dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-999349dc79214221aaf430c3096dbad1 | Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1.[N-]=C=O>>NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | [N-]=C=O.[K+].FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1.[N-]=C=O.[K+].O.C([O-])(O)=O.[Na+]>>FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N | [NH:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]2)[CH2:29][CH2:30]1.[N-:1]=[C:2]=[O:3]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:1... | Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1.[N-]=C=O | NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | C(C)(=O)O.C(C)O | Acylation | OtherReaction | 19b1a78eac5c11a7a6d62add8e898dd94b39712d8c09ceabf81d7e8d852d9904 | c12a5f5aa1bd3b17571900882f538b1b74958bac9a5fa2923f5c850cbafbf1dd | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [N-;H0;D1:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[c:4]-[C:5]1-[#16:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#16:6]-[C:5]-1-[c:4] | 87.3 | [{"value": 87.3, "product": "FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1.12 g of potassium isocyanate, 10 ml of water and 2 ml of acetic acid is added to a solution of 2.68 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of ethanol, and the mixture is stirred at room temperature for 2 hours. A mixture of 0.56 g of potassium isocyanate and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Urea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)(=O)O.C(C)O | null | 2 | Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1.[N-]=C=O>C(C)(=O)O.C(C)O>NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-99a875cbc0914ffc94f639c96f95744e | [N-]=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1>>NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | [N-]=C=O.[Na+].C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1.C(C)(=O)O.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N | [N-:1]=[C:2]=[O:3].[NH:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][CH2:... | [N-]=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | O.C(C)O | Acylation | OtherReaction | 19b1a78eac5c11a7a6d62add8e898dd94b39712d8c09ceabf81d7e8d852d9904 | c12a5f5aa1bd3b17571900882f538b1b74958bac9a5fa2923f5c850cbafbf1dd | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [N-;H0;D1:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[c:4]-[C:5]1-[#16:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#16:6]-[C:5]-1-[c:4] | 82.2 | [{"value": 82.2, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.2, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1.07 g of sodium isocyanate in 20 ml of water is added to a solution of 3.03 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine in 40 ml of ethanol, and 2.46 g of acetic acid are added thereto. The mixture is stirred at room temperature for 2 hours. 200 ml of water are added to the mixture,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Urea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | O.C(C)O | null | 2 | [N-]=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1>O.C(C)O>NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eaa3856354d9479ba50679c11149fbdb | CCOC(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>>CCOC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | O.C(C)OC(=O)N=C=O.FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1.C([O-])([O-])=O.[K+].[K+].C(C)OC(=O)N=C=O>>C(C)OC(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[C:7]=[O:8].[NH:9]1[CH2:10][CH2:11][S:12][CH:13]1[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[O:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][N:26]([c:27]2[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]2)[CH2:34][CH2:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][C:7](=[O:8])[N:9]1[CH2:10][CH2... | CCOC(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1 | CCOC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | O1CCCC1 | Protection | Urea synthesis via isocyanate and secondary amine | af73464e4ca701ed477f99651384f5203ed9f16c6f2ea7c05a137da8d8037a87 | 1577e03da21f550f17923074b07cedede3bd99110f882d7bcf67bf5b974e59bc | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[c:8]-[C:9]1-[#16:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#16:10]-[C:9]-1-[c:8] | 40.5 | [{"value": 40.5, "product": "C(C)OC(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 0.9 g of ethoxycarbonyl isocyanate is added to a solution of 2 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 30 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 18 hours. 3.1 g of ethoxycarbonyl isocyanate are added to the mixture, and the mixture is stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Carbamic ester.Urea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | O1CCCC1 | null | 18 | CCOC(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>O1CCCC1>CCOC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4309e47a359d4d8aa7980c2c2a42a140 | CS(=O)(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>>CS(=O)(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1.CS(=O)(=O)N=C=O>>CS(=O)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F | [CH3:1][S:2](=[O:3])(=[O:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH2:10][S:11][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]2)[CH2:33][CH2:34]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][S:11]... | CS(=O)(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1 | CS(=O)(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | CC(=O)C | Acylation | Urea synthesis via isocyanate and secondary amine | 4fc60b9212e2cd5fef4065a865923d912e694348c230069e34894dd7a40b5956 | c54c1ed6f5693fe7284d99bae8ce6ef1af2bc669c2b604d5d1041c83f556df82 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[c:8]-[C:9]1-[#16:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#16:10]-[C:9]-1-[c:8] | 61.3 | [{"value": 61.3, "product": "CS(=O)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.94 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine are dissolved in anhydrous acetone, and 0.73 g of methanesulfonyl isocyanate is added thereto at room temperature. After the mixture is stirred for 30 minutes, the mixture is concentrated under reduced pressure to remove solvent. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Sulfonamide.Urea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | CC(=O)C | null | 0.5 | CS(=O)(=O)N=C=O.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>CC(=O)C>CS(=O)(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1bfbce77124b4ef7b75e6c9cc7cb718a | CCP(=O)(CC)N=C=S.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>>CCP(=O)(CC)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | C(C)P(=O)(CC)N=C=S.FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1>>C(C)P(=O)(CC)NC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F | [CH3:1][CH2:2][P:3](=[O:4])([CH2:5][CH3:6])[N:7]=[C:8]=[S:9].[NH:10]1[CH2:11][CH2:12][S:13][CH:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][N:27]([c:28]2[cH:29][cH:30][cH:31][c:32]([F:33])[cH:34]2)[CH2:35][CH2:36]1>>[CH3:1][CH2:2][P:3](=[O:4])([CH2:5][CH3:6])[NH:7][C:8](=[... | CCP(=O)(CC)N=C=S.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1 | CCP(=O)(CC)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | db6efd8caa332621bc2f47da956ab9d93842b9ec246a2813d78b4744edee689e | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [C:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7].[c:8]-[C:9]1-[#16:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#16:10]-[C:9]-1-[c:8] | 85.2 | [{"value": 81.0, "product": "C(C)P(=O)(CC)NC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "C(C)P(=O)(CC)NC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | 0.68 g of diethylphosphoryl isothiocyanate is added to a solution of 1.23 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of acetone, and the mixture is stirred for one day. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chlorofor... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | CC(=O)C | null | 24 | CCP(=O)(CC)N=C=S.Fc1cccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)c1>CC(=O)C>CCP(=O)(CC)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc5689b69bf7423889aa61414394c6d6 | CC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>CC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | C(C)(=O)Cl.[H-].[Na+].CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F>>C(C)(=O)N(C(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([CH3:5])[C:6](=[O:7])[N:8]1[CH2:9][CH2:10][S:11][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]2)[CH2:33][CH2:34]1>>[CH3:1][C:2](=[O:3])[N:4]([CH3:5])[C:6](=[O:7])[N:8]1[CH2:9][CH2:10][S... | CC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | CCOCC.CN(C=O)C | Acylation | N-alkylation of secondary amines with alkyl halides | 996e0ddf2d6b57ad6b8e08b45c57ed86da0355f61815643564e670f244fe345b | ed2e2a2113014ef864b0a3bd063f004647b373e1f6820e0fdd5587d12a0e8460 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#16:4]-[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C;D1;H3:10])-[C:11]>>[#16:4]-[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:11] | null | [] | 50 | CELSIUS | 20 | HOUR | 0.1 g of sodium hydride (60% oil dispersion) is added to a solution of one g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide in 30 ml of dimethylformamide, and a solution of 0.19 g of acetyl chloride in 5 ml of ether is added thereto. After the mixture is stirred at 50° ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Urea | Urea.Substituted dicarboximide | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CCOCC.CN(C=O)C | 50 | 20 | CC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>CCOCC.CN(C=O)C>CC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-32f84dbb0b9d4ce7a27403d9bb0ba450 | CCC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>CCC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F.C(CC)(=O)Cl.C(C)N(CC)CC>>CN(C(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F)C(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH:5]([CH3:6])[C:7](=[O:8])[N:9]1[CH2:10][CH2:11][S:12][CH:13]1[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[O:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][N:26]([c:27]2[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]2)[CH2:34][CH2:35]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([CH3:6])[C:7](=[O:8])[N:9]1[C... | CCC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CCC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | C1(=CC=CC=C1)C | Acylation | N-alkylation of secondary amines with alkyl halides | 996e0ddf2d6b57ad6b8e08b45c57ed86da0355f61815643564e670f244fe345b | ed2e2a2113014ef864b0a3bd063f004647b373e1f6820e0fdd5587d12a0e8460 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[#16:5]-[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[C;D1;H3:11])-[C:12]>>[#16:5]-[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4])-[C:12] | 12 | [{"value": 12.0, "product": "CN(C(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.22 g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide, 1.39 g of propionyl chloride, 2.53 g of triethylamine and 50 ml of toluene is refluxed for 2.5 days with stirring. The mixture is concentrated under reduced pressure to remove solvent. Water is added to... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Urea | Urea.Substituted dicarboximide | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | CCC(=O)Cl.CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>C1(=CC=CC=C1)C>CCC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c55a82908a04847bac89c1a561b1980 | CC(=O)Cl.CC(=O)Cl.NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(=O)N.O1CCCC1.C(C)N(CC)CC.C(C)(=O)Cl.C(C)N(CC)CC.C(C)(=O)Cl.O1CCCC1>>C(C)(=O)N=C(OC(C)=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F | Cl[C:2]([CH3:1])=[O:3].Cl[C:7]([CH3:8])=[O:9].[NH2:4][C:5](=[O:6])[N:10]1[CH2:11][CH2:12][S:13][CH:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][N:27]([c:28]2[cH:29][cH:30][cH:31][c:32]([F:33])[cH:34]2)[CH2:35][CH2:36]1>>[CH3:1][C:2](=[O:3])[N:4]=[C:5]([O:6][C:7]([CH3:8])=[... | CC(=O)Cl.CC(=O)Cl.NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | null | Acylation | OtherReaction | 7cbab782ac1731d55afce8259d9230a293eafaaf2c8590fb5b21395b8697a775 | 24b7119c60fa8babfa147854c12206b2a2e456f249b6d16380d6c202d29d17da | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].Cl-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6].