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-01dbb772c5e249108f0b191ed17a2c0c | ord-e4dccccf09ef4bc5a00c348cf634def8 | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NCc1ccccc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[O:24])=[N:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][... | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NCc1ccccc1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NCc1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[C:10]-[c:11]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 20 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carboxamide and benzyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cbb96bc8b36a4161a95459638b80c7f3 | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccccc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C1(=CC=CC=C1)N=C=O>>C1(=CC=CC=C1)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[O:24])=[N:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[C... | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccccc1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 20 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carboxamide and phenyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9098d32bf1f346c9aebc376f14586cd8 | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.ClC1=CC=C(C=C1)N=C=O>>ClC1=CC=C(C=C1)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[O:24])=[N:25][c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][... | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 20 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carboxamide and 4-chlorophenyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d528eaedefc846aebb42fe733e14626e | CCN(CC)CC.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CN(C)C(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | C(C)N(CC)CC.N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.CCOCC>>CN(C(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1)C | C[CH2:1][N:2]([CH2:3]C)[CH2:4]C.[NH2:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18... | CCN(CC)CC.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CN(C)C(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | OtherReaction | 5c6b4f870e204e104c0f1499ec73c4ad5d6db6bd562919243dc377f536ff737a | cce708ea970b57f1f5ef6a8cd4b9f8b8b6fa55d74bb7d21faae338ef889ff0fb | c1ccc(CN2CCCCC2)cc1 | C-[CH2;D2;+0:1]-[#7:2](-[CH2;D2;+0:3]-C)-[CH2;D2;+0:4]-C.[#7:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[NH2;D1;+0:9]>>[#7:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[NH;D2;+0:9]-[C;H0;D3;+0:4](=[O;D1;H0:10])-[#7:2](-[CH3;D1;+0:1])-[CH3;D1;+0:3] | null | [] | null | null | 12 | HOUR | 0.6 ml (4 mmol) of triethylamine and 0.4 ml (4 mmol) of N,N-dimethyl-carbamide chloride are added to 1.2 g (4 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydrazine carboxamide in 20 ml of ether and the reaction mixture is stirred for 12 hours. Solid triethylammonium chloride is filtered off and the filtrate is... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | Other | null | null | 12 | CCN(CC)CC.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CN(C)C(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9220619335324543b39346a03e5120a5 | ClC(Cl)=Nc1ccccc1.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | C(C)N(CC)CC.C1=CC=C(C=C1)N=C(Cl)Cl.N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1>>C1(=CC=CC=C1)NC=1OC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | Cl[C:6](Cl)=[N:5][c:4]1[cH:3][cH:2][cH:1][cH:30][cH:29]1.[NH2:7][NH:8][C:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1)=[O:28]>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[n:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]3... | ClC(Cl)=Nc1ccccc1.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 9f57b8199da1a80915c6fb4e55729958b1db687e77260651dfc7cdd93e0d4b24 | 45c18f59b582ddb410ea5b0b11d63ec6882479579c1fdd7f9de8ce9d4d1c4f3c | c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | Cl-[C;H0;D3;+0:1](-Cl)=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[#7:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]):[o;H0;D2;+0:9]:1 | null | [] | null | null | null | null | 1.4 ml (10 mmol) of triethylamine and 0.7 ml (5 mmol) of phenyl isocyanide dichloride are added to 1.5 g (5 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carboxamide in 30 ml of THF and the mixture is stirred at room temperature until the reaction is quantitative. Solid triethylammonium chloride is fi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Alkenyl halide.Alkenyl halide.Urea | Secondary amine | null | c1nnco1 | c1ccccc1.c1nnco1.c1ccccc1.C1CC[NH]CC1 | HCl | C1CCOC1 | null | null | ClC(Cl)=Nc1ccccc1.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>C1CCOC1>c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1dc6b5574bd346ad89e9cac4f2b34550 | ClC(Cl)=Nc1ccccc1.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)s2)cc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C1=CC=C(C=C1)N=C(Cl)Cl>>C1(=CC=CC=C1)NC=1SC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | Cl[C:6](Cl)=[N:5][c:4]1[cH:3][cH:2][cH:1][cH:30][cH:29]1.[NH2:7][NH:8][C:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1)=[S:28]>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[n:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]3... | ClC(Cl)=Nc1ccccc1.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)s2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | aa99bb8db4a5478913b14b3c4eeefd2008610ccc458cc92cc8cbde68c7a6c88e | aca18d068646505ff58ab30128e34f04fd5a1250093d810d01f524cf99e531d0 | c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)s2)cc1 | Cl-[C;H0;D3;+0:1](-Cl)=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[#7:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]):[s;H0;D2;+0:9]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 29 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carbothioamide and phenyl isocyanide dichloride. The analytical values are summarized in Table II.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Alkenyl halide.Alkenyl halide.Thiourea | Secondary amine | null | c1nncs1 | c1ccccc1.c1nncs1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | ClC(Cl)=Nc1ccccc1.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)s2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e24ed27fe652417993abf3a0ffe56ba7 | CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | OO.CNC(=S)NNC(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S>>CNC=1SC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | S=[C:3]([NH:2][CH3:1])[NH:4][NH:5][C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1)=[S:25]>>[CH3:1][NH:2][c:3]1[n:4][n:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20][... | CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 9efb1688ef53e4f1ae2efb802981832b6e9fd4a1285d9ef76d5add7476a51aba | e4470a60f57ae49688bb34bad8a18ae9f2e3d4e4740a48dbb34995ca455f54ad | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | S=[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;H0;D1;+0:7])-[#7:8]-[C:9]>>[C:9]-[#7:8]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3]):[s;H0;D2;+0:7]:1 | null | [] | null | null | null | null | 2 ml of 30% Hydrogen peroxide are added to 1.58 g (4 mmol) of N-methyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarbothioamide in 30 ml of ethanol and the reaction mixture is briefly heated to boiling. The sulphur which separates is filtered off hot with the aid of active charcoal and the filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thiourea.Thiourea | null | null | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | Other | C(C)O | null | null | CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>C(C)O>CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9e8a6fca991c4f188febdba8ae9ce0c8 | NNC(=S)NCC(O)COc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1>>O=C(Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1)c1ccccc1 | C(C1=CC=CC=C1)(=O)N=C=S.OC(CNC(=S)NN)COC1=CC(=CC=C1)CN1CCCCC1>>C(C1=CC=CC=C1)(=O)NC=1SC(=NN1)NCC(COC1=CC(=CC=C1)CN1CCCCC1)O | [NH2:5][NH:6][C:7]([NH:8][CH2:9][CH:10]([OH:11])[CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1)=[S:27].S=[C:4]=[N:3][C:2](=[O:1])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][c:4]1[n:5][n:6][c:7]([NH:8][CH2:9][CH:10]([OH:11])[CH2:12][... | NNC(=S)NCC(O)COc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1 | O=C(Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1)c1ccccc1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | a850ded279b48aeec8587f403f629d6557305685dc71ce23b6f2b58a38d5d3d6 | 8be3ea1f5d7001eaaf02405042985ba52e4cd2780bdbfbe846421e561620dcdb | O=C(Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1)c1ccccc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5].[C:6]-[#7:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[NH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]):[s;H0;D2;+0:9]:1 | null | [] | null | null | 8 | HOUR | 0.33 g (2 mmol) of benzoyl isothiocyanate are added to 0.68 g (2 mmol) of N-[2-hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide in 20 ml of THF and the reaction mixture is stirred overnight at room temperature. After removal of the THF by evaporation, the solid residue is washed with ether and... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thiourea.Isothiocyanate | Secondary amide | null | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | null | 8 | NNC(=S)NCC(O)COc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1>C1CCOC1>O=C(Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d78e7903616a47b5a9621809086959ae | CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCCCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | C(CCC)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>C(CCC)NC=1SC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[NH:7][NH:8][C:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1)=[S:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[n:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:1... | CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CCCCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 172ec1d02d385dc1b37da6f3d7125d72ab9d6f3d78a23e67e4c38705b463a80f | 62b0c5ab2ca5e5d29f20dc74c77e75bb14f5ab313919f2151cec337439b9c55f | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;H0;D1;+0:7])-[#7:8]-[C:9]>>[C:9]-[#7:8]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:1](-[#7:2]-[C:3]):[s;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-butyl-2-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]aminothioxomethyl]hydrazine carboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Urea.Thiourea | null | null | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCCCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e67f7b9458324899aa2bf340325e6943 | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)NC1CCCCC1>>c1cc(CN2CCCCC2)cc(OCCCNc2nnc(NC3CCCCC3)s2)c1 | C1(CCCCC1)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCCC1)NC=1SC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:21]([NH:20][NH:19][C:18]([NH:17][CH2:16][CH2:15][CH2:14][O:13][c:12]1[cH:11][c:3]([CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:2][cH:1][cH:30]1)=[S:29])[NH:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1>>[cH:1]1[cH:2][c:3]([CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH2:... | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)NC1CCCCC1 | c1cc(CN2CCCCC2)cc(OCCCNc2nnc(NC3CCCCC3)s2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 172ec1d02d385dc1b37da6f3d7125d72ab9d6f3d78a23e67e4c38705b463a80f | 62b0c5ab2ca5e5d29f20dc74c77e75bb14f5ab313919f2151cec337439b9c55f | c1cc(CN2CCCCC2)cc(OCCCNc2nnc(NC3CCCCC3)s2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;H0;D1;+0:7])-[#7:8]-[C:9]>>[C:9]-[#7:8]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:1](-[#7:2]-[C:3]):[s;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-cyclohexyl-2-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]aminothioxomethyl]-hydrazine carboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Urea.Thiourea | null | null | c1nncs1 | c1ccccc1.C1CC[NH]CC1.c1nncs1.C1CCCCC1 | HO- | null | null | null | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)NC1CCCCC1>>c1cc(CN2CCCCC2)cc(OCCCNc2nnc(NC3CCCCC3)s2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-971b8e9f32ef4c168ef57c971277054d | CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | CNC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>CNC=1OC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:6]([NH:5][NH:4][C:3]([NH:2][CH3:1])=[O:25])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1>>[CH3:1][NH:2][c:3]1[n:4][n:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20][... | CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1cc(CN2CCCCC2)cc(OCCCNc2nnco2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[#7:8]-[C;D1;H3:9]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[#7:8]-[C;D1;H3:9]):[o;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-methyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-11086ec733244a54a276cc40317b0007 | CCNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | C(C)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>C(C)NC=1OC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:7]([NH:6][NH:5][C:4]([NH:3][CH2:2][CH3:1])=[O:26])[NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][n:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]3[... | CCNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1cc(CN2CCCCC2)cc(OCCCNc2nnco2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[#7:8]-[C:9]>>[C:9]-[#7:8]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:1](-[#7:2]-[C:3]):[o;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-ethyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CCNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CCNc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0b658159483d4944933cf94782ffab90 | CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | C(C)(C)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>C(C)(C)NC=1OC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:8]([NH:7][NH:6][C:5]([NH:4][CH:2]([CH3:1])[CH3:3])=[O:27])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[n:6][n:7][c:8]([NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][c:18... | CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CC(C)Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1cc(CN2CCCCC2)cc(OCCCNc2nnco2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[#7:8]-[C:9]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[#7:8]-[C:9]):[o;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-isopropyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f89ec35a77d24dec965a72076856b42d | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1>>Clc1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | ClC1=CC=C(C=C1)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1.P(=O)(Cl)(Cl)Cl>>ClC1=CC=C(C=C1)NC=1OC(=NN1)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | O=[C:10]([NH:9][NH:8][C:7]([NH:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:31][cH:30]1)=[O:29])[NH:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20]([CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][n:9][c:10]([NH:11][CH2:12][CH2:13][CH2:14][O:... | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1 | Clc1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[#7:8]-[c:9]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[#7:8]-[c:9]):[o;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-4-chlorophenyl-N'-[3-[3-(1piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide and phosphorus oxychloride. The analytical values are summarized in Table III.