C:12]-[C:11]-1-[C:9](=[O;D1;H0:8])-[O;D1;H1:10])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 56.4 | [{"value": 56.4, "product": "C(C1=CN=CC=C1)(=O)N1CSCC1C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 64 | CELSIUS | 16 | HOUR | Nicotinoyl chloride hydrochloride (534 g) is added over 1 hour at a temperature of between 30° and 52° C. to a solution of thiazolidine-4-carboxylic acid (400 g) and triethylamine (613 g) in chloroform (4,500 cc). The solution obtained is heated at a temperature of about 64° C. for 4 hours. After stirring at a temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccncc1 | HCl | C(Cl)(Cl)Cl | 64 | 16 | O=C(Cl)c1cccnc1.O=C(O)C1CSCN1>C(Cl)(Cl)Cl>O=C(O)C1CSCN1C(=O)c1cccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4a4238247c624393b3e38a48addec651 | Nc1ccccc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>>O=C(Nc1ccccc1)c1cc(-c2cccnc2)n2c1CSC2 | [OH-].[Na+].NC1=CC=CC=C1.Cl.ClC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2.C>>C1(=CC=CC=C1)NC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.Cl[C:2](=[O:1])[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[n:19]2[c:20]1[CH2:21][S:22][CH2:23]2>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[n:19]2[c:20]1[CH2:21][S:22][CH2:23... | Nc1ccccc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 | O=C(Nc1ccccc1)c1cc(-c2cccnc2)n2c1CSC2 | null | null | C(C)#N.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1cc(-c2cccnc2)n2c1CSC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2 | 57.8 | [{"value": 57.8, "product": "C1(=CC=CC=C1)NC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | A solution of aniline (11.2 g) in methylene chloride (50 cc) is added over 15 minutes at a temperature of about 24° C. and 29° C. to a suspension of 7-chloroformyl-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (12 g) in methylene chloride (200 cc). The suspension obtained is stirred at a temperature of about... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.c1cc2n(c1)CSC2 | HCl | C(C)#N.C(Cl)Cl | 20 | 16 | Nc1ccccc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>C(C)#N.C(Cl)Cl>O=C(Nc1ccccc1)c1cc(-c2cccnc2)n2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2dfe2c76b5b841aea8d11b048080f5c7 | N#Cc1cc(-c2cccnc2)n2c1CSC2.[OH-]>>NC(=O)c1cc(-c2cccnc2)n2c1CSC2 | C(C)O.C.N1=CC(=CC=C1)C1=CC(=C2N1CSC2)C#N.[OH-].[K+]>>N1=CC(=CC=C1)C1=CC(=C2N1CSC2)C(=O)N | [N:1]#[C:2][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][S:16][CH2:17]2.[OH-:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][S:16][CH2:17]2 | N#Cc1cc(-c2cccnc2)n2c1CSC2.[OH-] | NC(=O)c1cc(-c2cccnc2)n2c1CSC2 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1cncc(-c2ccc3n2CSC3)c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[OH-;D0:11]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:11])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2 | null | [] | 20 | CELSIUS | 16 | HOUR | A suspension of 5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carbonitrile (11.35 g) and of potassium hydroxide powder (14 g) in tert-butyl alcohol (100 cc) is heated at 85° C. for 1 hour. After 16 hours' stirring at a temperature of about 20° C., the reaction mixture is poured into distilled water (2 liters). The suspe... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccncc1.c1cc2n(c1)CSC2 | null | C(C)(C)(C)O | 20 | 16 | N#Cc1cc(-c2cccnc2)n2c1CSC2.[OH-]>C(C)(C)(C)O>NC(=O)c1cc(-c2cccnc2)n2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b36442ef1e0e427da9188dd8ef7623f7 | CN.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2>>CNC(=O)c1cc(-c2cccnc2)n2c1CCC2 | C.CN.Cl.ClC(=O)C=1C=C(N2CCCC12)C=1C=NC=CC1.C(C)#N>>CNC(=O)C=1C=C(N2CCCC12)C=1C=NC=CC1 | [CH3:1][NH2:2].Cl[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18]2>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18]2 | CN.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2 | CNC(=O)c1cc(-c2cccnc2)n2c1CCC2 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cncc(-c2ccc3n2CCC3)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](:[c:7]:1-[C:8])-[C:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C:8]-[c:7]1:[#7;a:6](:[c:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10])-[C:9] | null | [] | 20 | CELSIUS | 7 | HOUR | A suspension of 7-chloroformyl-5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine hydrochloride (14.1 g) in methylene chloride (250 cc) is saturated with a stream of anhydrous methylamine, while the temperature of the reaction mixture is kept at about 25° C. for 7 hours. The solution obtained is stirred at a temperature of about... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1cc2n(c1)CCC2 | HCl | C(Cl)Cl | 20 | 7 | CN.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2>C(Cl)Cl>CNC(=O)c1cc(-c2cccnc2)n2c1CCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a0e2495416b24776b0ff2e14038ce5c9 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCC2>>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2 | N1=CC(=CC=C1)C=1N2CCCC2=C(C1)C(=O)O.CN(C=O)C.ClCCCl>>Cl.ClC(=O)C=1C=C(N2CCCC12)C=1C=NC=CC1 | C(C[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18]2>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18]2 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCC2 | Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2 | null | null | C1CCCCC1.S(=O)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | cf8f2baf4bb848035eb10b6a611e1a1957d0ca765a4605f66fc3dd62ac8bf212 | d17829d7867afbdc103a0b2c7f35d7a0a76eb305fe44b655f945b9584718a72c | c1cncc(-c2ccc3n2CCC3)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](:[c:7]:1-[C:8])-[C:9].[Cl;H0;D1;+0:10]-C-C-[Cl;H0;D1;+0:11]>>[C:8]-[c:7]1:[#7;a:6](:[c:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:11])=[O;D1;H0:2])-[C:9].[ClH;D0;+0:10] | null | [] | 80 | CELSIUS | null | null | A suspension of 5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine-7-carboxylic acid (11.4 g) in a mixture of thionyl chloride (17.4 cc), dimethylformamide (0.05 cc) and 1,2-dichloroethane (150 cc) is heated at a temperature of about 80° C. for 3 hours. The reaction mixture is cooled to a temperature of about 20° C. and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1cc2n(c1)CCC2 | HO- | C1CCCCC1.S(=O)(Cl)Cl | 80 | null | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCC2>C1CCCCC1.S(=O)(Cl)Cl>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-98c4e0936fd54c8bbb7ca27429d6edc9 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCCC2>>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCCC2 | N1=CC(=CC=C1)C1=CC(=C2CCCCN12)C(=O)O.CN(C=O)C.ClCCCl>>Cl.ClC(=O)C=1C=C(N2CCCCC12)C=1C=NC=CC1 | C(C[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18][CH2:19]2>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14]2[c:15]1[CH2:16][CH2:17][CH2:18][CH2:19]2 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCCC2 | Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCCC2 | null | null | S(=O)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | cf8f2baf4bb848035eb10b6a611e1a1957d0ca765a4605f66fc3dd62ac8bf212 | d17829d7867afbdc103a0b2c7f35d7a0a76eb305fe44b655f945b9584718a72c | c1cncc(-c2ccc3n2CCCC3)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](:[c:7]:1-[C:8])-[C:9].[Cl;H0;D1;+0:10]-C-C-[Cl;H0;D1;+0:11]>>[C:8]-[c:7]1:[#7;a:6](:[c:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:11])=[O;D1;H0:2])-[C:9].[ClH;D0;+0:10] | null | [] | 70 | CELSIUS | 3 | HOUR | A solution of 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylic acid (13.3 g) in a mixture of thionyl chloride (19.2 cc), dimethylformamide (0.05 cc) and 1,2-dichloroethane (160 cc) is heated to a temperature of about 70° C. The suspension obtained is kept at a temperature of about 70° C. for 3 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1cc2n(c1)CCCC2 | HO- | S(=O)(Cl)Cl | 70 | 3 | ClCCCl.O=C(O)c1cc(-c2cccnc2)n2c1CCCC2>S(=O)(Cl)Cl>Cl.O=C(Cl)c1cc(-c2cccnc2)n2c1CCCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f11982bfa30746859d2d86d97b005c43 | N#Cc1cc(-c2cccnc2)n2c1CCCC2.OCCO.[OH-]>>O=C(O)c1cc(-c2cccnc2)n2c1CCCC2 | N1=CC(=CC=C1)C1=CC(=C2CCCCN12)C#N.[OH-].[K+].C(CO)O.C>>N1=CC(=CC=C1)C1=CC(=C2CCCCN12)C(=O)O | N#[C:2][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][CH2:16][CH2:17][CH2:18]2.OCC[OH:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][CH2:16][CH2:17][CH2:18]2 | N#Cc1cc(-c2cccnc2)n2c1CCCC2.OCCO.[OH-] | O=C(O)c1cc(-c2cccnc2)n2c1CCCC2 | null | null | O | Acylation | OtherReaction | 5e76f9eb1645dffa65f7e1b9c084dfced9f3cb65f8b76df935c174c7208ba236 | 3746af5ef2d46561e999a498fd7e2fe230c1b687b933f9146ccf2b5206980b7a | c1cncc(-c2ccc3n2CCCC3)c1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5](:[c:6]:1-[C:7])-[C:8].O-C-C-[OH;D1;+0:9].[OH-;D0:10]>>[C:7]-[c:6]1:[#7;a:5](:[c:4]:[c:3]:[c:2]:1-[C;H0;D3;+0:1](=[O;H0;D1;+0:9])-[OH;D1;+0:10])-[C:8] | null | [] | 20 | CELSIUS | 16 | HOUR | A solution of 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile (15.6 g) and of potassium hydroxide powder (15.8 g) in ethylene glycol (150 cc) is heated at a temperature of about 156° C. for 11 hours and 30 minutes. After 16 hours' stirring at a temperature of about 20° C., the solvent is evaporated off under ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol.Primary alcohol | Carboxylic acid | null | null | c1ccncc1.c1cc2n(c1)CCCC2 | HO- | O | 20 | 16 | N#Cc1cc(-c2cccnc2)n2c1CCCC2.OCCO.[OH-]>O>O=C(O)c1cc(-c2cccnc2)n2c1CCCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-be1d7015fa194ec1aee8172435d3fa3c | NCc1cccnc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>>O=C(NCc1cccnc1)c1cc(-c2cccnc2)n2c1CSC2 | C.NCC=1C=NC=CC1.C(C)N(CC)CC.Cl.ClC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2>>N1=CC(=CC=C1)CNC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[n:20]2[c:21]1[CH2:22][S:23][CH2:24]2>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[n:20]2[c:21]1[CH2:22... | NCc1cccnc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 | O=C(NCc1cccnc1)c1cc(-c2cccnc2)n2c1CSC2 | null | null | C(CCC)O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1cccnc1)c1cc(-c2cccnc2)n2c1CSC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[#7;a:11]:[c:12]:[c:13]-[C:14]-[NH2;D1;+0:15]>>[#7;a:11]:[c:12]:[c:13]-[C:14]-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2 | 59.1 | [{"value": 59.1, "product": "N1=CC(=CC=C1)CNC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | A solution of 3-aminomethylpyridine (5.5 g) and of triethylamine (10.1 g) in methylene chloride (100 cc) is added over 15 minutes at a temperature between 20° and 30° C. to a suspension of 7-chloroformyl-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (15 g) in methylene chloride (250 cc). The solution obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1.c1cc2n(c1)CSC2 | HCl | C(CCC)O.C(Cl)Cl | 20 | 16 | NCc1cccnc1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>C(CCC)O.C(Cl)Cl>O=C(NCc1cccnc1)c1cc(-c2cccnc2)n2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9a3504efdb64c92b1aeea28125c9957 | O=Cc1cc(-c2cccnc2)n2c1CSC2.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>N#CCc1cc(-c2cccnc2)n2c1CSC2 | CO.S(=O)(=O)(C1=CC=C(C)C=C1)C[N+]#[C-].CC(C)(C)[O-].[K+].N1=CC(=CC=C1)C1=CC(=C2N1CSC2)C=O>>N1=CC(=CC=C1)C1=CC(=C2N1CSC2)CC#N | O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][S:16][CH2:17]2.Cc1ccc(S(=O)(=O)C[N+:1]#[C-:2])cc1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]2[c:14]1[CH2:15][S:16][CH2:17]2 | O=Cc1cc(-c2cccnc2)n2c1CSC2.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | N#CCc1cc(-c2cccnc2)n2c1CSC2 | null | null | COCCOC | C-C Coupling | OtherReaction | 10f9d324cff21cc4d37a63bdf9fbfabb9ad49e9f3f28051ff2b53b0cda5d1082 | df3040bf3b8362a80f3d2edcc476b7684492c85dbd12b1ba9c2d3dbd94a9c0d7 | c1cncc(-c2ccc3n2CSC3)c1 | C-c1:c:c:c(-S(=O)(=O)-C-[N+;H0;D2:1]#[C-;H0;D1:2]):c:c:1.O=[CH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]2:[c:8]:1-[C:9]-[#16:10]-[C:11]-2>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[CH2;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]2:[c:8]:1-[C:9]-[#16:10]-[C:11]-2 | 71.6 | [{"value": 71.6, "product": "N1=CC(=CC=C1)C1=CC(=C2N1CSC2)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 1 | HOUR | A solution of tosylmethyl isocyanide (7.5 g) in 1,2-dimethoxyethane (50 cc) is added over 20 minutes at a temperature of about -30° C. to a solution of potassium tert-butylate (8.7 g) in 1,2-dimethoxyethane (140 cc) cooled to a temperature of about -30° C. The solution obtained is cooled to a temperature of about -60° ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Isocyanide | Nitrile | c1ccccc1 | null | c1ccncc1.c1cc2n(c1)CSC2 | TsOH.HO- | COCCOC | -30 | 1 | O=Cc1cc(-c2cccnc2)n2c1CSC2.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>COCCOC>N#CCc1cc(-c2cccnc2)n2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-824e7f9651f240e689a69529a68f3509 | C=C(Cl)C#N.O=C(O)[C@@H]1CC(O)CN1C(=O)c1cccnc1>>N#Cc1cc(-c2cccnc2)n2c1CC(O)C2 | [OH-].[Na+].ClC(C#N)=C.C(C1=CN=CC=C1)(=O)N1[C@H](C(=O)O)CC(C1)O.C(C)(=O)OC(C)=O.C(C)(C)O>>OC1CC2=C(C=C(N2C1)C=1C=NC=CC1)C#N | Cl[C:3]([C:2]#[N:1])=[CH2:4].O=C(O)[C@H:13]1[N:12]([C:5](=O)[c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[CH2:17][CH:15]([OH:16])[CH2:14]1>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[n:12]2[c:13]1[CH2:14][CH:15]([OH:16])[CH2:17]2 | C=C(Cl)C#N.O=C(O)[C@@H]1CC(O)CN1C(=O)c1cccnc1 | N#Cc1cc(-c2cccnc2)n2c1CC(O)C2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c95710789d1cdd89ba5f2ce9fde849f30b2083335c55d8155beab7505bfdcd26 | 8e1448c3647c7e9b55ba5077ceb62ca9e7c8e39a2901fbdd3aad031a0a841681 | c1cncc(-c2ccc3n2CCC3)c1 | Cl-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C:3]#[N;D1;H0:4].O-C(=O)-[C@@H;D3;+0:5]1-[C:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-[C;H0;D3;+0:10](=O)-[c;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1>>[N;D1;H0:4]#[C:3]-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11]2:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:2):[n;H0;D3;... | null | [] | 20 | CELSIUS | null | null | A suspension of N-nicotinoyl-4-hydroxyproline (34 g) in a mixture of 2-chloroacrylonitrile (115 cc) and of acetic anhydride (150 cc) is heated at a temperature of about 90° C. for 3 hours and 40 minutes. The solution obtained is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of abou... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Carboxylic acid.Tertiary amide.Vinyl | null | C1CC[NH]C1 | c1cc2n(c1)CCC2 | c1ccncc1.c1cc2n(c1)CCC2 | HCl | null | 20 | null | C=C(Cl)C#N.O=C(O)[C@@H]1CC(O)CN1C(=O)c1cccnc1>>N#Cc1cc(-c2cccnc2)n2c1CC(O)C2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a74cdf5f7cf24cd5b1c5653175416195 | COc1cccc(N)c1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>>COc1cccc(NC(=O)c2cc(-c3cccnc3)n3c2CSC3)c1 | C.COC=1C=C(N)C=CC1.C(C)N(CC)CC.Cl.ClC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2>>COC=1C=C(C=CC1)NC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:25]1.Cl[C:9](=[O:10])[c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[n:20]2[c:21]1[CH2:22][S:23][CH2:24]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18][cH:19]3)[n:20]3[c:21]2... | COc1cccc(N)c1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2 | COc1cccc(NC(=O)c2cc(-c3cccnc3)n3c2CSC3)c1 | null | null | C(CCC)O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1cc(-c2cccnc2)n2c1CSC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:3]1:[c:4]:[c:5]:[#7;a:6]2:[c:7]:1-[C:8]-[#16:9]-[C:10]-2 | 44.6 | [{"value": 44.6, "product": "COC=1C=C(C=CC1)NC(=O)C=1C=C(N2CSCC21)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | A solution of 3-methoxyaniline (3.1 g) and of triethylamine (5.1 g) in methylene chloride (50 cc) is added over 15 minutes at a temperature of between 21° and 28° C. to a suspension of 7-chloroformyl-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (7.5 g) in methylene chloride (125 cc). The solution obtained i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.c1cc2n(c1)CSC2 | HCl | C(CCC)O.C(Cl)Cl | 20 | 16 | COc1cccc(N)c1.O=C(Cl)c1cc(-c2cccnc2)n2c1CSC2>C(CCC)O.C(Cl)Cl>COc1cccc(NC(=O)c2cc(-c3cccnc3)n3c2CSC3)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-145a27aebfd74767a69e19e03a8c59f6 | CCCCC(CC)CCl.COC(=O)c1ccc(O)cc1>>CCCCC(CC)COc1ccc(C(=O)OC)cc1 | COC(C1=CC=C(C=C1)O)=O.C(C)C(CCl)CCCC.C[O-].[Na+]>>COC(C1=CC=C(C=C1)OCC(CCCC)CC)=O | Cl[CH2:8][CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH3:7].[OH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][cH:19]1 | CCCCC(CC)CCl.COC(=O)c1ccc(O)cc1 | CCCCC(CC)COc1ccc(C(=O)OC)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | A mixture of 51.7 g (0.34 mol) of 4-hydroxybenzoic acid methylester, 500 ml of dimethyl formamide, 60 g (0.40 mol) of 2-ethylhexylchloride and 21.8 g (0.40 mol) of sodium methylate was heated for 7 hours to boiling temperature and, after cooling and removal of the sodium chloride by filtration, was evaporated to drynes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | null | null | CCCCC(CC)CCl.COC(=O)c1ccc(O)cc1>CN(C=O)C>CCCCC(CC)COc1ccc(C(=O)OC)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b51e3c45dce24bd2a8edaa79ca6d4094 | CCCCCCCCCCCCOCCCl.COC(=O)c1ccc(O)cc1>>CCCCCCCCCCCCOCCOc1ccc(C(=O)OC)cc1 | COC(C1=CC=C(C=C1)O)=O.C(CCCCCCCCCCC)OCCCl.C[O-].[Na+]>>COC(C1=CC=C(C=C1)OCCOCCCCCCCCCCCC)=O | Cl[CH2:15][CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:16][c:17]1[cH:18][cH:19][c:20]([C:21](=[O:22])[O:23][CH3:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][c:17]1[cH:... | CCCCCCCCCCCCOCCCl.COC(=O)c1ccc(O)cc1 | CCCCCCCCCCCCOCCOc1ccc(C(=O)OC)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 20.4 g (0.134 mol) of 4-hydroxybenzoic acid methylester, 200 ml of dimethyl formamide, 40 g (0.160 mol) of 2-dodecyloxy ethylchloride (from 2-dodecyloxy ethanol and thionyl chloride) and 8.6 g (0.160 mol) of sodium methylate was heated for 7 hours to boiling temperature and, after cooling and removal of th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | null | null | CCCCCCCCCCCCOCCCl.COC(=O)c1ccc(O)cc1>CN(C=O)C>CCCCCCCCCCCCOCCOc1ccc(C(=O)OC)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-042c2ac25241438a9cc4967aa8083194 | CC(C)CCCCCCCCCCCl>>CC(C)CCCCCCCCCCO | COC(C1=CC=C(C=C1)O)=O.C(CCCCCCCCCC(C)C)Cl>>C(CCCCCCCCCC(C)C)O | Cl[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14] | CC(C)CCCCCCCCCCCl | CC(C)CCCCCCCCCCO | null | null | null | Functional Group Interconversion | Primary alkyl halide to alcohol | 4c480ae19804ad5cf02c2cb44a1909d952eb2f0debe381a021a63e61ede789dc | 05def2467bf3ab45f9f8ab94784b02043dfccd675fa03a71edc68bf348b4f536 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;D1;H1:4] | null | [] | null | null | null | null | This compound was prepared from 4-hydroxybenzoic acid methylester and isotridecylchloride, initially obtained from isotridecanol (an oxalcohol prepared from tetrapropylene) using known techniques. The product recovered exhibited a refractive index of