[#16:7]-[C:8]-[#7:9](-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;H0;D1;+0:12])-[C:13]>>[#16:7]-[C:8]-[#7:9](-[C;H0;D3;+0:10](=[N;H0;D2;+0:11]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[O;H0;D2;+0:12]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6... | 56 | [{"value": 56.0, "product": "C(C)(=O)N=C(OC(C)=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 1.08 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are dissolved in 20 ml of tetrahydrofuran, and 0.76 g of triethylamine is added thereto. A solution of 0.59 g of acetyl chloride in one ml of tetrahydrofuran is added to the mixture under ice-cooling, and the mixture is stirr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Urea | Ester | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | null | null | 72 | CC(=O)Cl.CC(=O)Cl.NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d0bb55d299664209bdb4fb168a9ad2a8 | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | C(C)(=O)N=C(OC(C)=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F.Cl>>C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F | CC(=O)[O:6][C:5](=[N:4][C:2]([CH3:1])=[O:3])[N:7]1[CH2:8][CH2:9][S:10][CH:11]1[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([c:25]2[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]2)[CH2:32][CH2:33]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][S:10][CH:11]1[c:12... | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | O1CCCC1.[OH-].[Na+].C(C)O | Miscellaneous | OtherReaction | 2e6fb0a3329693eca9c08ec9ab0da418063be847a6c403d46e63c08fc5041693 | 82a707dbab5460decf10b063efbab9ed39707af4af5e33ed675afdf1c19138af | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[#7:7](-[C:8])-[C:9]-[#16:10]>>[#16:10]-[C:9]-[#7:7](-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[NH;D2;+0:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:8] | 90.4 | [{"value": 90.0, "product": "C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 0.59 g of N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid is dissolved in a mixture of 15 ml of ethanol and 5 ml of tetrahydrofuran, and 1.34 ml of 10% aqueous sodium hydroxide solution is added thereto under ice-cooling. The mixture is stirred for 15 minutes, and... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Urea | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O1CCCC1.[OH-].[Na+].C(C)O | null | 0.25 | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>O1CCCC1.[OH-].[Na+].C(C)O>CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-aa76061cb7944db687e41e7774788579 | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1>>CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | Cl.C(C)(=O)N=C(OC(C)=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1.C(C)O.[OH-].[Na+]>>C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | CC(=O)[O:6][C:5](=[N:4][C:2]([CH3:1])=[O:3])[N:7]1[CH2:8][CH2:9][S:10][CH:11]1[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][S:10][CH:11]1[c:12]1[cH:1... | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | O1CCCC1.O | Miscellaneous | OtherReaction | 2e6fb0a3329693eca9c08ec9ab0da418063be847a6c403d46e63c08fc5041693 | 82a707dbab5460decf10b063efbab9ed39707af4af5e33ed675afdf1c19138af | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[#7:7](-[C:8])-[C:9]-[#16:10]>>[#16:10]-[C:9]-[#7:7](-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[NH;D2;+0:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:8] | 66.1 | [{"value": 66.1, "product": "C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "C(C)(=O)NC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of 1.19 g of N,O-diacetyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid, 20 ml of ethanol, 0.287 g of sodium hydroxide, 2.7 ml of water and 20 ml of tetrahydrofuran is stirred for 1.5 hours under ice-cooling. The mixture is neutralized with 10% hydrochloric acid, and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Urea | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O1CCCC1.O | null | 1.5 | CC(=O)N=C(OC(C)=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1>O1CCCC1.O>CC(=O)NC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f2ba0d33acd149c78f546b6cef92101a | CC(=O)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>>NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | C(C)(=O)NC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC(=CC=C1)F.[OH-].[Na+]>>FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(N)=S | CC(=O)[NH:1][C:2](=[S:3])[N:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]2)[CH2:29][CH2:30]1>>[NH2:1][C:2](=[S:3])[N:4]1[CH2:5][CH2:6][S:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][... | CC(=O)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | b7ab3e4f878ec88ccf9f24aa8ace9c0e9bd79c45879c7956fca4b89bfcf032d3 | eb308e50ea59a818e9be36da7e60c01d0f7ab2d0f39e89f35847ab33b6eb422f | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4](-[C:5])-[C:6]-[#16:7]>>[#16:7]-[C:6]-[#7:4](-[C:2](-[NH2;D1;+0:1])=[S;D1;H0:3])-[C:5] | 90 | [{"value": 90.0, "product": "FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(N)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "FC=1C=C(C=CC1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1C(N)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.87 g of N-acetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide, 7.3 ml of 10% aqueous sodium hydroxide solution and 60 ml of ethanol is refluxed for 20 hours and then concentrated under reduced pressure to remove solvent. The residue is extracted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Secondary amide | Thiourea | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | C(C)O | null | null | CC(=O)NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1>C(C)O>NC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-63d52bf819e7416a9fcd3ec481ab9c00 | CN(C(=O)C1CCCN1S(=O)(=O)c1ccc2ccccc2c1)C(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1>>CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CN(C(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1)C(=O)C1N(CCC1)S(=O)(=O)C1=CC2=CC=CC=C2C=C1.O1CCCC1.CO.[OH-].[Na+]>>CNC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | O=C(C1CCCN1S(=O)(=O)c1ccc2ccccc2c1)[N:2]([CH3:1])[C:3](=[S:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][NH:2][C:3](=[S:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:... | CN(C(=O)C1CCCN1S(=O)(=O)c1ccc2ccccc2c1)C(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | O | Reduction | Hydrogenolysis of tertiary amines | 4c88e43287aa5278815bca89984947d8fc6205bb3075a9603648c7c1700411ed | 5d07a16126cebdc2b1f430d06d117de6ba73811a47aaf39b506886f5cb1149fd | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | O=C(-C1-C-C-C-N-1-S(=O)(=O)-c1:c:c:c2:c:c:c:c:c:2:c:1)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[S;D1;H0:4])-[#7:5](-[C:6])-[C:7]-[#16:8]>>[#16:8]-[C:7]-[#7:5](-[C:3](=[S;D1;H0:4])-[NH;D2;+0:1]-[C;D1;H3:2])-[C:6] | 94.2 | [{"value": 94.2, "product": "CNC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "CNC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.05 g of (-)-N-methyl-N-[1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl]-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide, 40 ml of tetrahydrofuran, 40 ml of methanol, 120 mg of sodium hydroxide and 3 ml of water are treated in the same manner as described in Example 148-(2). 600 mg of (-)-N... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Tertiary amide.Tertiary amine | Thiourea | C1CCNC1.c1ccc2ccccc2c1 | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O | null | null | CN(C(=O)C1CCCN1S(=O)(=O)c1ccc2ccccc2c1)C(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1>O>CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0a61adb5089146bbaafb86e29a4c179b | Cc1ccc(S(=O)(=O)OCCCl)cc1.O=Cc1ccccc1O>>O=Cc1ccccc1OCCCl | OC1=C(C=O)C=CC=C1.ClCCOS(=O)(=O)C1=CC=C(C)C=C1.C([O-])([O-])=O.[K+].[K+]>>ClCCOC1=C(C=O)C=CC=C1 | Cc1ccc(S(=O)(=O)O[CH2:10][CH2:11][Cl:12])cc1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][Cl:12] | Cc1ccc(S(=O)(=O)OCCCl)cc1.O=Cc1ccccc1O | O=Cc1ccccc1OCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3]):c:c:1.[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 86 | [{"value": 86.0, "product": "ClCCOC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "ClCCOC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 40.0 g of 2-hydroxybenzaldehyde, 84 g of 1-chloro-2-tosyloxyethane and 50 g of potassium carbonate are added to 270 ml of dimethylformamide, and the mixture is stirred at room temperature for 3 days. After the reaction, half of the solvent is removed under reduced pressure. About 600 ml of water are added to the residu... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1 | TsOH.HO- | CN(C=O)C | null | 72 | Cc1ccc(S(=O)(=O)OCCCl)cc1.O=Cc1ccccc1O>CN(C=O)C>O=Cc1ccccc1OCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a487da4d0ad342668dd109913a8681fe | CNC(=S)N1CCSC1c1ccc(O)cc1.Cc1ccc(S(=O)(=O)OCCCl)cc1>>CNC(=S)N1CCSC1c1ccc(OCCCl)cc1 | CNC(=S)N1C(SCC1)C1=CC=C(C=C1)O.ClCCOS(=O)(=O)C1=CC=C(C)C=C1.C([O-])([O-])=O.[K+].[K+]>>CNC(=S)N1C(SCC1)C1=CC=C(C=C1)OCCCl | [CH3:1][NH:2][C:3](=[S:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:18][cH:19]1.Cc1ccc(S(=O)(=O)O[CH2:15][CH2:16][Cl:17])cc1>>[CH3:1][NH:2][C:3](=[S:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][Cl:17])[cH:18][cH:19]1 | CNC(=S)N1CCSC1c1ccc(O)cc1.Cc1ccc(S(=O)(=O)OCCCl)cc1 | CNC(=S)N1CCSC1c1ccc(OCCCl)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccc(C2NCCS2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3]):c:c:1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Cl;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 51.9 | [{"value": 51.9, "product": "CNC(=S)N1C(SCC1)C1=CC=C(C=C1)OCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.4, "product": "CNC(=S)N1C(SCC1)C1=CC=C(C=C1)OCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A mixture of 5 g of N-methyl-2-(4-hydroxyphenyl)thiazolidine-3-carbothioamide, 4.6 g of 1-chloro-2-tosyloxyethane, 4 g of potassium carbonate and 20 ml of dimethylformamide is stirred at room temperature for 2 days and further stirred at 50° C. for 20 hours. The mixture is concentrated under reduced pressure to remove ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | C1CSC[NH]1.c1ccccc1 | TsOH.HO- | CN(C=O)C | null | 48 | CNC(=S)N1CCSC1c1ccc(O)cc1.Cc1ccc(S(=O)(=O)OCCCl)cc1>CN(C=O)C>CNC(=S)N1CCSC1c1ccc(OCCCl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1ab0649934ff468ca3ce4dfc173e5293 | ClCCCBr.OCc1ccccc1S>>OCc1ccccc1SCCCCl | OCC1=C(C=CC=C1)S.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>>ClCCCSC1=C(CO)C=CC=C1 | Br[CH2:10][CH2:11][CH2:12][Cl:13].[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[SH:9]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][CH2:12][Cl:13] | ClCCCBr.OCc1ccccc1S | OCc1ccccc1SCCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 93 | [{"value": 93.0, "product": "ClCCCSC1=C(CO)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "ClCCCSC1=C(CO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 11.9 g of 2-(hydroxymethyl)thiophenol, 35.44 g of 1-bromo-3-chloropropane, 11.58 g of potassium carbonate and 150 ml of dimethylformamide is stirred at room temperature for 2 hours. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. Water is add... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 2 | ClCCCBr.OCc1ccccc1S>CN(C=O)C>OCc1ccccc1SCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-60e4dc598c6f440faebfb4ac0e619073 | COC(=O)c1ccc(SCCCCl)cc1>>OCc1ccc(SCCCCl)cc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCCSC1=CC=C(C(=O)OC)C=C1.O>>ClCCCSC1=CC=C(CO)C=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([S:7][CH2:8][CH2:9][CH2:10][Cl:11])[cH:12][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([S:7][CH2:8][CH2:9][CH2:10][Cl:11])[cH:12][cH:13]1 | COC(=O)c1ccc(SCCCCl)cc1 | OCc1ccc(SCCCCl)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 85.3 | [{"value": 85.3, "product": "ClCCCSC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | 5 g of lithium aluminum hydride are suspended in 200 ml of tetrahydrofuran, and a solution of 31.9 g of methyl 4-(3-chloro-propylthio)benzoate in 200 ml of tetrahydrofuran is added thereto at 5° to 15° C. The mixture is stirred at the same temperature for 45 minutes. Water is added to the mixture at a temperature of be... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | 0.75 | COC(=O)c1ccc(SCCCCl)cc1>O1CCCC1>OCc1ccc(SCCCCl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7f4ccdacd2124c509852605e00d848bd | OCc1ccccc1SCCCl>>O=Cc1ccccc1SCCCl | CS(=O)C.C(C(=O)Cl)(=O)Cl.C(C)N(CC)CC.ClCCSC1=C(CO)C=CC=C1>>ClCCSC1=C(C=O)C=CC=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][Cl:12]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][Cl:12] | OCc1ccccc1SCCCl | O=Cc1ccccc1SCCCl | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 91.7 | [{"value": 91.6, "product": "ClCCSC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "ClCCSC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 27.8 g of dimethylsulfoxide in 50 ml of methylene chloride is added to a solution of 22.6 g of oxalyl chloride in 450 ml of methylene chloride at -60° C. during one hour, and a solution of 32.7 g of 2-(2-chloroethylthio)benzylalcohol in 50 ml of methylene chloride is added thereto. The mixture is stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O.C(Cl)Cl | null | 0.25 | OCc1ccccc1SCCCl>O.C(Cl)Cl>O=Cc1ccccc1SCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-84c56ccc3d8f4af7b42a8396c4f681d0 | ClCCCN1CCN(c2ccccc2)CC1.O=Cc1ccccc1O>>O=Cc1ccccc1OCCCN1CCN(c2ccccc2)CC1 | [Na].OC1=C(C=O)C=CC=C1.Cl.Cl.ClCCCN1CCN(CC1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N1CCN(CC1)CCCOC1=C(C=O)C=CC=C1 | Cl[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:... | ClCCCN1CCN(c2ccccc2)CC1.O=Cc1ccccc1O | O=Cc1ccccc1OCCCN1CCN(c2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCN2CCN(c3ccccc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 74.4 | [{"value": 74.4, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCOC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A mixture of 3.88 g of 2-hydroxybenzaldehyde sodium salt, 7.00 g of 1-(3-chloropropyl)-4-phenylpiperazine dihydrochloride, 6.80 g of potassium carbonate and 50 ml of dimethylformamide is stirred at 60° to 70° C. for 15 hours under nitrogen atmosphere, and is concentrated under reduced pressure to remove solvent. Water ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CN(C=O)C | null | 15 | ClCCCN1CCN(c2ccccc2)CC1.O=Cc1ccccc1O>CN(C=O)C>O=Cc1ccccc1OCCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f5b0b9287b1249399995fc70dd4ff6e7 | O=Cc1ccccc1OCCCl.OCCO>>ClCCOc1ccccc1C1OCCO1 | C([O-])(O)=O.[Na+].ClCCOC1=C(C=O)C=CC=C1.C(CO)O.P(O)(O)(O)=O>>C1COC(C2=C(C=CC=C2)OCCCl)O1 | [Cl:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:12].O[CH2:13][CH2:14][OH:15]>>[Cl:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]1[O:12][CH2:13][CH2:14][O:15]1 | O=Cc1ccccc1OCCCl.OCCO | ClCCOc1ccccc1C1OCCO1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1):[c:8] | 97.2 | [{"value": 97.0, "product": "C1COC(C2=C(C=CC=C2)OCCCl)O1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "C1COC(C2=C(C=CC=C2)OCCCl)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 46.5 g of 2-(2-chloroethyloxy)benzaldehyde and 33.2 g of ethylene glycol in 500 ml of benzene in added 0.5 ml of 85% phosphoric acid, and the mixture is refluxed with stirring for about 18 hours while removing the produced water. After the reaction, the reaction mixture is cooled with ice and is made a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | C1=CC=CC=C1 | null | 18 | O=Cc1ccccc1OCCCl.OCCO>C1=CC=CC=C1>ClCCOc1ccccc1C1OCCO1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5ac80b0aa0e5432ea6f8cf1cb67bf4af | ClCCOc1ccccc1C1OCCO1.c1ccc(N2CCNCC2)cc1>>O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1 | C1COC(C2=C(C=CC=C2)OCCCl)O1.C1(=CC=CC=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=O)C=CC=C1 | Cl[CH2:11][CH2:10][O:9][c:8]1[c:3]([CH:2]2OCC[O:1]2)[cH:4][cH:5][cH:6][cH:7]1.[NH:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:... | ClCCOc1ccccc1C1OCCO1.c1ccc(N2CCNCC2)cc1 | O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | CN(C=O)C | Acylation | OtherReaction | e4ef4aeaaf8934513c8e22bceb9f0c076aecff470acc174043e72c9f596892d3 | 3fea7cb017cc7c3c2d30466649a837ff1527347fa4d748b5fc13e5f58792738d | c1ccc(OCCN2CCN(c3ccccc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[c:4]:[c:5](-[CH;D3;+0:6]1-O-C-C-[O;H0;D2;+0:7]-1):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[O;H0;D1;+0:7]=[CH;D2;+0:6]-[c:5](:[c:8]):[c:4]-[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | 42.8 | [{"value": 42.8, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A suspension of 2.29 g of 2-(2-chloroethyloxy)benzaldehyde ethyleneacetal, 1.73 g of N-phenylpiperazine, 1.50 g of anhyrous potassium carbonate and 15 ml of dimethylformamide is stirred at 70°-80° C. for about 18 hours under argon atmosphere. The reaction mixture is concentrated under reduced pressure to remove dimethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Secondary amine | Aldehyde.Tertiary amine | C1COCO1.C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CN(C=O)C | null | 18 | ClCCOc1ccccc1C1OCCO1.c1ccc(N2CCNCC2)cc1>CN(C=O)C>O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-55e7ad6b22ff44e29d699b8a2b766ad4 | ClCCCN1CCN(c2ccccc2)CC1.OCc1ccccc1S>>OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1 | OCC1=C(C=CC=C1)S.Cl.Cl.ClCCCN1CCN(CC1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(CO)C=CC=C1 | Cl[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1.[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[SH:9]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][c... | ClCCCN1CCN(c2ccccc2)CC1.OCc1ccccc1S | OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(SCCCN2CCN(c3ccccc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 91 | [{"value": 91.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(CO)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(CO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 6 | HOUR | A mixture of 1.56 g of 2-(hydroxymethyl)thiophenol, 3.77 g of 1-(3-chloropropyl)-4-phenylpiperazine dihydrochloride, 5.02 g of potassium carbonate and 40 ml of dimethylformamide is stirred at 50° C. for 6 hours. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solv... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CN(C=O)C | 50 | 6 | ClCCCN1CCN(c2ccccc2)CC1.OCc1ccccc1S>CN(C=O)C>OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e1eec7f7add74932a65c6586620a67b0 | OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1>>O=Cc1ccccc1SCCCN1CCN(c2ccccc2)CC1 | C(C)N(CC)CC.CS(=O)C.C(C(=O)Cl)(=O)Cl.C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(CO)C=CC=C1>>C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(C=O)C=CC=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]... | OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1 | O=Cc1ccccc1SCCCN1CCN(c2ccccc2)CC1 | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(SCCCN2CCN(c3ccccc3)CC2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.5 | [{"value": 90.5, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCSC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1.1 g of dimethylsulfoxide in 5 ml of methylene chloride is added to a solution of 0.894 g of oxalyl chloride in 20 ml of methylene chloride at -50° C. A solution of 2.19 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzylalcohol in 10 ml of methylene chloride is added to the mixture at -50° C., and the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | O.C(Cl)Cl | null | 0.25 | OCc1ccccc1SCCCN1CCN(c2ccccc2)CC1>O.C(Cl)Cl>O=Cc1ccccc1SCCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eb12f920bec740a89ef3f6602f83b842 | OCc1ccccc1SCCN1CCN(c2ccccc2)CC1>>O=Cc1ccccc1SCCN1CCN(c2ccccc2)CC1 | C1(=CC=CC=C1)N1CCN(CC1)CCSC1=C(CO)C=CC=C1.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C1(=CC=CC=C1)N1CCN(CC1)CCSC1=C(C=O)C=CC=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:2... | OCc1ccccc1SCCN1CCN(c2ccccc2)CC1 | O=Cc1ccccc1SCCN1CCN(c2ccccc2)CC1 | null | null | C(C)N(CC)CC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(SCCN2CCN(c3ccccc3)CC2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93.1 | [{"value": 93.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCSC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCSC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6.0 g of 2-[2-(4-phenylpiperazin-1-yl)ethylthio]benzylalcohol, 2.60 g of oxalyl chloride, 3.2 g of dimethylsulfoxide and 9.3 g of triethylamine are treated in the same manner as described above. 5.55 g of 2-[2-(4-phenylpiperazin-1-yl)ethylthio]benzaldehyde are obtained. Yield: 93%.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)N(CC)CC | null | null | OCc1ccccc1SCCN1CCN(c2ccccc2)CC1>C(C)N(CC)CC>O=Cc1ccccc1SCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-46245ad98a7644dbbba7e7b2ed233ffd | NCCS.O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1>>c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=O)C=CC=C1.[OH-].[Na+].Cl.NCCS>>C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1 | [NH2:19][CH2:20][CH2:21][SH:22].O=[CH:18][c:17]1[c:12]([O:11][CH2:10][CH2:9][N:8]2[CH2:7][CH2:6][N:5]([c:4]3[cH:3][cH:2][cH:1][cH:26][cH:25]3)[CH2:24][CH2:23]2)[cH:13][cH:14][cH:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH:18]3[NH:19]... | NCCS.O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 15efb05380d8debf7bab56597d1fa9b0622ee8622ff23260de9add0344b89365 | 5d87d269e927a5d4c4d7957f00c75ee007fdf5209a75b4d446e6fde136a78f70 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[C:6]-[C:7]-[SH;D1;+0:8]>>[c:3]:[c:2](-[CH;D3;+0:1]1-[NH;D2;+0:5]-[C:6]-[C:7]-[S;H0;D2;+0:8]-1):[c:4] | 91.4 | [{"value": 91.4, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2.21 g of sodium hydroxide are added to a solution of 5.75 g of cysteamine hydrochloride in 200 ml of ethanol, and a solution of 14.28 g of 2-[2-(4-phenylpiperazin-1-yl)ethyloxy]benzaldehyde in 100 ml of ethanol is added thereto. After the mixture is stirred at room temperature for 2 hours, the mixture is concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Aliphatic thiol | Secondary amine.Monosulfide | null | C1CSCN1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.C1CSCN1 | HO- | C(C)O | null | 2 | NCCS.O=Cc1ccccc1OCCN1CCN(c2ccccc2)CC1>C(C)O>c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-09c579e755e541c2b07caf3e5cd2741f | COc1ncccc1C(=O)O>>COC(=O)c1cccnc1OC | S(=O)(Cl)Cl.COC1=NC=CC=C1C(=O)O.C(Cl)(Cl)(Cl)Cl>>COC1=NC=CC=C1C(=O)OC | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[O:11][CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[O:11][CH3:12] | COc1ncccc1C(=O)O | COC(=O)c1cccnc1OC | null | null | null | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[C;D1;H3:7] | null | [] | null | null | 16 | HOUR | Thionyl chloride (50 ml.) was added to 2-methoxypyridine-3-carboxylic acid (5 g.) in 50 ml. of carbon tetrachloride and the mixture refluxed for 2 hours. The reaction mixture was cooled, evaporated to solids and chased with multiple portions of fresh carbon tetrachloride. The resulting acid chloride hydrochloride was d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccncc1 | Other | null | null | 16 | COc1ncccc1C(=O)O>>COC(=O)c1cccnc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-29e55984d1184720b127405ae4f45163 | CCN(CC)CC.COc1ncc(Cl)cc1C(=O)O>>COC(=O)c1cc(Cl)cnc1OC | ClC=1C=C(C(=NC1)OC)C(=O)O.C(C)N(CC)CC>>ClC=1C=C(C(=NC1)OC)C(=O)OC | CCN(CC)C[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[O:12][CH3:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[O:12][CH3:13] | CCN(CC)CC.COc1ncc(Cl)cc1C(=O)O | COC(=O)c1cc(Cl)cnc1OC | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 8ba133f06c4c0df103dfa8d83a3ae1c8f954a895eb15a5679d75dae29435b369 | 99f5e58a6f94b05681979232ec71674baa8e98488f497e30fe94f5f9a191f8d9 | c1ccncc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | null | [] | null | null | null | null | By the procedure of Example 1, 5-chloro-2- methoxypyridine-3-carboxylic acid [Sarges et al., J. Med. Chem. 19, 709 (1976); 10 g.]was converted to its acid chloride, which was added in one portion to 150 ml. of methanol (slight exotherm), then made basic with triethylamine (approximately 1.1 equivalents). The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Ester | null | null | c1ccncc1 | Other | CO | null | null | CCN(CC)CC.COc1ncc(Cl)cc1C(=O)O>CO>COC(=O)c1cc(Cl)cnc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-610cc48c92ef4b2b91d458584a284769 | CCOC(=O)C(O)c1cc(F)cc2cccnc12.[NH4+]>>NC(=O)C(O)c1cc(F)cc2cccnc12 | FC=1C=C2C=CC=NC2=C(C1)C(C(=O)OCC)O.[OH-].[NH4+]>>FC=1C=C2C=CC=NC2=C(C1)C(C(=O)N)O | CCO[C:2](=[O:3])[CH:4]([OH:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]12.[NH4+:1]>>[NH2:1][C:2](=[O:3])[CH:4]([OH:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]12 | CCOC(=O)C(O)c1cc(F)cc2cccnc12.[NH4+] | NC(=O)C(O)c1cc(F)cc2cccnc12 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2ncccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[O;D1;H1:4])-[c:5]:[c:6]:[#7;a:7].[NH4+;D0:8]>>[#7;a:7]:[c:6]:[c:5]-[C:3](-[O;D1;H1:4])-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2] | null | [] | null | null | null | null | Ethyl 2-(6-fluoro-8-quinolyl)-2-hydroxyacetate (1.1 g.) was refluxed for 10 minutes in 300 ml. of conc. ammonium hydroxide. The reaction mixture was cooled slightly, clarified by filtration and evaporated to solids. Trituration of the residue with 25 ml. of toluene gave the title product (860 mg., m.p. 169°-171° C.).
C... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2ncccc2c1 | HO- | null | null | null | CCOC(=O)C(O)c1cc(F)cc2cccnc12.[NH4+]>>NC(=O)C(O)c1cc(F)cc2cccnc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7eb2b9b7af004b369a2532d9aacf93e1 | Cn1cccc1.O=C1NC(=O)C(=O)C(=O)N1>>Cn1cccc1C1(O)C(=O)NC(=O)NC1=O | O.N1C(=O)NC(=O)C(=O)C1=O.CN1C=CC=C1.Cl>>OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)C | [CH3:1][n:2]1[cH:3][cH:4][cH:5][cH:6]1.[C:7]1(=[O:8])[C:9](=[O:10])[NH:11][C:12](=[O:13])[NH:14][C:15]1=[O:16]>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1[C:7]1([OH:8])[C:9](=[O:10])[NH:11][C:12](=[O:13])[NH:14][C:15]1=[O:16] | Cn1cccc1.O=C1NC(=O)C(=O)C(=O)N1 | Cn1cccc1C1(O)C(=O)NC(=O)NC1=O | null | null | C(C)O | C-C Coupling | OtherReaction | a4c1a46ff012305b9e5a76446fe231f2c1c5f443a6c3c3af74a1ce06988920dd | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=C1NC(=O)C(c2ccc[nH]2)C(=O)N1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[O;D1;H0:7]=[C:8]1-[#7:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13](=[O;D1;H0:14])-[C;H0;D3;+0:15]-1=[O;H0;D1;+0:16]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:15]1(-[OH;D1;+0:16])-[C:13](=[O;D1;H0:14])-[#7:12]-[C:10](=[O;D1;H0:11])-[#7:9]-[C:... | 65 | [{"value": 5.0, "product": "OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | Alloxan hydrate (3.2 g., 0.02 mole) was dissolved in 50 ml. of ethanol by warming. 1-Methylpyrrole (1.6 g., 0.02 mole) was added and the mixture warmed for 5 minutes on a steam bath, while perfusing with hydrogen chloride. After standing at room temperature for 0.5 hour, the reaction mixture was evaporated to dryness a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cc[nH]c1.C1CNCNC1 | c1ccc[nH]1.C1CNCNC1 | c1ccc[nH]1.C1CNCNC1 | null | C(C)O | null | 0.5 | Cn1cccc1.O=C1NC(=O)C(=O)C(=O)N1>C(C)O>Cn1cccc1C1(O)C(=O)NC(=O)NC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a21960842da8446c8bd423f866a07849 | CCCCI.O=C1NC(=O)C(=O)C(=O)N1.c1cc[nH]c1>>CCCCn1cccc1C1(O)C(=O)NC(=O)NC1=O | Cl.N1C=CC=C1.[K].ICCCC.N1C(=O)NC(=O)C(=O)C1=O>>OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)CCCC | I[CH2:4][CH2:3][CH2:2][CH3:1].[C:10]1(=[O:11])[C:12](=[O:13])[NH:14][C:15](=[O:16])[NH:17][C:18]1=[O:19].[nH:5]1[cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[C:10]1([OH:11])[C:12](=[O:13])[NH:14][C:15](=[O:16])[NH:17][C:18]1=[O:19] | CCCCI.O=C1NC(=O)C(=O)C(=O)N1.c1cc[nH]c1 | CCCCn1cccc1C1(O)C(=O)NC(=O)NC1=O | null | null | O1CCCC1.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 220be84d22102020d0dc799ad96f73134274c484ba4a32d0b1715b3d6dcb7ffb | 589c80aa999ad622b2d6aa7f4cdee3f946916a025ab7700e5ceb34432777049f | O=C1NC(=O)C(c2ccc[nH]2)C(=O)N1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12]-1=[O;H0;D1;+0:13].[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[nH;D2;+0:18]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:14]:[c:15]:[c:16]:[c;H0;D3;+0:17]:1-[C;H0;D4;+0:12]1(-[OH;D1;+0:13])-[C:5](=[O;D1;H0... | 64.1 | [{"value": 64.1, "product": "OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium pyrrole (3.0 g., 0.03 mole), 1-iodobutane (9.2 g., 0.05 moles) and 10 ml. of tetrahydrofuran were combined and refluxed for 1.5 hours by which time the reaction mixture had become a thick mass. The reaction mixture was diluted with 30 ml. of water and extracted with 35 ml. of ether. The ether was backwashed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | C1CNCNC1.c1cc[nH]c1 | c1ccc[nH]1.C1CNCNC1 | c1ccc[nH]1.C1CNCNC1 | HI | O1CCCC1.C(C)O | null | null | CCCCI.O=C1NC(=O)C(=O)C(=O)N1.c1cc[nH]c1>O1CCCC1.C(C)O>CCCCn1cccc1C1(O)C(=O)NC(=O)NC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-95069968247c44b2ab51ec34ff101153 | O=C1NC(=O)C(=O)C(=O)N1.c1ccc(-n2cccc2)cc1>>O=C1NC(=O)C(O)(c2cccn2-c2ccccc2)C(=O)N1 | O.N1C(=O)NC(=O)C(=O)C1=O.C1(=CC=CC=C1)N1C=CC=C1.O.N1C(=O)NC(=O)C(=O)C1=O.Cl>>OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)C1=CC=CC=C1 | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[O:7])[C:19](=[O:20])[NH:21]1.[cH:8]1[cH:9][cH:10][cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6]([OH:7])([c:8]2[cH:9][cH:10][cH:11][n:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:19](=[O:20])[NH:21]1 | O=C1NC(=O)C(=O)C(=O)N1.c1ccc(-n2cccc2)cc1 | O=C1NC(=O)C(O)(c2cccn2-c2ccccc2)C(=O)N1 | null | null | C(C)O | C-C Coupling | OtherReaction | a4c1a46ff012305b9e5a76446fe231f2c1c5f443a6c3c3af74a1ce06988920dd | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=C1NC(=O)C(c2cccn2-c2ccccc2)C(=O)N1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#7:10]-1.[c:11]-[#7;a:12]1:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:1>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6](-[OH;D1;+0:7])(-[c;H0;D3;+0:16]2:[c:15]:[c:14]:[c:13]:[#7;a:12]:2-[c:11])-[C:8](=[O;D1;H0:9])-[... | 80.6 | [{"value": 80.6, "product": "OC1(C(NC(NC1=O)=O)=O)C=1N(C=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Phenylpyrrole (1.4 g., 0.01 mole), alloxan hydrate (1.6 g., 0.01 mole) and 50 ml. of ethanol were combined and refluxed for 15 minutes. No reaction was noted by tlc. 1N Hydrochloric acid (10 ml., 0.01 mole) was added and the acidified mixture refluxed for 15 minutes. Incomplete reaction was noted by tlc. A second por... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CNCNC1.c1cc[nH]c1 | C1CNCNC1.c1ccc[nH]1 | C1CNCNC1.c1ccc[nH]1.c1ccccc1 | null | C(C)O | null | null | O=C1NC(=O)C(=O)C(=O)N1.c1ccc(-n2cccc2)cc1>C(C)O>O=C1NC(=O)C(O)(c2cccn2-c2ccccc2)C(=O)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cea0023b4b3542e7b1758742907c3ede | Brc1ccc2[nH]ccc2c1.O=C1NC(=O)C(=O)C(=O)N1>>O=C1NC(=O)C(O)(c2c[nH]c3ccc(Br)cc23)C(=O)N1 | O.N1C(=O)NC(=O)C(=O)C1=O.BrC=1C=C2C=CNC2=CC1.Cl>>OC1(C(NC(NC1=O)=O)=O)C1=CNC2=CC=C(C=C12)Br | [cH:8]1[cH:9][nH:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]12.[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[O:7])[C:18](=[O:19])[NH:20]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6]([OH:7])([c:8]2[cH:9][nH:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]23)[C:18](=[O:19])[NH:20]1 | Brc1ccc2[nH]ccc2c1.O=C1NC(=O)C(=O)C(=O)N1 | O=C1NC(=O)C(O)(c2c[nH]c3ccc(Br)cc23)C(=O)N1 | null | null | C(C)O | C-C Coupling | OtherReaction | 7c628cde874505d70066b03c9296773cfbcdc40c0f4563afcdc554abdd3b32c8 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=C1NC(=O)C(c2c[nH]c3ccccc23)C(=O)N1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[c:11]:[c:12]1:[#7;a:13]:[c:14]:[cH;D2;+0:15]:[c:16]:1:[c:17]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9]-1(-[OH;D1;+0:10])-[c;H0;D3;+0:15]1:[c:14]:[#7;a:13]:[c:12](:[c:... | 93.8 | [{"value": 93.8, "product": "OC1(C(NC(NC1=O)=O)=O)C1=CNC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Alloxan hydrate (1.6 g., 0.01 mole) was dissolved in 40 ml. of ethanol by heating. 5-Bromoindole (1.96 g., 0.01 mole) was added and heating near reflux continued for 15 minutes. Tlc did not indicate that reaction had occured. 1N Hydrochloric acid (10 ml.) was then added while maintaining the reaction near reflux. After... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1ccc2[nH]ccc2c1.C1CNCNC1 | C1CNCNC1.c1ccc2[nH]ccc2c1 | C1CNCNC1.c1ccc2[nH]ccc2c1 | null | C(C)O | null | 0.25 | Brc1ccc2[nH]ccc2c1.O=C1NC(=O)C(=O)C(=O)N1>C(C)O>O=C1NC(=O)C(O)(c2c[nH]c3ccc(Br)cc23)C(=O)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8a9b468035a9458e96d4a4f5d9967faa | O=C1NC(=O)C(=O)C(=O)N1.c1ccc2scnc2c1>>O=C1NC(=O)C(O)(c2nc3ccccc3s2)C(=O)N1 | S1C=NC2=C1C=CC=C2.N1C(=O)NC(=O)C(=O)C1=O>>OC1(C(NC(NC1=O)=O)=O)C=1SC2=C(N1)C=CC=C2 | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[O:7])[C:17](=[O:18])[NH:19]1.[cH:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[s:16]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6]([OH:7])([c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[s:16]2)[C:17](=[O:18])[NH:19]1 | O=C1NC(=O)C(=O)C(=O)N1.c1ccc2scnc2c1 | O=C1NC(=O)C(O)(c2nc3ccccc3s2)C(=O)N1 | null | null | null | C-C Coupling | OtherReaction | d9aa83a883a197037fdd31c3d054c7bd874ee758a6aa8bcdd6296a903ccc5f38 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=C1NC(=O)C(c2nc3ccccc3s2)C(=O)N1 | [#16;a:1]1:[c:2]:[c:3]:[#7;a:4]:[cH;D2;+0:5]:1.[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12](=[O;D1;H0:13])-[C;H0;D3;+0:14]-1=[O;H0;D1;+0:15]>>[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12](=[O;D1;H0:13])-[C;H0;D4;+0:14]-1(-[OH;D1;+0:15])-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[#7;a:4]:1 | null | [] | null | null | null | null | By the procedure of Example 38, benzthiazole (2.7 g., 0.02 moles) was converted to its 2-lithio derivative and then reacted with anhydrous alloxan to yield title product, initially isolated as an oil. The latter was crystallized from ether-hexane [2.2 g.; Rf 0.55 (1:1 ethyl acetate:hexane/5% acetic acid)].
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CNCNC1.c1ccc2scnc2c1 | C1CNCNC1.c1ccc2scnc2c1 | C1CNCNC1.c1ccc2scnc2c1 | null | null | null | null | O=C1NC(=O)C(=O)C(=O)N1.c1ccc2scnc2c1>>O=C1NC(=O)C(O)(c2nc3ccccc3s2)C(=O)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc968f431e0a486dbfd6bbc5f8b29349 | C[O-].O=C(O)c1cccnc1Cl>>COc1ncccc1C(=O)O | ClC1=NC=CC=C1C(=O)O.C[O-].[Na+]>>COC1=NC=CC=C1C(=O)O | [CH3:1][O-:2].Cl[c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[OH:11]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[OH:11] | C[O-].O=C(O)c1cccnc1Cl | COc1ncccc1C(=O)O | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 600484490705932a09b3fac6538a42c6f3fc156ab44a4ea0bbd020dd3eafd6ff | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[C;D1;H3:9]-[O-;H0;D1:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8] | null | [] | 110 | CELSIUS | 30 | MINUTE | A stainless steel stirred autoclave was charged sequentially with methanol (2.8 1.), sodium methoxide (259 g.) (in portions, keeping the temperature less than 35° C.), and 2-chloro-3-pyridinecarboxylic acid (190 g.). The autoclave was sealed and the reaction mixture heated at 110° C. (50 psig) for 48 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CO | 110 | 0.5 | C[O-].O=C(O)c1cccnc1Cl>CO>COc1ncccc1C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3792b8f5158c4708b58669947fcd21e1 | CCOC(=O)C(=O)OCC.Clc1cc(Br)c2ncccc2c1>>CCOC(=O)C(=O)c1cc(Cl)cc2cccnc12 | C(CCC)[Li].BrC=1C=C(C=C2C=CC=NC12)Cl.C(C(=O)OCC)(=O)OCC>>ClC=1C=C2C=CC=NC2=C(C1)C(C(=O)OCC)=O | CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].Br[c:8]1[cH:9][c:10]([Cl:11])[cH:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][c:10]([Cl:11])[cH:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]12 | CCOC(=O)C(=O)OCC.Clc1cc(Br)c2ncccc2c1 | CCOC(=O)C(=O)c1cc(Cl)cc2cccnc12 | null | null | O1CCCC1 | C-C Coupling | Ester and halide to ketone | 3dbcbbaf463d6c40c5052a565558cc24c1b64e60a3b9034219110c98b23faabc | dd03ca4e617545414fae7e22c410ecd4f78e4fd10d5a86bce7e36a4a1d0f1e9d | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].C-C-O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | 0 | CELSIUS | 30 | MINUTE | 8-Bromo-6-chloroquinoline [J. Het. Chem. 6, pp. 243-245 (1969); 6 g., 0.025 mole]in 50 ml. of tetrahydrofuran was added dropwise over a 10 minute period to a mixture of butyl lithium (2.3 M in hexane, 12.2 ml., 0.028 mole) and 40 ml. of tetrahydrofuran held at -70° C. After an additional 30 minutes at this temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ketone | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | O1CCCC1 | 0 | 0.5 | CCOC(=O)C(=O)OCC.Clc1cc(Br)c2ncccc2c1>O1CCCC1>CCOC(=O)C(=O)c1cc(Cl)cc2cccnc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-88edf4562ff1434b84869e91d827f11b | O.Oc1ccc2ncccc2c1>>O=Cc1c(O)ccc2ncccc12 | C(Cl)(Cl)Cl.[OH-].[Na+].O.C(Cl)(Cl)Cl.OC=1C=C2C=CC=NC2=CC1>>OC1=C(C=2C=CC=NC2C=C1)C=O | [OH2:1].