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1ccccc1.c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)Nc1ccc(Cl)cc1>>Clc1ccc(Nc2nnc(NCCCOc3cccc(CN4CCCCC4)c3)o2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8eb4fc42e2804d748fd87ba8aac6a162 | NCC=CCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCC=CCOc2cccc(CN3CCCCC3)c2)s1 | N1(CCCCC1)CC=1C=C(OCC=CCN)C=CC1.C(C)N(CC)CC.BrC1=NN=C(S1)N>>N1(CCCCC1)CC=1C=C(OCC=CCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH:8]=[CH:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:25]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH:8]=[CH:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20][C... | NCC=CCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCC=CCOc2cccc(CN3CCCCC3)c2)s1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | C(=CCOc1cccc(CN2CCCCC2)c1)CNc1nncs1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]=[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:7]-[C:8]=[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | 0.6 g (2.3 mmol) of 4-[3-(1-piperidinylmethyl)phenoxy]2-butene-1-amine, 0.35 ml of triethylamine and 0.42 g (2.3 mmol) of 5-bromo-1,3,4-thiadiazole-2-amin are heated under reflux in 20 ml of THF for 3 hours. Solid triethylammonium bromide is filtered off, the filtrate is concentrated by evaporation and the oily residue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HBr | C1CCOC1 | null | null | NCC=CCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>C1CCOC1>Nc1nnc(NCC=CCOc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6a7ed01635ed4c138cea3a4b01da5ca5 | NCC(O)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1 | BrC1=NN=C(S1)N.C(C)N(CC)CC.NCC(COC1=CC(=CC=C1)CN1CCCCC1)O>>NC1=NN=C(S1)NCC(COC1=CC(=CC=C1)CN1CCCCC1)O | [NH2:6][CH2:7][CH:8]([OH:9])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:25]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH:8]([OH:9])[CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20]... | NCC(O)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | 0.54 g (3 mmol) of 5-bromo-1,3,4-thiadiazole-2-amine and 0.45 ml of triethylamine are added to 0.8 g (3 mmol) of 1-amino-3-[3-(1-piperidinylmethyl)phenoxy]-2-propanol in 20 ml of THF and the mixture is reacted in a manner analogous to Example 51. The oil obtained is purified by column chromatography (silica gel; ammoni... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HBr | C1CCOC1 | null | null | NCC(O)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>C1CCOC1>Nc1nnc(NCC(O)COc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c587ea1f6afa47de97166c863f4d86d1 | CC(CN)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>CC(CNc1nnc(N)s1)COc1cccc(CN2CCCCC2)c1 | CC(CN)COC1=CC(=CC=C1)CN1CCCCC1.BrC1=NN=C(S1)N>>CC(CNC=1SC(=NN1)N)COC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH:2]([CH2:3][NH2:4])[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25]1.Br[c:5]1[n:6][n:7][c:8]([NH2:9])[s:10]1>>[CH3:1][CH:2]([CH2:3][NH:4][c:5]1[n:6][n:7][c:8]([NH2:9])[s:10]1)[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]2[CH2:2... | CC(CN)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1 | CC(CNc1nnc(N)s1)COc1cccc(CN2CCCCC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to Example 51 from 2-methyl-3-[3-(1-piperidinylmethyl) phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | CC(CN)COc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>CC(CNc1nnc(N)s1)COc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5aa43ab20cb0403ab1a162f7107fcb04 | CN(C)Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1>>CN(C)Cc1cccc(OCCCNc2nnc(N)s2)c1 | CN(C)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CN(C)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][NH2:14])[cH:21]1.Br[c:15]1[n:16][n:17][c:18]([NH2:19])[s:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][NH:14][c:15]2[n:16][n:17][c:18]([NH2:19])[s:20]2)[cH:21]1 | CN(C)Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1 | CN(C)Cc1cccc(OCCCNc2nnc(N)s2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(OCCCNc2nncs2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(dimethylamino)methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1ccccc1.c1nncs1 | HBr | null | null | null | CN(C)Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1>>CN(C)Cc1cccc(OCCCNc2nnc(N)s2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-aba52494f2a54ca8be4f2454e2d88a82 | NCCCOc1cccc(CN2CCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCC3)c2)s1 | N1(CCCC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>N1(CCCC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:22]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:23]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[cH:22... | NCCCOc1cccc(CN2CCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCCCOc2cccc(CN3CCCC3)c2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-(1-pyrrolidinylmethyl)-phenoxy]1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]C1 | HBr | null | null | null | NCCCOc1cccc(CN2CCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-be78e38a63a04e01bcbdccac00953061 | NCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | N1(CCCCC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>N1(CCCCC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:24]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]... | NCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-(1-piperidinylmethyl)phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine. The product obtained is identical to the substance described in Example 50.
Conditions: See reaction.notes.procedure_details.
Workup: The product obtained | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | NCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f3d2f9b9941c47908aaa472759580848 | NCCCOc1cccc(CN2CCCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCCCC3)c2)s1 | N1(CCCCCC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>N1(CCCCCC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:25]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20]... | NCCCOc1cccc(CN2CCCCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCCCOc2cccc(CN3CCCCCC3)c2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(hexahydro-1H-azepin-1-yl) methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CCC[NH]CC1 | HBr | null | null | null | NCCCOc1cccc(CN2CCCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bcd6c58213474e3e95f3d43538841d42 | NCCCOc1cccc(CN2CCOCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCOCC3)c2)s1 | N1(CCOCC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>N1(CCOCC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[cH:23]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:24]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2... | NCCCOc1cccc(CN2CCOCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCCCOc2cccc(CN3CCOCC3)c2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCOCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-(4-morpholinylmethyl)phenoxy]1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1COCC[NH]1 | HBr | null | null | null | NCCCOc1cccc(CN2CCOCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCOc2cccc(CN3CCOCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c23299e4c56f495ea8bb7cfb36122b35 | CN1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1>>CN1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 | CN1CCN(CC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CN1CCN(CC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[cH:23]2)[CH2:24][CH2:25]1.Br[c:17]1[n:18][n:19][c:20]([NH2:21])[s:22]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH:16][c:17]3[n:18][n:19][c:20]([... | CN1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1 | CN1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCNCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(4-methyl-1-piperazinyl) methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1C[NH]CC[NH]1.c1ccccc1.c1nncs1 | HBr | null | null | null | CN1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1>>CN1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ab50ca1c8ca943ada3827a0b5fa3b8c3 | NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NNC(=O)N)C=CC1.P(=O)(Cl)(Cl)Cl>>N1(CCCCC1)CC=1C=C(OCCCNC=2OC(=NN2)N)C=CC1 | O=[C:5]([NH:4][NH:3][C:2]([NH2:1])=[O:24])[NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21... | NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1cc(CN2CCCCC2)cc(OCCCNc2nnco2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](-[N;D1;H2:7])=[O;H0;D1;+0:8]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[N;D1;H2:7]):[o;H0;D2;+0:8]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 40 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-1,2-hydrazine dicarboxamide and phosphorus oxychloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>Nc1nnc(NCCCOc2cccc(CN3CCCCC3)c2)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-19bba1e04b7a4a7cafd3ccb58c5285a5 | CC(CNC(=O)NNC(N)=O)COc1cccc(CN2CCCCC2)c1>>CC(CNc1nnc(N)o1)COc1cccc(CN2CCCCC2)c1 | CC(CNC(=O)NNC(=O)N)COC1=CC(=CC=C1)CN1CCCCC1.N>>CC(CNC=1OC(=NN1)N)COC1=CC(=CC=C1)CN1CCCCC1 | O=[C:5]([NH:4][CH2:3][CH:2]([CH3:1])[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25]1)[NH:6][NH:7][C:8]([NH2:9])=[O:10]>>[CH3:1][CH:2]([CH2:3][NH:4][c:5]1[n:6][n:7][c:8]([NH2:9])[o:10]1)[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]2[CH2:... | CC(CNC(=O)NNC(N)=O)COc1cccc(CN2CCCCC2)c1 | CC(CNc1nnc(N)o1)COc1cccc(CN2CCCCC2)c1 | null | null | P(=O)(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1cc(CN2CCCCC2)cc(OCCCNc2nnco2)c1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](-[N;D1;H2:7])=[O;H0;D1;+0:8]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[N;D1;H2:7]):[o;H0;D2;+0:8]:1 | null | [] | null | null | null | null | 7 mmol of N-[2-Methyl-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide in 30 ml of phosphorus oxychloride are stirred for 6 hours at 50°-60° C. When cooled, the reaction mixture is poured out on 300 ml of ice water and neutralized by the addition of concentrated ammonia solution with cooling. The p... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1.C1CC[NH]CC1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CC(CNC(=O)NNC(N)=O)COc1cccc(CN2CCCCC2)c1>P(=O)(Cl)(Cl)Cl>CC(CNc1nnc(N)o1)COc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-424437dd939048d781b5e36f7d3f50fa | NCCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCCOc2cccc(CN3CCCCC3)c2)s1 | N1(CCCCC1)CC=1C=C(OCCCCN)C=CC1.BrC1=NN=C(S1)N>>N1(CCCCC1)CC=1C=C(OCCCCNC=2SC(=NN2)N)C=CC1 | [NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.Br[c:5]1[n:4][n:3][c:2]([NH2:1])[s:25]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20]... | NCCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1 | Nc1nnc(NCCCCOc2cccc(CN3CCCCC3)c2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 4-[3-(1-piperidinylmethyl)phenoxy]1-butanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | c1nncs1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | NCCCCOc1cccc(CN2CCCCC2)c1.Nc1nnc(Br)s1>>Nc1nnc(NCCCCOc2cccc(CN3CCCCC3)c2)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e9c53b21b5524c4296badbb52530d5b3 | CC1CCCNC1.O=Cc1cccc(O)c1>>CC1CCCN(Cc2cccc(O)c2)C1 | N.OC=1C=C(C=O)C=CC1.CC1CNCCC1.C(=O)O>>CC1CN(CCC1)CC=1C=C(C=CC1)O | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:15]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]2)[CH2:15]1 | CC1CCCNC1.O=Cc1cccc(O)c1 | CC1CCCN(Cc2cccc(O)c2)C1 | null | null | O | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCCCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | 120 | CELSIUS | 2 | HOUR | 24.4 g (0.2 mol) of 3-hydroxybenzaldehyde are mixed with 40 ml (about 0.4 mol) of 3-methylpiperidine and 20 ml (about 0.52 mol) of 100% formic acid with cooling and then stirred for 2 hours at 120° C. When the reaction mixture has cooled to room temperature, it is poured into water and rendered alkaline with ammonia, a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | O | 120 | 2 | CC1CCCNC1.O=Cc1cccc(O)c1>O>CC1CCCN(Cc2cccc(O)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-055eb18c1384484c97946551c03e5d3e | CC1CCCN(Cc2cccc(O)c2)C1>>CC1CCCN(Cc2cccc(OCCCN)c2)C1 | CC1CN(CCC1)CC=1C=C(C=CC1)O.[H-].[Na+].[O-]S(=O)(=O)[O-].[Na+].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1CN(CCC1)CC=1C=C(OCCCN)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:18]2)[CH2:19]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][NH2:17])[cH:18]2)[CH2:19]1 | CC1CCCN(Cc2cccc(O)c2)C1 | CC1CCCN(Cc2cccc(OCCCN)c2)C1 | null | null | CN(C)C=O.CCOCC.O | Miscellaneous | OtherReaction | c064ccf2aeb19a92171fe5bb69a62bd4fb9d23edbcb2d7ff13044aad3a0a8f21 | 19c3ce621148306217a46f5ad572c92027fba322132f3439aba66afd1bdfad9c | c1ccc(CN2CCCCC2)cc1 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C:5]-[C:6]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | 5.13 g (0.025 mol) of 3-[(3-Methylpiperidin-1-yl) methyl]phenol are introduced into a suspension of 1.0 g (0.025 mol) of sodium hydride (60%) in absolute DMF and stirred overnight at room temperature. After the addition of 2.23 g (0.025 mol) of 3-chloropropionic acid nitrile, the reaction mixture is stirred for 7 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether.Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | Other | CN(C)C=O.CCOCC.O | null | 8 | CC1CCCN(Cc2cccc(O)c2)C1>CN(C)C=O.CCOCC.O>CC1CCCN(Cc2cccc(OCCCN)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a74a4d08ee934a7985e29a4219f4899c | CC1CCCCN1Cc1cccc(O)c1.N#CCCCCl>>CC1CCCN(Cc2cccc(OCCCCN)c2)C1 | CC1N(CCCC1)CC=1C=C(C=CC1)O.[H-].[Na+].CN(C)C=O.[O-]S(=O)(=O)[O-].[Na+].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3].ClCCCC#N>>CC1CN(CCC1)CC=1C=C(OCCCCN)C=CC1 | [CH3:1][CH:2]1[N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:19]2)[CH2:5][CH2:4][CH2:3][CH2:20]1.Cl[CH2:14][CH2:15][CH2:16][C:17]#[N:18]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[cH:19]2)[CH2:20]1 | CC1CCCCN1Cc1cccc(O)c1.N#CCCCCl | CC1CCCN(Cc2cccc(OCCCCN)c2)C1 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | OtherReaction | 6fae8570ef9a11365228971d73364cc0836419b1a1e0db3a5860a0489c5eaf9c | 48d64ef5f17dc6cf6d34f3e1c417d8a500850f0d060c2118dbdafc68b185ec4c | c1ccc(CN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[C;D1;H3:6]-[CH;D3;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[C:13]-[c:14]:[c:15]:[c:16](-[OH;D1;+0:17]):[c:18]>>[C;D1;H3:6]-[CH;D3;+0:7]1-[CH2;D2;+0:8]-[N;H0;D3;+0:12](-[C:13]-[c:14]:[c:15]:[c:16](-[O;H0;D2;+0:17]-[CH2;D2;+0:1]-[C:2]-[... | null | [] | null | null | 8 | HOUR | 5.13 g (0.025 mol) of 3-((methylpiperidin-1-yl)methyl) phenol (Example 64 a) are added to a suspension of 1.0 g (0.025 mol) of sodium hydride (60%) in absolute DMF and the mixture is stirred overnight at room temperature. After the addition of 2.58 g (0.025 mol) of 4chlorobutyronitrile, the reaction mixture is stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile.Aromatic alcohol.Tertiary amine | Ether.Primary amine.Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | CCOCC.O | null | 8 | CC1CCCCN1Cc1cccc(O)c1.N#CCCCCl>CCOCC.O>CC1CCCN(Cc2cccc(OCCCCN)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eb4404a529524bbaaeb145c12af0db55 | CC1CCCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 | CC1CN(CCC1)CC=1C=C(OCCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1CN(CCC1)CC=1C=C(OCCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[cH:25]2)[CH2:26]1.Br[c:19]1[n:20][n:21][c:22]([NH2:23])[s:24]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][... | CC1CCCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1 | CC1CCCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | 54 | [{"value": 54.0, "product": "CC1CN(CCC1)CC=1C=C(OCCCCNC=2SC(=NN2)N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 4-[3-[(3-methylpiperidin-1-yl) methyl]phenoxy]-butanamine and 5-bromo-1,3,4-thiadiazole2-amine. Yield: 54% of theoretical: melting point: 123°-124° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]CC1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CCCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-505171a282c949038b31467505f1365b | CC1CCN(Cc2cccc(O)c2)C1.C[N+](C)(C)Cc1ccccc1>>CC1CCN(Cc2cccc(OCCCN)c2)C1 | [OH-].C(C1=CC=CC=C1)[N+](C)(C)C.CC1CN(CC1)CC=1C=C(C=CC1)O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1CN(CC1)CC=1C=C(OCCCN)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:17]2)[CH2:18]1.C[N+:16](C)([CH3:13])[CH2:15][c:14]1ccccc1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[cH:17]2)[CH2:18]1 | CC1CCN(Cc2cccc(O)c2)C1.C[N+](C)(C)Cc1ccccc1 | CC1CCN(Cc2cccc(OCCCN)c2)C1 | null | null | C(C=C)#N | C-C Coupling | OtherReaction | b033e4f5e55984718aa9f47c36b1beb517a4f1ad0a2807093e4f64a2bcbbbcc3 | dd64ca0ce7acc002e65e6435052ec87de38ffaa6b522877289e848391d0f3e83 | c1ccc(CN2CCCC2)cc1 | C-[N+;H0;D4:1](-C)(-[CH3;D1;+0:2])-[C:3]-[c;H0;D3;+0:4]1:c:c:c:c:c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:2]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 28.7 g (0.15 mol) of 3-[(3-methylpyrrolidin-1-yl) methyl]phenol are heated under reflux together with 100 ml of acrylonitrile and 1.5 ml of 40% methanolic benzyltrimethylammonium hydroxide solution for 18 hours. The excess acrylonitrile is evaporated off under vacuum and the residue is taken up with ether, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether.Primary amine | c1ccccc1 | null | C1CC[NH]C1.c1ccccc1 | Other | C(C=C)#N | null | null | CC1CCN(Cc2cccc(O)c2)C1.C[N+](C)(C)Cc1ccccc1>C(C=C)#N>CC1CCN(Cc2cccc(OCCCN)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0006ecc213bc472e9ba0b4816a5ec055 | CC1CCN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 | CC1CN(CC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1CN(CC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[cH:23]2)[CH2:24]1.Br[c:17]1[n:18][n:19][c:20]([NH2:21])[s:22]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH:16][c:17]3[n:18][n:19][c:20]([NH2:21... | CC1CCN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1 | CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(3-methylpyrrolidin-1-yl) methyl]phenoxy]propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]C1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CCN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf3b640751c84f7a99cdc5a255094fe4 | CC1CCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 | CC1CN(CC1)CC=1C=C(OCCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1CN(CC1)CC=1C=C(OCCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[cH:24]2)[CH2:25]1.Br[c:18]1[n:19][n:20][c:21]([NH2:22])[s:23]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][c:18]3[n:19][n:2... | CC1CCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1 | CC1CCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCC2)cc(OCCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 4-[3-[(3-methylpyrrolidin-1-yl) methyl]-phenoxy]-butanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]C1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CCN(Cc2cccc(OCCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCCNc3nnc(N)s3)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-292aa25057144f35afec883a6f5179f1 | CC1CCCC(C)N1Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1>>CC1CCCC(C)N1Cc1cccc(OCCCNc2nnc(N)s2)c1 | CC1N(C(CCC1)C)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1N(C(CCC1)C)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[N:8]1[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][CH2:18][NH2:19])[cH:26]1.Br[c:20]1[n:21][n:22][c:23]([NH2:24])[s:25]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[N:8]1[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][CH2:18]... | CC1CCCC(C)N1Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1 | CC1CCCC(C)N1Cc1cccc(OCCCNc2nnc(N)s2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(2,6-dimethyl-1-piperidinyl) methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]CC1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CCCC(C)N1Cc1cccc(OCCCN)c1.Nc1nnc(Br)s1>>CC1CCCC(C)N1Cc1cccc(OCCCNc2nnc(N)s2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-aaf7956a33af4e4cbdda27dc4ddd228e | CC1CC(C)CN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CC(C)CN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 | CC1CN(CC(C1)C)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1CN(CC(C1)C)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH:4]([CH3:5])[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[cH:25]2)[CH2:26]1.Br[c:19]1[n:20][n:21][c:22]([NH2:23])[s:24]1>>[CH3:1][CH:2]1[CH2:3][CH:4]([CH3:5])[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][NH:18... | CC1CC(C)CN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1 | CC1CC(C)CN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(3,5-dimethyl-1-piperidinyl) methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]CC1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CC(C)CN(Cc2cccc(OCCCN)c2)C1.Nc1nnc(Br)s1>>CC1CC(C)CN(Cc2cccc(OCCCNc3nnc(N)s3)c2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-240cfb306ec74f67bf05dd8b84d5b09c | CC1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 | CC1CCN(CC1)CC=1C=C(OCCCN)C=CC1.BrC1=NN=C(S1)N>>CC1CCN(CC1)CC=1C=C(OCCCNC=2SC(=NN2)N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[cH:23]2)[CH2:24][CH2:25]1.Br[c:17]1[n:18][n:19][c:20]([NH2:21])[s:22]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][NH:16][c:17]3[n:18][n:19][c:20]... | CC1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1 | CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | a5a25331c98f53fcb8c1245a1f93616c8ad6d4eafdf0b4a25825ce875023e7f0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(OCCCNc2nncs2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[#7;a:6]:1 | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 51 from 3-[3-[(4-methyl-1-piperidinyl)methyl]phenoxy]-1-propanamine and 5-bromo-1,3,4-thiadiazole-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1nncs1 | c1nncs1 | C1CC[NH]CC1.c1ccccc1.c1nncs1 | HBr | null | null | null | CC1CCN(Cc2cccc(OCCCN)c2)CC1.Nc1nnc(Br)s1>>CC1CCN(Cc2cccc(OCCCNc3nnc(N)s3)c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-345b767ded454aba98cfa55ad8b0d94c | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.CS(=O)(=O)c1ccc(OCCCCBr)c(C=O)c1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCBr | BrCCCCOC1=C(C=O)C=C(C=C1)S(=O)(=O)C.C(CC(=O)C)(=O)OC.COC(\C=C(\C)/N)=O>>BrCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC | [NH2:8]/[C:9]([CH3:10])=[CH:11]\[C:12](=[O:13])[O:14][CH3:15].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH3:7].O=[CH:16][c:17]1[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25][c:26]1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:... | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.CS(=O)(=O)c1ccc(OCCCCBr)c(C=O)c1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCBr | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]/[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]/[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C;D1;H3:12]-[C:13]1=[C;H0;D3;+0:15](-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19])-[CH;D3;+0:8](-[c:9](:[... | 53 | [{"value": 53.0, "product": "BrCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.6 g of 2-(4-bromobutoxy)-5-methylsulfonylbenzaldehyde, 2.6 g of methyl acetoacetate and 2.9 g of 3-aminocrotonic acid methyl ester were dissolved in 16 ml of isopropanol, and the solution was heated for 5 hours. After cooling, precipitated crystals were collected by filtration, and recrystallized from methanol to giv... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | C(C)(C)O | null | null | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.CS(=O)(=O)c1ccc(OCCCCBr)c(C=O)c1>C(C)(C)O>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3665349bb73843b2bd458f0e58887d4d | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN1C(=O)c2ccccc2C1=O>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN | C1(C=2C(C(N1CCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)=O)=CC=CC2)=O.O.NN>>NCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC | O=C1c2ccccc2C(=O)[N:32]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27][c:26]1[c:17]([CH:16]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]2[C:12](=[O:13])[O:14][CH3:15])[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10]... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN1C(=O)c2ccccc2C1=O | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | C1=CC(c2ccccc2)C=CN1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 48.2 | [{"value": 48.2, "product": "NCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6.9 g of dimethyl 4-[2-(4-phthalimidobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 5.9 g of hydrazine monohydrate in 170 ml of % ethanol(water: 5%) was refluxed under heating for 6 hours. After cooling, the reaction solution was concentrated under reduced pressure.... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1=CNC=CC1.c1ccccc1 | HO- | C(C)O | null | null | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN1C(=O)c2ccccc2C1=O>C(C)O>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f9daf0c7d744415583c393b130452832 | C1CCNCC1.CC(=O)O.CCOC(=O)CC(=O)CC.O=Cc1cc([N+](=O)[O-])ccc1OCCCCCl>>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCCl | ClCCCCOC1=C(C=O)C=C(C=C1)[N+](=O)[O-].C(CC)(=O)CC(=O)OCC.N1CCCCC1.C(C)(=O)O.C1=CC=CC=C1>>C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCCl)C(=O)OCC)C | C1[CH2:1][CH2:2][NH:9][CH2:7][CH2:8]1.[OH:3][C:4](=[O:5])[CH3:6].O=[C:10]([CH2:11][CH3:12])[CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18].O=[CH:19][c:20]1[cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27][c:28]1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C... | C1CCNCC1.CC(=O)O.CCOC(=O)CC(=O)CC.O=Cc1cc([N+](=O)[O-])ccc1OCCCCCl | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCCl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a2fd69c662911dd719907b7d2e097ca28d6af203cc3e753f2c7367b1677f0008 | e1ee724b20b39aa585c68c2275a6171afd6c7eee6c4b0bfb8a3e8094e9eeb7a6 | C1=CC(c2ccccc2)C=CN1 | C1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[NH;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-1.O=[C;H0;D3;+0:6](-[C:7]-[C;D1;H3:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13].O=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17].[CH3;D1;+0:18]-[C:19](=[O;D1;H0:20])-[OH;D1;+0:21]>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:9]1=[C;H0;D3;+0:6]... | null | [] | null | null | null | null | In 106 ml of dry benzene were dissolved 13.0 g of 2-(4-chlorobutoxy)-5-nitrobenzaldehyde, 7.28 g of ethyl propionylacetate, 0.20 ml of piperidine and 0.62 ml of acetic acid, and the solution was refluxed for 9 hours while removing water using a Dean-Stark trap. After cooling the reaction solution, 6.52 g of ethyl 3-ami... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Ketone.Ester.Secondary amine | Enamine.Enamine.Ester.Ester | C1CCNCC1 | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | null | C1CCNCC1.CC(=O)O.CCOC(=O)CC(=O)CC.O=Cc1cc([N+](=O)[O-])ccc1OCCCCCl>>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ae47bef14953469995ecbc681d8031ce | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN1C(=O)c2ccccc2C1=O>>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN | C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCN1C(C=2C(C1=O)=CC=CC2)=O)C(=O)OCC)C.O.NN>>NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)CC)C(=O)OCC | O=C1c2ccccc2C(=O)[N:34]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29][c:28]1[c:20]([CH:19]2[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:7]([CH3:8])[NH:9][C:10]([CH2:11][CH3:12])=[C:13]2[C:14](=[O:15])[O:16][CH2:17][CH3:18])[cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8... | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN1C(=O)c2ccccc2C1=O | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | C1=CC(c2ccccc2)C=CN1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 65.7 | [{"value": 65.7, "product": "NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)CC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 12.4 g of diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 10.4 g of hydrazine monohydrate in 270 ml of 95% ethanol (water: 5%) was refluxed under heating for 10 hours. After cooling the reaction solution, the solution was concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1=CNC=CC1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN1C(=O)c2ccccc2C1=O>C(C)O>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d45e5598631844f08585adfaf6246f37 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCN.c1ccc(C2CO2)cc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCNCC(O)c1ccccc1 | NCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC.C1C(C2=CC=CC=C2)O1>>OC(CNCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:13])[O:14][CH3:15])[CH:16]1[c:17]1[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][c:25]1[O:26][CH2:27][CH2:28][NH2:29].[CH2:30]1[CH:31]([c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[O:32]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([C... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCN.c1ccc(C2CO2)cc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCNCC(O)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCNCCc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[c:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[OH;D1;+0:7])-[c:4] | 19.3 | [{"value": 19.3, "product": "OC(CNCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | In 30 ml of N,N-dimethylformamide were dissolved 2 g of dimethyl 4-[2-(2-aminoethoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.6 g of styrene oxide, and the solution thus formed was allowed to stand for 2 days at room temperature. The reaction solution was concentrated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CN(C=O)C | null | 48 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCN.c1ccc(C2CO2)cc1>CN(C=O)C>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCNCC(O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3c162ac0662642e38fab20fffb0079d3 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC.C1(=CC=CC=C1)OCC1CO1>>OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:13])[O:14][CH3:15])[CH:16]1[c:17]1[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][c:25]1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31].[CH2:32]1[CH:33]([CH2:35][O:36][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[O:34]1>>[CH3:1][O:... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCCCNCCCOc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 51.5 | [{"value": 51.5, "product": "OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 1,300 ml of methanol were dissolved 13 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 4.5 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CO | null | null | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>CO>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f7d6b5a0a92348dbad2bb63286d5a2ea | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC.C1(=CC=CC=C1)OCC1CO1>>OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC)COC1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[CH:18]1[c:19]1[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26][c:27]1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33].[CH2:34]1[CH:35]([CH2:37][O:38][c:39]2[cH:40][cH:41][cH:42][cH:43][cH:44]2)[O:... | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1 | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCCCNCCCOc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 31.9 | [{"value": 31.9, "product": "OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC)COC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 500 ml of methanol were dissolved 5.2 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.7 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was sub... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CO | null | null | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>CO>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-95616be347ab446d930fbf2dcab17c14 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN.c1ccc(OCC2CO2)cc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCNCC(O)COc1ccccc1 | NCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC.C1(=CC=CC=C1)OCC1CO1>>OC(CNCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:13])[O:14][CH3:15])[CH:16]1[c:17]1[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25][c:26]1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32].[CH2:33]1[CH:34]([CH2:36][O:37][c:38]2[cH:39][cH:40][cH:41][cH:42][cH:43]2)[O:35]1>>[... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN.c1ccc(OCC2CO2)cc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCNCC(O)COc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCCCNCCCOc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 30.9 | [{"value": 30.9, "product": "OC(CNCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 44 ml of methanol were dissolved 2.57 g of dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (obtained in Reference Example 2) and 0.83 g of glycidyl phenyl ether, and the solution formed was allowed to react at room temperature for 43 hours and concentrated und... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CO | null | null | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCN.c1ccc(OCC2CO2)cc1>CO>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc(S(C)(=O)=O)ccc1OCCCCNCC(O)COc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-065611ec619f447a9db829eeb34ff8e9 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.COc1ccc(OCC2CO2)cc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccc(OC)cc1 | NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC.COC1=CC=C(C=C1)OCC1CO1>>OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=C(C=C1)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:13])[O:14][CH3:15])[CH:16]1[c:17]1[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][c:25]1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31].