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary alcohol | null | null | null | null | null | null | null | CC(C)CCCCCCCCCCCl>>CC(C)CCCCCCCCCCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9ae755645b74495cba90521e9eaebb2c | O=P([O-])([O-])O>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | [N+](=O)([O-])[O-].[Ca+2].[N+](=O)([O-])[O-].P(=O)(O)([O-])[O-].[NH4+].[NH4+].N>>P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | [O:1]=[P:2]([O-:3])([O-:4])[OH:5]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])([O-])O | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [O;-;D1;H0:1]-[#15:2](-[O;-;D1;H0:3])(=[O;D1;H0:4])-[OH;D1;+0:5]>>[O-;H0;D1:5]-[#15:2](-[O;-;D1;H0:1])(-[O;-;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | The reaction of 3 l of 0.5 mol/l aqueous solution of calcium nitrate [Ca(NO3)2 ] with 2 l of 0.5 mol/l aqueous solution of ammonium hydrogen phosphate [(NH4)2HPO4 ] was carried out by mixing them under nitrogen gas stream at a temperature equal to or less than 5° C., while adjusting pH to 11 by the addition of aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | null | null | null | O=P([O-])([O-])O>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-80585d3d1f174a07a8ac26c8d81210d5 | CCO.O=C(O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl>>CCOC(=O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl | O.ClC=1C(=C(SC1CC(=O)O)F)N1C(C=2CCCCC2C1=O)=O.C(C)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C(=C(SC1CC(=O)OCC)F)N1C(C=2CCCCC2C1=O)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][c:7]1[s:8][c:9]([F:10])[c:11]([N:12]2[C:13](=[O:14])[C:15]3=[C:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)[C:21]2=[O:22])[c:23]1[Cl:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[s:8][c:9]([F:10])[c:11]([N:12]2[C:13](=[O:14])[C:15]3=[C:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)[C:2... | CCO.O=C(O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl | CCOC(=O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl | null | null | C1(=CC=CC=C1)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C1C2=C(CCCC2)C(=O)N1c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#16;a:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[#16;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | To a solution of 2-(4-chloro-2-fluoro-5-carboxymethylthiophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (1.2 g) and ethanol (1.0 g) in toluene (20 ml), there was added a small amount of p-toluenesulfonic acid, and the mixture was refluxed for 3 hours. Water was added to the reaction mixture. The toluene layer was se... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccsc1.C1CCC2=C(C1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | null | null | CCO.O=C(O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl>C1(=CC=CC=C1)C>CCOC(=O)Cc1sc(F)c(N2C(=O)C3=C(CCCC3)C2=O)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-66918d79d0a84c83a3cb9be01a6051a0 | CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F>>Nc1cc(CC(O)=S)c(Cl)cc1F | C(C)(=O)NC=1C(=CC(=C(C1)CC(=S)O)Cl)F.Cl.[OH-].[Na+]>>NC=1C(=CC(=C(C1)CC(=S)O)Cl)F | CC(=O)[NH:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([OH:7])=[S:8])[c:9]([Cl:10])[cH:11][c:12]1[F:13]>>[NH2:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([OH:7])=[S:8])[c:9]([Cl:10])[cH:11][c:12]1[F:13] | CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F | Nc1cc(CC(O)=S)c(Cl)cc1F | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 73 | [{"value": 73.0, "product": "NC=1C(=CC(=C(C1)CC(=S)O)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5-(N-acetylamino)-2-chloro-4-fluorophenylthioacetic acid (89.8 g) in a 10% aqueous hydrochloric acid solution was refluxed for 2 hours under heating. After being allowed to cool, an aqueous solution of sodium hydroxide was added to make the suspension at pH 4. After ice-cooling, the precipitated crystal... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F>>Nc1cc(CC(O)=S)c(Cl)cc1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-314841d8e7144a3383cf73952ae86a5e | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O>>CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | [N+](=O)(O)[O-].S(O)(O)(=O)=O.C(C)(=O)NC1=C(C=C(C=C1)Cl)F>>C(C)(=O)NC1=CC(=C(C=C1F)Cl)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:11]([Cl:12])[cH:13][c:14]1[F:15].O[N+:8](=[O:9])[O-:10]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([Cl:12])[cH:13][c:14]1[F:15] | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | 99.5 | [{"value": 99.5, "product": "C(C)(=O)NC1=CC(=C(C=C1F)Cl)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 20% ice-cooled fuming sulfuric acid (50 g), 4-(N-acetylamino)-1-chloro-3-fluorobenzene (9.4 g) was dissolved, followed by gradual addition of fuming nitric acid (3.5 g) while keeping the temperature at 0° to 5° C. The resultant mixture was stirred at the same temperature for 1 hour and poured into ice (50 g). The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O>>CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c23a4513b82d45e09e99a39aac139faa | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F>>CC(=O)Nc1cc(N)c(Cl)cc1F | C(C)(=O)NC1=CC(=C(C=C1F)Cl)[N+](=O)[O-]>>C(C)(=O)NC1=CC(=C(C=C1F)Cl)N | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[c:12]([F:13])[cH:11][c:9]1[Cl:10]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11][c:12]1[F:13] | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | CC(=O)Nc1cc(N)c(Cl)cc1F | null | [Fe] | C(C)(=O)O.C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 60.4 | [{"value": 60.4, "product": "C(C)(=O)NC1=CC(=C(C=C1F)Cl)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | Iron powder (31.9 g) were suspended in a 5% acetic acid solution (60 ml), and the suspension was heated to 90° C. A solution of 4-(N-acetylamino)-1-chloro-5-fluoro-2-nitrobenzene (13.3 g) in acetic acid (100 l ml) and ethyl acetate (70 ml) was dropwise added thereto, and the resultant mixture was refluxed at 80° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].C(C)(=O)O.C(C)(=O)OCC | 90 | null | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F>[Fe].C(C)(=O)O.C(C)(=O)OCC>CC(=O)Nc1cc(N)c(Cl)cc1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d8cc237945574052a6d5fb822976a17c | CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(O)CS>>CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F | C(C(=O)O)S.N(=O)[O-].[Na+].C(C)(=O)NC1=CC(=C(C=C1F)Cl)N.Cl.[OH-].[Na+].S(N)(O)(=O)=O>>C(C)(=O)NC=1C(=CC(=C(C1)CC(=S)O)Cl)F | N[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[c:15]([F:16])[cH:14][c:12]1[Cl:13].O=[C:9]([CH2:8][SH:11])[OH:10]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([CH2:8][C:9]([OH:10])=[S:11])[c:12]([Cl:13])[cH:14][c:15]1[F:16] | CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(O)CS | CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 883928d542c9648afb18ee171e788bfedb6971fec38eb060208ce14a90f845ea | 0a479965227def53da1b53ebee7774bac4e68ae016c7e895a59ff807fed83dd3 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].O=[C;H0;D3;+0:7](-[O;D1;H1:8])-[CH2;D2;+0:9]-[SH;D1;+0:10]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH2;D2;+0:9]-[C;H0;D3;+0:7](-[O;D1;H1:8])=[S;H0;D1;+0:10]):[c:2]:[c:3] | null | [] | null | null | 1 | HOUR | 4-(N-Acetylamino)-2-amino-1-chloro-5-fluorobenzene (7.0 g) was suspended in a mixture of conc. hydrochloric acid (9 ml), water (40 ml) and ice (60 g), and the suspension was kept at -5° to 10° C., preferably at 0° C. A solution of sodium nitrite (2.5 g) in water (8 ml) was dropwise added to the suspension, which was th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Aliphatic thiol | Thiocarbonyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | null | 1 | CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(O)CS>O>CC(=O)Nc1cc(CC(O)=S)c(Cl)cc1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-24917a9021f944739cf6948b30a8a80d | CC(=O)Nc1ccc(Br)cc1F.O=S(=O)(O)O>>CC(=O)Nc1cc(S(=O)(=O)O)c(Br)cc1F | S(O)(O)(=O)=O.BrC1=CC(=C(C=C1)NC(C)=O)F.S(O)(O)(=O)=O>>C(C)(=O)NC=1C(=CC(=C(C1)S(=O)(=O)O)Br)F | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:12]([Br:13])[cH:14][c:15]1[F:16].O[S:8](=[O:9])(=[O:10])[OH:11]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([S:8](=[O:9])(=[O:10])[OH:11])[c:12]([Br:13])[cH:14][c:15]1[F:16] | CC(=O)Nc1ccc(Br)cc1F.O=S(=O)(O)O | CC(=O)Nc1cc(S(=O)(=O)O)c(Br)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4de7a411ca4a8e56f858115b27e6157e074d8465bf6f118cb7ff1cf307084c04 | a824d87b0e6c732faabe155a548de29df954da8631ad9b191cacb2d591bbcaa7 | c1ccccc1 | O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4].[Br;D1;H0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[Br;D1;H0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4]):[c:9]:[c:10] | null | [] | 20 | CELSIUS | 2 | HOUR | N-(4-Bromo-2-fluorophenyl)acetamide (173.2 g) was suspended in conc. sulfuric acid (80 ml), and 60% fuming sulfuric acid (340 ml) was dropwise added thereto at 10° to 20° C., followed by stirring at 20° C., for 2 hours. The reaction mixture was dropwise added to ice water (500 g) at 10° to 20° C., and the precipitated ... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 20 | 2 | CC(=O)Nc1ccc(Br)cc1F.O=S(=O)(O)O>>CC(=O)Nc1cc(S(=O)(=O)O)c(Br)cc1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-14408afd0ea04118a6b2aec746408141 | Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1.Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1>>Cc1cc(Cc2cc(C)cc(-c3cccc4[nH]nnc34)c2O)c(O)c(-c2cccc3[nH]nnc23)c1 | CC1=CC=C(C(=C1)C1=CC=CC=2NN=NC21)O.CC1=CC=C(C(=C1)C1=CC=CC=2NN=NC21)O.C[O-].[Na+]>>C(C1=C(C(=CC(=C1)C)C1=CC=CC=2NN=NC21)O)C2=C(C(=CC(=C2)C)C2=CC=CC=1NN=NC12)O | [CH3:1][c:2]1[cH:3][cH:4][c:23]([OH:24])[c:25](-[c:26]2[cH:27][cH:28][cH:29][c:30]3[nH:31][n:32][n:33][c:34]23)[cH:35]1.[cH:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]3[nH:17][n:18][n:19][c:20]23)[c:21]1[OH:22]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][c:6]2[cH:7][c:8]([CH3:9])[cH:10][c:11](-[c:12]... | Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1.Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1 | Cc1cc(Cc2cc(C)cc(-c3cccc4[nH]nnc34)c2O)c(O)c(-c2cccc3[nH]nnc23)c1 | null | null | C=1(C(=CC=CC1)C)C | C-C Coupling | OtherReaction | eb2908ed4d02b1e0b8609625a74eaabea2a238c68aadec547cb47821958dd9a8 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1cc(Cc2cccc(-c3cccc4[nH]nnc34)c2)cc(-c2cccc3[nH]nnc23)c1 | [O;D1;H1:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[O;D1;H1:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H1:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[C:13]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[O;D1;H1:1]):[c:3]):[c:11]:[c:12] | 95 | [{"value": 95.0, "product": "C(C1=C(C(=CC(=C1)C)C1=CC=CC=2NN=NC21)O)C2=C(C(=CC(=C2)C)C2=CC=CC=1NN=NC12)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 6.2 g of the Mannich base obtained in Example 1 and 4-methyl-6benzotriazolyl-phenol 4.5 g were dissolved in 200 ml of xylene, and sodium methylate (28% methanol solution) 0.2 g was added. The solution was heated with stirring under reflux at 140°-150° C. for 10 hours with a stream of nitrogen. After distilling of the s... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2[nH]nnc2c1.c1ccc2[nH]nnc2c1 | Other | C=1(C(=CC=CC1)C)C | null | null | Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1.Cc1ccc(O)c(-c2cccc3[nH]nnc23)c1>C=1(C(=CC=CC1)C)C>Cc1cc(Cc2cc(C)cc(-c3cccc4[nH]nnc34)c2O)c(O)c(-c2cccc3[nH]nnc23)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d903185401c6425592f4f674eacdfc7e | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)O)=C.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1.C(C)(=O)O.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1>>O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C | [CH2:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[C:15](=[O:16])[OH:17].[N-]=[N+]=[C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH2:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[C:15](... | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 8531b6eb3abfd6846ce0cb8d79abac610072134e0cc0be40cc269196cd4eea5b | d6eab3abd961fdb019332f17e55277b8a7c7f7a1f79c71be7a6248f0a0e6a15e | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | [#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].[N-]=[N+]=[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]>>[#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13] | 99.1 | [{"value": 99.1, "product": "O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[(1,3-Dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid (1.54 g, 4.8 mmole) was dissolved in 25 ml of acetonitrile and a solution of diphenyldiazomethane (1.17 g, 5.94 mmole/50 ml acetonitrile) was added dropwise. After approximately 1.1 equivalents of diphenyldiazomethane had been added, tlc showed no starting material r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo | Ester | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccccc1 | Other | C(C)#N | null | null | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>C(C)#N>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-326a1ef3e0824d60a1db186de1402dca | CC(C)(C)OC(=O)NC1C(=O)N(OCc2ccccc2)C1(C)C>>CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C | C(C)(C)(C)OC(=O)NC1C(N(C1(C)C)OCC1=CC=CC=C1)=O>>C(C)(C)(C)OC(=O)NC1C(N(C1(C)C)O)=O | c1ccc(C[O:13][N:12]2[C:10](=[O:11])[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:14]2([CH3:15])[CH3:16])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[C:10](=[O:11])[N:12]([OH:13])[C:14]1([CH3:15])[CH3:16] | CC(C)(C)OC(=O)NC1C(=O)N(OCc2ccccc2)C1(C)C | CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C | null | [Pd] | CO | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1CCN1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[#7:5]-1-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[#7:5]-1-[OH;D1;+0:6] | 100.4 | [{"value": 100.4, "product": "C(C)(C)(C)OC(=O)NC1C(N(C1(C)C)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-3-[(t-Butyloxycarbonyl)amino]-4,4-dimethyl-1-(phenylmethoxy)-2-azetidinone (8.07 g, 25 mmol) was hydrogenated at atmospheric pressure and ambient temperature in 40 ml of methanol with 0.6 g of 10% palladium on charcoal as catalyst for 2 hours. The reaction mixture was filtered through a pad of Celite and the filtra... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | C1C[NH]C1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)NC1C(=O)N(OCc2ccccc2)C1(C)C>[Pd].CO>CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-372b48998a944947acdc316bd1e13103 | CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C.O=S(=O)(O)Cl.c1ccncc1>>CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)[O-])C1(C)C.CCCC[N+](CCCC)(CCCC)CCCC | O.C(C)(C)(C)OC(=O)NC1C(N(C1(C)C)O)=O.ClS(=O)(=O)O.N1=CC=CC=C1>>C(CCC)[N+](CCCC)(CCCC)CCCC.S(=O)(=O)(ON1C(C(C1(C)C)NC(=O)OC(C)(C)C)=O)[O-] | [CH3:1][C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]1[C:10](=[O:11])[N:12]([OH:13])[C:18]1([CH3:19])[CH3:20])([CH3:35])[CH3:36].Cl[S:14](=[O:15])(=[O:16])[OH:17].[cH:22]1[cH:23][cH:24][n:25][cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[C:10](=[O:11])[N:12]([O:13][S:14](=[O:15])(=[O:16])[O-:17])[... | CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C.O=S(=O)(O)Cl.c1ccncc1 | CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)[O-])C1(C)C.CCCC[N+](CCCC)(CCCC)CCCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | ClCCl | Acylation | OtherReaction | ce7d354dca39d756db2846188614927bd4293b709a269ae75ac42d8d12a93b22 | 03c431cf9c388e566f0e58c89e54434d4ef9b7340e6b9a612b938fb432b9d26a | O=C1CCN1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[C;D1;H3:5]-[C;H0;D4;+0:6](-[CH3;D1;+0:7])(-[CH3;D1;+0:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13]1-[C:14]-[#7:15](-[OH;D1;+0:16])-[C:17]-1=[O;D1;H0:18].