[cH:3]1[c:4]([OH:5])[cH:6][cH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[CH:2][c:3]1[c:4]([OH:5])[cH:6][cH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12 | O.Oc1ccc2ncccc2c1 | O=Cc1c(O)ccc2ncccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b448291d461d839ae70a6a1ab399b0e7d61d1ad82e7df41b54a00ef11e9f4879 | be117abed4a0a0378ea43d3a5c1ccf903b86823ade7e92fcb09d68743e45d19a | c1ccc2ncccc2c1 | [O;D1;H1:1]-[c:2]1:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8](:[c:9]):[cH;D2;+0:10]:1.[OH2;D0;+0:11]>>[O;D1;H1:1]-[c:2]1:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:10]:1-[C:12]=[O;H0;D1;+0:11] | null | [] | 90 | CELSIUS | 6 | HOUR | Sodium hydroxide (25 g.) was dissolved in 35 ml. of water with cooling, 6-hydroxyquinoline (5 g.) in 15 ml. of chloroform was added and the reaction mixture heated to reflux (about 90° C.) for 12 hours, during which two further 15 ml. portions of chloroform were added - one after 2 hours and the other after 6 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | null | 90 | 6 | O.Oc1ccc2ncccc2c1>>O=Cc1c(O)ccc2ncccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-49296d2357364b18b0d51fff59527d15 | O=C(O)c1cc2ccc(Cl)cc2o1>>O=C(O)c1cc2cc(Cl)ccc2o1 | ClC=1C=CC=C(C1C=O)O.FC1=CC2=C(OC(=C2)C(=O)O)C=C1.ClC=1C=CC2=C(OC(=C2)C(=O)O)C1>>ClC1=CC2=C(OC(=C2)C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:12]2[c:6]([cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[o:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]2[o:13]1 | O=C(O)c1cc2ccc(Cl)cc2o1 | O=C(O)c1cc2cc(Cl)ccc2o1 | null | null | null | Miscellaneous | OtherReaction | 6919e7905146bdc0c46835415551780572928af110d80d2e3da217b6e11a99fc | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2occc2c1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2:[o;H0;D2;+0:12]:1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:11]2:[c:10]:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:2:[o;H0;D2;+0:12]:1 | null | [] | null | null | null | null | By the same procedure, 5-fluorosalicyaldehyde and 6-chlorosalicylaldehyde are converted, respectively, to 5-fluorobenzo[b]furan-2-carboxylic acid and 6-chlorobenzo[b]furan-2-carboxylic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1 | null | null | null | null | O=C(O)c1cc2ccc(Cl)cc2o1>>O=C(O)c1cc2cc(Cl)ccc2o1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-75f04b9b625845f494cd468f75c57ffe | Cc1c(Cl)ccc2cccnc12.O=C1CCC(=O)N1Br>>Clc1ccc2cccnc2c1CBr | ClC1=CC=C2C=CC=NC2=C1C.BrN1C(CCC1=O)=O>>ClC1=CC=C2C=CC=NC2=C1CBr | [Cl:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[c:11]1[CH3:12].O=C1CCC(=O)N1[Br:13]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[c:11]1[CH2:12][Br:13] | Cc1c(Cl)ccc2cccnc12.O=C1CCC(=O)N1Br | Clc1ccc2cccnc2c1CBr | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2ncccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | 7-Chloro-8-methylquinoline (1 g.) [Bradford et al., J. Chem Soc., p. 437 (1947)]is dissolved in 20 ml. of benzene and brominated with one equivalent of N-bromosuccinimide in the presence of catalytic amounts of peroxide. The product, 7-chloro-8-(bromomethyl)quinoline is isolated by evaporation
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2ncccc2c1 | HO- | C1=CC=CC=C1 | null | null | Cc1c(Cl)ccc2cccnc12.O=C1CCC(=O)N1Br>C1=CC=CC=C1>Clc1ccc2cccnc2c1CBr |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5c24f2117d6a447bb1c6127ce54bb126 | BrBr.CC(=O)C1Cc2ccccc2C1>>O=C(CBr)C1Cc2ccccc2C1 | BrBr.BrBr.C1C(CC2=CC=CC=C12)C(C)=O.BrBr>>BrCC(=O)C1CC2=CC=CC=C2C1 | Br[Br:4].[O:1]=[C:2]([CH3:3])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1>>[O:1]=[C:2]([CH2:3][Br:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1 | BrBr.CC(=O)C1Cc2ccccc2C1 | O=C(CBr)C1Cc2ccccc2C1 | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc2c(c1)CCC2 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:3](-[C:2])=[O;D1;H0:5] | null | [] | null | null | null | null | Bromine (6.8 g) is slowly added to a stirred solution of 1-(2,3-dihydro-1H-inden-2-yl)ethanone (6.8 g) in 200 ml of dry ether, while keeping the temperature at +10° C. The rate of the addition of bromine is controlled so that the colour due to one added portion of bromine has been discharged before another portion is a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccc2c(c1)CCC2 | HBr | CCOCC | null | null | BrBr.CC(=O)C1Cc2ccccc2C1>CCOCC>O=C(CBr)C1Cc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-831b47ccaa75402fb592e9fa15e798c2 | BrBr.CC(=O)c1cc2ccccc2o1>>O=C(CBr)c1cc2ccccc2o1 | CC(=O)C=1OC2=C(C1)C=CC=C2.BrBr>>O1C(=CC2=C1C=CC=C2)C(CBr)=O | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[o:13]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[o:13]1 | BrBr.CC(=O)c1cc2ccccc2o1 | O=C(CBr)c1cc2ccccc2o1 | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc2occc2c1 | Br-[Br;H0;D1;+0:1].[#8;a:2]:[c:3]-[C:4](-[CH3;D1;+0:5])=[O;D1;H0:6]>>[#8;a:2]:[c:3]-[C:4](=[O;D1;H0:6])-[CH2;D2;+0:5]-[Br;H0;D1;+0:1] | null | [] | null | null | 2 | HOUR | Benzofuran-2-yl methyl ketone (20 g) is dissolved in 100 ml of methylene chloride and 3.2 ml of bromine in methylene chloride is added at 5°-10° C. Then the reaction mixture is stirred at +15° C. for 2 hours. Then it is washed with water, with diluted sodium bicarbonate solution and again with water. The organic phase ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccc2occc2c1 | HBr | C(Cl)Cl | null | 2 | BrBr.CC(=O)c1cc2ccccc2o1>C(Cl)Cl>O=C(CBr)c1cc2ccccc2o1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5a05f21af04347eba8fca34c13fc77a3 | C[C@@H]1c2ccccc2C[C@@H]1C(=O)O.O=S(Cl)Cl>>C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl | C[C@H]1[C@H](CC2=CC=CC=C12)C(=O)O.S(=O)(Cl)Cl>>C[C@H]1[C@H](CC2=CC=CC=C12)C(=O)Cl | O[C:11]([C@@H:10]1[C@H:2]([CH3:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9]1)=[O:12].O=S(Cl)[Cl:13]>>[CH3:1][C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@@H:10]1[C:11](=[O:12])[Cl:13] | C[C@@H]1c2ccccc2C[C@@H]1C(=O)O.O=S(Cl)Cl | C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)CCC2 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:6] | null | [] | null | null | null | null | cis-2,3-Dihydro-1-methyl-1H-indene-2-carboxylic acid (52.6 g) is converted to its acid chloride by treatment with thionyl chloride (130 ml). Excess thionyl chloride is distilled off and the acid chloride is distilled, b.p. 86°-89° C./0.45 mmHg. The yield is 47.9 g, 83%.
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)CCC2 | HCl | null | null | null | C[C@@H]1c2ccccc2C[C@@H]1C(=O)O.O=S(Cl)Cl>>C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0c8bd1726a624b558cf9760fcb686e24 | C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl>>CC(=O)[C@H]1Cc2ccccc2[C@H]1C | C[C@H]1[C@H](CC2=CC=CC=C12)C(=O)Cl.CCOCC.S(O)(O)(=O)=O>>C[C@H]1[C@H](CC2=CC=CC=C12)C(C)=O | Cl[C:2](=[O:3])[C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C@H:12]1[CH3:13]>>[CH3:1][C:2](=[O:3])[C@H:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C@H:12]1[CH3:13] | C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl | CC(=O)[C@H]1Cc2ccccc2[C@H]1C | null | null | null | Functional Group Interconversion | OtherReaction | 4e817a5ec78c6c2a6f84aedb26a0e8811be631b20b7d07ec665e1c596667189c | f6f1db2fb6b7641a5cc9b525399565f319b23dea2171a8a2e15ad3fed644bcab | c1ccc2c(c1)CCC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[C;D1;H3:6])=[O;D1;H0:2])-[C:5] | 92 | [{"value": 92.0, "product": "C[C@H]1[C@H](CC2=CC=CC=C12)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | cis-1-(2,3-Dihydro-1-methyl-1H-inden-2-yl)ethanone is prepared by the treatment of cis-2,3-dihydro-1-methyl-1H-indene-2-carboxylic acid chloride with ethoxymagnesiummalonic acid ethyl ester in dry ether and thereafter by the treatment of sulfuric acid according to the publication (Reynolds G. A. and Hauser, C. B., Org.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | null | null | c1ccc2c(c1)CCC2 | null | null | null | null | C[C@@H]1c2ccccc2C[C@@H]1C(=O)Cl>>CC(=O)[C@H]1Cc2ccccc2[C@H]1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8626b45b275c4e28bae2be02833668e2 | CC(=O)C1(Br)Cc2ccccc2C1C.C[C@@H]1c2ccccc2C[C@@H]1C(=O)CBr>>CC1c2ccccc2CC1(Br)C(=O)CBr | BrCC(=O)[C@@H]1[C@@H](C2=CC=CC=C2C1)C.BrBr.BrBr.C[C@H]1[C@H](CC2=CC=CC=C12)C(C)=O.BrC1(C(C2=CC=CC=C2C1)C)C(C)=O>>BrCC(=O)C1(C(C2=CC=CC=C2C1)C)Br | [CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C:10]1([Br:11])[C:12](=[O:13])[CH3:14].C[C@@H]1c2ccccc2C[C@@H]1C(=O)C[Br:15]>>[CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C:10]1([Br:11])[C:12](=[O:13])[CH2:14][Br:15] | CC(=O)C1(Br)Cc2ccccc2C1C.C[C@@H]1c2ccccc2C[C@@H]1C(=O)CBr | CC1c2ccccc2CC1(Br)C(=O)CBr | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 02a16af959daa02973ed686e9293b78635f4a648224716be7230eeabbda243ff | e75d27ba56381d95767cb1073c9e300bbe7fb0cf89d3bae527844cbd5245737b | c1ccc2c(c1)CCC2 | C-[C@H]1-[C@H](-C(=O)-C-[Br;H0;D1;+0:1])-C-c2:c:c:c:c:c:2-1.[C:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:3](-[C:2])=[O;D1;H0:5] | null | [] | null | null | null | null | Bromine in methylene chloride is slowly added to a stirred solution of cis-1-(2,3-dihydro-1-methyl-1H-inden-2-yl)ethanone (34.8 g) in methylene chloride (835 ml), while keeping the temperature at +10° C. The reaction is followed by GLC. The first products are the isomers of 1-(2-bromo-2,3-dihydro-1-methyl-1H-inden-2-yl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Primary halide | c1ccc2c(c1)CCC2 | null | c1ccc2c(c1)CCC2 | HO- | C(Cl)Cl | null | null | CC(=O)C1(Br)Cc2ccccc2C1C.C[C@@H]1c2ccccc2C[C@@H]1C(=O)CBr>C(Cl)Cl>CC1c2ccccc2CC1(Br)C(=O)CBr |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7ea4f8fc554c4262acbd33d788d8a118 | Cc1ccc2c(c1)C(C)C(C(=O)O)=C2>>CC1=C(C(=O)O)Cc2ccc(C)cc21 | CC1C(=CC2=CC=C(C=C12)C)C(=O)O.C(C)OC(C(CC1=CC=C(C=C1)C)C(C)=O)=O.S(O)(O)(=O)=O>>CC1=C(CC2=CC=C(C=C12)C)C(=O)O | [CH3:1][CH:2]1[C:3]([C:4](=[O:5])[OH:6])=[CH:7][c:8]2[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]21>>[CH3:1][C:2]1=[C:3]([C:4](=[O:5])[OH:6])[CH2:7][c:8]2[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]21 | Cc1ccc2c(c1)C(C)C(C(=O)O)=C2 | CC1=C(C(=O)O)Cc2ccc(C)cc21 | null | null | null | Miscellaneous | OtherReaction | a7595144baf9ed16d69ef1cd82fd2cf6644c447d3eba2ace35dfdcca34f79f0f | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1=Cc2ccccc2C1 | [C;D1;H3:1]-[CH;D3;+0:2]1-[C;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C;D1;H3:1]-[C;H0;D3;+0:2]1=[C;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11] | 59 | [{"value": 59.0, "product": "CC1=C(CC2=CC=C(C=C12)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The 1,6-dimethyl-indene-2-carboxylic acid can be prepared by the treatment of α-acetyl-4-methylbenzenepropanoic acid ethyl ester with sulfuric acid (Shadbolt, R. S., J. Chem. Soc. (C), (1970) 920). Recrystallization from ethanol, m.p. 174°-182° C. Yield 59%.
Conditions: See reaction.notes.procedure_details.
Workup: Rec... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | null | null | null | null | Cc1ccc2c(c1)C(C)C(C(=O)O)=C2>>CC1=C(C(=O)O)Cc2ccc(C)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-87df338463cf4ff9b0aae301b7d4b2ce | CC1=C(C(=O)O)Cc2ccc(C)cc21.O=S(Cl)Cl>>CC1=C(C(=O)Cl)Cc2ccc(C)cc21 | CC1=C(CC2=CC=C(C=C12)C)C(=O)O.S(=O)(Cl)Cl>>CC1=C(CC2=CC=C(C=C12)C)C(=O)Cl | O[C:4]([C:3]1=[C:2]([CH3:1])[c:14]2[c:8]([cH:9][cH:10][c:11]([CH3:12])[cH:13]2)[CH2:7]1)=[O:5].O=S(Cl)[Cl:6]>>[CH3:1][C:2]1=[C:3]([C:4](=[O:5])[Cl:6])[CH2:7][c:8]2[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]21 | CC1=C(C(=O)O)Cc2ccc(C)cc21.O=S(Cl)Cl | CC1=C(C(=O)Cl)Cc2ccc(C)cc21 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | C1=Cc2ccccc2C1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](=[C:5](-[C;D1;H3:6])-[c:7])-[C:8]>>[C:8]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])=[C:5](-[C;D1;H3:6])-[c:7] | null | [] | null | null | null | null | 3,5-Dimethyl-indene-2-carboxylic acid (37.3 g) is converted to its acid chloride by treatment with thionyl chloride (580 ml). Excess thionyl chloride is distilled off. Yield 40.5 g, 99%.
Conditions: See reaction.notes.procedure_details.