[CH2:32]1[CH:33]([CH2:35][O:36][c:37]2[cH:38][cH:39][c:40]([O:41][CH3:42])[cH:43][cH:44]2)[O:3... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.COc1ccc(OCC2CO2)cc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccc(OC)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCCCNCCCOc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 30 | [{"value": 30.0, "product": "OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 200 ml of methanol were dissolved 2 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.84 g of glycidyl 4-methoxyphenyl ether, and the solution was refluxed under heating for 3 hours. The solvent was distilled off under reduced pressure. The residue was subject... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CO | null | null | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.COc1ccc(OCC2CO2)cc1>CO>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccc(OC)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f3c02f79686496e8840329c81d3621d | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)CC)C(=O)OCC.C1(=CC=CC=C1)OCC1CO1>>C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCNCC(COC1=CC=CC=C1)O)C(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH2:11][CH3:12])=[C:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[CH:19]1[c:20]1[cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27][c:28]1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34].[CH2:35]1[CH:36]([CH2:38][O:39][c:40]2[cH:41][cH:42][cH:43][cH:44][cH:... | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1 | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | C1=CC(c2ccccc2OCCCCNCCCOc2ccccc2)C=CN1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[CH2;D2;+0:6]-[C:5](-[C:4])-[OH;D1;+0:7] | 20.1 | [{"value": 20.1, "product": "C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCNCC(COC1=CC=CC=C1)O)C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 46 ml of methanol were dissolved 4.62 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.46 g of glycidyl phenyl ether, and the solution formed was refluxed under heating for 15 hours. After cooling the reaction solution, the solution was concentrated under ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | CO | null | null | CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCN.c1ccc(OCC2CO2)cc1>CO>CCOC(=O)C1=C(C)NC(CC)=C(C(=O)OCC)C1c1cc([N+](=O)[O-])ccc1OCCCCNCC(O)COc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-42e9e6685d48461cbe538debba22bce7 | ClC/C=C/CCl.O=Cc1cc([N+](=O)[O-])ccc1O>>O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl | O.[N+](=O)([O-])C1=CC=C(C(C=O)=C1)O.ClC\C=C\CCl.C([O-])([O-])=O.[K+].[K+]>>ClC/C=C/COC1=C(C=O)C=C(C=C1)[N+](=O)[O-] | Cl[CH2:13]/[CH:14]=[CH:15]/[CH2:16][Cl:17].[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][c:11]1[OH:12]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][c:11]1[O:12][CH2:13]/[CH:14]=[CH:15]/[CH2:16][Cl:17] | ClC/C=C/CCl.O=Cc1cc([N+](=O)[O-])ccc1O | O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl | 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]-[Cl;D1;H0:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[Cl;D1;H0:5]-[C:4]/[C:3]=[C:2]/[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:7]=[O;D1;H0:6] | 43.3 | [{"value": 43.3, "product": "ClC/C=C/COC1=C(C=O)C=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 8 g of 5-nitrosalicylaldehyde, 30.8 g of trans-1,4-dichloro-2-butene and 13.2 g of potassium carbonate in 35 ml of dimethylformamide was stirred at room temperature for 19 hours, and further stirred at 80°-87° C. (outside temperature) for 2 hours. The mixture was allowed to cool, poured into 80 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 2 | ClC/C=C/CCl.O=Cc1cc([N+](=O)[O-])ccc1O>CN(C=O)C>O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-062c826e74c641139e59148b875c82f5 | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl | ClC/C=C/COC1=C(C=O)C=C(C=C1)[N+](=O)[O-].C(CC(=O)C)(=O)OC.N\C(=C/C(=O)OC)\C>>ClC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC | [NH2:8]/[C:9]([CH3:10])=[CH:11]\[C:12](=[O:13])[O:14][CH3:15].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH3:7].O=[CH:16][c:17]1[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][c:25]1[O:26][CH2:27]/[CH:28]=[CH:29]/[CH2:30][Cl:31]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:... | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]/[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]/[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C;D1;H3:12]-[C:13]1=[C;H0;D3;+0:15](-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19])-[CH;D3;+0:8](-[c:9](:[... | 48.8 | [{"value": 48.8, "product": "ClC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.2 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde, 2.4 g of methyl acetoacetate and 2.3 g of methyl 3-aminocrotonate was dissolved in 30 ml of iso-propanol, and the solution obtained was refluxed for 3.5 hours under heating. After cooling, the precipitated crystals were collected by filtration to give 4.4 g of... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | C(C)(C)O | null | null | COC(=O)/C=C(/C)N.COC(=O)CC(C)=O.O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl>C(C)(C)O>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-90c6a3b9e7fa46c781833496bc0982aa | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl.NC[C@H](O)COc1ccccc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CNC[C@H](O)COc1ccccc1.Cl | ClC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC.O[C@@H](CN)COC1=CC=CC=C1>>Cl.O[C@@H](CNC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3:10])=[C:11]([C:12](=[O:13])[O:14][CH3:15])[CH:16]1[c:17]1[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][c:25]1[O:26][CH2:27]/[CH:28]=[CH:29]/[CH2:30][Cl:43].[NH2:31][CH2:32][C@H:33]([OH:34])[CH2:35][O:36][c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1>>[C... | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl.NC[C@H](O)COc1ccccc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CNC[C@H](O)COc1ccccc1.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C1=CC(c2ccccc2OC/C=C/CNCCCOc2ccccc2)C=CN1 | [#8:1]-[C:2]/[C:3]=[C:4]/[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8:1]-[C:2]/[C:3]=[C:4]/[CH2;D2;+0:5]-[NH;D2;+0:9]-[C:8]-[C:7].[ClH;D0;+0:6] | 42.4 | [{"value": 42.4, "product": "Cl.O[C@@H](CNC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.1 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 5.8 g (S)-2-hydroxy-3-phenoxypropylamine were dissolved in 35 ml of acetonitrile, and the resultant solution was refluxed under heating for 2 hours. The reaction solution was concentrated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1=CNC=CC1.c1ccccc1.c1ccccc1 | null | C(C)#N | null | null | COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl.NC[C@H](O)COc1ccccc1>C(C)#N>COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CNC[C@H](O)COc1ccccc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d49eb61e2fd44989265dbcff16dd028 | COC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1>>COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | CC=1N=C(NC(C1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=CC=C1>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[N:8]=[C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[NH:16][CH:17]1[c:18]1[cH:19][cH:20][cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]1-[c:18]1[cH:19][cH:2... | COC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1 | COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 452876530f92c752f96ca55adf3cb89bf603ee57951274f00f7008f3d6ae24dd | f5606b90db756ee719828c8eb5153bc09c7b83b577c3581dd077ec45190954cf | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5]1=[C;H0;D3;+0:6](-[C;D1;H3:7])-[N;H0;D2;+0:8]=[C;H0;D3;+0:9](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[NH;D2;+0:15]-[CH;D3;+0:16]-1-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[c;H0;D3;+0:16](-[c;H0;D3;... | 67.8 | [{"value": 67.8, "product": "CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl 4-methyl-2-phenyl-6-(3-nitrophenyl)-1,6-dihydro-5-pyrimidinecarboxylate (475 g) in chloroform (5 l) was added activated manganese dioxide (1.9 kg) and the mixture was refluxed for two hours with stirring vigorously. After allowing to cool to room temperature, manganese dioxide was filtered off. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Ester | C1=CN=CNC1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | COC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-75a16eec411946899f802c923c0a7c7d | COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO | [H-].[Al+3].[Li+].[H-].[H-].[H-].CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC.C(C)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | CO[C:23]([c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)=[O:24]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c... | COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4](-[c:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[C;D1;H3:10]>>[C;D1;H3:10]-[c:9]1:[#7;a:8]:[c:7]:[#7;a:6]:[c:4](-[c:5]):[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 72.5 | [{"value": 72.5, "product": "OCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of lithium aluminum hydride (12.24 g) in a mixture of dry tetrahydrofuran (180 ml) and diethyl ether (360 ml) was dropwise added a solution of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (45 g) in dry tetrahydrofuran (180 ml) under cooling at -50°~-40° C. The excess lithium alumin... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | null | COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>O1CCCC1>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5445957897b14e47a375be80f7ca2538 | BrP(Br)Br.CC1=C(O)C(c2cccc([N+](=O)[O-])c2)=NC(c2ccccc2)N1C>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr | C([O-])([O-])=O.[K+].[K+].P(Br)(Br)Br.O1CCCC1.OC=1C(=NC(N(C1C)C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].O1CCCC1>>BrCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | BrP(Br)[Br:24].O[C:22]1=[C:2]([CH3:1])[N:3]([CH3:23])[CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[N:11]=[C:12]1[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[... | BrP(Br)Br.CC1=C(O)C(c2cccc([N+](=O)[O-])c2)=NC(c2ccccc2)N1C | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 0569c10d54a7ed4c88674f90d24c0b6d31fe5f6538ec1f20678cbdda06acd18d | ff8a48637e4a3e8c893fa0884b576c04f6c8615006ce9c5e4c1e66a3c62f9c37 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[C;H0;D3;+0:2]1=[C;H0;D3;+0:3](-[C;D1;H3:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:6])-[CH;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[N;H0;D2;+0:13]=[C;H0;D3;+0:14]-1-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:6]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:14](-[c;H0;D3;+0:1... | null | [] | null | null | 4 | HOUR | To a solution of phosphorus tribromide (16.85 g) in a mixture of benzene (150 ml) and tetrahydrofuran (150 ml) was dropwise added a solution of 5-hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g) in tetrahydrofuran (150 ml) under cooling at 7°-10° C. After stirring for 4 hours at the same temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Substituted imine.Enol | Primary halide | C1=C[NH]CN=C1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HBr | C1=CC=CC=C1 | null | 4 | BrP(Br)Br.CC1=C(O)C(c2cccc([N+](=O)[O-])c2)=NC(c2ccccc2)N1C>C1=CC=CC=C1>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-48a09d41fff04695972f49c0700533bc | CC(=O)CC(C)=O.O=Cc1cccc([N+](=O)[O-])c1>>CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O | C(C)OCC.[N+](=O)([O-])C=1C=C(C=O)C=CC1.C(C)(=O)CC(C)=O.C(C)(=O)O>>C(C)(=O)C(C(=O)C)=CC1=CC(=CC=C1)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[CH2:4][C:15]([CH3:16])=[O:17].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]1>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]1)[C:15]([CH3:16])=[O:17] | CC(=O)CC(C)=O.O=Cc1cccc([N+](=O)[O-])c1 | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O | null | N1CCCCC1 | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | 8b042f2e077bfb0959f760e380accd55e8432e0734286e7ddad30bd56258afda | 861adc1a1cbf8a1d99b16533e8a5effc5c1b49887bf237eff94531749e0a81b9 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](-[C;D1;H3:10])=[O;D1;H0:11] | 53.5 | [{"value": 53.5, "product": "C(C)(=O)C(C(=O)C)=CC1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-nitrobenzaldehyde (20 g), acetylacetone (13.25 g), acetic acid (1.58 g), and piperidine (0.45 g) in benzene (20 ml) was refluxed for 1 hour under azeotropic dehydration. To the reaction mixture was added diethyl ether (100 ml). The mixture was washed with water (50 ml) and a saturated aqueous solution of... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ketone | Ketone.Ketone | null | null | c1ccccc1 | HO- | N1CCCCC1.C1=CC=CC=C1 | null | null | CC(=O)CC(C)=O.O=Cc1cccc([N+](=O)[O-])c1>N1CCCCC1.C1=CC=CC=C1>CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c3b37e31e5d14c2ab67233d672266e5e | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.N=C(N)c1ccccc1>>CC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1 | C(C)(=O)OCC.C(C)(=O)C(C(=O)C)=CC1=CC(=CC=C1)[N+](=O)[O-].Cl.C(C1=CC=CC=C1)(=N)N.C(C)N(CC)CC>>C(C)(=O)C1=C(N=C(NC1C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=CC=C1)C | O=[C:5]([C:4]([C:2]([CH3:1])=[O:3])=[CH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1)[CH3:6].[NH:7]=[C:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[NH2:15]>>[CH3:1][C:2](=[O:3])[C:4]1=[C:5]([CH3:6])[N:7]=[C:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15][CH:16]1[c:17]1[cH:18][cH:19][cH... | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.N=C(N)c1ccccc1 | CC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1 | null | null | C(CCC)O | Functional Group Addition | OtherReaction | 743b321ea466c3b99e8043e5a7282d758af73b19a6ca0ed8b03d5e2870baf66f | 2bf067cc07383211e0c461d3787cd2d22c0bd5189d7d20d0b5ee9274e5599b01 | C1=CC(c2ccccc2)NC(c2ccccc2)=N1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])=[O;D1;H0:10].[NH2;D1;+0:11]-[C:12](=[NH;D1;+0:13])-[c:14]>>[C;D1;H3:9]-[C:8](=[O;D1;H0:10])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[N;H0;D2;+0:13]=[C:12](-[c:14])-[NH;D2;+0:11]-[CH;D3;+0:4]-1-[c:5](:[c:6]):[c:7] | 31 | [{"value": 31.0, "product": "C(C)(=O)C1=C(N=C(NC1C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 1-acetyl-1-(3-nitrobenzyliden)acetone (10 g), benzamidine hydrochloride (8.06 g) and triethylamine (8.4 ml) in n-butanol (100 ml) was refluxed for 2 hours. The reaction mixture was added ethyl acetate (100 ml), washed with water (100 ml) and 5% hydrochloric acid (100 ml) successively. The solvent was evapo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | Ketone.Secondary amine | null | C1=CN=CNC1 | C1=CN=CNC1.c1ccccc1.c1ccccc1 | HO- | C(CCC)O | null | 1 | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.N=C(N)c1ccccc1>C(CCC)O>CC(=O)C1=C(C)N=C(c2ccccc2)NC1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-85ec00ae73394616852dbd4678f08fe0 | CC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O | C(C)(=O)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].[BH4-].[Na+]>>OC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c:22]1[C:23]([CH3:24])=[O:25]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:2... | CC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[CH;D3;+0:9](-[C;D1;H3:10])-[OH;D1;+0:11] | 76.2 | [{"value": 76.2, "product": "OC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 5-acetyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (3 g) and sodium borohydride (0.34 g) in methanol (110 ml) was stirred at room temperature for 4 hours. The reaction mixture was evaporated in vacuo and the residue was poured into a mixture of ethyl acetate and water. The separated organic layer was d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | null | CO | null | 4 | CC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>CO>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d873a469a1aa4c19a659d20fa347bd64 | BrP(Br)Br.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br | OC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].P(Br)(Br)Br>>BrC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | BrP(Br)[Br:25].O[CH:23]([c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)[CH3:24]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-... | BrP(Br)Br.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH;D3;+0:2](-[C;D1;H3:3])-[c:4]1:[c:5](-[c:6]):[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-[C;D1;H3:11]>>[Br;H0;D1;+0:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[c:4]1:[c:5](-[c:6]):[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-[C;D1;H3:11] | null | [] | null | null | 5 | HOUR | A solution of 5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.8 g) in tetrahydrofuran (10 ml) was dropped to a solution of phosphorus tribromide (0.34 ml) in tetrahydrofuran (20 ml) under ice cooling. The reaction mixture was stirred for 5 hours at the same condition and poured into ice water and ex... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | 5 | BrP(Br)Br.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)O>O1CCCC1>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b39cab3995b64be78950e30111b58cac | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.COC(OC)N(C)C>>CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1 | COC=1C=C(C(=O)CC(=O)OCC)C=CC1OC.COC(N(C)C)OC>>COC=1C=C(C(=O)C(C(=O)OCC)=CN(C)C)C=CC1OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1.CO[CH:7](OC)[N:8]([CH3:9])[CH3:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([CH3:9])[CH3:10])[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1 | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.COC(OC)N(C)C | CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 2070759bbd858ab0921591417d06ceb70d9ac10faec59de73877361a6f0f54fd | 20445ba43f0305567ebc2de9a9cc93201db418c8c15029402df1028694739caf | c1ccccc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:10](=[O;D1;H0:11])-[c:12] | null | [] | null | null | null | null | A solution of ethyl 2-(3,4-dimethoxybenzoyl)-acetate (25.2 g) and N,N-dimethylformamide dimethyl acetal (17.9 g) in tetrahydrofuran (100 ml) was refluxed for 18 hours under stirring. The reaction mixture was evaporated in vacuo to give ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31.09) as an oil.
... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether | Enamine | null | null | c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.COC(OC)N(C)C>O1CCCC1>CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-341f97577ef543daa52fec737b242a18 | CC(=N)N.CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1>>CCOC(=O)c1cnc(C)nc1-c1ccc(OC)c(OC)c1 | COC=1C=C(C(=O)C(C(=O)OCC)=CN(C)C)C=CC1OC.Cl.C(C)(=N)N.C(C)N(CC)CC>>CC1=NC=C(C(=N1)C1=CC(=C(C=C1)OC)OC)C(=O)OCC | [NH2:8][C:9]([CH3:10])=[NH:11].CN(C)[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:12](=O)[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([CH3:10])[n:11][c:12]1-[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1 | CC(=N)N.CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1 | CCOC(=O)c1cnc(C)nc1-c1ccc(OC)c(OC)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 576c2e9a4ba3e1d4269bea118a69f80f88e096d0937ca7bcd23052a0802705e0 | 886f2e85a82b0f3d3beb2dddeeecea7badac2f543d0f6e9b3d49c4063123e7c7 | c1ccc(-c2ccncn2)cc1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[NH;D1;+0:16]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:15]:[c;H0;D3;+0:14](-[C;D1;H3:13]):[n;H0;D2;+0:16]:... | 45.9 | [{"value": 45.9, "product": "CC1=NC=C(C(=N1)C1=CC(=C(C=C1)OC)OC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31 g), acetoamidine hydrochloride (13.3 g) and triethylamine (16.2 g) in ethanol (200 ml) was refluxed for 10 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Primary amine | Ester | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O | null | null | CC(=N)N.CCOC(=O)C(=CN(C)C)C(=O)c1ccc(OC)c(OC)c1>C(C)O>CCOC(=O)c1cnc(C)nc1-c1ccc(OC)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8bcae92e09434b79989104d97d819e5f | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(=O)N1CCN(C)CC1.N=C(N)c1ccccc1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(=O)N1CCN(C)CC1 | CN1CCN(CC1)C(=O)C(=CC1=CC(=CC=C1)[N+](=O)[O-])C(C)=O.Cl.C(C1=CC=CC=C1)(=N)N.C(C)N(CC)CC>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)N1CCN(CC1)C | O=[C:2]([CH3:1])[C:22](=[CH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)[C:23](=[O:24])[N:25]1[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]1.[NH:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH2:11]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[c... | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(=O)N1CCN(C)CC1.N=C(N)c1ccccc1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(=O)N1CCN(C)CC1 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 033592cf85bde1eecf5df9a935388df53853b5e27177177b6d392deee27485d9 | 8182c33d66a1c51620dac2e3d5b839c3fec60d5b5668262efc6be8b10c115a58 | O=C(c1cnc(-c2ccccc2)nc1-c1ccccc1)N1CCNCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[C:14].[NH2;D1;+0:15]-[C;H0;D3;+0:16](=[NH;D1;+0:17])-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22]>>[C:13]-[#7:12](-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[c;H0;D3... | null | [] | null | null | null | null | A mixture of 2-(4-methylpiperazin-1-ylcarbonyl)-1-(3-nitrophenyl)-1-buten-3-one (20 g), benzamidine hydrochloride (9.9 g) and triethylamine (11.4 ml) in n-butanol (200 ml) was refluxed for 2 hours. After evaporating the solvent, the residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml). The se... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HO- | C(CCC)O | null | null | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(=O)N1CCN(C)CC1.N=C(N)c1ccccc1>C(CCC)O>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(=O)N1CCN(C)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-58f90a0544c441568e26fdbf9e238eb3 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C=O | OCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]>>C(=O)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c:22]1[CH2:23][OH:24]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c:2... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C=O | null | [O-2].[O-2].[Mn+4] | C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[CH2;D2;+0:9]-[OH;D1;+0:10]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[CH;D2;+0:9]=[O;H0;D1;+0:10] | 50.3 | [{"value": 50.3, "product": "C(=O)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g) in ethyl acetate (10 ml) was added activated manganese dioxide (2.4 g) and the mixture was refluxed for 2 hours under stirring vigorously. After allowing to stand to room temperature, manganese dioxide was filtered off. The filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(C)(=O)OCC | null | null | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO>[O-2].[O-2].[Mn+4].C(C)(=O)OCC>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dcd8d2b7abf04ce0bdd51fdc309fc6a6 | Br.COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>>COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC.Br.C(C)(=O)O>>BrCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC | [BrH:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][Br:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]1-[c:19... | Br.COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | null | null | C(C)(=O)O | Functional Group Addition | Bromination | ca537da020427de460728e4a46844f31fb9ac78bacba6b64ec890c6a63cf7c56 | 814107e7eb6098cbc76bc1ba0b008fd579e7d14ef25761860dc78b2c0289c23e | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[CH3;D1;+0:10].[BrH;D0;+0:11]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[CH2;D2;+0:10]-[Br;H0;D1;+0:11] | 66.4 | [{"value": 66.4, "product": "BrCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (5 g), pyridinium bromide perbromide (5.6 g) and 25% hydrogen bromide-acetic acid (5 ml) in acetic acid (200 ml) was stirred for 2 hours at room temperature. The reaction mixture was poured into ice water (200 ml) and stirred for 10 minutes... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary halide | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | null | C(C)(=O)O | null | 2 | Br.COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>C(C)(=O)O>COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f9e672f1e9b44c4186cfbb5036d7a208 | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C)CC1 | BrCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].CN1CCNCC1>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C | [NH:24]1[CH2:25][CH2:26][N:27]([CH3:28])[CH2:29][CH2:30]1.Br[CH2:23][c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:1... | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2ncc(CN3CCNCC3)c(-c3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3](-[c:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C;D1;H3:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:3](-[c:4]):[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | null | null | null | null | A mixture of 5-bromomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g), N-methylpiperazine (1.17 g) in isopropyl alcohol (15 ml) was refluxed for 6 hours. After evaporating the solvent, the residue was dissolved in chloroform, washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cncnc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(C)(C)O | null | null | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CBr>C(C)(C)O>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7f820da542c94a05a709cf0743a91157 | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)N1CCN(C)CC1 | BrC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].CN1CCNCC1>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)N1CCN(CC1)C | [NH:25]1[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]1.Br[CH:23]([c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)[CH3:24]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH... | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)N1CCN(C)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1ede6a7f71bc7355bda22d7fae3c2f7f89530aa6d4f0e909f8f73998c65893f6 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | c1ccc(-c2ncc(CN3CCNCC3)c(-c3ccccc3)n2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4](-[c:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[C;D1;H3:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C;D1;H3:10]-[c:9]1:[#7;a:8]:[c:7]:[#7;a:6]:[c:4](-[c:5]):[c:3]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 32.4 | [{"value": 32.4, "product": "CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g) and N-methylpiperazine (1.13 g) in isopropylalcohol (15 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on allumina eluting with a mixture of ethyl acetate and n-hexane (1:20... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cncnc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(C)(C)O | null | null | CN1CCNCC1.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br>C(C)(C)O>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)N1CCN(C)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bc3a3701e39b42c0a3d5a904d9d85908 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN.N#C[S-].O=C(Cl)c1ccccc1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1 | [S-]C#N.[NH4+].C(C1=CC=CC=C1)(=O)Cl.C(Cl)(Cl)Cl.NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]>>C(C1=CC=CC=C1)(=O)NC(NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])=S | [CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c:22]1[CH2:23][NH2:24].[C:25]([S-:26])#[N:27].Cl[C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN.N#C[S-].O=C(Cl)c1ccccc1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1 | null | null | O.CC(=O)C | Acylation | OtherReaction | ba32abf48e55d53ef6e0af57f1d7169ed0ac841ff7858c991011fd961a061dc2 | b88d5f877c80e8bb46ad5808630e5b77d7f3aea35cbafadf6b92b5b8202ff7a7 | O=C(NC(=S)NCc1cnc(-c2ccccc2)nc1-c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]:[c:8](-[C:9]-[NH2;D1;+0:10]):[c:11]:[#7;a:12].[N;H0;D1;+0:13]#[C;H0;D2;+0:14]-[S-;H0;D1:15]>>[#7;a:6]:[c:7]:[c:8](-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:14](=[S;H0;D1;+0:15])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:11]:[#7;a:12] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)(=O)NC(NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of ammonium thiocyanate (0.25 g) and benzoyl chloride (0.41 g) in acetone (20 ml) was refluxed for 2 hours, and 5-aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.9 g) in acetone (5 ml) was added thereto. After refluxing for 2 hours, the reaction mixture was poured into a mixture of chloroform (10... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitrile.Primary amine | Thiourea.Secondary amide | null | null | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | O.CC(=O)C | null | null | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN.N#C[S-].O=C(Cl)c1ccccc1>O.CC(=O)C>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f619641739a748e89b0fd89a05ea9aa1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S | C(C1=CC=CC=C1)(=O)NC(NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])=S.[OH-].[Na+]>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CNC(=S)N | O=C(c1ccccc1)[NH:26][C:25]([NH:24][CH2:23][c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)=[S:27]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S | null | null | CO.O | Reduction | Hydrogenolysis of amides/imides/carbamates | 6328dabafc97dccec70704aeab9949d588a2e027ae7e309e707f818d6bad9dae | eb308e50ea59a818e9be36da7e60c01d0f7ab2d0f39e89f35847ab33b6eb422f | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | O=C(-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[#7:4]-[C:2](-[NH2;D1;+0:1])=[S;D1;H0:3] | 95.6 | [{"value": 95.6, "product": "CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CNC(=S)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5-(3-benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.0 g) and sodium hydroxide (0.089 g) in methanol (20 ml) and water (10 ml) was stirred for 1 hour at a room temperature. After evaporating the solvent, water (20 ml) was added thereto and stirred for 30 minutes. The resulting pre... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Secondary amide | Thiourea | c1ccccc1 | null | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | CO.O | null | 1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(=S)NC(=O)c1ccccc1>CO.O>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ef17da84c683468391c7243b8c369f7e | CI.CN(C)C=O.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC1=NCCN1 | CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CNC(=S)N.CI.CN(C=O)C>>N1=C(NCC1)NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | I[CH3:28].C[N:26](C=O)[CH3:27].S=[C:25]([NH:24][CH2:23][c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1)[NH2:29]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][c... | CI.CN(C)C=O.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC1=NCCN1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aa01b8c85c6a5022b17fadf89208d9da413839c60ede86abcc6cb07431ac19d2 | 06ee8f288d420ac865a49d2a78379d3cbe7ef9fd7b532d51e4cc19e6ee099591 | c1ccc(-c2ncc(CNC3=NCCN3)c(-c3ccccc3)n2)cc1 | C-[N;H0;D3;+0:1](-[CH3;D1;+0:2])-C=O.I-[CH3;D1;+0:3].S=[C;H0;D3;+0:4](-[NH2;D1;+0:5])-[#7:6]-[C:7]>>[C:7]-[#7:6]-[C;H0;D3;+0:4]1=[N;H0;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[NH;D2;+0:5]-1 | null | [] | null | null | 7 | HOUR | A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine (0.7 g) and methyl iodide (0.31 g) in N,N-dimethylformamide (20 ml) was stirred for 7 hours at a room temperature. After evaporating the solvent in vacuo, the residual product was dissolved in ethanol (14 ml). Ethylenediamine (0.33 g) was add... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Tertiary amide | Secondary amine | null | C1=NCCN1 | c1cncnc1.c1ccccc1.c1ccccc1.C1=NCCN1 | HI | null | null | 7 | CI.CN(C)C=O.Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC(N)=S>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CNC1=NCCN1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-56106b27cb394ea38b97cd41472b5458 | CN1CCNCC1.COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>>COC(=O)c1c(CN2CCN(C)CC2)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | BrCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC.CN1CCNCC1>>CN1CCN(CC1)CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC | [NH:8]1[CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14]1.Br[CH2:7][c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24](-[c:25]2[cH:26][cH:27][cH:28][c:29]([N+:30](=[O:31])[O-:32])[cH:33]2)[n:23][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C... | CN1CCNCC1.COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | COC(=O)c1c(CN2CCN(C)CC2)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc(CN3CCNCC3)nc(-c3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[#8:9])=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[c:6]:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:14]1-[C:15]-[C:16]-[#7:11]-[C:12]-[C:13]-1 | 23.6 | [{"value": 23.6, "product": "CN1CCN(CC1)CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (1.5 g) in isopropyl alcohol (15 ml) was added N-methylpiperazine (0.88 g) at 70° C. The reaction mixture was stirred for 10 minutes at the same temperature. After evaporating the solvent, the residue was dissolved in a mixture o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | C(C)(C)O | null | 0.166667 | CN1CCNCC1.COC(=O)c1c(CBr)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>C(C)(C)O>COC(=O)c1c(CN2CCN(C)CC2)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1b0e899e852c46f697084b105512427c | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCNCC1.O=C(Cl)c1ccco1>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C(=O)c2ccco2)CC1 | Cl.Cl.CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCNCC1.ClCCl.O1C(=CC=C1)C(=O)Cl>>CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C(=O)C=1OC=CC1 | [CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]2)[c:22]1[CH2:23][N:24]1[CH2:25][CH2:26][NH:27][CH2:35][CH2:36]1.Cl[C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][o:34]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCNCC1.O=C(Cl)c1ccco1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C(=O)c2ccco2)CC1 | null | null | C(C)N(CC)CC | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccco1)N1CCN(Cc2cnc(-c3ccccc3)nc2-c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#8;a:5]:[c:6] | 97.5 | [{"value": 97.5, "product": "CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C(=O)C=1OC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 6-methyl-5-(1-piperazinylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine dihydrochloride (1 g), dichloromethane (10 ml) and triethylamine (0.48 g), was added 2-furoyl chloride (0.31 g) at 5° C. under ice cooling. After stirring for 1 hour at the same temperature, the reaction mixture was concentrated under... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1cncnc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccoc1 | HCl | C(C)N(CC)CC | null | 1 | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCNCC1.O=C(Cl)c1ccco1>C(C)N(CC)CC>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1CCN(C(=O)c2ccco2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-875c847cb5274fd89a51931bb3c68eed | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1C(=O)c2ccccc2C1=O>>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN | CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1C(C=2C(C1=O)=CC=CC2)=O.O.NN>>NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-] | O=C1c2ccccc2C(=O)[N:24]1[CH2:23][c:22]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1C(=O)c2ccccc2C1=O | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3](:[c:4]:[#7;a:5]):[c:6]:[#7;a:7])-C(=O)-c2:c:c:c:c:c:2-1>>[#7;a:5]:[c:4]:[c:3](-[C:2]-[NH2;D1;+0:1]):[c:6]:[#7;a:7] | 22.8 | [{"value": 22.8, "product": "NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 6-methyl-4-(3-nitrophenyl)-5-phthalimidomethyl-2-phenylpyrimidine (6.9 g) and hydrazine monohydrate (0.8 g) in ethanol (140 ml) was refluxed for 6 hours. After filtering off the insolubles, the filtrate was poured into a suspension of chloroform (200 ml) and water (300 ml) under stirring. The organic la... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN1C(=O)c2ccccc2C1=O>C(C)O>Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CN |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-39086401e8144ed4a96b7c62ec12a729 | CC(=O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>>CC(O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | C(C)(=O)C=1C(=NC(=NC1CCN(C)C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-].[BH4-].[Na+].O.C(Cl)(Cl)Cl>>CN(CCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)O)C | [CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH2:6][CH2:7][N:8]([CH3:9])[CH3:10])[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][c:20]1-[c:21]1[cH:22][cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29]1>>[CH3:1][CH:2]([OH:3])[c:4]1[c:5]([CH2:6][CH2:7][N:8]([CH3:9])[CH3:10])[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:1... | CC(=O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | CC(O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ccnc(-c3ccccc3)n2)cc1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11]>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1-[CH;D3;+0:9](-[C;D1;H3:10])-[OH;D1;+0:11] | 19.9 | [{"value": 19.9, "product": "CN(CCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5-acetyl-6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (1 g) and sodium borohydride (0.1 g) in methanol (40 ml) was stirred for 1 hour. The reaction mixture was poured into a mixture of water and chloroform and adjusted the pH to 9. The extract was dried over magnesium sulfate and evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | null | CO | null | 1 | CC(=O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1>CO>CC(O)c1c(CCN(C)C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-03a3e9fdc377495d8579edee92e18c46 | Cl>>Cl | CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C=O.Cl>>Cl.CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C=O | [ClH:32]>>[ClH:32] | Cl | Cl | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 10 | CELSIUS | 2 | HOUR | A mixture of 6-methyl-5-(4-formylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (4.5 g) and hydrochloric acid (2 ml) in methyl alcohol (45 ml) was stirred at 10° C. for 2 hours. The resulting precipitates were collected by filtration, washed with methyl alcohol and dried in vacuo to give 6-methyl-5-(4-formy... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | 10 | 2 | Cl>CO>Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0970fc1f0ddc4dc68f97748679c31c19 | C=O.CC(C)(C)c1ccc(O)cc1.Oc1ccccc1.[OH-]>>CC(C)(C)c1cc(CO)c(O)c(CO)c1 | C=O.[OH-].[Na+].C(C)(C)(C)C1=CC=C(C=C1)O.Cl.C1(=CC=CC=C1)O>>C(C)(C)(C)C1=CC(=C(C(=C1)CO)O)CO | [CH2:13]=[O:14].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:10]([OH:11])[cH:12][cH:15]1.Oc1cccc[cH:8]1.[OH-:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][OH:9])[c:10]([OH:11])[c:12]([CH2:13][OH:14])[cH:15]1 | C=O.CC(C)(C)c1ccc(O)cc1.Oc1ccccc1.[OH-] | CC(C)(C)c1cc(CO)c(O)c(CO)c1 | null | null | C(Cl)(Cl)Cl.O | Heteroatom Alkylation and Arylation | OtherReaction | 0e2e08bcfeb94fbc7851869a08248baad1394a086907daebda731e4c7bf65f8c | 04626bf3ac4338ffa447e71355fb787257e7f59940514ea44a235f793b80d636 | c1ccccc1 | O-c1:[cH;D2;+0:1]:c:c:c:c:1.[CH2;D1;+0:2]=[O;H0;D1;+0:3].[O;D1;H1:4]-[c:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1.[OH-;D0:11]>>[O;D1;H1:4]-[c:5]1:[c;H0;D3;+0:6](-[CH2;D2;+0:2]-[OH;D1;+0:3]):[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[OH;D1;+0:11] | null | [] | null | null | null | null | 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Aromatic alcohol | Primary alcohol.Primary alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(Cl)(Cl)Cl.O | null | null | C=O.CC(C)(C)c1ccc(O)cc1.Oc1ccccc1.[OH-]>C(Cl)(Cl)Cl.O>CC(C)(C)c1cc(CO)c(O)c(CO)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-90f1210b5010478582a8b8c2ecc022ac | C=C(C)C(=O)OCCN=C=O.OCCNCCO>>C=C(C)C(=O)OCCNC(=O)N(CCO)CCO | C(C(=C)C)(=O)OCCN=C=O.N(CCO)CCO.CC1=C(O)C=CC(=C1)O>>C(C(=C)C)(=O)OCCNC(=O)N(CCO)CCO | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11].[NH:12]([CH2:13][CH2:14][OH:15])[CH2:16][CH2:17][OH:18]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[N:12]([CH2:13][CH2:14][OH:15])[CH2:16][CH2:17][OH:18] | C=C(C)C(=O)OCCN=C=O.OCCNCCO | C=C(C)C(=O)OCCNC(=O)N(CCO)CCO | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and secondary amine | 288f31369c46060b9009e57afc96d52a76d6a0243a2e1197ab47b0221bb8a3ee | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | null | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | null | [] | null | null | 105 | MINUTE | A one liter flask, under a N2 blanket, was charged with 105 gm of diethanolamine (1 mole) and 20 mg of methylhydroquinone. One molar of 2-isocyanatoethyl methacrylate (IEM) containing 2 ml of DBTDL (2% solution in toluene) was dropped slowly in the flask with moderate stirring over a period of 105 minutes, while the te... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | null | null | null | null | C1(=CC=CC=C1)C | null | 1.75 | C=C(C)C(=O)OCCN=C=O.OCCNCCO>C1(=CC=CC=C1)C>C=C(C)C(=O)OCCNC(=O)N(CCO)CCO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-02d791137985462297a555d94c554095 | COc1ccc(CC2[NH2+]CCC3CCCC=C32)cc1>>COc1ccc(C[C@H]2[NH2+]CC[C@@H]3CCCC=C32)cc1 | C(C)(=O)[O-].COC1=CC=C(CC2[NH2+]CCC3CCCC=C23)C=C1>>C(C)(=O)[O-].COC1=CC=C(C[C@H]2[NH2+]CC[C@@H]3CCCC=C23)C=C1 | [CH3:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH:12]2[NH2+:13][CH2:14][CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH:20]=[C:21]23)[cH:22][cH:23]1>>[CH3:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][C@H:12]2[NH2+:13][CH2:14][CH2:15][C@@H:16]3[CH2:17][CH2:18][CH2:19][CH:20]=[C:21]23)[cH:22][cH:23]1 | COc1ccc(CC2[NH2+]CCC3CCCC=C32)cc1 | COc1ccc(C[C@H]2[NH2+]CC[C@@H]3CCCC=C32)cc1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1=C2[C@@H](CCC1)CC[NH2+][C@@H]2Cc1ccccc1 | null | null | [] | null | null | null | null | Sufficient racemic (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate is dissolved in isopropanol to form a 52.6% by weight (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate solution. The solution is seeded at 20° C. with about 1%, relative to the weight of the solution, of (S)-acetate and is stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1=C2C[NH+]CC[C@@H]2CCC1 | null | C(C)(C)O | null | null | COc1ccc(CC2[NH2+]CCC3CCCC=C32)cc1>C(C)(C)O>COc1ccc(C[C@H]2[NH2+]CC[C@@H]3CCCC=C32)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8be19d99101940f8b611464ff0ecf239 | COc1ccc(C[C@@H]2[NH2+]CCC3CCCC=C32)cc1>>COc1ccc(C[C@@H]2NCCC3CCCC=C32)cc1 | C(C)(=O)[O-].COC1=CC=C(C[C@@H]2[NH2+]CCC3CCCC=C23)C=C1.[OH-].[Na+]>>COC1=CC=C(C[C@@H]2NCCC3CCCC=C23)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@@H:8]2[NH2+:9][CH2:10][CH2:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH:16]=[C:17]23)[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@@H:8]2[NH:9][CH2:10][CH2:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH:16]=[C:17]23)[cH:18][cH:19]1 | COc1ccc(C[C@@H]2[NH2+]CCC3CCCC=C32)cc1 | COc1ccc(C[C@@H]2NCCC3CCCC=C32)cc1 | null | null | O | Reduction | OtherReaction | 90a6f4de7f82bd5a4029ce8b0912f320ad7381ea35cdb33ec487e0d88c2ca0ed | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1=C2C(CCC1)CCN[C@H]2Cc1ccccc1 | [C:1]-[C:2]=[C:3]1-[C:4]-[C:5]-[C:6]-[NH2+;D2:7]-[C:8]-1-[C:9]>>[C:1]-[C:2]=[C:3]1-[C:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-1-[C:9] | 97.3 | [{"value": 97.3, "product": "COC1=CC=C(C[C@@H]2NCCC3CCCC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "COC1=CC=C(C[C@@H]2NCCC3CCCC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 31.7 g of (S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate in 250 ml of water is brought by addition of concentrated sodium hydroxide solution to pH 12. The free base is extracted twice with 150 ml of diethyl ether each time. Washing of the combined extracts with water, drying over sodium sulfate a... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | C1=C2C[NH+]CCC2CCC1 | C1=C2CNCCC2CCC1 | c1ccccc1.C1=C2CNCCC2CCC1 | null | O | null | null | COc1ccc(C[C@@H]2[NH2+]CCC3CCCC=C32)cc1>O>COc1ccc(C[C@@H]2NCCC3CCCC=C32)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bc81acde98bc4b1fabc531c70cdf4325 | CC1=CCC2CC1C2(C)C>>CC1=C2CC(CC1)C2(C)C | [B](C1CC2CC(C1C)C2(C)C)C3CC4CC(C3C)C4(C)C.CC1=CCC2CC1C2(C)C.B.C1NCCC2=CC=CC=C12>>C12=C(CCC(C1(C)C)C2)C | [CH3:1][C:2]1=[CH:7][CH2:6][CH:5]2[CH2:4][CH:3]1[C:8]2([CH3:9])[CH3:10]>>[CH3:1][C:2]1=[C:3]2[CH2:4][CH:5]([CH2:6][CH2:7]1)[C:8]2([CH3:9])[CH3:10] | CC1=CCC2CC1C2(C)C | CC1=C2CC(CC1)C2(C)C | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 063528f3a3cdebf359e2820779cca11e887cd7e7c144ea6ef56ce715549397ed | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1=C2CC(CC1)C2 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]2-[C:5]-[CH;D3;+0:6]-1-[C;H0;D3;+0:7](-[C;D1;H3:8])=[CH;D2;+0:9]-[C:10]-2>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]2-[C:5]-[C;H0;D3;+0:6]-1=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[C:10]-2 | null | [] | null | null | null | null | Another way to accomplish this assymetric reduction of compound 4' to optically active tetrahydroisoquinolines is to reduce the compound in tetrahydrofuran with the reagent which is obtained by reacting 2 moles of optically active alpha pinene with borane in tetrahydrofuran. The solution of the diisopinocampheylborane ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC2CC(C1)C2 | C1=C2CC(CC1)C2 | C1=C2CC(CC1)C2 | null | O1CCCC1 | null | null | CC1=CCC2CC1C2(C)C>O1CCCC1>CC1=C2CC(CC1)C2(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d549740ce134666822d464aa2a445ae | CCCO.Cc1cc([N+](=O)[O-])cc[n+]1[O-]>>CCCOc1cc[n+]([O-])c(C)c1 | CC1=[N+](C=CC(=C1)[N+](=O)[O-])[O-].C(CC)O.[Na].C(CC)O>>CC1=[N+](C=CC(=C1)OCCC)[O-] | [CH3:1][CH2:2][CH2:3][OH:4].O=[N+]([O-])[c:5]1[cH:6][cH:7][n+:8]([O-:9])[c:10]([CH3:11])[cH:12]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n+:8]([O-:9])[c:10]([CH3:11])[cH:12]1 | CCCO.Cc1cc([N+](=O)[O-])cc[n+]1[O-] | CCCOc1cc[n+]([O-])c(C)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 936d99471ea23de6bb74bd9dfa4853c4e7f9ce3385bfcedd89499f7c22b9b426 | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a;+:5](-[O;-;D1;H0:6]):[c:7]:[c:8]:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a;+:5](-[O;-;D1;H0:6]):[c:7]:[c:8]:1 | null | [] | null | null | null | null | To a solution of sodium n-propoxide solution prepared by dissolving sodium (1.7 g) in n-propanol (200 ml) was added to a hot solution of 2-methyl-4-nitropyridine-1-oxide (5.2 g) in n-propanol (210 ml). The mixture was stirred for ten minutes, then n-propanol was evaporated off. To the residue was added chloroform under... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | null | null | null | CCCO.Cc1cc([N+](=O)[O-])cc[n+]1[O-]>>CCCOc1cc[n+]([O-])c(C)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fcfef2d239354cdaa1521ec40209288e | CCCO.Cc1c([N+](=O)[O-])cc[n+]([O-])c1C>>CCCOc1cc[n+]([O-])c(C)c1C | CC1=[N+](C=CC(=C1C)[N+](=O)[O-])[O-].C(CC)O.C([O-])([O-])=O.[K+].[K+]>>CC1=[N+](C=CC(=C1C)OCCC)[O-] | [CH3:1][CH2:2][CH2:3][OH:4].O=[N+]([O-])[c:5]1[cH:6][cH:7][n+:8]([O-:9])[c:10]([CH3:11])[c:12]1[CH3:13]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n+:8]([O-:9])[c:10]([CH3:11])[c:12]1[CH3:13] | CCCO.Cc1c([N+](=O)[O-])cc[n+]([O-])c1C | CCCOc1cc[n+]([O-])c(C)c1C | null | null | null | Functional Group Interconversion | OtherReaction | 936d99471ea23de6bb74bd9dfa4853c4e7f9ce3385bfcedd89499f7c22b9b426 | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9] | null | [] | 80 | CELSIUS | 22 | HOUR | In n-propanol (42 ml) was dissolved 2,3-dimethyl-4-nitropyridine-1-oxide (841 mg). To the solution was added anhydrous potassium carbonate (2.1 g), and the mixture was stirred at 80° C. for 22 hours, followed by filtration with celite. The filtrate was concentrated, and the residue was chromatographed on a column of si... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | null | 80 | 22 | CCCO.Cc1c([N+](=O)[O-])cc[n+]([O-])c1C>>CCCOc1cc[n+]([O-])c(C)c1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-167b86074bc5488b9fcafaa508255281 | CCCOc1cc[n+]([O-])c(C)c1>>CCCOc1ccnc(CO)c1 | C([O-])([O-])=O.[Na+].