[cH;D2;+0:19]1:[cH;D2;+0:20]:[cH;D2;+0:21]:[n;H0;D2;+0:22]:[cH;D2;+0:23]:[cH;D2;+0:24]:1>>[C;D1;H3:5]-[C... | null | [] | 25 | CELSIUS | 10 | MINUTE | A solution of chlorosulfonic acid (12.27 g, 0.105 mole) in 210 ml of dichloromethane at -40° C. under argon was treated with 20.5 g (0.26 mole) of pyridine dropwise over 10 minutes. The mixture is stirred for 10 more minutes at 0° C. and 10 minutes at 25° C. A slurry of (±)-3-[(t-butyloxycarbonyl)amino]-1-hydroxy-4,4-d... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | Ether.Boc | c1ccncc1 | null | C1C[NH]C1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl | 25 | 0.166667 | CC(C)(C)OC(=O)NC1C(=O)N(O)C1(C)C.O=S(=O)(O)Cl.c1ccncc1>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl>CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)[O-])C1(C)C.CCCC[N+](CCCC)(CCCC)CCCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8c0e7bba371b45db9636a661c316681f | C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)OC(c1ccccc1)c1ccccc1>>C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)O | FC(C(=O)O)(F)F.NC=1SC=C(N1)/C(/C(=O)NC1C(N(C1(C)C)OS(=O)(=O)O)=O)=N/OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C.C(Cl)Cl.C1(=CC=CC=C1)OC>>NC=1SC=C(N1)/C(/C(=O)NC1C(N(C1(C)C)OS(=O)(=O)O)=O)=N/OC(C(=O)O)=C | c1ccc(C(c2ccccc2)[O:29][C:27]([C:2](=[CH2:1])[O:3]/[N:4]=[C:5](\[C:6](=[O:7])[NH:8][CH:9]2[C:10](=[O:11])[N:12]([O:13][S:14](=[O:15])(=[O:16])[OH:17])[C:18]2([CH3:19])[CH3:20])[c:21]2[cH:22][s:23][c:24]([NH2:25])[n:26]2)=[O:28])cc1>>[CH2:1]=[C:2]([O:3]/[N:4]=[C:5](\[C:6](=[O:7])[NH:8][CH:9]1[C:10](=[O:11])[N:12]([O:13]... | C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)OC(c1ccccc1)c1ccccc1 | C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)O | null | null | C1(=CC=CC=C1)C | Deprotection | Ester saponification (alkyl deprotection) | 6c6fe281a466ba3015c862d0079f398ca54d13fe39ff38458258f53accd43d52 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | N=C(C(=O)NC1CNC1=O)c1cscn1 | [#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6] | null | [] | -5 | CELSIUS | 45 | MINUTE | To the flask containing (±)-(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-[[4,4-dimethyl-2-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-propenoic acid, diphenylmethyl ester was added methylene chloride (10 ml) and anisole (10 ml). After cooling to -5° C., trifluoroacetic acid (8 ml) was added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1.c1ccccc1 | null | C1C[NH]C1.c1cscn1 | Other | C1(=CC=CC=C1)C | -5 | 0.75 | C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)OC(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>C=C(O/N=C(\C(=O)NC1C(=O)N(OS(=O)(=O)O)C1(C)C)c1csc(N)n1)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c3f14a8fcf3b4b7497e5d9c212404b51 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C>>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O | O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C)(C)C)=C.FC(C(=O)O)(F)F.C1(=CC=CC=C1)C>>O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)O)=C | CC(C)(C)[O:17][C:15]([C:2](=[CH2:1])[O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])=[O:16]>>[CH2:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[C:15](=[O:16])[OH:17] | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O | null | null | C1(=CC=CC=C1)OC.C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NC(=O)c2ccccc21 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[#8:5])=[C;D1;H2:6]>>[#8:5]-[C:4](=[C;D1;H2:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 98.2 | [{"value": 98.2, "product": "O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)O)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-[(1,3-dioxo-2H-isoindol-2-yl)-oxy]-2-propenoic acid, t-butyl ester (49.9 g, 0.173 mole) in methylene chloride (300 ml) and anisole (150 ml) was treated with trifluoroacetic acid (300 ml). After stirring overnight at room temperature, 800 ml of dry toluene was added and the reaction mixture was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2c(c1)C[NH]C2 | Other | C1(=CC=CC=C1)OC.C(Cl)Cl | null | 8 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C>C1(=CC=CC=C1)OC.C(Cl)Cl>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-62540daf740f4ebdb0f0fb22e0de0d65 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)O)=C.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1>>O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C | [CH2:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[C:15](=[O:16])[OH:17].[N-]=[N+]=[C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH2:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14])[C:15](... | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 8531b6eb3abfd6846ce0cb8d79abac610072134e0cc0be40cc269196cd4eea5b | d6eab3abd961fdb019332f17e55277b8a7c7f7a1f79c71be7a6248f0a0e6a15e | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | [#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].[N-]=[N+]=[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]>>[#8:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13] | 70.3 | [{"value": 70.3, "product": "O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[(1,3-Dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid (39.6 g, 0.17 mole) was dissolved in 800 ml of acetonitrile and a solution of diphenyldiazomethane (43.4 g, 0.224 mole/1000 ml acetonitrile) was added dropwise over 3 hours at 0° C. The reaction solution was evaporated to a solid which was triturated with hexane. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo | Ester | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccccc1 | Other | C(C)#N | null | null | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>C(C)#N>C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-81a98eb62d3a4e8db0a1240526ed7b45 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1>>C=C(ON)C(=O)OC(c1ccccc1)c1ccccc1 | O=C1N(C(C2=CC=CC=C12)=O)OC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C.O.NN>>NOC(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)=C | O=C1c2ccccc2C(=O)[N:4]1[O:3][C:2](=[CH2:1])[C:5](=[O:6])[O:7][CH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[C:2]([O:3][NH2:4])[C:5](=[O:6])[O:7][CH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1 | C=C(ON)C(=O)OC(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl.C(C)O | Reduction | Phthalimide deprotection | 8c6c904eae7a7d528fa3eeedb7e9706448ab9f7df249a16fa865a9210a6adc85 | 892f9aeb7d80035b81a0f5a363c9ed6a90780ba9faa3f0708093fa283b8c9a24 | c1ccc(Cc2ccccc2)cc1 | O=C1-[N;H0;D3;+0:1](-[#8:2]-[C:3](=[C;D1;H2:4])-[C:5](-[#8:6])=[O;D1;H0:7])-C(=O)-c2:c:c:c:c:c:2-1>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:3](=[C;D1;H2:4])-[#8:2]-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a solution of 2-[(1,3-dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid, diphenylmethyl ester (6.07 g, 15.2 mmole) in 375 ml of methylene chloride under argon at 0° C. was added hydrazine hydrate (0.76 g, 15.2 mmole) in 4 ml absolute ethanol. After one hour at 0° C., the mixture was evaporated to dryness at +10° C. and t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C(C)O | null | 1 | C=C(ON1C(=O)c2ccccc2C1=O)C(=O)OC(c1ccccc1)c1ccccc1>C(Cl)Cl.C(C)O>C=C(ON)C(=O)OC(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b8abfc5399164ec0b2d27d6533f14659 | CC(C)(C)OC(=O)N[C@@H]1C(=O)N(OCc2ccccc2)C1(C)C>>CC(C)(C)OC(=O)N[C@@H]1C(=O)N(O)C1(C)C | C(C)(C)(C)OC(=O)N[C@@H]1C(N(C1(C)C)OCC1=CC=CC=C1)=O>>C(C)(C)(C)OC(=O)N[C@@H]1C(N(C1(C)C)O)=O | c1ccc(C[O:13][N:12]2[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:14]2([CH3:15])[CH3:16])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[C:10](=[O:11])[N:12]([OH:13])[C:14]1([CH3:15])[CH3:16] | CC(C)(C)OC(=O)N[C@@H]1C(=O)N(OCc2ccccc2)C1(C)C | CC(C)(C)OC(=O)N[C@@H]1C(=O)N(O)C1(C)C | null | [Pd] | C(C)(=O)OCC.C(C)O | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1CCN1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[#7:5]-1-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[#7:5]-1-[OH;D1;+0:6] | 83.1 | [{"value": 83.1, "product": "C(C)(C)(C)OC(=O)N[C@@H]1C(N(C1(C)C)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 14.77 g (0.0461 mole) of (3S)-3-[(t-butyloxycarbonyl)amino]-4,4-dimethyl-1-(phenylmethoxy)-2-azetidinone in 15 ml of ethanol and 85 ml of ethyl acetate was hydrogenated over 0.75 g of 5% palladium-on-carbon catalyst for 1.5 hours at 1 atmosphere. The reaction mixture was filtered and concentrated to give ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | C1C[NH]C1 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | null | CC(C)(C)OC(=O)N[C@@H]1C(=O)N(OCc2ccccc2)C1(C)C>[Pd].C(C)(=O)OCC.C(C)O>CC(C)(C)OC(=O)N[C@@H]1C(=O)N(O)C1(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-065deac20e75456784ee84a24854b3d8 | CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)O)C12CCC2>>NC1C(=O)N(OS(=O)(=O)O)C12CCC2 | C(C)(C)(C)OC(=O)NC1C(N(C12CCC2)OS(=O)(=O)O)=O.[Na].C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>NC1C(N(C12CCC2)OS(=O)(=O)O)=O | CC(C)(C)OC(=O)[NH:1][CH:2]1[C:3](=[O:4])[N:5]([O:6][S:7](=[O:8])(=[O:9])[OH:10])[C:11]12[CH2:12][CH2:13][CH2:14]2>>[NH2:1][CH:2]1[C:3](=[O:4])[N:5]([O:6][S:7](=[O:8])(=[O:9])[OH:10])[C:11]12[CH2:12][CH2:13][CH2:14]2 | CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)O)C12CCC2 | NC1C(=O)N(OS(=O)(=O)O)C12CCC2 | null | null | ClCCl.C1(=CC=CC=C1)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CC2(CCC2)N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[#7:4](-[#8:5]-[#16:6]-[O;D1;H1:7])-[C:8]-1=[O;D1;H0:9]>>[NH2;D1;+0:1]-[C:2]1-[C:3]-[#7:4](-[#8:5]-[#16:6]-[O;D1;H1:7])-[C:8]-1=[O;D1;H0:9] | null | [] | null | null | 0.5 | HOUR | 3-[(t-Butoxycarbonyl)amino]-2-oxo-1-(sulfooxy)-1-azaspiro[3.3]heptane, monosodium salt (0.3 g, 0.87 mmole) was slurried in 2.5 ml of dry dichloromethane and 1.0 ml of anisole at -10° C. under argon, and then treated with 4.0 ml of trifluoroacetic acid. After 0.5 hour, a solid had formed. After 1.5 hours, 4 ml of dry to... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC2(C1)CC[NH]2 | HO- | ClCCl.C1(=CC=CC=C1)C | null | 0.5 | CC(C)(C)OC(=O)NC1C(=O)N(OS(=O)(=O)O)C12CCC2>ClCCl.C1(=CC=CC=C1)C>NC1C(=O)N(OS(=O)(=O)O)C12CCC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-14cd47dd92304a94895a0eed6473f454 | BrBr.O=c1cc(O)c2cccnc2n1-c1ccccc1>>O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 | OC1=CC(N(C2=NC=CC=C12)C1=CC=CC=C1)=O.BrBr>>BrC=1C(N(C2=NC=CC=C2C1O)C1=CC=CC=C1)=O | Br[Br:4].[O:1]=[c:2]1[cH:3][c:5]([OH:6])[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[n:13]1-[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[c:2]1[c:3]([Br:4])[c:5]([OH:6])[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[n:13]1-[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrBr.O=c1cc(O)c2cccnc2n1-c1ccccc1 | O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 931b303f1bd4c9a087dc1eb2dc5143889aed01c01237ad614920721faf93f5b4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ccc2cccnc2n1-c1ccccc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[c:5](-[O;D1;H1:6]):[cH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[c:11]>>[#7;a:2]:[c:3]1:[c:4]:[c:5](-[O;D1;H1:6]):[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[c:11] | 65.4 | [{"value": 65.4, "product": "BrC=1C(N(C2=NC=CC=C2C1O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (1 g) in CH2Cl2 (20 mL) was added, dropwise and with stirring, a solution of bromine (0.7 g) in CH2Cl2 (5 mL). The mixture was stirred at room temperature overnight, after which time the product was filtered off, dried in air and recrystallized from aceto... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2ncccc2c1 | c1cnc2ncccc2c1 | c1cnc2ncccc2c1.c1ccccc1 | HBr | C(Cl)Cl | null | null | BrBr.O=c1cc(O)c2cccnc2n1-c1ccccc1>C(Cl)Cl>O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8cc4dd16c7654ef9a2223720cf302a31 | CN1CCCC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>>C[N+]1(c2c(O)c3cccnc3n(-c3ccccc3)c2=O)CCCC1.[OH-] | BrC=1C(N(C2=NC=CC=C2C1O)C1=CC=CC=C1)=O.CN1CCCC1>>[OH-].OC1=C(C(N(C2=NC=CC=C12)C1=CC=CC=C1)=O)[N+]1(CCCC1)C | [CH3:1][N:2]1[CH2:21][CH2:22][CH2:23][CH2:24]1.Br[c:3]1[c:4]([OH:5])[c:6]2[cH:7][cH:8][cH:9][n:10][c:11]2[n:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1=[O:20]>>[CH3:1][N+:2]1([c:3]2[c:4]([OH:5])[c:6]3[cH:7][cH:8][cH:9][n:10][c:11]3[n:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]2=[O:20])[CH2:21][... | CN1CCCC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 | C[N+]1(c2c(O)c3cccnc3n(-c3ccccc3)c2=O)CCCC1.[OH-] | null | null | N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | e088ee06debd1768d6a7b49fef1c393c335ddbf966a3c2930c1cbe2912e5a136 | 4e785b123c30fe1e471eaa628309cb7fdb2dcbe05b4ffc27bd0436c6801b9115 | O=c1c([NH+]2CCCC2)cc2cccnc2n1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[c:5]):[c:6](:[#7;a:7]):[c:8]:[c:9]:1-[O;D1;H1:10].[C;D1;H3:11]-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1>>[#7;a:7]:[c:6]1:[c:8]:[c:9](-[O;D1;H1:10]):[c;H0;D3;+0:1](-[N+;H0;D4:12]2(-[C;D1;H3:11])-[C:13]-[C:14]-[C:15]-[C:16]-2):[c:2](=[O;D1;H0:3]):[#7;a:4]:1-[c:5] | null | [] | null | null | 33 | HOUR | In dry pyridine (30 mL), 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (10 g) was suspended. N-methyl pyrrolidine (20 mL) was added to the suspension. The mixture was heated to 95°-100° C. with stirring, and was kept there for about 33 hours. The product was evaporated under high vacuum to provide a dark oil. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | null | C1CC[NH]C1.c1cnc2ncccc2c1 | c1cnc2ncccc2c1.C1CC[NH+]C1 | c1cnc2ncccc2c1.c1ccccc1.C1CC[NH+]C1 | null | N1=CC=CC=C1 | null | 33 | CN1CCCC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>N1=CC=CC=C1>C[N+]1(c2c(O)c3cccnc3n(-c3ccccc3)c2=O)CCCC1.[OH-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1a63051189a64827a0e1e208f850bb1d | C1CCNC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>>O=c1c([NH+]2CCCC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] | BrC=1C(N(C2=NC=CC=C2C1O)C1=CC=CC=C1)=O.N1CCCC1>>[OH-].OC1=C(C(N(C2=NC=CC=C12)C1=CC=CC=C1)=O)[NH+]1CCCC1 | [NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1.Br[c:3]1[c:2](=[O:1])[n:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:16]2[c:11]([c:9]1[OH:10])[cH:12][cH:13][cH:14][n:15]2>>[O:1]=[c:2]1[c:3]([NH+:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[c:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[n:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:2... | C1CCNC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 | O=c1c([NH+]2CCCC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] | null | null | CN(C)C=O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 0de7eb20484a3f91e640898ecef4af7974e8385696e6cd2373f8565ddad78a13 | 629eabbde8e9e7fb44d82efe8f99784bd824d43dc9f8e1860cea90fe5325d9b5 | O=c1c([NH+]2CCCC2)cc2cccnc2n1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[c:5]):[c:6](:[#7;a:7]):[c:8]:[c:9]:1-[O;D1;H1:10].[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[#7;a:7]:[c:6]1:[c:8]:[c:9](-[O;D1;H1:10]):[c;H0;D3;+0:1](-[NH+;D3:15]2-[C:11]-[C:12]-[C:13]-[C:14]-2):[c:2](=[O;D1;H0:3]):[#7;a:4]:1-[c:5] | null | [] | 100 | CELSIUS | null | null | A solution of 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (2 g) in a mixture of pyrrolidine (10 mL) and DMF (5 mL) was stirred and heated at 100° C. for 2 days. The resulting mixture was then cooled, diluted with CH2Cl2 (100 mL) and filtered. The solid was triturated with hot CHCl3, filtered, and dried to yie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | null | C1CCNC1.c1cnc2ncccc2c1 | C1CC[NH+]C1.c1cnc2ncccc2c1 | C1CC[NH+]C1.c1cnc2ncccc2c1.c1ccccc1 | null | CN(C)C=O.C(Cl)Cl | 100 | null | C1CCNC1.O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>CN(C)C=O.C(Cl)Cl>O=c1c([NH+]2CCCC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3f7c40f113fd4fd48511e36981e2c6a7 | O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>>O=c1c([NH+]2CCC(O)CC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] | BrC=1C(N(C2=NC=CC=C2C1O)C1=CC=CC=C1)=O>>[OH-].OC1=C(C(N(C2=NC=CC=C12)C1=CC=CC=C1)=O)[NH+]1CCC(CC1)O | Br[c:3]1[c:2](=[O:1])[n:4](-[c:20]2[cH:5][cH:24][cH:23][cH:22][cH:21]2)[c:18]2[c:13]([c:11]1[OH:12])[cH:14][cH:15][cH:16][n:17]2>>[O:1]=[c:2]1[c:3]([NH+:4]2[CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10]2)[c:11]([OH:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[n:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[OH-:26] | O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1 | O=c1c([NH+]2CCC(O)CC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] | null | null | N1=C(C=CC=C1C)C.OC1CCNCC1 | Aromatic Heterocycle Formation | OtherReaction | c0857e3387d83aa1e3e8272b2f93c681ee7f22de4670677c0e8791fe379a529a | 9f963a7ceedcacba8bff3744c93bc22895e3751f804d727222d55e99a5bb086d | O=c1c([NH+]2CCCCC2)cc2cccnc2n1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[O;D1;H1:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[n;H0;D3;+0:9](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:2):[c;H0;D3;+0:16]:1=[O;D1;H0:17]>>[O;D1;H0:17]=[c;H0;D3;+0:16]1:[#7;a:18](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[c:19]:2):[c;H0;D3;+0:6](... | null | [] | 100 | CELSIUS | null | null | A solution of 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (1 g) in a mixture of 2,6-lutidine (5 mL) and 4-hydroxy-piperidine (3.12 g) was heated at 100° C. for 32 hours. The lutidine was removed by evaporation under high vacuum. The residue was dissolved in CH3CN(20): H2O(80): CH3CO2H(1) and separated by reve... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Secondary alcohol | c1ccccc1.c1cnc2ncccc2c1 | C1CC[NH+]CC1.c1cnc2ncccc2c1.c1ccccc1 | C1CC[NH+]CC1.c1cnc2ncccc2c1.c1ccccc1 | Br- | N1=C(C=CC=C1C)C.OC1CCNCC1 | 100 | null | O=c1c(Br)c(O)c2cccnc2n1-c1ccccc1>N1=C(C=CC=C1C)C.OC1CCNCC1>O=c1c([NH+]2CCC(O)CC2)c(O)c2cccnc2n1-c1ccccc1.[OH-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2a9efe2e38d441bdb33e0120ea48ea1f | CCOc1cc2c(c(OCC)c1OCC)COC2=O.O=[N+]([O-])O>>CCOc1c2c(c([N+](=O)[O-])c(OCC)c1OCC)C(=O)OC2 | C(C)(=O)O.C(C)OC1=C2COC(=O)C2=CC(=C1OCC)OCC.[N+](=O)(O)[O-]>>C(C)OC1=C2COC(=O)C2=C(C(=C1OCC)OCC)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][c:4]1[c:5]2[c:6]([cH:7][c:11]([O:12][CH2:13][CH3:14])[c:15]1[O:16][CH2:17][CH3:18])[C:19](=[O:20])[O:21][CH2:22]2.O[N+:8](=[O:9])[O-:10]>>[CH3:1][CH2:2][O:3][c:4]1[c:5]2[c:6]([c:7]([N+:8](=[O:9])[O-:10])[c:11]([O:12][CH2:13][CH3:14])[c:15]1[O:16][CH2:17][CH3:18])[C:19](=[O:20])[O:21][CH2:22]2 | CCOc1cc2c(c(OCC)c1OCC)COC2=O.O=[N+]([O-])O | CCOc1c2c(c([N+](=O)[O-])c(OCC)c1OCC)C(=O)OC2 | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | ee3ad82349d0ec639a2d273ef62f31226e87972cc0517103400f7bde30591a6c | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1OCc2ccccc21 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]1:[c:9]-[C:10]-[#8:11]-[C:12]-1=[O;D1;H0:13]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]1:[c:9]-[C:10]-[#8:11]-[C:12]-1=[O;D1;H0:13] | 35 | [{"value": 35.0, "product": "C(C)OC1=C2COC(=O)C2=C(C(=C1OCC)OCC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Glacial acetic acid (14 ml) was added to 5.32 g (0.02 mole) of 4,5,6-triethoxyphthalide. Into the reaction mixture on a water bath at 30-35° C., 14 ml of fuming nitric acid, d=1.52, was gradually added dropwise over a time period of 9 hours. After completion of the addition, the reaction mixture was allowed to stand ov... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HO- | O | null | 8 | CCOc1cc2c(c(OCC)c1OCC)COC2=O.O=[N+]([O-])O>O>CCOc1c2c(c([N+](=O)[O-])c(OCC)c1OCC)C(=O)OC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-39e3a70ecded4f8ea6d40804995deae2 | CO.O=C1OC([N+](=O)[O-])c2ccccc21>>O=C1OCc2ccccc21.c1ccc2cnccc2c1 | [N+](=O)([O-])C1OC(=O)C2=CC=CC=C12.CO>>C1=NC=CC2=CC=CC=C12.C1(=O)OCC2=CC=CC=C12 | O[CH3:4].O=[N+:16]([O-])[CH:17]1[O:3][C:2](=[O:1])[c:10]2[c:5]1[cH:6][cH:7][cH:8][cH:9]2>>[O:1]=[C:2]1[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21.[cH:11]1[cH:12][cH:13][c:14]2[cH:15][n:16][cH:17][cH:18][c:19]2[cH:20]1 | CO.O=C1OC([N+](=O)[O-])c2ccccc21 | O=C1OCc2ccccc21.c1ccc2cnccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f9a5a1d5d598abfebf99033f479fa9fc5ec64164c0038edd6c13b7a0160aecd8 | dae788f4a1f4377f83595fb07b32c0e1335ba5803d0ca58b98d832eeef4ad9ce | O=C1OCc2ccccc21.c1ccc2cnccc2c1 | O-[CH3;D1;+0:1].O=[N+;H0;D3:2](-[O-])-[CH;D3;+0:3]1-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c;H0;D3;+0:9]-1:[c:10]:[c:11]>>[O;D1;H0:6]=[C:5]1-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7]-1:[c:8].[c:12]1:[c:13]:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[c:14]:[c:15]:1 | null | [] | null | null | null | null | wherein R4 to R7 are as defined above, in methanol in an amount of 1.5 to 10 times by volume of nitrophthalide and a reaction temperature of 50° to 80° C. for a reaction period of 8 to 36 hours to produce a phthalide isoquinoline represented by the general formula (III): ##STR11##
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group.Methanol | Ester | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2.c1ccc2cnccc2c1 | c1ccc2c(c1)COC2.c1ccc2cnccc2c1 | null | null | null | null | CO.O=C1OC([N+](=O)[O-])c2ccccc21>>O=C1OCc2ccccc21.c1ccc2cnccc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ae4597ad267b47eb9940dcaad6564230 | COc1nc(C)nc(N)n1.O=C([O-])N(c1ccccc1)S(=O)(=O)c1ccc(Cl)nn1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccc(Cl)nn2)n1 | ClC=1N=NC(=CC1)S(=O)(=O)N(C([O-])=O)C1=CC=CC=C1.NC1=NC(=NC(=N1)OC)C>>ClC=1N=NC(=CC1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)C | [CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:23]1.[O-][C:10](=[O:11])[N:12](c1ccccc1)[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[n:21][n:2... | COc1nc(C)nc(N)n1.O=C([O-])N(c1ccccc1)S(=O)(=O)c1ccc(Cl)nn1 | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccc(Cl)nn2)n1 | null | null | O1CCOCC1 | Acylation | OtherReaction | c711cd1efb286da599cb4f6d31ebc08e3e00fafe8cc5f1f83ddfd8a6db9b39ec | d376f5b2bb9d4421ae0e8d656f00ea10021a6d76153a24b5fa5e6591c71665a7 | O=C(Nc1ncncn1)NS(=O)(=O)c1cccnn1 | [#7;a:1]:[#7;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[N;H0;D3;+0:7](-[C;H0;D3;+0:8](-[O-])=[O;D1;H0:9])-c1:c:c:c:c:c:1.[NH2;D1;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:[#7;a:16]:1>>[#7;a:1]:[#7;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[c:11]1:... | 43.3 | [{"value": 43.3, "product": "ClC=1N=NC(=CC1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 14.2 g of N-(3-chloropyridazine-6-sulfonyl)phenylcarbamate and 6.3 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are refluxed for 1 hour in 120 ml of absolute dioxan. When the reaction is complete, the mixture is concentrated in vacuo and the residue is taken up in a saturated aqueous solution of sodium b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Primary amine | Sulfonamide.Urea | c1ccccc1 | null | c1ncncn1.c1ccnnc1 | HO- | O1CCOCC1 | null | null | COc1nc(C)nc(N)n1.O=C([O-])N(c1ccccc1)S(=O)(=O)c1ccc(Cl)nn1>O1CCOCC1>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccc(Cl)nn2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a8d6626d43bf43faa9840510eb71c657 | N#CC1NC(=O)[C@H]1N.O=C(Cl)Cc1ccccc1>>N#C[C@H]1NC(=O)[C@H]1NC(=O)Cc1ccccc1 | C1(=CC=CC=C1)CC(=O)Cl.CC=1C=CC(=CC1)S(=O)(=O)O.N[C@@H]1C(NC1C#N)=O.N1=CC=CC=C1>>C(#N)[C@@H]1[C@@H](C(N1)=O)NC(CC1=CC=CC=C1)=O | [N:1]#[C:2][CH:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH2:8].Cl[C:9](=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[N:1]#[C:2][C@H:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9](=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | N#CC1NC(=O)[C@H]1N.O=C(Cl)Cc1ccccc1 | N#C[C@H]1NC(=O)[C@H]1NC(=O)Cc1ccccc1 | null | null | O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)N[C@H]1CNC1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[C:6]1-[C:7]-[#7:8]-[C:9]-1=[O;D1;H0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[C:6]1-[C:7]-[#7:8]-[C:9]-1=[O;D1;H0:10] | null | [] | 25 | CELSIUS | null | null | In 100 ml of methylene chloride were dissolved under ice-cooling 5 g of p-toluenesulfonate of (3S, 4RS)-3-amino-4-cyano-2-azetidinone and 4.2 g of pyridine. To the solution was added 3 g of phenylacetyl chloride. The mixture was stirred at room temperature (about 25° C.) for ten minutes, which was shaken with water. Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CNC1.c1ccccc1 | HCl | O.C(Cl)Cl | 25 | null | N#CC1NC(=O)[C@H]1N.O=C(Cl)Cc1ccccc1>O.C(Cl)Cl>N#C[C@H]1NC(=O)[C@H]1NC(=O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-188d82f13f314cc0b26d94522c8c649d | CC(C)(ON=C(C(=O)Cl)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.N#C[C@H]1NC(=O)[C@H]1N>>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 | C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)O)C.N[C@@H]1C(N[C@@H]1C#N)=O.Cl.ClCC(=O)NC=1SC=C(N1)C(C(=O)Cl)=NOC(C)(C)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]>>ClCC(=O)NC=1SC=C(N1)C(C(=O)N[C@@H]1C(N[C@@H]1C#N)=O)=NOC(C)(C)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-] | Cl[C:7]([C:6](=[N:5][O:4][C:2]([CH3:1])([CH3:3])[C:27](=[O:28])[O:29][CH2:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1)[c:17]1[cH:18][s:19][c:20]([NH:21][C:22](=[O:23])[CH2:24][Cl:25])[n:26]1)=[O:8].[NH2:9][C@@H:10]1[C:11](=[O:12])[NH:13][C@@H:14]1[C:15]#[N:16]>>[CH3:1][C:2]([CH3:3])([O:4][N:5... | CC(C)(ON=C(C(=O)Cl)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.N#C[C@H]1NC(=O)[C@H]1N | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CON=C(C(=O)N[C@H]1CNC1=O)c1cscn1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[#7:4]-[#8:5])-[c:6](:[#7;a:7]):[c:8]:[#16;a:9].[NH2;D1;+0:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-1=[O;D1;H0:15]>>[#16;a:9]:[c:8]:[c:6](-[C:3](=[#7:4]-[#8:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-1=[O;D1;H0:15]):[#7;a:7] | 44.1 | [{"value": 44.1, "product": "ClCC(=O)NC=1SC=C(N1)C(C(=O)N[C@@H]1C(N[C@@H]1C#N)=O)=NOC(C)(C)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | In 12 ml of tetrahydrofuran was dissolved 0.30 g of (3S, 4S)-3-amino-4-cyano-2-azetidinone p-toluenesulfonate. To the solution were added, under ice-cooling, 0.12 g of triethylamine and, subsequently 0.60 g of 2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetyl chloride hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CNC1.c1cscn1.c1ccccc1 | HCl | O1CCCC1 | null | 0.666667 | CC(C)(ON=C(C(=O)Cl)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.N#C[C@H]1NC(=O)[C@H]1N>O1CCCC1>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9b042347b36c4a3287150473876816b6 | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | CS(=O)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[C-]#N.[K+].C(C)(=O)OCC.C(C)(=O)OCC>>C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CS(=O)(=O)[C@H:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17]... | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | 4e2b6fe3999f8013b5d72b11baedbb086b0bf3517953db3002e7a90160212e1f | afc317b75dc27dd96f8b185a6d88494042f714247ebd3d6ce3b0e647608c4473 | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | C-S(=O)(=O)-[C@H;D3;+0:1]1-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-1-[#7:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[#7:6]-[C:5]1-[C:3](=[O;D1;H0:4])-[#7:2]-[CH;D3;+0:1]-1-[C;H0;D2;+0:7]#[N;D1;H0:8] | 77.2 | [{"value": 77.2, "product": "C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 30 | MINUTE | To a solution of 12.3 g of (3R, 4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 150 ml of DMF is added a solution of 1.6 g of potassium cyanide in 24 ml of water under ice-cooling and the mixture is stirred at room temperature (approx. 25° C.) for 30 minutes. To the reaction mixture are added ice water and ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Nitrile | C1CNC1 | C1CNC1 | C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O.CN(C)C=O | 25 | 0.5 | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>O.CN(C)C=O>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1554984ff1894fc28fe6a21cbc9b7c15 | CC(C)(C)[Si](C)(C)Cl.N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)(C)[Si](C)(C)N1C(=O)[C@@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1C#N | C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)N1C([C@H](C1C#N)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[NH:8]1[C:9](=[O:10])[C@@H:11]([NH:12][C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH:32]1[C:33]#[N:34]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[N:8]1[C... | CC(C)(C)[Si](C)(C)Cl.N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)(C)[Si](C)(C)N1C(=O)[C@@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1C#N | null | null | C(Cl)Cl | Protection | OtherReaction | 571205ba0a22d3d60d9a45b3b137645dbca02e496a419b6be1f95f33017d0b79 | f67e5eeebc56cd2b347c1c8f322829d7af5cd2d5682d82dce87a0ff304294500 | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12](=[O;D1;H0:13])-[NH;D2;+0:14]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[N;H0;D3;+0:14]1-[C:10](-[C:9]#[N;D1;H0:8])-[C:11]-[C:12]-1=[O;D1... | 44 | [{"value": 44.0, "product": "[Si](C)(C)(C(C)(C)C)N1C([C@H](C1C#N)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 1.10 g of (3s, 4RS)-4-cyano-3-tritylamino-2-azetidinone, 0.50 g of triethylamine and 20 ml of methylene chloride is added 0.56 g of tert-butyldimethylsilyl chloride under ice-cooling and stirring. The mixture is stirred at room temperature (approx. 25° C.) for 30 minutes and the reaction mixture is conc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Silyl protective group | Tertiary amide.Silyl protective group | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(C)(C)[Si](C)(C)Cl.N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CC(C)(C)[Si](C)(C)N1C(=O)[C@@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1C#N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f9d3196cf5bc4df3bc21273101cc2edd | CC(C)(ON=C(C(=O)NC1C(=O)NC1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.OO>>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C(N)=O)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 | OO.[OH-].[Na+].ClCC(=O)NC=1SC=C(N1)C(C(=O)NC1C(NC1C#N)=O)=NOC(C)(C)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]>>C(N)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C(=NOC(C)(C)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C=1N=C(SC1)NC(CCl)=O)=O | [CH3:1][C:2]([CH3:3])([O:4][N:5]=[C:6]([C:7](=[O:8])[NH:9][CH:10]1[C:11](=[O:12])[NH:13][CH:14]1[C:15]#[N:16])[c:18]1[cH:19][s:20][c:21]([NH:22][C:23](=[O:24])[CH2:25][Cl:26])[n:27]1)[C:28](=[O:29])[O:30][CH2:31][c:32]1[cH:33][cH:34][c:35]([N+:36](=[O:37])[O-:38])[cH:39][cH:40]1.O[OH:17]>>[CH3:1][C:2]([CH3:3])([O:4][N:... | CC(C)(ON=C(C(=O)NC1C(=O)NC1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.OO | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C(N)=O)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | O=C(CON=C(C(=O)N[C@H]1CNC1=O)c1cscn1)OCc1ccccc1 | O-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[CH;D3;+0:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1-[#7:9]-[C:10]=[O;D1;H0:11]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[C@H;D3;+0:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1-[#7:9]-[C:10]=[O;D1;H0:11] | null | [] | 25 | CELSIUS | 30 | MINUTE | In 2 ml of dimethyl sulfoxide is dissolved 0.38 g of (3S,4S)-b 3-[2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetamido]-4-cyano-2-azetidinone and, following addition of 0.1 ml of 30% aqueous hydrogen peroxide and 0.1 ml of 1N sodium hydroxide, the mixture is stirred at approx. 2... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | C1CNC1.c1cscn1.c1ccccc1 | Other | CS(=O)C | 25 | 0.5 | CC(C)(ON=C(C(=O)NC1C(=O)NC1C#N)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1.OO>CS(=O)C>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N[C@@H]1C(N)=O)c1csc(NC(=O)CCl)n1)C(=O)OCc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ef45cd8e19f346a2939b798513a0897d | N#C[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO>>NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | C(#N)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl.OO.[OH-].[Na+]>>C(N)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [N:1]#[C:2][C@H:4]1[NH:5][C:6](=[O:7])[C@H:8]1[NH:9][C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.O[OH:3]>>[NH2:1][C:2](=[O:3])[C@H:4]1[NH:5][C:6](=[O:7])[C@H:8]1[NH:9][C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]... | N#C[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO | NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | ClCCl | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | O-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[C:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[C:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1 | null | [] | null | null | null | null | In 2 ml of dichloromethane is dissolved 160 mg of (3S,4S)-4-cyano-3-triphenylmethylamino-2-azetidinone and, following addition of 154 mg of tetra-n-butylammonium hydrogen sulfate, 0.103 ml of 30% aqueous hydrogen peroxide and 0.68 ml of 1N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirre... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl | null | null | N#C[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl>NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-98f46b24b7374845b869dde97ca1bcc2 | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | [C-]#N.