Workup: Excess thionyl chloride is distilled off | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | C1=Cc2ccccc2C1 | HCl | null | null | null | CC1=C(C(=O)O)Cc2ccc(C)cc21.O=S(Cl)Cl>>CC1=C(C(=O)Cl)Cc2ccc(C)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ab458a1226a44a2ab6a4a788fe7dda8f | CC(=O)[C@H]1Cc2ccccc2[C@H]1C>>CC(=O)C1=C(C)c2cc(C)ccc2C1 | CCOCC.C[C@H]1[C@H](CC2=CC=CC=C12)C(C)=O>>CC1=C(CC2=CC=C(C=C12)C)C(C)=O | [CH3:1][C:2](=[O:3])[C@@H:4]1[C@H:5]([CH3:6])[c:7]2[cH:8][cH:9][cH:11][cH:12][c:13]2[CH2:14]1>>[CH3:1][C:2](=[O:3])[C:4]1=[C:5]([CH3:6])[c:7]2[cH:8][c:9]([CH3:10])[cH:11][cH:12][c:13]2[CH2:14]1 | CC(=O)[C@H]1Cc2ccccc2[C@H]1C | CC(=O)C1=C(C)c2cc(C)ccc2C1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 1428ddf264ea39b942080957ee8b8fd9368b1a5c11740576518d93da93c2dd22 | f394080031812a9c0cde55fa330311dfe42bea38dbdf0b4621700859838ffa32 | C1=Cc2ccccc2C1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[C@H;D3;+0:4]1-[C:5]-[c:6]2:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:2-[C@H;D3;+0:12]-1-[C;D1;H3:13]>>[C;D1;H3:14]-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]2:[c:11](:[c:10]:1)-[C;H0;D3;+0:12](-[C;D1;H3:13])=[C;H0;D3;+0:4](-[C:2](-[C;D1;H3:1])=[O;D1;H0:3])-[C:5]-2 | 84 | [{"value": 84.0, "product": "CC1=C(CC2=CC=C(C=C12)C)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(3,5-Dimethyl-inden-2-yl)ethanone is prepared by the same procedure as cis-1-(2,3-dihydro-1-methyl-1H-inden-2-yl)ethanone in Example 4b. A mixture of dry ether and tetrahydrofuran is used as solvent. Yield 84%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | Other | O1CCCC1 | null | null | CC(=O)[C@H]1Cc2ccccc2[C@H]1C>O1CCCC1>CC(=O)C1=C(C)c2cc(C)ccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-87ac3ca1a6a44205a81100de76b418af | BrBr.CC(=O)C1=C(C)c2cc(C)ccc2C1>>Cc1ccc2c(c1)C(C)C(C(=O)CBr)=C2 | BrBr.CC1=C(CC2=CC=C(C=C12)C)C(C)=O>>BrCC(=O)C=1C(C2=CC(=CC=C2C1)C)C | Br[Br:14].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8]([CH3:9])=[C:10]([C:11](=[O:12])[CH3:13])[CH2:15]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH:8]([CH3:9])[C:10]([C:11](=[O:12])[CH2:13][Br:14])=[CH:15]2 | BrBr.CC(=O)C1=C(C)c2cc(C)ccc2C1 | Cc1ccc2c(c1)C(C)C(C(=O)CBr)=C2 | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 63511e44f801465d677c29ade9e74644ea21572114dd81cfb6199c9456c67fab | eb663644836e52c1f41296c3f69eb0e554d5dc7739685ba436d901c3ef080ab9 | C1=Cc2ccccc2C1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[C:5](-[CH3;D1;+0:6])=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]-1:[c:12]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:6]-[C:5](=[O;D1;H0:7])-[C;H0;D3;+0:4]1=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11](:[c:12])-[CH;D3;+0:3]-1-[C;D1;H3:2] | 59.5 | [{"value": 59.0, "product": "BrCC(=O)C=1C(C2=CC(=CC=C2C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "BrCC(=O)C=1C(C2=CC(=CC=C2C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromine (2.80 g) is added to 1-(3,5-dimethyl-inden-2-yl)ethanone (3.00 g) in dry ether (30 ml), while keeping the temperature at +10° C. The mixture is extracted with water, several times with the diluted NaHCO3 solution, again with water, dried and evaporated under reduced pressure to afford the product (2.54 g, 59%).... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide.Ketone | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | HBr | CCOCC | null | null | BrBr.CC(=O)C1=C(C)c2cc(C)ccc2C1>CCOCC>Cc1ccc2c(c1)C(C)C(C(=O)CBr)=C2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-444387114cd14a4393559ebdbf1888ba | Cc1cccc2c1C=C(C(=O)O)C2C.O=S(Cl)Cl>>Cc1cccc2c1C=C(C(=O)Cl)C2C | CC1C(=CC2=C(C=CC=C12)C)C(=O)O.S(=O)(Cl)Cl>>CC1C(=CC2=C(C=CC=C12)C)C(=O)Cl | O[C:10]([C:9]1=[CH:8][c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[CH:13]1[CH3:14])=[O:11].O=S(Cl)[Cl:12]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]=[C:9]([C:10](=[O:11])[Cl:12])[CH:13]2[CH3:14] | Cc1cccc2c1C=C(C(=O)O)C2C.O=S(Cl)Cl | Cc1cccc2c1C=C(C(=O)Cl)C2C | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | C1=Cc2ccccc2C1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](=[C:5]-[c:6])-[C:7]>>[C:7]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])=[C:5]-[c:6] | 100 | [{"value": 100.0, "product": "CC1C(=CC2=C(C=CC=C12)C)C(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,4-Dimethyl-indene-2-carboxylic acid is converted to its acid chloride by treatment with thionyl chloride. Yield 100%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | C1=Cc2ccccc2C1 | HCl | null | null | null | Cc1cccc2c1C=C(C(=O)O)C2C.O=S(Cl)Cl>>Cc1cccc2c1C=C(C(=O)Cl)C2C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-28e41baf097a49e6ac6270dddced12dd | Cc1cccc2c1C=C(C(=O)O)C2C>>Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C | CC1C(=CC2=C(C=CC=C12)C)C(=O)O>>C[C@H]1[C@H](CC2=C(C=CC=C12)C)C(=O)O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]=[C:9]([C:10](=[O:11])[OH:12])[CH:13]2[CH3:14]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][C@H:9]([C:10](=[O:11])[OH:12])[C@@H:13]2[CH3:14] | Cc1cccc2c1C=C(C(=O)O)C2C | Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C | null | [Pd] | C(C)O.O | Reduction | Hydrogenation (double to single) | e5689a02f639e60b4fe706a412d3f57570263b52462fa8286db9a999fcbf7a7c | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(c1)CCC2 | [C;D1;H3:1]-[CH;D3;+0:2]1-[C;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C;D1;H3:1]-[C@H;D3;+0:2]1-[C@@H;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11] | null | [] | null | null | null | null | 1,4-Dimethyl-indene-2-carboxylic acid (35.5 g) is hydrogenated in ethanol-water (700 ml-70 ml) over 10% palladium on carbon at ambient temperature. After filtration ethanol is evaporated. Water is added and the precipitated cis-2,3-dihydro-1,4-dimethyl-1H-indene-2-carboxylic acid is filrated. Yield 33.3 g, 93% M.p. 132... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2C1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | [Pd].C(C)O.O | null | null | Cc1cccc2c1C=C(C(=O)O)C2C>[Pd].C(C)O.O>Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a6468257cde240678537a92584eedbfd | Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C.O=S(Cl)Cl>>Cc1cccc2c1C[C@H](C(=O)Cl)[C@@H]2C | C[C@H]1[C@H](CC2=C(C=CC=C12)C)C(=O)O.S(=O)(Cl)Cl>>C[C@H]1[C@H](CC2=C(C=CC=C12)C)C(=O)Cl | O[C:10]([C@H:9]1[CH2:8][c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[C@H:13]1[CH3:14])=[O:11].O=S(Cl)[Cl:12]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][C@H:9]([C:10](=[O:11])[Cl:12])[C@@H:13]2[CH3:14] | Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C.O=S(Cl)Cl | Cc1cccc2c1C[C@H](C(=O)Cl)[C@@H]2C | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)CCC2 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:6] | 92 | [{"value": 92.0, "product": "C[C@H]1[C@H](CC2=C(C=CC=C12)C)C(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | cis-2,3-Dihydro-1,4-dimethyl-1H-indene-2-carboxylic acid is converted to its acid chloride by treatment with thionyl chloride. Yield 92%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)CCC2 | HCl | null | null | null | Cc1cccc2c1C[C@H](C(=O)O)[C@@H]2C.O=S(Cl)Cl>>Cc1cccc2c1C[C@H](C(=O)Cl)[C@@H]2C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1b094d5a56494e2da452893b6b974dbc | CC1(C(=O)O)Cc2ccccc2C1.O=S(Cl)Cl>>CC1(C(=O)Cl)Cc2ccccc2C1 | CC1(CC2=CC=CC=C2C1)C(=O)O.S(=O)(Cl)Cl>>CC1(CC2=CC=CC=C2C1)C(=O)Cl | O[C:3]([C:2]1([CH3:1])[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1)=[O:4].O=S(Cl)[Cl:5]>>[CH3:1][C:2]1([C:3](=[O:4])[Cl:5])[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1 | CC1(C(=O)O)Cc2ccccc2C1.O=S(Cl)Cl | CC1(C(=O)Cl)Cc2ccccc2C1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)CCC2 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])(-[C:6])-[C:7]>>[C:6]-[C:4](-[C;D1;H3:5])(-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:7] | null | [] | null | null | null | null | A stirred mixture of 2,3-dihydro-2-methyl-1H-indene-2-carboxylic acid (6.70 g) and thionyl chloride (70 ml) is heated under reflux for 14 hr. The ecess of thionyl chloride is removed and the acid chloride is distilled. Yield 5.35 g, 72%, bp. 93°-98° C./3 mmHg.
Conditions: See reaction.notes.procedure_details.
Workup: i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)CCC2 | HCl | null | null | null | CC1(C(=O)O)Cc2ccccc2C1.O=S(Cl)Cl>>CC1(C(=O)Cl)Cc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-85a2fa7645354306a0bcb4aae40fe67f | BrBr.CC(=O)C1(C)Cc2ccccc2C1>>CC1(C(=O)CBr)Cc2ccccc2C1 | CC1(CC2=CC=CC=C2C1)C(C)=O.BrBr>>BrCC(=O)C1(CC2=CC=CC=C2C1)C | Br[Br:6].[CH3:1][C:2]1([C:3](=[O:4])[CH3:5])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1>>[CH3:1][C:2]1([C:3](=[O:4])[CH2:5][Br:6])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1 | BrBr.CC(=O)C1(C)Cc2ccccc2C1 | CC1(C(=O)CBr)Cc2ccccc2C1 | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc2c(c1)CCC2 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:3](-[C:2])=[O;D1;H0:5] | null | [] | null | null | null | null | 1-(2,3-Dihydro-2-methyl-1H-inden-2-yl)ethanone (3.69 g) in methylene chloride (40 ml) is stirred and cooled at 10° C. during the dropwise addition of bromine (2.82 g)/methylene chloride (10 ml). Work-up of the resultant solution gives 2-bromo-1-(2,3-dihydro-2-methyl-1H-inden-2-yl)ethanone.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccc2c(c1)CCC2 | HBr | C(Cl)Cl | null | null | BrBr.CC(=O)C1(C)Cc2ccccc2C1>C(Cl)Cl>CC1(C(=O)CBr)Cc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e661ba1483df42c9a16946f9259de1b6 | BrC1Cc2ccccc2C1.CCOC(OCC)C(=O)NN1CCCCC1>>CCOC(C=O)(OCC)C1Cc2ccccc2C1 | N1(CCCCC1)NC(C(OCC)OCC)=O.[Mg].[Mg].S(O)(O)(=O)=O.BrC1CC2=CC=CC=C2C1>>C(C)OC(C=O)(C1CC2=CC=CC=C2C1)OCC | Br[CH:10]1[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18]1.C1CCN(N[C:5]([CH:4]([O:3][CH2:2][CH3:1])[O:7][CH2:8][CH3:9])=[O:6])CC1>>[CH3:1][CH2:2][O:3][C:4]([CH:5]=[O:6])([O:7][CH2:8][CH3:9])[CH:10]1[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18]1 | BrC1Cc2ccccc2C1.CCOC(OCC)C(=O)NN1CCCCC1 | CCOC(C=O)(OCC)C1Cc2ccccc2C1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 33ad6fc0f5c61ff6e607266e8535db15f86926f49630c404b02f60eb84280f5c | 96d7be43d301ef432c38e0dcab15db38e6b746a28e4247b22cb5e21a9e836c25 | c1ccc2c(c1)CCC2 | Br-[CH;D3;+0:1]1-[C:2]-[c:3]:[c:4]-[C:5]-1.[C:6]-[#8:7]-[CH;D3;+0:8](-[#8:9]-[C:10])-[C;H0;D3;+0:11](=[O;D1;H0:12])-N-N1-C-C-C-C-C-1>>[C:6]-[#8:7]-[C;H0;D4;+0:8](-[#8:9]-[C:10])(-[CH;D2;+0:11]=[O;D1;H0:12])-[CH;D3;+0:1]1-[C:2]-[c:3]:[c:4]-[C:5]-1 | null | [] | null | null | 2 | HOUR | 0.73 g of magnesium turnings are covered with 90 ml of dry diethylether. To that mixture is then added 6 g of 2-bromoindane in 20 ml of dry diethylether at such a rate that a gentle boiling is maintained. When the magnesium turnings have reacted the solution containing the Grignard reagent is cooled to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Secondary halide.Ether.Ether | Aldehyde.Ether.Ether | c1ccc2c(c1)CCC2.C1CCNCC1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HBr | C(C)OCC | null | 2 | BrC1Cc2ccccc2C1.CCOC(OCC)C(=O)NN1CCCCC1>C(C)OCC>CCOC(C=O)(OCC)C1Cc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-107362592a79411db3a3bb2ea321f094 | CCC1(C(=O)O)CCc2ccccc2C1.O=S(Cl)Cl>>CCC1(C(=O)Cl)CCc2ccccc2C1 | C(C)C1(CC2=CC=CC=C2CC1)C(=O)O.S(=O)(Cl)Cl>>C(C)C1(CC2=CC=CC=C2CC1)C(=O)Cl | O[C:4]([C:3]1([CH2:2][CH3:1])[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15]1)=[O:5].O=S(Cl)[Cl:6]>>[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[Cl:6])[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15]1 | CCC1(C(=O)O)CCc2ccccc2C1.O=S(Cl)Cl | CCC1(C(=O)Cl)CCc2ccccc2C1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)CCCC2 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])(-[C:6])-[C:7]>>[C:6]-[C:4](-[C:5])(-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[C:7] | null | [] | null | null | 5 | DAY | A mixture of 2-ethyl-1,2,3,4-tetrahydro-2-naphthoic acid (22,0 g) and thionyl chloride is boiled for 5 days. The acid chloride is distilled. B.p. 110°-115° C./0.2 mmHg. Yield 21.6 g, 90%.