[Na+].CC1=[N+](C=CC(=C1)OCCC)[O-].C(C)(=O)OC(C)=O>>OCC1=NC=CC(=C1)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n+:8]([O-:11])[c:9]([CH3:10])[cH:12]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n:8][c:9]([CH2:10][OH:11])[cH:12]1 | CCCOc1cc[n+]([O-])c(C)c1 | CCCOc1ccnc(CO)c1 | null | S(O)(O)(=O)=O | null | Miscellaneous | OtherReaction | 7e561d7afee9600ed6bdb2a097e47ef139bafb1884a12ad7f91414ba01df7b33 | 0607ce9ac404b7f992b14bf13602ccd36eb29bd5911f2b79cc25c0bfd203a764 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-;H0;D1:5]):[c:6]:[c:7]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:6]:[c:7] | null | [] | 100 | CELSIUS | 15 | MINUTE | A mixture of 2-methyl-4-propoxypyridine-1-oxide (8.6 g), acetic anhydride (8.6 ml) and concentrated sulfuric acid (two drops) was heated at 100° C. for five minutes, to which were added ice-water and an excess amount of sodium carbonate. The mixture was subjected to extraction with chloroform. The extract was dried wit... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | null | S(O)(O)(=O)=O | 100 | 0.25 | CCCOc1cc[n+]([O-])c(C)c1>S(O)(O)(=O)=O>CCCOc1ccnc(CO)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7ac2a232bc5f41229b38aabcef8b9704 | CCCOc1ccnc(CSc2nc3ccccc3[nH]2)c1C.O=C(OO)c1cccc(Cl)c1>>CCCOc1ccnc(CS(=O)c2nc3ccccc3[nH]2)c1C | CC=1C(=NC=CC1OCCC)CSC=1NC2=C(N1)C=CC=C2.ClC1=CC(=CC=C1)C(=O)OO>>CC=1C(=NC=CC1OCCC)CS(=O)C=1NC2=C(N1)C=CC=C2 | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n:8][c:9]([CH2:10][S:11][c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[nH:21]2)[c:22]1[CH3:23].O=C(O[OH:12])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n:8][c:9]([CH2:10][S:11](=[O:12])[c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[nH:21]2)[c... | CCCOc1ccnc(CSc2nc3ccccc3[nH]2)c1C.O=C(OO)c1cccc(Cl)c1 | CCCOc1ccnc(CS(=O)c2nc3ccccc3[nH]2)c1C | null | null | C(Cl)(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S(Cc1ccccn1)c1nc2ccccc2[nH]1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7;a:2]:[c:3]-[C:4]-[S;H0;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[#7;a:2]:[c:3]-[C:4]-[S;H0;D3;+0:5](=[O;H0;D1;+0:1])-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 39.5 | [{"value": 39.5, "product": "CC=1C(=NC=CC1OCCC)CS(=O)C=1NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(3-methyl-4-propoxy-2-pyridyl)methylthiobenzimidazole (1 g) in chloroform (20 ml) was added dropwise over 10 minutes under ice-cooling m-chloroperbenzoic acid (750 mg) dissolved in chloroform (10 ml). The solution was chromatographed directly on a column of silica gel (50 g), which was eluted with et... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | C(Cl)(Cl)Cl | null | null | CCCOc1ccnc(CSc2nc3ccccc3[nH]2)c1C.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>CCCOc1ccnc(CS(=O)c2nc3ccccc3[nH]2)c1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3f4e5fd49dba41ce9980468ba16d9ddd | NC(=O)Nc1ccccc1S.Nc1nc2ccccc2s1>>CC(=O)Cc1nc2ccccc2s1 | [Na].[K].SC1=C(C=CC=C1)NC(=O)N.NC=1SC2=C(N1)C=CC=C2.[OH-].[Na+]>>C(C(=O)C)C=1SC2=C(N1)C=CC=C2 | N[C:2](Nc1c(S)c[cH:1]c[cH:4]1)=[O:3].N[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[s:13]1>>[CH3:1][C:2](=[O:3])[CH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[s:13]1 | NC(=O)Nc1ccccc1S.Nc1nc2ccccc2s1 | CC(=O)Cc1nc2ccccc2s1 | null | null | C(C)(=O)O.C=C1CC(=O)O1.O | C-C Coupling | OtherReaction | 9f527bec22c82f1e5bb1eb088af5297471a9465f175b6fbf300540bbbc658b0d | 6c581d45dd22ba1ebcc082910c44a973a92ebd5c93756315a85a6b350616f64b | c1ccc2scnc2c1 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-N-c1:[cH;D2;+0:3]:c:[cH;D2;+0:4]:c:c:1-S.N-[c;H0;D3;+0:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1>>[CH3;D1;+0:4]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[c;H0;D3;+0:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1 | 79.4 | [{"value": 79.4, "product": "C(C(=O)C)C=1SC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The water-moist 2-mercaptophenylurea obtained according to European Pat. No. 0,039,483, Example 1, paragraph 1, by reacting 150 parts of 2-aminobenzothiazole with 150 parts of sodium hydroxide and working up the mixture with water, or an appropriate amount of the sodium or potassium salt of the said 2-mercaptophenylure... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine.Aromatic thiol | Ketone | c1ccccc1.c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | C(C)(=O)O.C=C1CC(=O)O1.O | null | 1 | NC(=O)Nc1ccccc1S.Nc1nc2ccccc2s1>C(C)(=O)O.C=C1CC(=O)O1.O>CC(=O)Cc1nc2ccccc2s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-933065a153024599baa544ac59e11817 | CC(=O)O.NC(=O)Nc1ccc(Cl)cc1S>>Cc1nc2ccc(Cl)cc2s1 | [Na].ClC1=CC(=C(C=C1)NC(=O)N)S.C(C)(=O)O>>ClC1=CC2=C(N=C(S2)C)C=C1 | O=[C:2](O)[CH3:1].NC(=O)[NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[SH:11]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[s:11]1 | CC(=O)O.NC(=O)Nc1ccc(Cl)cc1S | Cc1nc2ccc(Cl)cc2s1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | bf5666ed839f558fbabc30f3deafdf0e8f42efe324c62cf01e8603baca6cf789 | 45cf0d44644894990d05b34571ba8c7dcefb09b9928e416c8c8516bc57f9e1ed | c1ccc2scnc2c1 | N-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[SH;D1;+0:5]):[c:6].O-[C;H0;D3;+0:7](=O)-[C;D1;H3:8]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[s;H0;D2;+0:5]:1 | 93.3 | [{"value": 93.3, "product": "ClC1=CC2=C(N=C(S2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 112.25 parts of the sodium salt of 4-chloro-2-mercaptophenylurea, which salt is obtainable according to Example 6 of European Pat. No. 0,039,483, are suspended in 450 parts of glacial acetic acid in an autoclave. The pressure vessel is closed and heated slowly to 150° C.-160° C. in the course of 2 hours, a pressure of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Urea.Aromatic thiol | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HO- | O | null | 5 | CC(=O)O.NC(=O)Nc1ccc(Cl)cc1S>O>Cc1nc2ccc(Cl)cc2s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cd9cee84bbb34d60b58548e31996ec0e | NCC(=O)O.O=C(Cl)c1ccc(F)cc1>>O=C(O)CNC(=O)c1ccc(F)cc1 | Cl.NCC(=O)O.FC1=CC=C(C(=O)Cl)C=C1>>FC1=CC=C(C(NCC(=O)O)=O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][NH2:5].Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1 | NCC(=O)O.O=C(Cl)c1ccc(F)cc1 | O=C(O)CNC(=O)c1ccc(F)cc1 | null | null | [OH-].[Na+] | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[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;H0:9])-[O;D1;H1:10]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78.1 | [{"value": 78.1, "product": "FC1=CC=C(C(NCC(=O)O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "FC1=CC=C(C(NCC(=O)O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of glycine (15 g, 0.2 mol) in 175 mL of 5% aqueous sodium hydroxide is cooled to 10° C. to 15° C. p-Fluorobenzoyl chloride (31.6 g, 0.2 mol) is then added dropwise to the mixture and stirred vigorously for 0.5 hour while maintaining the temperature of the mixture of about 10° C. to 15° C. The pH of the react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | [OH-].[Na+] | null | 0.5 | NCC(=O)O.O=C(Cl)c1ccc(F)cc1>[OH-].[Na+]>O=C(O)CNC(=O)c1ccc(F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5eae9c249c2f4d548c00c56de8b74d45 | Cc1cccc2c1C(=O)N1CCC[C@H]1C(=O)N2>>COc1cccc2c1C(=O)N(C)CC(=O)N2 | CC1=CC=CC2=C1C(N1[C@H](C(N2)=O)CCC1)=O.N1[C@H](C(=O)O)CCC1>>COC1=CC=CC2=C1C(N(CC(N2)=O)C)=O | C1C[C@@H:13]2[N:11]([C:9](=[O:10])[c:8]3[c:3]([CH3:1])[cH:4][cH:5][cH:6][c:7]3[NH:16][C:14]2=[O:15])[CH2:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[N:11]([CH3:12])[CH2:13][C:14](=[O:15])[NH:16]2 | Cc1cccc2c1C(=O)N1CCC[C@H]1C(=O)N2 | COc1cccc2c1C(=O)N(C)CC(=O)N2 | null | null | null | Oxidation | OtherReaction | 98b9a2ac613282ee2baf86089cff62e06865446e63efcb5853aaf36e3f9eb2b8 | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=C1CNC(=O)c2ccccc2N1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]1:[c:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[C@@H;D3;+0:10]2-C-C-[CH2;D2;+0:11]-[#7:12]-2-[C:13]-1=[O;D1;H0:14]>>[CH3;D1;+0:11]-[#7:12]1-[CH2;D2;+0:10]-[C:8](=[O;D1;H0:9])-[#7:7]-[c:6]:[c:5](:[c;H0;D3;+0:2](-[#8:15]-[CH3;D1;+0:1]):[c:3]:[c:4])-[C:13]-1=[O;D1;H0:14] | null | [] | null | null | null | null | (S)-6-methyl-1,2,3,11a-tetrahydro-5H-pyrrolo (2,1-c) (1,4) benzodiazepine-5,11 (10H)-dione by reaction with L-proline. M.p. 207.6°-209.9° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2c(c1)CN1CCC[C@H]1CN2 | c1ccc2c(c1)C[NH]CCN2 | c1ccc2c(c1)C[NH]CCN2 | Other | null | null | null | Cc1cccc2c1C(=O)N1CCC[C@H]1C(=O)N2>>COc1cccc2c1C(=O)N(C)CC(=O)N2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-370e9da63cad4d6da5cf2183f76d801c | Cc1ccc2c(c1)C(=O)N1CCC[C@H]1C(=O)N2>>Cc1ccc2c(c1)C(=O)N(C)CC(=O)N2 | CC=1C=CC2=C(C(N3[C@H](C(N2)=O)CCC3)=O)C1.N1[C@H](C(=O)O)CCC1>>CC=1C=CC2=C(C(N(CC(N2)=O)C)=O)C1 | C1C[C@@H:12]2[N:10]([C:8](=[O:9])[c:6]3[c:5]([cH:4][cH:3][c:2]([CH3:1])[cH:7]3)[NH:15][C:13]2=[O:14])[CH2:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH3:11])[CH2:12][C:13](=[O:14])[NH:15]2 | Cc1ccc2c(c1)C(=O)N1CCC[C@H]1C(=O)N2 | Cc1ccc2c(c1)C(=O)N(C)CC(=O)N2 | null | null | null | Miscellaneous | OtherReaction | 602b3004fe526c8ffa4d9c5c1c62bd9303f43d040fae1edd376c975122123e84 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CNC(=O)c2ccccc2N1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[#7:8]2-[CH2;D2;+0:9]-C-C-[C@H;D3;+0:10]-2-1>>[CH3;D1;+0:9]-[#7:8]1-[CH2;D2;+0:10]-[C:2](=[O;D1;H0:1])-[#7:3]-[c:4]:[c:5]-[C:6]-1=[O;D1;H0:7] | null | [] | null | null | null | null | (S)-7-methyl-1,2,3,11a-tetrahydro-5H-pyrrolo (2,1-c) (1,4) benzodiazepine-5,11(10H)-dione by reaction with L-proline. M.p. 243.1°-244.5° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)CN1CCC[C@H]1CN2 | c1ccc2c(c1)C[NH]CCN2 | c1ccc2c(c1)C[NH]CCN2 | Other | null | null | null | Cc1ccc2c(c1)C(=O)N1CCC[C@H]1C(=O)N2>>Cc1ccc2c(c1)C(=O)N(C)CC(=O)N2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-60f2c1dc2ddc4f86a12118429b21f645 | O=CNCc1nc(C2CC2)no1>>[C-]#[N+]Cc1nc(C2CC2)no1 | C1(CC1)C1=NOC(=N1)CNC=O.C(C)N(CC)CC.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>>C1(CC1)C1=NOC(=N1)C[N+]#[C-] | O=[CH:1][NH:2][CH2:3][c:4]1[n:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[n:10][o:11]1>>[C-:1]#[N+:2][CH2:3][c:4]1[n:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[n:10][o:11]1 | O=CNCc1nc(C2CC2)no1 | [C-]#[N+]Cc1nc(C2CC2)no1 | null | null | C(Cl)Cl.O | Miscellaneous | OtherReaction | f7214d38106dea5486b0d6fc128153f0f3b957c1bb9d1fb6ea0a46d9542dfde8 | 29f2ff643c48789b889454614350e59bf34db9112de745283c27cc9bf82dca6d | c1nc(C2CC2)no1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[C:3]-[c:4](:[#7;a:5]):[#8;a:6]:[#7;a:7]>>[#7;a:7]:[#8;a:6]:[c:4](-[C:3]-[N+;H0;D2:2]#[C-;H0;D1:1]):[#7;a:5] | null | [] | null | null | 30 | MINUTE | A stirred solution of 3-cyclopropyl-5-formylaminomethyl-1,2,4-oxadiazole (60 mmol) and triethylamine (176 mmol) in CH2Cl2 (100 ml) was charged at 0° C. dropwise with POCl3 (60 mmol). The mixture was then left for 30 min. with stirring at 0° C., whereafter a solution of Na2CO3 (60 mmol) in H2O (50 ml) was added. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Isocyanide | null | null | c1ncon1.C1CC1 | HO- | C(Cl)Cl.O | null | 0.5 | O=CNCc1nc(C2CC2)no1>C(Cl)Cl.O>[C-]#[N+]Cc1nc(C2CC2)no1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-99eb61288cb4458ca343c64c8408c1ff | CN1OC(C2CC2)=NC1NC=O>>[C-]#[N+]Cc1noc(C2CC2)n1 | C1(CC1)C1=NC(N(O1)C)NC=O.C(C)N(CC)CC.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>>C1(CC1)C1=NC(=NO1)C[N+]#[C-] | O=[CH:1][NH:2][CH:4]1[N:5]([CH3:3])[O:6][C:7]([CH:8]2[CH2:9][CH2:10]2)=[N:11]1>>[C-:1]#[N+:2][CH2:3][c:4]1[n:5][o:6][c:7]([CH:8]2[CH2:9][CH2:10]2)[n:11]1 | CN1OC(C2CC2)=NC1NC=O | [C-]#[N+]Cc1noc(C2CC2)n1 | null | null | C(Cl)Cl.O | Aromatic Heterocycle Formation | OtherReaction | 5ba58d06433ab4c274aac81358c61bce81f77583d7857bd709dde88c66d0d4b8 | 74e3157d960a5b3232e0247f357eee950229c93dfc4694d1f6ac37272bd51dd2 | c1noc(C2CC2)n1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[CH;D3;+0:3]1-[N;H0;D2;+0:4]=[C;H0;D3;+0:5](-[C:6]2-[C:7]-[C:8]-2)-[O;H0;D2;+0:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:11]>>[C-;H0;D1:1]#[N+;H0;D2:2]-[CH2;D2;+0:11]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[C:6]2-[C:7]-[C:8]-2):[o;H0;D2;+0:9]:[n;H0;D2;+0:10]:1 | null | [] | null | null | 30 | MINUTE | A stirred solution of 5-cyclopropyl-3-formylamino-methyl-1,2,4-oxadiazole (60 mmol) and triethylamine (176 mmol) in CH2Cl2 (100 ml) was charged dropwise with POCl3 (60 mmol) at 0° C. The mixture was then left for 30 min. with stirring at 0° C., whereafter a solution of Na2CO3 (60 mmol) in H2O (50 ml) was added. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amine | Isocyanide | C1=NC[NH]O1 | c1ncon1 | c1ncon1.C1CC1 | HO- | C(Cl)Cl.O | null | 0.5 | CN1OC(C2CC2)=NC1NC=O>C(Cl)Cl.O>[C-]#[N+]Cc1noc(C2CC2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93b72a32055f4663a84ab26eb7211fd7 | C=CCSc1ccc(C)cc1.COc1cccc(C(Cn2ccnc2)=[N+](C)[O-])c1>>COc1cccc(C2(Cn3ccnc3)CC(CSc3ccc(C)cc3)ON2C)c1 | N1(C=NC=C1)CC(=[N+](C)[O-])C1=CC(=CC=C1)OC.CC1=CC=C(C=C1)SCC=C>>COC=1C=C(C=CC1)C1(N(OC(C1)CSC1=CC=C(C=C1)C)C)CN1C=NC=C1 | [CH2:15]=[CH:16][CH2:17][S:18][c:19]1[cH:20][cH:21][c:22]([CH3:23])[cH:24][cH:25]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([CH2:9][n:10]2[cH:11][cH:12][n:13][cH:14]2)=[N+:27]([O-:26])[CH3:28])[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2([CH2:9][n:10]3[cH:11][cH:12][n:13][cH:14]3)[CH2:15][CH:16]([C... | C=CCSc1ccc(C)cc1.COc1cccc(C(Cn2ccnc2)=[N+](C)[O-])c1 | COc1cccc(C2(Cn3ccnc3)CC(CSc3ccc(C)cc3)ON2C)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 033846290994884fa7fb48cc64e4e4283f06dc380ab6111c31eebe393f2d4ff9 | 067a43be9697e70dc891834395ddb80799577503a0096cc0b881fd0da6bd8a0a | c1ccc(SCC2CC(Cn3ccnc3)(c3ccccc3)NO2)cc1 | [#16:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[#7;a:5]-[C:6]-[C;H0;D3;+0:7](=[N+;H0;D3:8](-[C;D1;H3:9])-[O-;H0;D1:10])-[c:11](:[c:12]):[c:13]>>[#16:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[C;H0;D4;+0:7](-[C:6]-[#7;a:5])(-[c:11](:[c:12]):[c:13])-[N;H0;D3;+0:8](-[C;D1;H3:9])-[O;H0;D2;+0:10]-1 | null | [] | null | null | null | null | The title compound was prepared by a procedure similar to that described in Example 1 by reacting 2-(1H-imidazol-1-yl)-1-(3-methoxyphenyl)-N-methylethanimine N-oxide (1, R1 =3--OCH3) with allyl 4-methyphenyl sulfide (2: R2 =4--CH3). The resulting cis- and trans-diastereomeric mixture of compound 3 (R1 =3--OCH3, R2 =4--... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Tertiary amine | null | C1C[NH]OC1 | c1ccccc1.c1c[nH]cn1.C1C[NH]OC1.c1ccccc1 | null | null | null | null | C=CCSc1ccc(C)cc1.COc1cccc(C(Cn2ccnc2)=[N+](C)[O-])c1>>COc1cccc(C2(Cn3ccnc3)CC(CSc3ccc(C)cc3)ON2C)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f5ad352ed1c74d3988e13524a6474adc | C=CCOc1cccc(C)c1.Cc1cccc(C(Cn2cncn2)=[N+](C)[O-])c1>>CN1OC(COc2ccccc2)CC1(Cn1cncn1)c1ccccc1 | C[N+](=C(CN1N=CN=C1)C1=CC(=CC=C1)C)[O-].CC=1C=C(C=CC1)OCC=C>>C1(=CC=CC=C1)C1(N(OC(C1)COC1=CC=CC=C1)C)CN1N=CN=C1 | C[c:11]1[cH:10][cH:9][cH:8][c:7]([O:6][CH2:5][CH:4]=[CH2:13])[cH:12]1.C[c:23]1[cH:22][c:21]([C:14](=[N+:2]([CH3:1])[O-:3])[CH2:15][n:16]2[cH:17][n:18][cH:19][n:20]2)[cH:26][cH:25][cH:24]1>>[CH3:1][N:2]1[O:3][CH:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C:14]1([CH2:15][n:16]1[cH:17][n:18][cH:19][n... | C=CCOc1cccc(C)c1.Cc1cccc(C(Cn2cncn2)=[N+](C)[O-])c1 | CN1OC(COc2ccccc2)CC1(Cn1cncn1)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 3409b7e368e7ca2a388623e4ea90e60c2b61815bf7e277200a6b09b6f5b42304 | ff43c62789a32cd4dfc6a735ef0f0e222d66db86bd89fe68738f56cf637558c9 | c1ccc(OCC2CC(Cn3cncn3)(c3ccccc3)NO2)cc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#8:6]-[C:7]-[CH;D2;+0:8]=[CH2;D1;+0:9].C-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[C;H0;D3;+0:13](-[C:14]-[#7;a:15])=[N+;H0;D3:16](-[C;D1;H3:17])-[O-;H0;D1:18]):[c:19]:[c:20]:[c:21]:1>>[#7;a:15]-[C:14]-[C;H0;D4;+0:13]1(-[c:12]2:[c:11]:[cH;D2;+0:10]:[c:21]:[c:20]:[c:19]:2)-[CH2;D2;+0:9... | null | [] | null | null | null | null | Compound 3 (R1 =R2 =H) was prepared by a procedure similar to that described in Example 1 by reacting N-methyl-1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide (1, R1 =H) with allyl phenyl ether (2, R2 =H). The resulting cis- and trans-diastereomeric mixture of the title compound was flash-chromatographed on neutra... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Tertiary amine | c1ccccc1.c1ccccc1 | C1C[NH]OC1.c1ccccc1.c1ccccc1 | C1C[NH]OC1.c1ccccc1.c1nc[nH]n1.c1ccccc1 | Other | null | null | null | C=CCOc1cccc(C)c1.Cc1cccc(C(Cn2cncn2)=[N+](C)[O-])c1>>CN1OC(COc2ccccc2)CC1(Cn1cncn1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3497fce3c27c4a8183dd59dfdd64c3b5 | C=C(C)CC(C)(C)C.Nc1ccccc1[N+](=O)[O-]>>CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1 | [N+](=O)([O-])C1=C(N)C=CC=C1.CC(=C)CC(C)(C)C.