[K+].CS(=O)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CS(=O)(=O)[C@H:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17]... | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | [Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC | O.C(Cl)(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 4e2b6fe3999f8013b5d72b11baedbb086b0bf3517953db3002e7a90160212e1f | afc317b75dc27dd96f8b185a6d88494042f714247ebd3d6ce3b0e647608c4473 | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | C-S(=O)(=O)-[C@H;D3;+0:1]1-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-1-[#7:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[#7:6]-[C:5]1-[C:3](=[O;D1;H0:4])-[#7:2]-[CH;D3;+0:1]-1-[C;H0;D2;+0:7]#[N;D1;H0:8] | 72.2 | [{"value": 72.2, "product": "C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 120 ml of carbon tetrachloride are dissolved 12.2 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone and 2.44 g of tri-n-octylmethylammonium chloride and, under stirring, a solution of 2.15 g of potassium cyanide in 30 ml of water is added. The mixture is stirred vigorously at the same temperature for 15 minu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Nitrile | C1CNC1 | C1CNC1 | C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | [Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC.O.C(Cl)(Cl)(Cl)Cl | null | null | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>[Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC.O.C(Cl)(Cl)(Cl)Cl>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f19b343e797049888b9b1649d2bc69eb | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO>>NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | OO.[OH-].[Na+].C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(N)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [N:1]#[C:2][CH:4]1[NH:5][C:6](=[O:7])[C@H:8]1[NH:9][C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.O[OH:3]>>[NH2:1][C:2](=[O:3])[C@H:4]1[NH:5][C:6](=[O:7])[C@H:8]1[NH:9][C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1... | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO | NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | O-[OH;D1;+0:1].[#7:2]-[C:3]1-[C:4](=[O;D1;H0:5])-[#7:6]-[CH;D3;+0:7]-1-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[#7:2]-[C:3]1-[C:4](=[O;D1;H0:5])-[#7:6]-[C@@H;D3;+0:7]-1-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[O;H0;D1;+0:1] | 20.4 | [{"value": 20.4, "product": "C(N)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 40 ml of chloroform is dissolved 3.54 g of (3S,4RS)-4-cyano-3-tritylamino-2-azetidinone as obtained in Example 20 and, following addition of 3.4 g of tetra-n-butylammonium hydrogen sulfate, 2.3 g of 30% hydrogen peroxide and 15 ml of 1N sodium hydroxide are added under ice-cooling and stirring. The mixture is stirre... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(Cl)(Cl)Cl | null | null | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.OO>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(Cl)(Cl)Cl>NC(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ae461d73bcff45228281b4f8a3db474f | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | [C-]#N.[K+].CS(=O)(=O)[C@@H]1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)C1[C@@H](C(N1)=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CS(=O)(=O)[C@H:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH:3]1[NH:4][C:5](=[O:6])[C@H:7]1[NH:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17]... | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N | N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | CCCCC[N+](CCCCC)(CCCCC)CCCCC.[Br-] | C1=CC=CC=C1.O | C-C Coupling | OtherReaction | 4e2b6fe3999f8013b5d72b11baedbb086b0bf3517953db3002e7a90160212e1f | afc317b75dc27dd96f8b185a6d88494042f714247ebd3d6ce3b0e647608c4473 | O=C1NC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | C-S(=O)(=O)-[C@H;D3;+0:1]1-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-1-[#7:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[#7:6]-[C:5]1-[C:3](=[O;D1;H0:4])-[#7:2]-[CH;D3;+0:1]-1-[C;H0;D2;+0:7]#[N;D1;H0:8] | null | [] | null | null | 15 | MINUTE | In 2 ml of benzene are dissolved 0.5 mmol of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone and 0.1 mmol of tetra-n-amylammonium bromide, and a solution of 0.55 mmol of potassium cyanide in 0.55 ml of water is added at 15° C. The mixture is stirred vigorously for 15 minutes and treated in the same manner as Examp... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Nitrile | C1CNC1 | C1CNC1 | C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CCCCC[N+](CCCCC)(CCCCC)CCCCC.[Br-].C1=CC=CC=C1.O | null | 0.25 | CS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#N>CCCCC[N+](CCCCC)(CCCCC)CCCCC.[Br-].C1=CC=CC=C1.O>N#CC1NC(=O)[C@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2a80223beefe44d9b08f195aabbc7f3b | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(O)cc1>>FC(F)(F)COc1ccc(OCC(F)(F)F)cc1 | C1(O)=CC=C(O)C=C1.C([O-])([O-])=O.[K+].[K+].FC(S(=O)(=O)OCC(F)(F)F)(F)F>>FC(COC1=CC=C(C=C1)OCC(F)(F)F)(F)F | O=S(=O)(O[CH2:5][C:2]([F:1])([F:3])[F:4])[C:13]([F:14])([F:15])[F:16].[OH:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:17][cH:18]1>>[F:1][C:2]([F:3])([F:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1 | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(O)cc1 | FC(F)(F)COc1ccc(OCC(F)(F)F)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 40e52addd69bfb60edf49cf338a3e101168e05048346fdb8a656fea7da57757c | 2966f4b83ace9b36068d1786a601e1728bcf23c7155547a11ed2d75bfe3b84a3 | c1ccccc1 | O=S(=O)(-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[OH;D1;+0:10]-[c:11]1:[c:12]:[c:13]:[c:14](-[OH;D1;+0:15]):[c:16]:[c:17]:1>>[F;D1;H0:7]-[C;H0;D4;+0:6](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:18]-[O;H0;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[c:14](-[O;H0;D2;... | 88 | [{"value": 88.0, "product": "FC(COC1=CC=C(C=C1)OCC(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 2.42 moles (334.4 g.) of potassium carbonate, 2.2 moles (510.6 g.) of 2,2,2-trifluoroethyl trifluoromethanesulfonate in 1.02 liter of acetone is added a solution of 1.0 mole (110 g.) of hydroquinone in 1.1 liter of acetone, slowly over a 2 hour period. The reaction is then heated at reflux for 24 hours,... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic alcohol.Aromatic alcohol | Trifluoro group.Ether.Ether | null | null | c1ccccc1 | Other | CC(=O)C | null | 2 | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(O)cc1>CC(=O)C>FC(F)(F)COc1ccc(OCC(F)(F)F)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bd78296ee7604ae9bddbd1b3c3be1a26 | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1>>CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | Cl.[Cl-].[Al+3].[Cl-].[Cl-].FC(COC1=CC=C(C=C1)OCC(F)(F)F)(F)F.C(C)(=O)OC(C)=O>>CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1 | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | ClCCl.CCCCCC | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | 90 | [{"value": 90.0, "product": "CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 2.43 moles (324 g.) of aluminum chloride in 648 ml. of dichloromethane is added a solution 0.88 mole (274 g.) of 1,4-bis(2,2,2-trifluoroethoxy)benzene and 0.97 mole (92 ml.) of acetic anhydride in 880 ml. of dichloromethane over a 3 hour period while maintaining the temperature at above 0° C. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl.CCCCCC | null | null | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1>ClCCl.CCCCCC>CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-335d4ec0845a4042ae6c145b2c618492 | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1>>CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | FC(COC1=CC=C(C=C1)OCC(F)(F)F)(F)F.C(C)(=O)OC(C)=O.Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1 | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | 82 | [{"value": 82.0, "product": "CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a mixture of 4.367 kilograms (32.75 moles) of aluminum chloride and 8.8 liters of dichloromethane at 0° C. is added gradually a solution of 3,267 kilograms of 1,4-bis(2,2,2-trifluoroethoxy)benzene and 1.899 kilograms (13.7 moles) of acetic anhydride in 1.3 liters of dichloromethane. The reaction temperature is maint... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl | null | 16 | CC(=O)OC(C)=O.FC(F)(F)COc1ccc(OCC(F)(F)F)cc1>ClCCl>CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e8cf184961434382a1570af4c29666d4 | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[OH-]>>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F.[OH-].[Na+].ClCl.[OH-].[Na+]>>FC(COC1=C(C(=O)O)C=C(C=C1)OCC(F)(F)F)(F)F | C[C:2](=[O:1])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[OH-] | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | O | Acylation | OtherReaction | e1d216f9ec5d1e0ab04cbd7e284acaaebe679828044d718ad57104584ff5302e | 7b5bc8122b5027b4d965c982eed9443b26b90bd801407eec9b2b367c037fc8de | c1ccccc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | 94.5 | [{"value": 94.5, "product": "FC(COC1=C(C(=O)O)C=C(C=C1)OCC(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 7.3 moles (292 g.) of sodium hydroxide in 600 ml. of water is added ice to make the total volume of 1.75 liters. Chlorine gas is passed into the solution while maintaining the temperature below 10° C. until it is neutral to litmus, and 2.19 moles (87.6 g.) of sodium hydroxide dissolved in 200 ml. of wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Carboxylic acid | null | null | c1ccccc1 | Other | O | 50 | null | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[OH-]>O>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-91f05881152f4417803aa3e3b341a28e | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.O=S(Cl)Cl>>O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | FC(COC1=C(C(=O)O)C=C(C=C1)OCC(F)(F)F)(F)F.S(=O)(Cl)Cl>>FC(COC1=C(C(=O)Cl)C=C(C=C1)OCC(F)(F)F)(F)F | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.O=S(Cl)Cl | O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | To a solution of 0.688 mole (219 g.) of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid in 657 ml. of benzene is added 1.376M. (100.4 ml.) of thionyl chloride slowly over 1 hour while heating to about 60° C. The mixture is then heated at reflux for about 8 hours, then evaporated to provide the desired product, 2,5-bis(2,2,2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | C1=CC=CC=C1 | null | null | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.O=S(Cl)Cl>C1=CC=CC=C1>O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c720cf44b01b4661bc3a257853320079 | O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F>>O=C(NCC1CCCCN1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | FC(COC1=C(C(=O)NCC2=NC=CC=C2)C=C(C=C1)OCC(F)(F)F)(F)F.C(C)(=O)O.[H][H]>>C(C)(=O)O.FC(COC1=C(C(=O)NCC2NCCCC2)C=C(C=C1)OCC(F)(F)F)(F)F | [O:5]=[C:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[c:15]1[cH:16][c:17]([O:18][CH2:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][c:26]1[O:27][CH2:28][C:29]([F:30])([F:31])[F:32]>>[O:5]=[C:6]([NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]1)[c:15]1[cH:16][c:17]([O:18][CH2:19][C:20]([F:21])([... | O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | O=C(NCC1CCCCN1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | [Pt] | CCCCCC | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | O=C(NCC1CCCCN1)c1ccccc1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1>>[O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1 | 71 | [{"value": 71.0, "product": "C(C)(=O)O.FC(COC1=C(C(=O)NCC2NCCCC2)C=C(C=C1)OCC(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6.5 | HOUR | A mixture of 0.33 mole (134.7 g.) 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide, 1.347 liter of glacial acetic acid and 13.5 g. of 5 percent platinum on carbon is reduced in a Parr apparatus at a pressure of about 10 pounds of hydrogen at room temperature. The reaction is complete in 6-7 hours. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1.c1ccccc1 | null | [Pt].CCCCCC | null | 6.5 | O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F>[Pt].CCCCCC>O=C(NCC1CCCCN1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dc7bfbb943914b4989841cde9342f1f2 | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl>>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | Cl[O-].C(C)(=O)C1=CC=CC=C1.CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F>>FC(COC1=C(C(=O)O)C=C(C=C1)OCC(F)(F)F)(F)F | C[C:2](=[O:1])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21].Cl[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | null | Acylation | OtherReaction | e1d216f9ec5d1e0ab04cbd7e284acaaebe679828044d718ad57104584ff5302e | 7b5bc8122b5027b4d965c982eed9443b26b90bd801407eec9b2b367c037fc8de | c1ccccc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[O-;H0;D1:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | replacing the methyl moiety of the acetophenone function of said 2,5-bis(2,2,2-trifluoroethoxy)acetophenone using hypochlorite to yield 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Carboxylic acid | null | null | c1ccccc1 | HCl | null | null | null | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl>>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-472b66ff9eef40b493ae1e06eec8e701 | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl>>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | Cl[O-].C(C)(=O)C1=CC=CC=C1.CC(=O)C1=C(C=CC(=C1)OCC(F)(F)F)OCC(F)(F)F>>FC(COC1=C(C(=O)O)C=C(C=C1)OCC(F)(F)F)(F)F | C[C:2](=[O:1])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21].Cl[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][C:18]([F:19])([F:20])[F:21] | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl | O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | null | Acylation | OtherReaction | e1d216f9ec5d1e0ab04cbd7e284acaaebe679828044d718ad57104584ff5302e | 7b5bc8122b5027b4d965c982eed9443b26b90bd801407eec9b2b367c037fc8de | c1ccccc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[O-;H0;D1:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | replacing the methyl moiety of the acetophenone function of said 2,5-bis(2,2,2-trifluoroethoxy)acetophenone using hypochlorite to yield 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Carboxylic acid | null | null | c1ccccc1 | HCl | null | null | null | CC(=O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F.[O-]Cl>>O=C(O)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dce6f4e2248c4163ba66fcf4d334a273 | NCc1ccccn1.O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F>>O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | FC(COC1=C(C(=O)Cl)C=C(C=C1)OCC(F)(F)F)(F)F.NCC1=NC=CC=C1>>FC(COC1=C(C(=O)NCC2=NC=CC=C2)C=C(C=C1)OCC(F)(F)F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][c:13]([O:14][CH2:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][c:22]1[O:23][CH2:24][C:25]([F:26])([F:27])[F:28]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1)[c:11]1[cH:12][c:13]([O:14][CH2:15][C:16]([F:17])([F:18])[F:1... | NCc1ccccn1.O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccn1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | contacting said 2,5-bis(2,2,2trifluoroethoxy)benzoic acid chloride with 2-aminomethylpyridine to provide 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | null | null | null | NCc1ccccn1.O=C(Cl)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F>>O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6075e750f58d40a38d75ded2154666e1 | O=C(c1ccc(C(=O)O)c(C(=O)O)c1)c1ccc(C(=O)O)c(C(=O)O)c1>>O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O | C1=CC(=C(C=C1C(=O)C2=CC(=C(C=C2)C(=O)O)C(=O)O)C(=O)O)C(=O)O.C1=CC(=C(C=C1C(=O)C2=CC(=C(C=C2)C(=O)O)C(=O)O)C(=O)O)C(=O)O.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1>>C1=CC2=C(C=C1C(=O)C3=CC4=C(C=C3)C(=O)OC4=O)C(=O)OC2=O | O[C:9]([c:7]1[c:6]([C:12]([OH:11])=[O:13])[cH:5][cH:4][c:3]([C:2](=[O:1])[c:14]2[cH:15][cH:16][c:17]([C:23](O)=[O:24])[c:18]([C:20](=[O:21])[OH:22])[cH:19]2)[cH:8]1)=[O:10]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[O:11][C:12]2=[O:13])[c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19]1)[C:20](=[O:21])[O... | O=C(c1ccc(C(=O)O)c(C(=O)O)c1)c1ccc(C(=O)O)c(C(=O)O)c1 | O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O | null | null | null | Miscellaneous | OtherReaction | 01fc45a364070fbd541127169777f7bd59cd6fb39434dc4c20a62ecba22d8cdc | e83a95bc3ef3bbc28a0f9ce60ccfbd3725429b901b391dbfdf0df35bff2f3261 | O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[O;D1;H0:10]=[C;H0;D3;+0:9]1-[O;H0;D2;+0:16]-[C:14](=[O;D1;H0:15])-[c:13]:[c:11]-1:[c:12].[O;D1;H0:7]=[C:6]1-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D... | null | [] | null | null | null | null | A process for producing benzophenone tetracarboxylic dianhydride, which comprises adding benzophenone tetracarboxylic acid to a solvent comprising, as the main constituent, an organic compound having a boiling point of more than 100° C. and being inert to benzophenone tetracarboxylic acid and benzophenone tetracarboxyl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | Anhydride.Anhydride | null | c1ccc2c(c1)COC2.c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2.c1ccc2c(c1)COC2 | HO- | null | null | null | O=C(c1ccc(C(=O)O)c(C(=O)O)c1)c1ccc(C(=O)O)c(C(=O)O)c1>>O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db112047c19e43b3a1f1f3e0cc3d9b0d | BrCCCBr.Oc1ccc2c(c1)OCO2>>BrCCCOc1ccc2c(c1)OCO2 | C(C)(C)(C)O.[OH-].