Conditions: See reaction.notes.procedure_details.
Workup: The acid chloride is distilled | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)CCCC2 | HCl | null | null | 120 | CCC1(C(=O)O)CCc2ccccc2C1.O=S(Cl)Cl>>CCC1(C(=O)Cl)CCc2ccccc2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b78c327e1a3641088d5f502f89c88f70 | CO.C[C@@H]1c2ccccc2C[C@@H]1C(=O)O>>COC(=O)[C@H]1Cc2ccccc2[C@H]1C | S(O)(O)(=O)=O.C[C@H]1[C@H](CC2=CC=CC=C12)C(=O)O.CO>>COC(=O)[C@@H]1[C@@H](C2=CC=CC=C2C1)C | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C@H:13]1[CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C@H:13]1[CH3:14] | CO.C[C@@H]1c2ccccc2C[C@@H]1C(=O)O | COC(=O)[C@H]1Cc2ccccc2[C@H]1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2c(c1)CCC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6])-[C:5] | 91 | [{"value": 91.0, "product": "COC(=O)[C@@H]1[C@@H](C2=CC=CC=C2C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | cis-2,3-Dihydro-1-methyl-1H-indene-2-carboxylic acid methyl ester is prepared from cis-2,3-dihydro-1-methyl-1H-indene-2-carboxylic acid (see Example 4) by the standard methods using methanol and concentrated sulphuric acid. Yield 91%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2c(c1)CCC2 | HO- | null | null | null | CO.C[C@@H]1c2ccccc2C[C@@H]1C(=O)O>>COC(=O)[C@H]1Cc2ccccc2[C@H]1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9d4ebd8e481047809b51612b904aa6b8 | BrBr.CCC1(C(C)=O)Cc2ccccc2C1C>>CCC1(C(=O)CBr)Cc2ccccc2C1C | C(C)C1(C(C2=CC=CC=C2C1)C)C(C)=O.BrBr>>BrCC(=O)C1(C(C2=CC=CC=C2C1)C)CC | Br[Br:7].[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[CH3:6])[CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH:15]1[CH3:16]>>[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[CH2:6][Br:7])[CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH:15]1[CH3:16] | BrBr.CCC1(C(C)=O)Cc2ccccc2C1C | CCC1(C(=O)CBr)Cc2ccccc2C1C | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc2c(c1)CCC2 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:3](-[C:2])=[O;D1;H0:5] | 65 | [{"value": 65.0, "product": "BrCC(=O)C1(C(C2=CC=CC=C2C1)C)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-1-(2,3-dihydro-2-ethyl-1-methyl-1H-inden-2-yl)ethanone is prepared from 1-(2,3-dihydro-2-ethyl-1-methyl-1H-inden-2-yl)ethanone (21.6 g) by treatment with bromine (17.6 g) in methylene chloride (300 ml). Yield 65%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccc2c(c1)CCC2 | HBr | C(Cl)Cl | null | null | BrBr.CCC1(C(C)=O)Cc2ccccc2C1C>C(Cl)Cl>CCC1(C(=O)CBr)Cc2ccccc2C1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0c50a0db96974d4e998373adf507d6e8 | CC(=O)OC(C)=O.Nc1ccc(S(=O)(=O)O)c2ccccc12>>CC(=O)Nc1ccc(S(=O)(=O)O)c2ccccc12 | NC1=CC=C(C2=CC=CC=C12)S(=O)(=O)O.N1=CC=CC=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=C(C2=CC=CC=C12)S(=O)(=O)O.N1=CC=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CC(=O)OC(C)=O.Nc1ccc(S(=O)(=O)O)c2ccccc12 | CC(=O)Nc1ccc(S(=O)(=O)O)c2ccccc12 | null | null | C(C)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2ccccc2c1 | 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] | 59.4 | [{"value": 59.4, "product": "C(C)(=O)NC1=CC=C(C2=CC=CC=C12)S(=O)(=O)O.N1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 12 g (0.05 mole) of 1-amino-4-naphthalenesulphonic acid, 7.2 ml of pyridine and 15 ml of acetic anhydride are placed in a flask provided with a stirrer and heater. The mixture is heated until the solution is clear, at which point 10 ml of absolute ethanol is added and the mixture is allowed to cool, first to ambient te... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1 | HO- | C(C)O | null | 3 | CC(=O)OC(C)=O.Nc1ccc(S(=O)(=O)O)c2ccccc12>C(C)O>CC(=O)Nc1ccc(S(=O)(=O)O)c2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-633630798e4d4a5bb72b060b5562efd4 | CCN.CSC(=NC#N)NC1CCCc2ccccc21>>CCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(C)N>>C(#N)N=C(NCC)NC1CCCC2=CC=CC=C12 | [CH3:1][CH2:2][NH2:3].CS[C:4](=[N:5][C:6]#[N:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][NH:3][C:4](=[N:5][C:6]#[N:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CCN.CSC(=NC#N)NC1CCCc2ccccc21 | CCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7] | null | [] | null | null | 20 | HOUR | A solution of 6.13 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 10 ml of 70% aqueous ethylamine in 90 ml of ethanol was heated at reflux with stirring for 20 hours. The reaction mixture was cooled in a refrigerator to give 2.44 g of N"-cyano-N-ethyl-N'-(1,2,3,4-tetrahydro-1-naphthyl)guanidine... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | 20 | CCN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)O>CCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4b4b32ae47a846a4bd3b2b48f365e3b5 | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21>>CC(C)NC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(C)(C)N>>C(#N)N=C(NC(C)C)NC1CCCC2=CC=CC=C12 | [CH3:1][CH:2]([CH3:3])[NH2:4].CS[C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21 | CC(C)NC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:10]-[C:8](-[C;D1;H3:7])-[C;D1;H3:9] | null | [] | null | null | 154 | HOUR | A solution of 30.0 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-napthyl)-S-methylisothiourea and 40 ml of isopropylamine in 300 ml of acetonitrile was heated at reflux with stirring for 154 hours. The solvent and excess isopropylamine were removed by evaporation in vacuo, leaving the crude product as a tacky, white solid. Cry... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 154 | CC(C)N.CSC(=NC#N)NC1CCCc2ccccc21>C(C)#N>CC(C)NC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-304c38d018044bb286d8a97c383e9f1c | CCCN.CSC(=NC#N)NC1CCCc2ccccc21>>CCCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(CC)N>>C(#N)N=C(NCCC)NC1CCCC2=CC=CC=C12 | [CH3:1][CH2:2][CH2:3][NH2:4].CS[C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CCCN.CSC(=NC#N)NC1CCCc2ccccc21 | CCCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | 20 | HOUR | A solution of 12.3 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-napthyl)-S-methylisothiourea and 16 ml of n-propylamine in 100 ml of acetonitrile was heated at reflux with stirring for 20 hours. The reaction mixture was then allowed to stand in a refrigerator to give 8.63 g of N"-cyano-N-n-propyl-N'-(1,2,3,4-tetrahydro-1-naph... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)#N | null | 20 | CCCN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)#N>CCCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7f6895ba5ca84377a6aeef1d151e9b4b | CN.CSC(=NC#N)NC1CCCc2ccccc21>>CNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.CN>>C(#N)N=C(NC)NC1CCCC2=CC=CC=C12 | [CH3:1][NH2:2].CS[C:3](=[N:4][C:5]#[N:6])[NH:7][CH:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[CH3:1][NH:2][C:3](=[N:4][C:5]#[N:6])[NH:7][CH:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | CN.CSC(=NC#N)NC1CCCc2ccccc21 | CNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:8]-[C;D1;H3:7] | null | [] | null | null | 22 | HOUR | A solution of 12.3 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 20 ml of 33% ethanolic methylamine in 200 ml of ethanol was heated at reflux with stirring for 22 hours. The solvent was then removed by evaporation in vacuo, leaving the crude product as a glassy, amorphous solid. Crystallizatio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | 22 | CN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)O>CNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b9959cbcabf24a84aa148b8ecad25cdc | C=CCN.CSC(=NC#N)NC1CCCc2ccccc21>>C=CCNC(=NC#N)NC1CCCc2ccccc21 | C(#N)N=C(NC1CCCC2=CC=CC=C12)SC.C(C=C)N>>C(C=C)NC(=NC#N)NC1CCCC2=CC=CC=C12 | [CH2:1]=[CH:2][CH2:3][NH2:4].CS[C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[N:6][C:7]#[N:8])[NH:9][CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | C=CCN.CSC(=NC#N)NC1CCCc2ccccc21 | C=CCNC(=NC#N)NC1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc2c(c1)CCCC2 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5]-[C:6].[C;D1;H2:7]=[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:6]-[#7:5]-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:10]-[C:9]-[C:8]=[C;D1;H2:7] | null | [] | null | null | null | null | A solution of 24.5 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 38 ml of allylamine in 400 ml of ethanol was heated at reflux for 87 hours. The solvent was removed from the reaction mixture by evaporation in vacuo, leaving a pale yellow semisolid which was crystallized from isopropyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccc2c(c1)CCCC2 | Other | C(C)O | null | null | C=CCN.CSC(=NC#N)NC1CCCc2ccccc21>C(C)O>C=CCNC(=NC#N)NC1CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2a25a670f29446a8bcfed9c8a1b1ea10 | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].C(C(C)C)N>>C(C(C)C)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].Cl[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl | CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | null | [] | null | null | null | null | To a stirred solution of 50.Og (0.24 mole) of 4-chloro-3-nitroquinoline in 300 ml of tetrahydrofuran was added, in small portions, 52.7g (0.72 mole) of isobutylamine. The mixture was heated at its reflux temperature for one hour, and was then evaporated in vacuo. Water was added to the residue and the solid was separat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | O1CCCC1 | null | null | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>O1CCCC1>CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-701fcea6be6145faa217161bfc2ee4fd | CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CNc1c([N+](=O)[O-])cnc2ccccc12 | CN.ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>CNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [CH3:1][NH2:2].Cl[c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[CH3:1][NH:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | CN.O=[N+]([O-])c1cnc2ccccc2c1Cl | CNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[C;D1;H3:10] | null | [] | null | null | null | null | To a stirred solution of 40% aqueous methylamine was added, in small portions, 30.Og (0.144 mole) of 4-chloro-3-nitroquinoline. The reaction mixture was heated at its reflux temperature for about 0.75 hour. After cooling, the mixture was poured into 300 ml of water. The solid was separated by filtration, and was then s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | O | null | null | CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>O>CNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-140b435f511a4d6abe847ad623279805 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl>>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 | C(C(C)C)N1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-].P(=O)(Cl)(Cl)Cl>>ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C | [O-][n+:11]1[cH:9][c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([Cl:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 | null | null | null | Miscellaneous | OtherReaction | c5cfc3e69c2d1a66a8560034fe025f449600689a18546e68a564dc97632a28be | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[n+;H0;D3:8](-[O-]):[c:9](:[c:10]):[c:11]:[c:12]:1:2>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[c:12]:1:[c:11]:[c:9](:[c:10]):[n;H0;D2;+0:8]:[c;H0;D3;+0:7]:2-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | A mixture of 9.95 g (0.0412 mole) of 1-isobutyl-1H-imidazo [4,5-c]quinolin-5-oxide (from Example 54) and 100 ml of phosphorus oxychloride was heated at its reflux temperature for 2.5 hours, and was then cooled and poured into ice with stirring. Basification (to pH 9-10) with 50% aqueous sodium hydroxide solution was fo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)[n+]cc1[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | null | null | null | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl>>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dbffeec5148f4326a5a271f967528eb5 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.[NH4+]>>CC(C)Cn1cnc2c(N)nc3ccccc3c21 | ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C.[OH-].[NH4+]>>C(C(C)C)N1C=NC=2C(=NC=3C=CC=CC3C21)N | Cl[c:9]1[c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]([n:11]1)[cH:13][cH:14][cH:15][cH:16]2.[NH4+:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.