[N+](=O)([O-])C1=C(N)C=CC=C1>>C(C)(C)(CC(C)(C)C)C1=CC(=C(N)C=C1)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6](=[CH2:7])[CH3:8].[cH:9]1[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | C=C(C)CC(C)(C)C.Nc1ccccc1[N+](=O)[O-] | CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1 | null | [Cl-].[Zn+2].[Cl-] | null | C-C Coupling | Friedel-Crafts alkylation | f6021e53f57d07d48a856391b21137517c9bd669381174a55381b6219a6afd68 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[CH2;D1;+0:5].[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[CH3;D1;+0:5])-[c;H0;D3;+0:8](:[c:7]:[c:6]):[c:9]:[c:10] | null | [] | 60 | CELSIUS | null | null | In a 2-liter reaction flask fitted with a condenser, nitrogen inlet, stirrer, thermometer and addition funnel is placed 272 grams (2.0 moles) of anhydrous zinc chloride. The flask is placed under a nitrogen atmosphere and 166 ml (2.0 moles) of concentrated (12 N) hydrochloric acid is added over a 10-minute period with ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | [Cl-].[Zn+2].[Cl-] | 60 | null | C=C(C)CC(C)(C)C.Nc1ccccc1[N+](=O)[O-]>[Cl-].[Zn+2].[Cl-]>CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fc12ecb0226845b88b3d342b93ad0cfa | CC(=O)OC(C)=O.CCCCCCCCCCCCc1ccc(N)cc1>>CCCCCCCCCCCCc1ccc(NC(C)=O)cc1 | C(CCCCCCCCCCC)C1=CC=C(N)C=C1.C(C)(=O)OC(C)=O.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C=C1)CCCCCCCCCCCC | CC(=O)O[C:18]([CH3:19])=[O:20].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:21][cH:22]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][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[c... | CC(=O)OC(C)=O.CCCCCCCCCCCCc1ccc(N)cc1 | CCCCCCCCCCCCc1ccc(NC(C)=O)cc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 40 | CELSIUS | 3 | HOUR | In a 1-liter flask fitted with a stirrer and reflux condenser is added 137.5 grams (0.525 mole) of p-n-dodecylaniline, dissolved in 138 ml of tolune. To this is added over a 15-minute period 57.5 ml of acetic anhydride. The temperature rises from 40° to 80° C. After all the acetic anhydride is added, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | 40 | 3 | CC(=O)OC(C)=O.CCCCCCCCCCCCc1ccc(N)cc1>>CCCCCCCCCCCCc1ccc(NC(C)=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-988f9d1f7f0e4e7b89b7025738b61397 | CCCCCCCCCCCCc1ccc(NC(C)=O)c([N+](=O)[O-])c1>>CCCCCCCCCCCCc1ccc(N)c([N+](=O)[O-])c1 | C(C)(=O)NC1=C(C=C(C=C1)CCCCCCCCCCCC)[N+](=O)[O-].C(C)O.[OH-].[K+]>>C(CCCCCCCCCCC)C1=CC(=C(N)C=C1)[N+](=O)[O-] | CC(=O)[NH:17][c:16]1[cH:15][cH:14][c: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])[cH:22][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[c:18]([N+:19](=[O:20])[O-:2... | CCCCCCCCCCCCc1ccc(NC(C)=O)c([N+](=O)[O-])c1 | CCCCCCCCCCCCc1ccc(N)c([N+](=O)[O-])c1 | null | null | O | 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] | null | [] | null | null | null | null | In a 1-liter flask fitted with a stirrer and reflux condenser, 61.8 grams of N-acetyl-4-n-dodecyl-2-nitroaniline (prepared in Example 2b), 320 ml of ethanol and 64 ml of 40% aqueous potassium hydroxide solution are heated for 1 hour under reflux. The reaction mixture is cooled and then poured into 1.5 liters of water. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | O | null | null | CCCCCCCCCCCCc1ccc(NC(C)=O)c([N+](=O)[O-])c1>O>CCCCCCCCCCCCc1ccc(N)c([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ed583ce98fe146e3998e1fa263b5c10e | C=C(C)c1ccccc1.Oc1ccccc1>>CC(C)(c1ccccc1)c1ccc(O)c(C(C)(C)c2ccccc2)c1 | C1(=CC=CC=C1)O.CC(=C)C1=CC=CC=C1>>CC(C1=CC=CC=C1)(C)C1=C(C=CC(=C1)C(C1=CC=CC=C1)(C)C)O | [CH3:3][C:16](=[CH2:17])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[cH:1]1[cH:2][cH:6][cH:5][c:13]([OH:14])[cH:15]1>>[CH3:1][C:2]([CH3:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([C:16]([CH3:17])([CH3:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25]1 | C=C(C)c1ccccc1.Oc1ccccc1 | CC(C)(c1ccccc1)c1ccc(O)c(C(C)(C)c2ccccc2)c1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3a96e938de4ed6d1e9f38305f05a65a7fb3235750174878c3942fe0b6f84506a | 2b87f1579c9923b177e03e39c742898edee768f61e024e0fb04b09c6181f59f2 | c1ccc(Cc2cccc(Cc3ccccc3)c2)cc1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6].[O;D1;H1:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[C;D1;H3:14]-[C;H0;D4;+0:2](-[CH3;D1;+0:1])(-[c:4](:[c:5]):[c:6])-[c;H0;D3;+0:9]1:[c:15]:[c:16](-[C;H0;D4;+0:11](-[CH3;D1;+0:10])(-[CH3;D1;+0:3])-[c:17]2:[... | null | [] | 140 | CELSIUS | null | null | This intermediate is made by reacting a mixture of 705.8 grams (7.5 moles) of phenol with 1772.7 grams (15 moles) of alpha-methylstyrene in the presence of 25.7 grams (0.135 moles) of p-toluenesulfonic acid monohydrate catalyst. This mixture is heated under nitrogen at 140° C. for 2.5 hours. The reaction mixture is coo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Vinyl | Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C | 140 | null | C=C(C)c1ccccc1.Oc1ccccc1>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C>CC(C)(c1ccccc1)c1ccc(O)c(C(C)(C)c2ccccc2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-40e6f1d5d42a4cd08132d0bdb6e46fe3 | CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1.Cl>>CC(C)(C)CC(C)(C)c1ccc([N+]#N)c([N+](=O)[O-])c1.[Cl-] | C(C)(C)(CC(C)(C)C)C1=CC(=C(N)C=C1)[N+](=O)[O-].N(=O)[O-].[Na+].Cl>>[Cl-].C(C)(C)(CC(C)(C)C)C1=CC(=C(C=C1)[N+]#N)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([NH2:13])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1.[ClH:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([N+:13]#[N:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1.[Cl-:20] | CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1.Cl | CC(C)(C)CC(C)(C)c1ccc([N+]#N)c([N+](=O)[O-])c1.[Cl-] | null | null | C1(=CC=CC=C1)C.O | Functional Group Interconversion | OtherReaction | 4b9613e8eb03ba0ca635945a60e7b18985445e9967460b2f7cd3bfa7398bb2a3 | ca5105ff0b33557e585dc54e7cfdd7fa7df4e7f9c3edc13b706f4674b75a100e | c1ccccc1 | [ClH;D0;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl-;H0;D0:1].[N;D1;H0:6]#[N+;H0;D2:2]-[c:3](:[c:4]):[c:5] | null | [] | 38 | CELSIUS | 1 | HOUR | In a 100-ml flask fitted with a stirrer and thermometer, 15.0 grams (0.06 mole) of 4-tert-octyl-2-nitroaniline is suspended in 20 ml of toluene. To this is added at 25° C. 17.3 grams (0.18 mole) of concentrated hydrochloric acid. The suspension is stirred at 38° C. for 1 hour followed by the addition of 6 ml of water. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | null | c1ccccc1 | null | C1(=CC=CC=C1)C.O | 38 | 1 | CC(C)(C)CC(C)(C)c1ccc(N)c([N+](=O)[O-])c1.Cl>C1(=CC=CC=C1)C.O>CC(C)(C)CC(C)(C)c1ccc([N+]#N)c([N+](=O)[O-])c1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-538b2fa95db549c3b201e8be5d8840ea | O=C(Cl)c1ccccc1.O=Cc1ccccc1.c1ccncc1>>O=C(OC(c1ccccc1)[n+]1ccccc1)c1ccccc1.[Cl-] | C(C1=CC=CC=C1)(=O)Cl.N1=CC=CC=C1.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)[N+]1=CC=CC=C1 | [O:1]=[C:2]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[Cl:23].[O:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[n:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([O:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[n+: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.[Cl-:23] | O=C(Cl)c1ccccc1.O=Cc1ccccc1.c1ccncc1 | O=C(OC(c1ccccc1)[n+]1ccccc1)c1ccccc1.[Cl-] | null | null | null | Acylation | OtherReaction | ad14ca8728026f215811ec24885d6596e878bcab549b96d4e5f8f86cae6792a3 | 87eac71efa029453313efa310b9d8329d8a6df445da04bd2b097e9709482abb9 | O=C(OC(c1ccccc1)[n+]1ccccc1)c1ccccc1 | [Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[c:12]:[c:13]:[n;H0;D2;+0:14]:[c:15]:[c:16]>>[Cl-;H0;D0:1].[O;D1;H0:3]=[C;H0;D3;+0:2](-[O;H0;D2;+0:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[n+;H0;D3:14](:[c:13]:[c:12]):[c:15]:[c:16])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 4 | DAY | Benzoyl chloride 3.0 g (0.021 mol) and 1.69 g (0.021 mol) pyridine were mixed together under nitrogen and allowed to react at room temperature overnite. Benzaldehyde 2.23 g (0.021 mol) was added and the mixture was allowed to stand at ambient temperature for 4 days. Recrystallization from ethanol:ether gave 4.27 g (0.0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde | Ester | c1ccncc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1.c1ccccc1 | null | null | null | 96 | O=C(Cl)c1ccccc1.O=Cc1ccccc1.c1ccncc1>>O=C(OC(c1ccccc1)[n+]1ccccc1)c1ccccc1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b567ad629031415c975ad17d8c230aff | CCOC(=O)c1cccnc1.O=C(OCCl)c1ccccc1>>CCOC(=O)c1ccc[n+](COC(=O)c2ccccc2)c1.[Cl-] | C(C1=CN=CC=C1)(=O)OCC.C(C1=CC=CC=C1)(=O)OCCl>>[Cl-].C(C1=CC=CC=C1)(=O)OC[N+]1=CC(=CC=C1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][cH:21]1.[CH2:11]([O:12][C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[Cl:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n+:10]([CH2:11][O:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1.[Cl-:22] | CCOC(=O)c1cccnc1.O=C(OCCl)c1ccccc1 | CCOC(=O)c1ccc[n+](COC(=O)c2ccccc2)c1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | 2d791a2b039e837e4469f29a9d3f5eea0f6387e4a716127f06460215c532571d | e2072b513d16b3f8a4f047ad38a1d6ba3729e124ecb5f77bb47b58b6d8e00ecf | O=C(OC[n+]1ccccc1)c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n;H0;D2;+0:6]:[c:7]:[c:8].[Cl;H0;D1;+0:9]-[CH2;D2;+0:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n+;H0;D3:6](-[CH2;D2;+0:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[c:14]):[c:7]:[c:8].[Cl-;H0;D0:9] | null | [] | null | null | null | null | A mixture of 3.00 g (0.02 mol) ethyl nicotinate and 3.50 g (0.02 mol) chloromethyl benzoate was heated at 70° under nitrogen for 10 hrs. Trituration in anhydrous ether and recrystallization from ethanol-ether gave 2.18 g (0.007 mol), 35%, 1-benzoyloxymethyl-3-carboethoxypyridinium chloride, mp 138°-141°; ir (KBr) 1730 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | null | null | null | null | CCOC(=O)c1cccnc1.O=C(OCCl)c1ccccc1>>CCOC(=O)c1ccc[n+](COC(=O)c2ccccc2)c1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-61f54da028b24a72bc1f764a9ad4f9e4 | Cn1ccnc1.O=C(Cl)c1ccccc1.O=Cc1ccccc1>>Cn1cc[n+](C(OC(=O)c2ccccc2)c2ccccc2)c1.[Cl-] | [K+].[Br-].C(C1=CC=CC=C1)(=O)Cl.CN1C=NC=C1.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)[N+]1=CN(C=C1)C | [CH3:1][n:2]1[cH:3][cH:4][n:5][cH:22]1.[C:8](=[O:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[Cl:23].[CH:6](=[O:7])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][n:2]1[cH:3][cH:4][n+:5]([CH:6]([O:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1.[C... | Cn1ccnc1.O=C(Cl)c1ccccc1.O=Cc1ccccc1 | Cn1cc[n+](C(OC(=O)c2ccccc2)c2ccccc2)c1.[Cl-] | null | null | CCOCC | Acylation | OtherReaction | c2271b51ff2709b7714dfd8e7b89f272db45be328d9556d894dfb483cdd52b83 | 87eac71efa029453313efa310b9d8329d8a6df445da04bd2b097e9709482abb9 | O=C(OC(c1ccccc1)[n+]1cc[nH]c1)c1ccccc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[Cl;H0;D1;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12].[O;H0;D1;+0:13]=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[n+;H0;D3:4](-[CH;D3;+0:14](-[O;H0;D2;+0:13]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12])-[c:15](:[c:16])... | null | [] | null | null | null | null | To an ether solution of benzoyl chloride 2.81 g (0.02 mol) there was added dropwise 1.67 g (0.02 mol) 1-methylimidazole with stirring. The resulting mixture was evaporated in vacuo and the residue was allowed to react with 2.12 g (0.02 mol) benzaldehyde at 70° overnite. After cooling, the reaction mixture was triturate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde | Ester | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1.c1ccccc1 | null | CCOCC | null | null | Cn1ccnc1.O=C(Cl)c1ccccc1.O=Cc1ccccc1>CCOCC>Cn1cc[n+](C(OC(=O)c2ccccc2)c2ccccc2)c1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5fbff02ec4284b1fb6155cc592812eba | CCCCCCCCCCCC(=O)OCCl.Cn1ccnc1>>CCCCCCCCCCCC(=O)OC[n+]1ccn(C)c1.[Cl-] | C(CCCCCCCCCCC)(=O)OCCl.CN1C=NC=C1.[K+].[Br-]>>[Cl-].C(CCCCCCCCCCC)(=O)OC[N+]1=CN(C=C1)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][Cl:22].[n:16]1[cH:17][cH:18][n:19]([CH3:20])[cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][n+:16]1[cH:17][cH:18][n:19]([CH3:20])[cH:21]1.[C... | CCCCCCCCCCCC(=O)OCCl.Cn1ccnc1 | CCCCCCCCCCCC(=O)OC[n+]1ccn(C)c1.[Cl-] | null | null | CCOCC | Functional Group Interconversion | OtherReaction | f252edd4cf72edae965a18ce7754be124e45d9f40ad89b3e180ed497b3af0851 | e2072b513d16b3f8a4f047ad38a1d6ba3729e124ecb5f77bb47b58b6d8e00ecf | c1c[nH+]c[nH]1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[n;H0;D2;+0:5]:[c:6]:1.[C:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12]>>[C:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[CH2;D2;+0:11]-[n+;H0;D3:5]1:[c:4]:[c:3]:[#7;a:2](-[C;D1;H3:1]):[c:6]:1.[Cl-;H0;D0:12] | null | [] | null | null | null | null | A mixture of 2.49 g (0.01 mol) chloromethyl n-dodecanoate and 0.82 g (0.01 mol) 1-methylimidazole were mixed and heated together at 90° for 3 hrs. On cooling to room temperature, anhydrous ether was added to the mixture and the mixture was triturated in anhydrous ether overnite. The solid was isolated by filtration und... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1 | null | CCOCC | null | null | CCCCCCCCCCCC(=O)OCCl.Cn1ccnc1>CCOCC>CCCCCCCCCCCC(=O)OC[n+]1ccn(C)c1.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fa1c20f388e948989dd21b012d79f7a9 | C1CN2CCC1CC2.CCCCCCCCCCCC(=O)OCCl>>CCCCCCCCCCCC(=O)OC[N+]12CCC(CC1)CC2.[Cl-] | C(CCCCCCCCCCC)(=O)OCCl.N12CCC(CC1)CC2.[K+].[Br-]>>[Cl-].C(CCCCCCCCCCC)(=O)OC[N+]12CCC(CC1)CC2 | [N:16]12[CH2:17][CH2:18][CH:19]([CH2:20][CH2:21]1)[CH2:22][CH2:23]2.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][Cl:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][N+:16]12[CH2:17][CH2:18][C... | C1CN2CCC1CC2.CCCCCCCCCCCC(=O)OCCl | CCCCCCCCCCCC(=O)OC[N+]12CCC(CC1)CC2.[Cl-] | null | null | CCOCC | Functional Group Interconversion | OtherReaction | f3baafa4c262bc918490361fc8002a63a56026d60ea77f62ff81e987bd919351 | fd941d9ad33e23092aeb6b2781ccbe493e0d631be1192cef7ff376091800d17a | C1C[NH+]2CCC1CC2 | [C:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[C:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[N+;H0;D4:9](-[C:8]-[C:7])(-[C:10]-[C:11])-[C:12]-[C:13].[Cl-;H0;D0:6] | null | [] | null | null | null | null | 2.49 g (0.01 mol) chloromethyl n-dodecanoate and 1.12 g (0.01 mol) quinuclidine were mixed and allowed to react together at room temperature for 48 hrs. Anhydrous ether was added to the mixture and the mixture was triturated in anydrous ether overnite. The solid was isolated by filtration under a nitrogen atmosphere an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Tertiary amine | Ester | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | C1C[NH+]2CCC1CC2 | null | CCOCC | null | null | C1CN2CCC1CC2.CCCCCCCCCCCC(=O)OCCl>CCOCC>CCCCCCCCCCCC(=O)OC[N+]12CCC(CC1)CC2.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d6803dbfbc1e4f0fbfab242ee261a3d9 | O=C(OCCl)c1ccccc1.c1ccncc1>>O=C(OC[n+]1ccccc1)c1ccccc1.[Cl-] | N1=CC=CC=C1.C(C1=CC=CC=C1)(=O)OCCl.[K+].[Br-]>>[Cl-].C(C1=CC=CC=C1)(=O)OC[N+]1=CC=CC=C1 | [O:1]=[C:2]([O:3][CH2:4][Cl:17])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[n:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([O:3][CH2:4][n+:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[Cl-:17] | O=C(OCCl)c1ccccc1.c1ccncc1 | O=C(OC[n+]1ccccc1)c1ccccc1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | 2d791a2b039e837e4469f29a9d3f5eea0f6387e4a716127f06460215c532571d | e2072b513d16b3f8a4f047ad38a1d6ba3729e124ecb5f77bb47b58b6d8e00ecf | O=C(OC[n+]1ccccc1)c1ccccc1 | [Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[Cl-;H0;D0:1].[O;D1;H0:5]=[C:4](-[c:6])-[#8:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:10]:[c:11]):[c:8]:[c:7] | null | [] | null | null | null | null | A mixture containing 0.79 g (0.01 mol) pyridine and 1.7 g (0.01 mol) chloromethyl benzoate was allowed to react at ambient temperature for 24 hr. Trituration in anhydrous ether followed by filtration under nitrogen gave 1.2 g (0.005 mol), 50%, 29, mp 197°-199° (dec); ir (KBr) 3440, 3020, 1710, 1610, 1475, 1265, 1150, 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | null | null | null | null | O=C(OCCl)c1ccccc1.c1ccncc1>>O=C(OC[n+]1ccccc1)c1ccccc1.[Cl-] |
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