[K+].C1OC=2C=C(C=CC2O1)O.BrCCCBr>>BrCCCOC1=CC2=C(OCO2)C=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)[O:12][CH2:13][O:14]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)[O:12][CH2:13][O:14]2 | BrCCCBr.Oc1ccc2c(c1)OCO2 | BrCCCOc1ccc2c(c1)OCO2 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)OCO2 | 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] | 81.7 | [{"value": 81.7, "product": "BrCCCOC1=CC2=C(OCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution prepared by dissolving 7.3 g of potassium hydroxide in 7 ml of water and then adding 120 ml of t-butanol are added 15 g of 3,4-methylenedioxyphenol and 88 g of 1,3-dibromopropane and the mixture is stirred for 3 hours under heating at reflux. After completion of the reaction, the solvent is distilled off ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)OCO2 | HBr | O | null | 3 | BrCCCBr.Oc1ccc2c(c1)OCO2>O>BrCCCOc1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-89aa6ffc9f4d4c8db3519910dae0cdda | O=C(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2>>OC(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2 | [OH-].[Na+].Cl.O1C(COC2=C1C=CC=C2)CNCC(=O)C2=CC1=C(OCO1)C=C2.[BH4-].[Na+]>>O1C(COC2=C1C=CC=C2)CNCC(O)C2=CC1=C(OCO1)C=C2 | [O:1]=[C:2]([CH2:3][NH:4][CH2:5][CH:6]1[CH2:7][O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[O:15]1)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][O:24]2>>[OH:1][CH:2]([CH2:3][NH:4][CH2:5][CH:6]1[CH2:7][O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[O:15]1)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][C... | O=C(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2 | OC(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)OCC(CNCCc1ccc3c(c1)OCO3)O2 | [#7:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[#7:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 89 | [{"value": 89.0, "product": "O1C(COC2=C1C=CC=C2)CNCC(O)C2=CC1=C(OCO1)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "O1C(COC2=C1C=CC=C2)CNCC(O)C2=CC1=C(OCO1)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | In 15 ml of methanol is dissolved 1.0 g of 5-[2-{(1,4-benzodioxan-2-ylmethyl)amino}acetyl]-1,3-benzodioxole hydrochloride prepared according to the procedure described in Example 3 and the solution is neutralized with 2N sodium hydroxide. Thereafter, 100 mg of sodium borohydride is added and the mixture is stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCO2 | null | CO | null | 6 | O=C(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2>CO>OC(CNCC1COc2ccccc2O1)c1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb6902f9bbd442ae9d8ee9ad3797bedb | NCC1COc2ccccc2O1.O=C(CCCl)Nc1ccc2c(c1)OCO2>>O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2 | O.ClCCC(=O)NC1=CC2=C(C=C1)OCO2.O1C(COC2=C1C=CC=C2)CN.C(C)N(CC)CC>>O1C(COC2=C1C=CC=C2)CNCCC(=O)NC2=CC1=C(C=C2)OCO1 | [NH2:5][CH2:6][CH:7]1[CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[O:16]1.Cl[CH2:4][CH2:3][C:2](=[O:1])[NH:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2>>[O:1]=[C:2]([CH2:3][CH2:4][NH:5][CH2:6][CH:7]1[CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[O:16]1)[NH:17][c:18]1[cH:19][cH:2... | NCC1COc2ccccc2O1.O=C(CCCl)Nc1ccc2c(c1)OCO2 | O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6].[#8:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | 87.5 | [{"value": 77.0, "product": "O1C(COC2=C1C=CC=C2)CNCCC(=O)NC2=CC1=C(C=C2)OCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "O1C(COC2=C1C=CC=C2)CNCCC(=O)NC2=CC1=C(C=C2)OCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 20 | HOUR | To a solution of 10 g of N-(3-chloropropionyl)-3,4-methylenedioxyaniline in 50 ml of dimethylformamide are added 8.7 g of 1,4-benzodioxan-2-ylmethylamine and 8.9 g of triethylamine and the mixture is stirred for 20 hours at 50° C. After completion of the reaction, water is added and the mixture is extracted with ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | 50 | 20 | NCC1COc2ccccc2O1.O=C(CCCl)Nc1ccc2c(c1)OCO2>CN(C=O)C>O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ee7884ce19df458082f8329aee02b602 | O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2>>c1ccc2c(c1)OCC(CNCCCNc1ccc3c(c1)OCO3)O2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O1C(COC2=C1C=CC=C2)CNCCC(=O)NC2=CC1=C(C=C2)OCO1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O1C(COC2=C1C=CC=C2)CNCCCNC2=CC1=C(C=C2)OCO1 | O=[C:14]([CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:8][O:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)[O:25]1)[NH:15][c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][O:24]2>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][CH:9]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][NH:15][c:16]1[cH:17][cH:18][c:19]3[c:20]([c... | O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2 | c1ccc2c(c1)OCC(CNCCCNc1ccc3c(c1)OCO3)O2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)OCC(CNCCCNc1ccc3c(c1)OCO3)O2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 97.1 | [{"value": 80.0, "product": "O1C(COC2=C1C=CC=C2)CNCCCNC2=CC1=C(C=C2)OCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "O1C(COC2=C1C=CC=C2)CNCCCNC2=CC1=C(C=C2)OCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | In 50 ml of tetrahydrofuran is suspended 1.5 g of lithium aluminum hydride and a solution of 6.0 g of N-[3-{(1,4-benzodioxan-2-yl}methyl)amino propionyl]-3,4-methylenedioxyaniline prepared according to the procedure described in Example 6 dissolved in 10 ml of tetrahydrofuran is added dropwise to the suspension. After ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCO2 | Other | O1CCCC1 | 50 | 4 | O=C(CCNCC1COc2ccccc2O1)Nc1ccc2c(c1)OCO2>O1CCCC1>c1ccc2c(c1)OCC(CNCCCNc1ccc3c(c1)OCO3)O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f4b2f6b895ea49ca973111d860418a32 | C=CC.CC(C)C=O.CCCC=O>>CCCC(O)C(C=O)CC | C=CC.C(CCC)=O.C(C(C)C)=O>>CCCC(C(CC)C=O)O | C=C[CH3:10].C[CH:6]([CH:7]=[O:8])[CH3:9].[CH3:1][CH2:2][CH2:3][CH:4]=[O:5]>>[CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[CH:6]([CH:7]=[O:8])[CH2:9][CH3:10] | C=CC.CC(C)C=O.CCCC=O | CCCC(O)C(C=O)CC | null | null | null | C-C Coupling | OtherReaction | 80e1f0b18ea95959b98505afff5c2aa33a934f4b772e171c0da1076665a6ad5b | c9897ef6c812d57d5114df5e38a5a8945d9f218ddf57db27ecece1bf741ab026 | null | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3]=[O;D1;H0:4].C=C-[CH3;D1;+0:5].[C:6]-[C:7]-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[C:6]-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[CH;D3;+0:1](-[C:3]=[O;D1;H0:4])-[CH2;D2;+0:2]-[CH3;D1;+0:5] | null | [] | null | null | null | null | This compound is usually prepared by the hydroformylation of propene yielding a reaction mixture which contains n-butanal, as well as i-butanal and other reaction products. The pure n-butanal is separated from the reaction mixture by distillation and is subsequently subjected to aldolisation to form the corresponding b... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Vinyl | Aldehyde.Secondary alcohol | null | null | null | Other | null | null | null | C=CC.CC(C)C=O.CCCC=O>>CCCC(O)C(C=O)CC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5f1172c237c240db90b4e91212b88ef5 | Cc1cc(C(=O)O)cc(C)c1[N+](=O)[O-].Cc1ccccc1CN>>Cc1ccccc1CNC(=O)c1cc(C)c([N+](=O)[O-])c(C)c1 | CC=1C=C(C(=O)Cl)C=C(C1[N+](=O)[O-])C.CC=1C=C(C(=O)O)C=C(C1[N+](=O)[O-])C.CC1=C(CN)C=CC=C1.C(C)N(CC)CC>>CC=1C=C(C(=O)NCC2=C(C=CC=C2)C)C=C(C1[N+](=O)[O-])C | O[C:10](=[O:11])[c:12]1[cH:13][c:14]([CH3:15])[c:16]([N+:17](=[O:18])[O-:19])[c:20]([CH3:21])[cH:22]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([CH3:15])[c:16]([N+:17](=[O:18])[O-:19])[c:20]([CH3:21])[cH:22]1 | Cc1cc(C(=O)O)cc(C)c1[N+](=O)[O-].Cc1ccccc1CN | Cc1ccccc1CNC(=O)c1cc(C)c([N+](=O)[O-])c(C)c1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | A solution of 3,5-dimethyl-4-nitrobenzoyl chloride in tetrahyrofuran, generated from 7.0 g of 3,5-dimethyl-4-nitrobenzoic acid by standard procedures, was added to 4.3 g of 2-methylbenzyl amine and 5.0 ml of triethylamine in tetrahydrofuran. The reaction was stirred at ambient temperature overnight, chilled, and filter... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 8 | Cc1cc(C(=O)O)cc(C)c1[N+](=O)[O-].Cc1ccccc1CN>O1CCCC1>Cc1ccccc1CNC(=O)c1cc(C)c([N+](=O)[O-])c(C)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a117bc2fbc444d72b33f591291414928 | BrBr.Cc1c(O)c(C)c(Br)c(C)c1Br>>CC1=C(Br)C(C)(Br)C(Br)=C(C)C1=O | CC1=C(C(=CC(=C1)C)C)O.BrBr.BrC=1C(=C(C(=C(C1C)Br)C)O)C.BrCC1=C(C(=C(C(=C1Br)C)O)C)Br>>BrC1=C(C(C(=C(C1(C)Br)Br)C)=O)C | Br[Br:7].[CH3:1][c:2]1[c:3]([Br:4])[c:5]([CH3:6])[c:8]([Br:9])[c:10]([CH3:11])[c:12]1[OH:13]>>[CH3:1][C:2]1=[C:3]([Br:4])[C:5]([CH3:6])([Br:7])[C:8]([Br:9])=[C:10]([CH3:11])[C:12]1=[O:13] | BrBr.Cc1c(O)c(C)c(Br)c(C)c1Br | CC1=C(Br)C(C)(Br)C(Br)=C(C)C1=O | null | null | O.C(C)(=O)[O-].[Na+].C(C)(=O)O.C(C)(=O)O | Acylation | OtherReaction | cd7b2d41b2cd4da3c6fbe252952f2a86818177d86729a91505440f6eb12ff42e | 30b22b6f50ed5709786636242f968e27ffd86e89894ab3f87a968d3be413a783 | O=C1C=CCC=C1 | Br-[Br;H0;D1;+0:1].[Br;D1;H0:2]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[C;D1;H3:5]):[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c;H0;D3;+0:8](-[C;D1;H3:9]):[c;H0;D3;+0:10](-[Br;D1;H0:11]):[c;H0;D3;+0:12]:1-[C;D1;H3:13]>>[Br;D1;H0:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C;H0;D3;+0:8](-[C;D1;H3:9])=[... | null | [] | null | null | null | null | The preparation of a halogenated phenol such as 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol (tribromomesitol) can involve the following sequence: bromination of 2, 4, 6-trimethylphenol (mesitol) with 2 moles of bromine in acetic acid to prepare 3, 5-dibromo-2, 4, 6-trimethylphenol (dibromometisol) which is isolated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic alcohol | Tertiary halide.Alkenyl halide.Alkenyl halide.Ketone | c1ccccc1 | C1=CCC=CC1 | C1=CCC=CC1 | HBr | O.C(C)(=O)[O-].[Na+].C(C)(=O)O.C(C)(=O)O | null | null | BrBr.Cc1c(O)c(C)c(Br)c(C)c1Br>O.C(C)(=O)[O-].[Na+].C(C)(=O)O.C(C)(=O)O>CC1=C(Br)C(C)(Br)C(Br)=C(C)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2a36e49790914d26a529926870d300df | Cc1c(O)c(C)c(Br)c(C)c1Br.Cc1cc(C(Br)(Br)Br)cc(C)c1O>>Cc1c(O)c(C)c(Br)c(CBr)c1Br | BrC(C=1C=C(C(=C(C1)C)O)C)(Br)Br.BrC1=C(C(=C(C(=C1C)O)C)Br)C>>BrCC1=C(C(=C(C(=C1Br)C)O)C)Br | [CH3:1][c:2]1[c:3]([OH:4])[c:5]([CH3:6])[c:7]([Br:8])[c:9]([CH3:10])[c:12]1[Br:13].Cc1cc(C(Br)(Br)[Br:11])cc(C)c1O>>[CH3:1][c:2]1[c:3]([OH:4])[c:5]([CH3:6])[c:7]([Br:8])[c:9]([CH2:10][Br:11])[c:12]1[Br:13] | Cc1c(O)c(C)c(Br)c(C)c1Br.Cc1cc(C(Br)(Br)Br)cc(C)c1O | Cc1c(O)c(C)c(Br)c(CBr)c1Br | null | null | null | Functional Group Interconversion | Bromination | c283c4d3091aa0534b9b612860bbb8e64790c700dbfcc856a7f4baab20059420 | ae02e01962cf9daf34585e5708190b4128615578bb6c86f760dd7705559059a3 | c1ccccc1 | Br-C(-Br)(-[Br;H0;D1;+0:1])-c1:c:c(-C):c(-O):c(-C):c:1.[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 25 | CELSIUS | 3 | HOUR | The temperature is increased to 70° C. -75° C., and a solution is obtained. The solution is held at 70° C. -75° C. for 3 hours. The unreacted bromine is removed by distillation with the aid of 1 liter of carbon tetrachloride. When 1 liter of solvent remains with the product, the solution is cooled to 25° C. The light b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Aromatic alcohol | Primary halide | c1ccccc1 | null | c1ccccc1 | HBr | null | 25 | 3 | Cc1c(O)c(C)c(Br)c(C)c1Br.Cc1cc(C(Br)(Br)Br)cc(C)c1O>>Cc1c(O)c(C)c(Br)c(CBr)c1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7974117b850745ce99478a14fbf8fabe | O=C(O)C(O)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl>>O=C(O)C(O)c1cc(O)c(O)cc1Cl | S(=O)(=O)(Cl)Cl.OC=1C=C(C(C(=O)O)O)C=CC1O.O>>ClC1=C(C(C(=O)O)O)C=C(C(=C1)O)O | [O:1]=[C:2]([OH:3])[CH:4]([OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12][cH:13]1.O=S(=O)(Cl)[Cl:14]>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12][c:13]1[Cl:14] | O=C(O)C(O)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl | O=C(O)C(O)c1cc(O)c(O)cc1Cl | null | null | C(C)(=O)O | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[C:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[C:5]-[C:3](=[O;D1;H0:2])-[O;D1;H1:4]):[c:7] | null | [] | null | null | 2 | HOUR | Sulphuryl chloride (0.8 ml) was added to a solution of 3,4-dihydroxymandelic acid (1.84 g, 10 mmol) in warm acetic acid (20 ml). The mixture was stirred for two hours then poured into water and extracted with ethyl acetate (6×40 ml). The extracts were washed with saturated brine (50 ml), dried and evaporated to a cryst... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(C)(=O)O | null | 2 | O=C(O)C(O)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl>C(C)(=O)O>O=C(O)C(O)c1cc(O)c(O)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-28fadf5ad4b9498fb212d6eaee09c186 | N.O=CC(=O)O.Oc1ccc(Cl)cc1O>>O=C(O)CNc1cc(O)c(O)cc1Cl | N.C(C=O)(=O)O.ClC=1C=C(C(O)=CC1)O.N.C>>ClC1=C(C=C(C(=C1)O)O)NCC(=O)O | [NH3:5].O=[CH:4][C:2](=[O:1])[OH:3].[cH:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12][c:13]1[Cl:14]>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12][c:13]1[Cl:14] | N.O=CC(=O)O.Oc1ccc(Cl)cc1O | O=C(O)CNc1cc(O)c(O)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c11d733b1d378c2ca8935818f43643986c21b09db71b80282f52fa3887fa4a14 | 8883936783e332626550746e6de6ae2ae8af6a13e88264ea7bb1baff157737c0 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[Cl;D1;H0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10].[NH3;D0;+0:11]>>[Cl;D1;H0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[NH;D2;+0:11]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4]):[c:9]:[c:10] | null | [] | null | null | 8 | HOUR | Aqueous ammonia (Sp.Gr 0.88, 37.5 ml) was added dropwise to an ice bath cooled 50% w/v aqueous glyoxylic acid solution (11.25 ml) at <10°. When the addition was complete the solution was heated at 50° for 15 minutes, 4-chlorocatechol (21.7 g) and more aqueous ammonia (12.5 ml) added, then heated at 60° for 4 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 8 | N.O=CC(=O)O.Oc1ccc(Cl)cc1O>>O=C(O)CNc1cc(O)c(O)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-87ff1aaf786d4dafa35d8815afcd33ec | O=C(NC(O)C(=O)O)OCc1ccccc1.Oc1ccc(Cl)cc1O>>O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl | C([O-])([O-])=O.[Na+].[Na+].S(O)(O)(=O)=O.ClC=1C=C(C(O)=CC1)O.C(C1=CC=CC=C1)OC(=O)NC(C(=O)O)O>>C(C1=CC=CC=C1)OC(=O)N(CC(=O)O)C1=C(C=C(C(=C1)O)O)Cl | O[CH:4]([C:2](=[O:1])[OH:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[cH:16]1[cH:17][c:18]([OH:19])[c:20]([OH:21])[cH:22][c:23]1[Cl:24]>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][c:18]([OH:19])[c:20]([OH:21])[cH:... | O=C(NC(O)C(=O)O)OCc1ccccc1.Oc1ccc(Cl)cc1O | O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl | null | null | C(C)(=O)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 82bd85c6da7b44e60eeaaedb2361d3b39244ecd3f218fee1ba2ec03dd1fa5d10 | ecf89c6cf8e87d34d1bce0363f2597a3a5f86e83f56c6da8dc45241096b01ba6 | O=C(Nc1ccccc1)OCc1ccccc1 | O-[CH;D3;+0:1](-[NH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9].[Cl;D1;H0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:2](-[CH2;D2;+0:1]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:11](-[Cl;D1;H0:10]):[c:12] | null | [] | null | null | 1 | HOUR | Acetic acid (27 ml), concentrated sulphuric acid (3 ml) then 4-chlorocatechol (5.06 g. 35 mmole) were added to N-benzyloxycarbonyl 2-hydroxyglycine (6.75 g, 30 mmole) cooled in an ice bath. The mixture was stirred for one hour then poured onto ice and ethyl acetate and adjusted to pH7 with saturated sodium carbonate so... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Secondary alcohol | Carbamic ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | null | 1 | O=C(NC(O)C(=O)O)OCc1ccccc1.Oc1ccc(Cl)cc1O>C(C)(=O)O.C(C)(=O)OCC>O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8be6c565ef5649d1915be6fdfbac7331 | O=C(O)CN(C(=O)OCc1ccccc1)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl>>O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl | C(C1=CC=CC=C1)OC(=O)N(CC(=O)O)C1=CC(=C(C=C1)O)O.S(=O)(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC(=O)N(CC(=O)O)C1=C(C=C(C(=C1)O)O)Cl | [O:1]=[C:2]([OH:3])[CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][c:18]([OH:19])[c:20]([OH:21])[cH:22][cH:23]1.O=S(=O)(Cl)[Cl:24]>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][c:18]([OH:19])[c:20]([O... | O=C(O)CN(C(=O)OCc1ccccc1)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl | O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl | null | null | C(C)(=O)O.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(Nc1ccccc1)OCc1ccccc1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[#7:4]-[C:3]=[O;D1;H0:2]):[c:6] | null | [] | null | null | 2 | HOUR | N-Benzyloxycarbonyl 3,4-dihydroxyphenylglycine (0.79 g, 2.5 mmole) in acetic acid (10 ml) was treated with sulphuryl chloride (0.2 ml), stirred at room temperature for two hours then diluted with ethyl acetate (50 ml), washed with water (2×3 ml) and brine (20 ml), dried and evaporated to a gum which was crystallized fr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(C)(=O)O.C(C)(=O)OCC | null | 2 | O=C(O)CN(C(=O)OCc1ccccc1)c1ccc(O)c(O)c1.O=S(=O)(Cl)Cl>C(C)(=O)O.C(C)(=O)OCC>O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f891e300ccd949b285d97d069a945d6c | CC(=O)OC(C)=O.O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl>>CC(=O)Oc1cc(Cl)c(N(CC(=O)O)C(=O)OCc2ccccc2)cc1OC(C)=O | C1CCOC1.C(C1=CC=CC=C1)OC(=O)N(CC(=O)O)C1=C(C=C(C(=C1)O)O)Cl.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OC(C)=O.C(C)(=O)OC(C)=O>>C(C1=CC=CC=C1)OC(=O)N(CC(=O)O)C1=C(C=C(C(=C1)OC(C)=O)OC(C)=O)Cl | O([C:2]([CH3:1])=[O:3])[C:28]([CH3:29])=[O:30].[OH:4][c:5]1[cH:6][c:7]([Cl:8])[c:9]([N:10]([CH2:11][C:12](=[O:13])[OH:14])[C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][c:26]1[OH:27]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([Cl:8])[c:9]([N:10]([CH2:11][C:12](=[O:13])[OH:14])[C:15](=... | CC(=O)OC(C)=O.O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl | CC(=O)Oc1cc(Cl)c(N(CC(=O)O)C(=O)OCc2ccccc2)cc1OC(C)=O | null | null | O | Acylation | OtherReaction | 9fe842616fe8c5fa0bf72ff72cbb7e6f269a35f85453c588a379d45816b954fa | 23705b28103bfefc76c3f909cff1028dc7a10b9fbc3b8b8a232f6d46c105cee3 | O=C(Nc1ccccc1)OCc1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:8](-[O;H0;D2;+0:7]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6]):[c:9] | null | [] | null | null | null | null | N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine (1.76 g, 5 mmole) in water (30 ml) and THF (20 ml) was adjusted to pH 7.5 with saturated sodium carbonate solution. Acetic anhydride (1.2 ml) was added and pH 6.5 maintained with saturated sodium carbonate solution, after 15 minutes and again after a further 15 mi... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol.Aromatic alcohol | Ester.Ester | null | null | c1ccccc1.c1ccccc1 | HO- | O | null | null | CC(=O)OC(C)=O.O=C(O)CN(C(=O)OCc1ccccc1)c1cc(O)c(O)cc1Cl>O>CC(=O)Oc1cc(Cl)c(N(CC(=O)O)C(=O)OCc2ccccc2)cc1OC(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-114a2a5a1d2948c59ca0ec05a0544bd0 | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(Br)cc1O>>CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2Br)C(=O)C1=O | O=C1N(CCN(C1=O)CC)C(=O)NC(C(=O)O)O.BrC=1C=C(C(O)=CC1)O.C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC.C([O-])([O-])=O.[Na+].[Na+]>>O=C1N(CCN(C1=O)CC)C(=O)NC(C(=O)O)C1=C(C=C(C(=C1)O)O)Br | O[CH:10]([NH:9][C:7]([N:6]1[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:25](=[O:26])[C:23]1=[O:24])=[O:8])[C:11](=[O:12])[OH:13].[cH:14]1[cH:15][c:16]([OH:17])[c:18]([OH:19])[cH:20][c:21]1[Br:22]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[NH:9][CH:10]([C:11](=[O:12])[OH:13])[c:14]2[cH:15][c:16]([OH:17])[c:18]([OH:... | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(Br)cc1O | CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2Br)C(=O)C1=O | null | null | C(C)(=O)O.S(O)(O)(=O)=O | C-C Coupling | OtherReaction | 353f6f3410bb939815e396d07868f2feb4b967c7c280d70099400ec8589322b5 | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | O=C1NCCN(C(=O)NCc2ccccc2)C1=O | O-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[Br;D1;H0:11]-[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:[c:16]>>[Br;D1;H0:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:15]:[c:1... | null | [] | null | null | 18 | HOUR | 4-Bromocatechol (4.77 g, 25.2 mmole) was added to an ice bath cooled suspension of N-(2,3-dioxo-4-ethylpiperazin-1-yl-carbonyl)-2-hydroxyglycine (2.59 g. 10 mmole) in glacial acetic acid (9 ml) and concentrated sulphuric acid (1 ml). The mixture was stirred for 18 hours then poured onto a mixture of ice, saturated sodi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HO- | C(C)(=O)O.S(O)(O)(=O)=O | null | 18 | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(Br)cc1O>C(C)(=O)O.S(O)(O)(=O)=O>CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2Br)C(=O)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dea297abfbc740adb41576c657c7bfec | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(F)cc1O>>CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2F)C(=O)C1=O | FC=1C=C(C(O)=CC1)O.O=C1N(CCN(C1=O)CC)C(=O)NC(C(=O)O)O.C([O-])([O-])=O.[Na+].[Na+]>>OC1=CC(=C(C=C1O)C(NC(=O)N1C(C(N(CC1)CC)=O)=O)C(=O)O)F | O[CH:10]([NH:9][C:7]([N:6]1[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:25](=[O:26])[C:23]1=[O:24])=[O:8])[C:11](=[O:12])[OH:13].[cH:14]1[cH:15][c:16]([OH:17])[c:18]([OH:19])[cH:20][c:21]1[F:22]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[NH:9][CH:10]([C:11](=[O:12])[OH:13])[c:14]2[cH:15][c:16]([OH:17])[c:18]([OH:1... | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(F)cc1O | CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2F)C(=O)C1=O | null | null | O.C(C)(=O)O.S(O)(O)(=O)=O | C-C Coupling | OtherReaction | 353f6f3410bb939815e396d07868f2feb4b967c7c280d70099400ec8589322b5 | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | O=C1NCCN(C(=O)NCc2ccccc2)C1=O | O-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[F;D1;H0:11]-[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:[c:16]>>[F;D1;H0:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:15]:[c:16] | null | [] | null | null | 8 | HOUR | 4-Fluorocatechol (3.06 g., 24 mmole) was added to a suspension of N-(2,3-dioxo-4-ethylpiperazin-1-ylcarbonyl)-2-hydroxyglycine (3.89 g, 15 mmole) in glacial acetic acid (13.5 ml) and concentrated sulphuric acid (1.5 ml). The mixture was stirred overnight, diluted with water (50 ml), adjusted to pH6 with saturated sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HO- | O.C(C)(=O)O.S(O)(O)(=O)=O | null | 8 | CCN1CCN(C(=O)NC(O)C(=O)O)C(=O)C1=O.Oc1ccc(F)cc1O>O.C(C)(=O)O.S(O)(O)(=O)=O>CCN1CCN(C(=O)NC(C(=O)O)c2cc(O)c(O)cc2F)C(=O)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a6cb9adcc92d41e3970945481aec0a42 | O=C(O)c1ccc(C(=O)O)c2c(C(=O)O)ccc(C(=O)O)c12>>O=C(O)c1ccc(C(=O)O)c2c3ccc(c(=O)oc3=O)c12 | C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.C1(=CC=C(C=2C(=CC=C(C12)C(=O)O)C(=O)O)C(=O)O)C(=O)O>>C12=CC=C(C=3C(=CC=C(C13)C(=O)O)C(=O)O)C(=O)OC2=O | O[C:16]([c:15]1[cH:14][cH:13][c:12]([C:19]([OH:18])=[O:20])[c:11]2[c:7]([C:8](=[O:9])[OH:10])[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[c:21]21)=[O:17]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]2[c:12]3[cH:13][cH:14][c:15]([c:16](=[O:17])[o:18][c:19]3=[O:20])[c:21]12 | O=C(O)c1ccc(C(=O)O)c2c(C(=O)O)ccc(C(=O)O)c12 | O=C(O)c1ccc(C(=O)O)c2c3ccc(c(=O)oc3=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 934f8084f78d0d57668b9bdfb8c4a326135833bbaa40eb5b5508d2fbbfa357fe | 63a2bae03e4c021ca09a5731c2cc874376b3b6ed89490f90594503c6ca351cff | O=c1oc(=O)c2ccc1c1ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]:[c:11]:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[o;H0;D2;+0:9]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c:6]2:[c:10]:[c:11]:[c:3]:1:[c:4]:[c:5]:2 | null | [] | null | null | null | null | The 1,3,6,8-tetrabromopyrene is obtained in an amount of 564 parts and a purity of about 83%, which corresponds to a yield of about 2% of theory, based on 100% pure pyrene, which on further processing to naphthalene-1,4,5,8-tetracarboxylic acid gives 258 parts of naphthalene-1,4,5,8-tetracarboxylic 1,4-monoanhydride.
C... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | null | c1ccc2ccccc2c1 | C1=c2ccc(c3ccccc23)=CO1 | C1=c2ccc(c3ccccc23)=CO1 | HO- | null | null | null | O=C(O)c1ccc(C(=O)O)c2c(C(=O)O)ccc(C(=O)O)c12>>O=C(O)c1ccc(C(=O)O)c2c3ccc(c(=O)oc3=O)c12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dad2eed20186402398cc850a972487d1 | C=CCS.CC(=O)OC1CC(=O)N1>>C=CCSC1CC(=O)N1 | [OH-].[Na+].C(C=C)S.C(C)(=O)OC1CC(N1)=O>>C(C=C)SC1CC(N1)=O | [CH2:1]=[CH:2][CH2:3][SH:4].CC(=O)O[CH:5]1[CH2:6][C:7](=[O:8])[NH:9]1>>[CH2:1]=[CH:2][CH2:3][S:4][CH:5]1[CH2:6][C:7](=[O:8])[NH:9]1 | C=CCS.CC(=O)OC1CC(=O)N1 | C=CCSC1CC(=O)N1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 20eec362e306239fc5d47a6d83bf174290e0e0295dfb6eb5816503ddec5d1c06 | 42b46623e04892eb7ae9d9dbbd3cf095172c8c83bd28d92882cec40cddf86ad3 | O=C1CCN1 | C-C(=O)-O-[CH;D3;+0:1]1-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-1.[C;D1;H2:6]=[C:7]-[C:8]-[SH;D1;+0:9]>>[C;D1;H2:6]=[C:7]-[C:8]-[S;H0;D2;+0:9]-[CH;D3;+0:1]1-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-1 | null | [] | null | null | 30 | MINUTE | A solution of 42.9 g of sodium hydroxide in 500 ml of water was made up under nitrogen and cooled to room temperature, 108 ml of allyl mercaptan was added and the mixture stirred under nitrogen for 30 minutes. 138.7 g of 4-acetoxyazetidin-2-one was added to the mixture over 10 minutes under nitrogen and the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Monosulfide | C1CNC1 | C1CNC1 | C1CNC1 | HO- | O | null | 0.5 | C=CCS.CC(=O)OC1CC(=O)N1>O>C=CCSC1CC(=O)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2367364d91d348c0b828b1a5a79f548f | C=CCSC1CC(=O)N1.O=C([O-])C(Br)Cc1ccc([N+](=O)[O-])cc1>>C=CCSC1CC(=O)N1CC(=O)OCc1ccc([N+](=O)[O-])cc1 | O.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=C(CC(C(=O)[O-])Br)C=C1.C(C=C)SC1CC(N1)=O.CN(C=O)C>>C(C=C)SC1CC(N1CC(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=O | [CH2:1]=[CH:2][CH2:3][S:4][CH:5]1[CH2:6][C:7](=[O:8])[NH:9]1.Br[CH:10]([C:11](=[O:12])[O-:13])[CH2:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23]1>>[CH2:1]=[CH:2][CH2:3][S:4][CH:5]1[CH2:6][C:7](=[O:8])[N:9]1[CH2:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[... | C=CCSC1CC(=O)N1.O=C([O-])C(Br)Cc1ccc([N+](=O)[O-])cc1 | C=CCSC1CC(=O)N1CC(=O)OCc1ccc([N+](=O)[O-])cc1 | null | null | null | Functional Group Addition | OtherReaction | 545cf93159254a46658cf2484b35c86399ce672b29d96daabbd4f480b69288e9 | 8ba69f4a715d9692dba0f9562b4fc4e2d2e9c98051fdd8045bc3496c17eac722 | O=C(CN1CCC1=O)OCc1ccccc1 | Br-[CH;D3;+0:1](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8].[#16:9]-[C:10]1-[C:11]-[C:12](=[O;D1;H0:13])-[NH;D2;+0:14]-1>>[#16:9]-[C:10]1-[C:11]-[C:12](=[O;D1;H0:13])-[N;H0;D3;+0:14]-1-[CH2;D2;+0:1]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | MINUTE | 11.5 g of 4-nitrobenzylbromoacetate in 30 ml of dimethylformamide was added to 5.0 g of 4-allylthioazetidin-2-one dissolved in 70 ml of dimethylformamide with stirring under argon at room temperature. After 5 mins, 10.61 g of potassium carbonate was added to the solution. During the following 20 mins there was a colour... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amide | Ester.Tertiary amide | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1 | Br- | null | null | 0.083333 | C=CCSC1CC(=O)N1.O=C([O-])C(Br)Cc1ccc([N+](=O)[O-])cc1>>C=CCSC1CC(=O)N1CC(=O)OCc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2a15c84a63fd4fae939388f85b41aae4 | C=CCSC1CC(=O)N1CC(=O)OC>>C=CCSC1CC(=O)N1CC(=O)O | [OH-].[K+].C(C=C)SC1CC(N1CC(=O)OC)=O.Cl>>C(C=C)SC1CC(N1CC(=O)O)=O | C[O:13][C:11]([CH2:10][N:9]1[CH:5]([S:4][CH2:3][CH:2]=[CH2:1])[CH2:6][C:7]1=[O:8])=[O:12]>>[CH2:1]=[CH:2][CH2:3][S:4][CH:5]1[CH2:6][C:7](=[O:8])[N:9]1[CH2:10][C:11](=[O:12])[OH:13] | C=CCSC1CC(=O)N1CC(=O)OC | C=CCSC1CC(=O)N1CC(=O)O | null | null | O.C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCN1 | 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 | 2.34 g of potassium hydroxide dissolved in a mixture of 285 ml of ethanol and 15 ml of water was added to 6.0 g of methyl 2-(4-allylthioazetidin-2-on-1-yl)acetate with stirring at room temperature. The solution was poured into 720 ml 1M hydrochloric acid, extracted into dichloromethane (2×650 ml), the organic layer ext... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]C1 | Other | O.C(C)O | null | null | C=CCSC1CC(=O)N1CC(=O)OC>O.C(C)O>C=CCSC1CC(=O)N1CC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d0305e3f8b44de28230f95fd82629e7 | Cc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>>Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=C(C=C1)C.C([O-])(O)=O.[Na+]>>O=C1CC2SC(=C(N12)C(=O)[O-])OC1=CC=C(C=C1)C.[Na+] | O=[N+]([O-])c1ccc(C[O:11][C:9]([C:8]2=[C:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]3)[S:17][CH:16]3[N:12]2[C:13](=[O:14])[CH2:15]3)=[O:10])cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][C:7]2=[C:8]([C:9](=[O:10])[O-:11])[N:12]3[C:13](=[O:14])[CH2:15][CH:16]3[S:17]2)[cH:18][cH:19]1 | Cc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | null | [Pd] | O1CCOCC1 | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#8:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#8:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | 90 | MINUTE | To a solution of 53 mg of 4-nitrobenzyl 7-oxo-3-(4-tolyloxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan was added an aqueous solution of 10 mg of sodium bicarbonate, and 50 mg of palladium on charcoal (10%). The mixture was hydrogenated with shaking at 50 p.s.i. for 90 minutes.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1 | null | 1.5 | Cc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>[Pd].O1CCOCC1>Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6d313810f4dd42a88f65f7287dd25216 | Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1>>Cc1ccc(OC2=C(C(=O)O)N3C(=O)CC3S2)cc1 | O=C1CC2SC(=C(N12)C(=O)[O-])OC1=CC=C(C=C1)C.[Na+].Cl>>O=C1CC2SC(=C(N12)C(=O)O)OC1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][C:7]2=[C:8]([C:9](=[O:10])[O-:11])[N:12]3[C:13](=[O:14])[CH2:15][CH:16]3[S:17]2)[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][C:7]2=[C:8]([C:9](=[O:10])[OH:11])[N:12]3[C:13](=[O:14])[CH2:15][CH:16]3[S:17]2)[cH:18][cH:19]1 | Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | Cc1ccc(OC2=C(C(=O)O)N3C(=O)CC3S2)cc1 | null | null | null | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | O=C1CC2SC(Oc3ccccc3)=CN12 | [#16:1]-[C:2](-[#8:3])=[C:4](-[C:5](-[O-;H0;D1:6])=[O;D1;H0:7])-[#7:8]-[C:9]=[O;D1;H0:10]>>[#16:1]-[C:2](-[#8:3])=[C:4](-[C:5](=[O;D1;H0:7])-[OH;D1;+0:6])-[#7:8]-[C:9]=[O;D1;H0:10] | 48.2 | [{"value": 48.2, "product": "O=C1CC2SC(=C(N12)C(=O)O)OC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | An aqueous solution of 32 mg of sodium 7-oxo-3-(4-tolyloxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate was acidified to pH 2.0 with dilute hydrochloric acid, and was then extracted with ethyl acetate. The organic layer was backwashed with water, and then dried and evaporated in vacuo to afford 14.3 mg of the ab... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.C1=CN2CCC2S1 | null | null | null | null | Cc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1>>Cc1ccc(OC2=C(C(=O)O)N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ff18f171073b41e1bae56734e71a1c01 | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1>>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C(C=C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=S)OC1=CC=CC=C1)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=CC=C1 | C=CC[S:23](=O)[CH:24]1[CH2:25][C:26](=[O:27])[N:28]1[CH:14]([C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:15](=S)[O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:14]1=[C:15]([O:16][c:... | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 09567d1fb0e06be53e411508137f88dfa4351f8b0b195081fb14c08fba224024 | fdbe926d598ab340f45c824667ff03d3ad5a17b984102931fa7371ce5bc3bef4 | O=C(OCc1ccccc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C=C-C-[S;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1-[CH;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:12](=S)-[#8:13]-[c:14]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:12](-[#8:13]-[c:14])-[S;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-2-1 | 18 | [{"value": 18.0, "product": "O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.7, "product": "O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 97 mg of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxopropionate and 52 mg of triphenylphosphine in 2 ml of dry dioxan was heated under an argon atmosphere under reflux for 15 minutes. The mixture was then evaporated in vacuo to dryness; chromatography over silica gel aff... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Thiocarbonyl.Sulfoxide.Allyl | Enamine.Ester.Ether.Monosulfide | null | C1=CN2CCC2S1 | c1ccccc1.c1ccccc1.C1=CN2CCC2S1 | Other | O1CCOCC1 | null | null | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1>O1CCOCC1>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5056db55fb364a0293765fbb38651319 | O=C([O-])C1=C(Oc2ccccc2)SC2(Cc3ccc([N+](=O)[O-])cc3)CC(=O)N12>>O=C([O-])C1=C(Oc2ccccc2)SC2CC(=O)N12 | [N+](=O)([O-])C1=CC=C(CC23SC(=C(N3C(C2)=O)C(=O)[O-])OC2=CC=CC=C2)C=C1.C([O-])(O)=O.[Na+]>>O=C1CC2SC(=C(N12)C(=O)[O-])OC1=CC=CC=C1.[Na+] | O=[N+]([O-])c1ccc(C[C:14]23[S:13][C:5]([O:6][c:7]4[cH:8][cH:9][cH:10][cH:11][cH:12]4)=[C:4]([C:2](=[O:1])[O-:3])[N:18]2[C:16](=[O:17])[CH2:15]3)cc1>>[O:1]=[C:2]([O-:3])[C:4]1=[C:5]([O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[S:13][CH:14]2[CH2:15][C:16](=[O:17])[N:18]12 | O=C([O-])C1=C(Oc2ccccc2)SC2(Cc3ccc([N+](=O)[O-])cc3)CC(=O)N12 | O=C([O-])C1=C(Oc2ccccc2)SC2CC(=O)N12 | null | [Pd] | O1CCOCC1.O | Reduction | OtherReaction | 1e1b471d1d417dd71781146706d5899f32e72e3e0d40425a6f5909f852d481ce | 7c6218583be997f699d95dfe65a34b687b1d229c78ffd736b05621faf29962fe | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[C;H0;D4;+0:1]23-[#16:2]-[C:3](-[#8:4])=[C:5](-[C:6](-[O;-;D1;H0:7])=[O;D1;H0:8])-[#7:9]-2-[C:10](=[O;D1;H0:11])-[C:12]-3):c:c:1>>[#8:4]-[C:3]1=[C:5](-[C:6](-[O;-;D1;H0:7])=[O;D1;H0:8])-[#7:9]2-[C:10](=[O;D1;H0:11])-[C:12]-[CH;D3;+0:1]-2-[#16:2]-1 | 74.6 | [{"value": 74.6, "product": "O=C1CC2SC(=C(N12)C(=O)[O-])OC1=CC=CC=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of a solution of 56 mg of 4-nitrobenzyl-7-oxo-3-phenoxy-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in 3 ml of dioxan and 12.5 mg of sodium bicarbonate in 2 ml of water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 90 minutes. The mixture was then filtered through Celite, and lyophi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Monosulfide | Monosulfide | c1ccccc1.C1=CN2CCC2S1 | C1=CN2CCC2S1 | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | O=C([O-])C1=C(Oc2ccccc2)SC2(Cc3ccc([N+](=O)[O-])cc3)CC(=O)N12>[Pd].O1CCOCC1.O>O=C([O-])C1=C(Oc2ccccc2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8210441576984f24a7766ee8b616321d | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1>>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C(C=C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=S)OC1=CC=CC=C1)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=CC=C1 | C=CC[S:23](=O)[CH:24]1[CH2:25][C:26](=[O:27])[N:28]1[CH:14]([C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:15](=S)[O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:14]1=[C:15]([O:16][c:... | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 09567d1fb0e06be53e411508137f88dfa4351f8b0b195081fb14c08fba224024 | fdbe926d598ab340f45c824667ff03d3ad5a17b984102931fa7371ce5bc3bef4 | O=C(OCc1ccccc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C=C-C-[S;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1-[CH;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:12](=S)-[#8:13]-[c:14]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:12](-[#8:13]-[c:14])-[S;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-2-1 | 17.3 | [{"value": 17.3, "product": "O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 1550 mg of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxo-propanate (containing 10% pivalic acid), 808 mg of triphenylphosphine and dioxan was heated under an argon atmosphere at 110° C. for 15 minutes. The mixture was evaporated in vacuo to dryness, and the resulting oil was chrom... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Thiocarbonyl.Sulfoxide.Allyl | Enamine.Ester.Ether.Monosulfide | null | C1=CN2CCC2S1 | c1ccccc1.c1ccccc1.C1=CN2CCC2S1 | Other | O1CCOCC1 | 110 | null | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccccc1>O1CCOCC1>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0bc59737e03a4de3845a019af7b8aba5 | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C>>C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)OC)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C=C)S(=O)C1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)OC)=O | [CH2:1]=[CH:2][CH2:3][S:4][CH:6]1[CH2:7][C:8](=[O:9])[N:10]1[C:11]([C:12](=[S:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)=[C:25]([O:26][c:27]1[cH:28][cH:29][c:30]([O:31][CH3:32])[cH:33][cH:34]1)[C:35](=[O:36])[C:37]([CH3:38])([CH3:39])[CH3:40]>>[CH2:1]=[CH:2][CH2:3][S:4](=[O:5... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C | C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C | null | null | C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C1CCN1C(=COc1ccccc1)C(=S)OCc1ccccc1 | [C:1]=[C:2]-[#7:3]1-[C:4](-[S;H0;D2;+0:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:1]=[C:2]-[#7:3]1-[C:4](-[S;H0;D3;+0:5](=[O;D1;H0:12])-[C:6]-[C:7]=[C;D1;H2:8])-[C:9]-[C:10]-1=[O;D1;H0:11] | 62 | [{"value": 62.0, "product": "C(C=C)S(=O)C1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.35 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-methoxyphenoxy)-3-trimethylacetylthio-propenate in ethyl acetate at -78° C. was added a solution of 0.128 g of 80% m-chloroperoxybenzoic acid in ethyl acetate over 10 minutes. The reaction mixture was washed with saturated sodium bicarbonat... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C>C(C)(=O)OCC>C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(OC)cc1)C(=O)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40f7e92ac98a48628919c3bb7ab3d772 | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(OC)cc1>>COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | C(C=C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=S)OC1=CC=C(C=C1)OC)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1 | C=CC[S:28](=O)[CH:27]1[N:23]([CH:9]([C:8](=S)[O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]2)[C:24](=[O:25])[CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]2=[C:9]([C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:... | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(OC)cc1 | COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 09567d1fb0e06be53e411508137f88dfa4351f8b0b195081fb14c08fba224024 | fdbe926d598ab340f45c824667ff03d3ad5a17b984102931fa7371ce5bc3bef4 | O=C(OCc1ccccc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C=C-C-[S;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1-[CH;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:12](=S)-[#8:13]-[c:14]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:12](-[#8:13]-[c:14])-[S;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-2-1 | 17.2 | [{"value": 17.2, "product": "COC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 422 mg of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-(4-methoxyphenoxy)-3-thioxopropanate, 214 mg of triphenylphosphine, and dioxan was heated under an argon atmosphere at 100° for 15 minutes. Then, the mixture was evaporated in vacuo to dryness, and the resulting oil was chromatographed on sil... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Thiocarbonyl.Sulfoxide.Allyl | Enamine.Ester.Ether.Monosulfide | null | C1=CN2CCC2S1 | c1ccccc1.c1ccccc1.C1=CN2CCC2S1 | Other | O1CCOCC1 | null | null | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(OC)cc1>O1CCOCC1>COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-682a8533f4c743c19b88d6287889b659 | COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>>COc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | COC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1.C([O-])(O)=O.[Na+]>>COC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+] | O=[N+]([O-])c1ccc(C[O:12][C:10]([C:9]2=[C:8]([O:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]3)[S:18][CH:17]3[N:13]2[C:14](=[O:15])[CH2:16]3)=[O:11])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]2=[C:9]([C:10](=[O:11])[O-:12])[N:13]3[C:14](=[O:15])[CH2:16][CH:17]3[S:18]2)[cH:19][cH:20]1 | COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | COc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | null | [Pd] | O1CCOCC1.O | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#8:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#8:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | null | null | A mixture of a solution of 60 mg of 4-nitrobenzyl 3-(4-methoxyphenoxy)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 15 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | COc1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>[Pd].O1CCOCC1.O>COc1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-682bf859e96f4071bbb1d613564a3977 | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C>>C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C=C)S(=O)C1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O | [CH2:1]=[CH:2][CH2:3][S:4][CH:6]1[CH2:7][C:8](=[O:9])[N:10]1[C:11]([C:12](=[S:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)=[C:25]([O:26][c:27]1[cH:28][cH:29][c:30]([F:31])[cH:32][cH:33]1)[C:34](=[O:35])[C:36]([CH3:37])([CH3:38])[CH3:39]>>[CH2:1]=[CH:2][CH2:3][S:4](=[O:5])[CH:6]... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C | C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C | null | null | C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C1CCN1C(=COc1ccccc1)C(=S)OCc1ccccc1 | [C:1]=[C:2]-[#7:3]1-[C:4](-[S;H0;D2;+0:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:1]=[C:2]-[#7:3]1-[C:4](-[S;H0;D3;+0:5](=[O;D1;H0:12])-[C:6]-[C:7]=[C;D1;H2:8])-[C:9]-[C:10]-1=[O;D1;H0:11] | 58.3 | [{"value": 58.3, "product": "C(C=C)S(=O)C1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4.0 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-trimethylacetylthio-propenate in ethyl acetate at -78° was added a solution of 1.5 g of 80% m-chloroperoxybenzoic acid in ethyl acetate over 10 minutes. The reaction mixture was washed with saturated sodium bicarbonate solut... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C>C(C)(=O)OCC>C=CCS(=O)C1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6d1cb58153a64ec1b34fdc9b4d50e442 | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(F)cc1>>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 | C(C=C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=S)OC1=CC=C(C=C1)F)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1 | C=CC[S:24](=O)[CH:25]1[CH2:26][C:27](=[O:28])[N:29]1[CH:14]([C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:15](=S)[O:16][c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:14]1=[C:15]([O... | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(F)cc1 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 09567d1fb0e06be53e411508137f88dfa4351f8b0b195081fb14c08fba224024 | fdbe926d598ab340f45c824667ff03d3ad5a17b984102931fa7371ce5bc3bef4 | O=C(OCc1ccccc1)C1=C(Oc2ccccc2)SC2CC(=O)N12 | C=C-C-[S;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1-[CH;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:12](=S)-[#8:13]-[c:14]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:12](-[#8:13]-[c:14])-[S;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-2-1 | 12.3 | [{"value": 12.3, "product": "FC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.15 g of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-thioxo-propanate, 600 mg of triphenylphosphine, and dioxan was heated under an argon atmosphere at 100° for 15 minutes. Then, the mixture was evaporated in vacuo to dryness, and the resulting oil was chromatographed on sil... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Thiocarbonyl.Sulfoxide.Allyl | Enamine.Ester.Ether.Monosulfide | null | C1=CN2CCC2S1 | c1ccccc1.c1ccccc1.C1=CN2CCC2S1 | Other | O1CCOCC1 | null | null | C=CCS(=O)C1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)C(=S)Oc1ccc(F)cc1>O1CCOCC1>O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bbae89eeb1164984848e253d3e573545 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CCN12>>O=C([O-])C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 | FC1=CC=C(OC2=C(N3CCC3S2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1.C([O-])(O)=O.[Na+]>>FC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+] | O=[N+]([O-])c1ccc(C[O:3][C:2](=[O:1])[C:4]2=[C:5]([O:6][c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]3)[S:14][CH:15]3[CH2:16][CH2:17][N:19]23)cc1>>[O:1]=[C:2]([O-:3])[C:4]1=[C:5]([O:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[S:14][CH:15]2[CH2:16][C:17](=[O:18])[N:19]12 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CCN12 | O=C([O-])C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 | null | [Pd] | O1CCOCC1.O | Functional Group Interconversion | OtherReaction | e822a636698cf3ba88c05a1f82fd94d3583383d400ee627bc2b661c38f2052de | 4690ed478d743360ccffbea7bd2623366965e371cf2283ac8c3868d9bc115d2f | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]2=[C:5](-[#8:6])-[#16:7]-[C:8]3-[C:9]-[CH2;D2;+0:10]-[#7:11]-3-2):c:c:1>>[#8:6]-[C:5]1=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:11]2-[C:8](-[#16:7]-1)-[C:9]-[C;H0;D3;+0:10]-2=[O;D1;H0:12] | 95.5 | [{"value": 95.5, "product": "FC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of a solution of 500 mg of 4-nitrobenzyl 3-(4-fluorophenoxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 101 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes. Then the reaction mixture was filtered through Celite, and then lyop... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Tertiary amide | c1ccccc1.C1=CN2CCC2S1 | C1=CN2CCC2S1 | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(F)cc2)SC2CCN12>[Pd].O1CCOCC1.O>O=C([O-])C1=C(Oc2ccc(F)cc2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9f382e08b304749b5efb94d5aeae9b9 | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C.ClCl>>CC(C)(C)C(=O)C(Oc1ccc(F)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O.ClCl>>ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O | C=CCS[CH:34]1[N:30]([C:16](=[C:7]([C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[O:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[C:17](=[S:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]2)[C:31](=[O:32])[CH2:33]1.Cl[Cl:35]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[C:7]([O:8]... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C.ClCl | CC(C)(C)C(=O)C(Oc1ccc(F)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | null | null | ClCCl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d4a1f45948ca6338d13758a8eb064414f490d5560b79b989b8f902e12590b6c8 | 7fecd9068ed121180c7c8f39a016405d4e3d2c3ae4d3dd36c097f13d461df37e | O=C1CCN1C(=COc1ccccc1)C(=S)OCc1ccccc1 | C=C-C-S-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[S;D1;H0:9])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13].Cl-[Cl;H0;D1;+0:14]>>[#8:8]-[C:7](=[S;D1;H0:9])-[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:14])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13] | 68.5 | [{"value": 68.5, "product": "ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7.2 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-trimethylacetylthio-propenate (prepared as described in Example 25) in dichloromethane at -20°, was added a solution of 25 mmol of chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Allyl | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.c1ccccc1.C1C[NH]C1 | HCl | ClCCl.C(Cl)(Cl)(Cl)Cl | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(F)cc1)C(=O)C(C)(C)C.ClCl>ClCCl.C(Cl)(Cl)(Cl)Cl>CC(C)(C)C(=O)C(Oc1ccc(F)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bee91b55d88744178ee3531d3b46f27f | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(Cl)cc1)C(=O)C(C)(C)C.ClCl>>CC(C)(C)C(=O)C(Oc1ccc(Cl)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)Cl)=O.ClCl>>ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)Cl)=O | C=CCS[CH:34]1[N:30]([C:16](=[C:7]([C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[O:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[C:17](=[S:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]2)[C:31](=[O:32])[CH2:33]1.Cl[Cl:35]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[C:7]([O:8... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(Cl)cc1)C(=O)C(C)(C)C.ClCl | CC(C)(C)C(=O)C(Oc1ccc(Cl)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | null | null | ClCCl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d4a1f45948ca6338d13758a8eb064414f490d5560b79b989b8f902e12590b6c8 | 7fecd9068ed121180c7c8f39a016405d4e3d2c3ae4d3dd36c097f13d461df37e | O=C1CCN1C(=COc1ccccc1)C(=S)OCc1ccccc1 | C=C-C-S-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[S;D1;H0:9])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13].Cl-[Cl;H0;D1;+0:14]>>[#8:8]-[C:7](=[S;D1;H0:9])-[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:14])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13] | 64.2 | [{"value": 64.2, "product": "ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.5 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-chlorophenoxy)-3-trimethylacetylthio-propenate in dichloromethane at -20° C. was added a solution of 1.7 mmol chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature, evaporated in vacuo, and the residua... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Allyl | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.c1ccccc1.C1C[NH]C1 | HCl | ClCCl.C(Cl)(Cl)(Cl)Cl | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(Cl)cc1)C(=O)C(C)(C)C.ClCl>ClCCl.C(Cl)(Cl)(Cl)Cl>CC(C)(C)C(=O)C(Oc1ccc(Cl)cc1)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2acad378d87448b983c09932cd48ed7b | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(Cl)cc2)SC2CCN12>>O=C([O-])C1=C(Oc2ccc(Cl)cc2)SC2CC(=O)N12 | ClC1=CC=C(OC2=C(N3CCC3S2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1.C([O-])(O)=O.[Na+]>>ClC1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+] | O=[N+]([O-])c1ccc(C[O:3][C:2](=[O:1])[C:4]2=[C:5]([O:6][c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]3)[S:14][CH:15]3[CH2:16][CH2:17][N:19]23)cc1>>[O:1]=[C:2]([O-:3])[C:4]1=[C:5]([O:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[S:14][CH:15]2[CH2:16][C:17](=[O:18])[N:19]12 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(Cl)cc2)SC2CCN12 | O=C([O-])C1=C(Oc2ccc(Cl)cc2)SC2CC(=O)N12 | null | [Pd] | O1CCOCC1.O | Functional Group Interconversion | OtherReaction | e822a636698cf3ba88c05a1f82fd94d3583383d400ee627bc2b661c38f2052de | 4690ed478d743360ccffbea7bd2623366965e371cf2283ac8c3868d9bc115d2f | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]2=[C:5](-[#8:6])-[#16:7]-[C:8]3-[C:9]-[CH2;D2;+0:10]-[#7:11]-3-2):c:c:1>>[#8:6]-[C:5]1=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:11]2-[C:8](-[#16:7]-1)-[C:9]-[C;H0;D3;+0:10]-2=[O;D1;H0:12] | null | [] | null | null | null | null | A mixture of a solution of 500 mg of 4-nitrobenzyl 3-(4-chlorophenoxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 97 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Tertiary amide | c1ccccc1.C1=CN2CCC2S1 | C1=CN2CCC2S1 | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2ccc(Cl)cc2)SC2CCN12>[Pd].O1CCOCC1.O>O=C([O-])C1=C(Oc2ccc(Cl)cc2)SC2CC(=O)N12 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.