[NH4+] | CC(C)Cn1cnc2c(N)nc3ccccc3c21 | null | null | null | Functional Group Interconversion | OtherReaction | 5180f216097ba9fb57e932c038efbe236ac4870417fb61da74fdffde0a3037cf | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH4+;D0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | 150 | CELSIUS | null | null | A mixture of 4.0 g (0.0154 mole) of 4-chloro-1-isobutyl-1H-imidazo [4,5-c]quinoline (from Example 77) and 25 cc of concentrated ammonium hydroxide was placed in a metal bomb and heated at 150° C. for about 16 hours. After cooling the solid was separated by filtration, washed with water and recrystallized from ethanol t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | null | 150 | null | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.[NH4+]>>CC(C)Cn1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e947c30edcac4d5f85af4d0febdc8b90 | O=C(OCCn1cnc2cnc3ccccc3c21)c1ccccc1.OO>>O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1 | C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C=NC=3C=CC=CC3C21.OO>>C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-] | [O:1]=[C:2]([O:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[cH:10][n:11][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.O[OH:12]>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[cH:10][n+:11]([O-:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12)[c:20]1[cH:21][cH:22... | O=C(OCCn1cnc2cnc3ccccc3c21)c1ccccc1.OO | O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1 | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | ad4e5886430ca643e61e33ce51381127eb6443ce8f7fd345eaa14b7a1d61bd3d | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | O=C(OCCn1cnc2c[nH+]c3ccccc3c21)c1ccccc1 | O-[OH;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | null | [] | 65 | CELSIUS | null | null | A mixture of 67.5 g (0.213 mole) of 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]quinoline (from Example 115), 36.3 g (0.32 mole) of 30% hydrogen peroxide and 450 ml of glacial acetic acid was heated at 65° C. for 2 days with stirring. The solution was evaporated in vacuo, and the residue was then added to water. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)[n+]cc1nc[nH]c12 | c1ccc2c(c1)[n+]cc1nc[nH]c12.c1ccccc1 | HO- | C(C)(=O)O | 65 | null | O=C(OCCn1cnc2cnc3ccccc3c21)c1ccccc1.OO>C(C)(=O)O>O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fd07e5c4703549e79fcc07e18a5b58b2 | O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1.O=P(Cl)(Cl)Cl>>O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1 | C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-].P(=O)(Cl)(Cl)Cl>>C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C(=NC=3C=CC=CC3C21)Cl | [O-][n+:12]1[cH:10][c:9]2[n:8][cH:7][n:6]([CH2:5][CH2:4][O:3][C:2](=[O:1])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:19]2[c:18]2[c:13]1[cH:14][cH:15][cH:16][cH:17]2.O=P(Cl)(Cl)[Cl:11]>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]([Cl:11])[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12)[c:20... | O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1.O=P(Cl)(Cl)Cl | O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | c5cfc3e69c2d1a66a8560034fe025f449600689a18546e68a564dc97632a28be | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | O=C(OCCn1cnc2cnc3ccccc3c21)c1ccccc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[n+;H0;D3:8](-[O-]):[c:9](:[c:10]):[c:11]:[c:12]:1:2>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[c:12]:1:[c:11]:[c:9](:[c:10]):[n;H0;D2;+0:8]:[c;H0;D3;+0:7]:2-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | A mixture of 50g (0.15 mole) of 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]quinolin-5-oxide (from Example 116) and 200 ml of phosphorus oxychloride was heated for two hours on a steam bath. The mixture was then partially evaporated in vacuo. The mixture was poured over ice, and the solution was neutralized with sodium hydr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)[n+]cc1[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12.c1ccccc1 | HCl | null | null | null | O=C(OCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1.O=P(Cl)(Cl)Cl>>O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-09412f2ea4984b9680a422f7d8c6366d | O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1>>OCCn1cnc2c(Cl)nc3ccccc3c21 | C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C(=NC=3C=CC=CC3C21)Cl.N>>ClC1=NC=2C=CC=CC2C2=C1N=CN2CCO | O=C(c1ccccc1)[O:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]12>>[OH:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]12 | O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1 | OCCn1cnc2c(Cl)nc3ccccc3c21 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 8df1b5c4ec88eb8f4e334a9ade2ac7fc0b3f460ea1450816d1758f28eee39662 | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2c(c1)ncc1nc[nH]c12 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | 20 | CELSIUS | 3 | DAY | A mixture of 25.3 g (0.072 mole) of 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 117) and 500 ml of 10% ammonia in methanol was stirred at about 20° C. for three days, and was then filtered and finally evaporated to low volume. The slurry was mixed with diethyl ether, and the solid was separa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | c1nc2ccccc2c2[nH]cnc12 | HO- | CO | 20 | 72 | O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1>CO>OCCn1cnc2c(Cl)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d55cf3cb02ba41bab50cae8993ff9059 | N.O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1>>Cl.Nc1nc2ccccc2c2c1ncn2CCO.O | C(C1=CC=CC=C1)(=O)OCCN1C=NC=2C(=NC=3C=CC=CC3C21)Cl.N>>O.Cl.OCCN1C=NC=2C(=NC=3C=CC=CC3C21)N | [NH3:2].c1ccc(C([O:18][CH2:17][CH2:16][n:15]2[c:11]3[c:10]4[c:5]([n:4][c:3]([Cl:1])[c:12]3[n:13][cH:14]2)[cH:6][cH:7][cH:8][cH:9]4)=[O:19])cc1>>[ClH:1].[NH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]2[c:12]1[n:13][cH:14][n:15]2[CH2:16][CH2:17][OH:18].[OH2:19] | N.O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1 | Cl.Nc1nc2ccccc2c2c1ncn2CCO.O | null | null | Cl.CO | Heteroatom Alkylation and Arylation | OtherReaction | 665ca0a8153959cf33011b69b672067ade7501393d2797d593ce4706bc4cf371 | a0d2810f2e52e72d80187445295033f9d64ed41da4af71c56901ee260d67fe3b | c1ccc2c(c1)ncc1nc[nH]c12 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]2:[#7;a:7](-[C:8]-[C:9]-[O;H0;D2;+0:10]-C(=[O;H0;D1;+0:11])-c3:c:c:c:c:c:3):[c:12]:[#7;a:13]:[c:14]:2:1.[NH3;D0;+0:15]>>[ClH;D0;+0:1].[NH2;D1;+0:15]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]2:[#7;a:7](-[C:8]-[C:9]-[OH;D1;+0:10]):[c:12]:[#7;a:13]:[c:14]:2:1.[OH2... | null | [] | null | null | null | null | A mixture of 1.3 g (0.0037 mole) of 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 117) in 60 ml of methanol was saturated with about 10g of ammonia gas. The mixture was heated at 150° C. in a steel bomb for ten hours. The mixture was evaporated, and the residue was slurried in diethyl ether an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Primary alcohol.Primary amine | c1ccccc1.c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2nc[nH]c12 | Other | Cl.CO | null | null | N.O=C(OCCn1cnc2c(Cl)nc3ccccc3c21)c1ccccc1>Cl.CO>Cl.Nc1nc2ccccc2c2c1ncn2CCO.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b1be4dfd6da4477da37761d7f80d972c | O=C(Cl)c1ccccc1.OCC(O)Cn1cnc2cnc3ccccc3c21>>O=C(OCC(Cn1cnc2cnc3ccccc3c21)OC(=O)c1ccccc1)c1ccccc1 | C(C1=CC=CC=C1)(=O)Cl.OC(CN1C=NC=2C=NC=3C=CC=CC3C21)CO>>C(C1=CC=CC=C1)(=O)OC(CN1C=NC=2C=NC=3C=CC=CC3C21)COC(C2=CC=CC=C2)=O | Cl[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:2][cH:27][cH:28]1.[OH:1][CH2:4][CH:5]([CH2:6][n:7]1[cH:8][n:9][c:10]2[cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12)[OH:20]>>[O:1]=[C:2]([O:3][CH2:4][CH:5]([CH2:6][n:7]1[cH:8][n:9][c:10]2[cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12)[O:20][C:2... | O=C(Cl)c1ccccc1.OCC(O)Cn1cnc2cnc3ccccc3c21 | O=C(OCC(Cn1cnc2cnc3ccccc3c21)OC(=O)c1ccccc1)c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6f2ba2a48e83b7d7a9ef833d61a803f978e1e5237808ad4cd37f7e0315e7bd3f | 8eb99b12d7d9bf3bf89650dc1a9dd90efde0b77ac3da22794c3abe4e413897c2 | O=C(OCC(Cn1cnc2cnc3ccccc3c21)OC(=O)c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:1.[C:9]-[C:10](-[OH;D1;+0:11])-[CH2;D2;+0:12]-[OH;D1;+0:13]>>[C:9]-[C:10](-[CH2;D2;+0:12]-[#8:14]-[C;H0;D3;+0:6](=[O;H0;D1;+0:13])-[c:15](:[c:16]):[c:17])-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[c:1... | null | [] | null | null | null | null | Using the method of Example 115, benzoyl chloride was reacted with 1-(2,3-dihydroxypropyl)-1H-imidazo[4,5-c]-quinoline (from Example 51) to provide 1-(2,3-dibenzoyloxypropyl)-1H-imidazo[4,5-c]quinoline.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol.Secondary alcohol | Ester.Ester | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2c(c1)ncc1nc[nH]c12.c1ccccc1.c1ccccc1 | null | null | null | null | O=C(Cl)c1ccccc1.OCC(O)Cn1cnc2cnc3ccccc3c21>>O=C(OCC(Cn1cnc2cnc3ccccc3c21)OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2c929c9ff91f46908204776551292b7d | CC(=O)OCC(Cn1cnc2c[n+]([O-])c3ccccc3c21)OC(C)=O>>[O-][n+]1cc2ncn(CC(O)CO)c2c2ccccc21 | C(C)(=O)OC(CN1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-])COC(C)=O>>OC(CN1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-])CO | CC(=O)[O:10][CH:9]([CH2:8][n:7]1[cH:6][n:5][c:4]2[cH:3][n+:2]([O-:1])[c:19]3[c:14]([c:13]21)[cH:15][cH:16][cH:17][cH:18]3)[CH2:11][O:12]C(C)=O>>[O-:1][n+:2]1[cH:3][c:4]2[n:5][cH:6][n:7]([CH2:8][CH:9]([OH:10])[CH2:11][OH:12])[c:13]2[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CC(=O)OCC(Cn1cnc2c[n+]([O-])c3ccccc3c21)OC(C)=O | [O-][n+]1cc2ncn(CC(O)CO)c2c2ccccc21 | null | C[O-].[Na+] | CO | Reduction | OtherReaction | 729bb4ff95e38c3d11c4da55fe3e362074025f1fba900386729c8f4837142b9a | f7eaf12d8ca7f7f33975963ce6d5d64e20763721d3f59f4cd8cae1a62b7f8497 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[O;H0;D2;+0:5]-C(-C)=O>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[OH;D1;+0:5] | null | [] | null | null | null | null | To a stirred solution of 4.0 g (0.0117 mole) of 1-(2,3-diacetoxypropyl)-1H-imidazo[4,5-c]quinolin-5-oxide (from Example 121, Part A) in 50 ml of methanol was added about 12 drops of 25% sodium methoxide solution. After one hour the product was collected by filtration, washed with methanol and recrystallized from ethano... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Secondary alcohol | null | null | c1ccc2c(c1)[n+]cc1[nH]cnc12 | HO- | C[O-].[Na+].CO | null | null | CC(=O)OCC(Cn1cnc2c[n+]([O-])c3ccccc3c21)OC(C)=O>C[O-].[Na+].CO>[O-][n+]1cc2ncn(CC(O)CO)c2c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc6dcb2adf4e4ae7a8c81d53c0d50ebb | NCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCc1ccccc1 | C(C1=CC=CC=C1)N.ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>C(C1=CC=CC=C1)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [NH2:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.Cl[c:13]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl | O=[N+]([O-])c1cnc2ccccc2c1NCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:10]-[C:11]-[c:12] | null | [] | null | null | null | null | Using the method of Example 1, benzylamine and 4-chloro-3-nitroquinoline were reacted to provide 4-benzylamino-3-nitroquinoline. The structural assignment for the crude product (m.p. 178°-196° C.) was supported by infrared spectral analysis.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | NCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f325f0d97a2d4a3d92dc24afc812f03e | Clc1nc2ccccc2c2c1ncn2Cc1ccccc1.N>>Nc1nc2ccccc2c2c1ncn2Cc1ccccc1 | C(C1=CC=CC=C1)N1C=NC=2C(=NC=3C=CC=CC3C21)Cl.N>>C(C1=CC=CC=C1)N1C=NC=2C(=NC=3C=CC=CC3C21)N | Cl[c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[c:11]1[n:12][cH:13][n:14]2[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[NH3:1]>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[c:11]1[n:12][cH:13][n:14]2[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | Clc1nc2ccccc2c2c1ncn2Cc1ccccc1.N | Nc1nc2ccccc2c2c1ncn2Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a67570e0a22d637a1d2a31207671ab3b6e569ccedb0b9b67428b6008b9e1da93 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(Cn2cnc3cnc4ccccc4c32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | Using the method of Example 100, 1-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 80) was reacted with ammonia to provide white solid 1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine after recrystallization from N,N-dimethylformamide, m.p. 257°-259° C. Analysis: Calculated for C17H14N4: % C, 74.4; % H, 5.1; % N, 20... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2nc[nH]c12.c1ccccc1 | HCl | null | null | null | Clc1nc2ccccc2c2c1ncn2Cc1ccccc1.N>>Nc1nc2ccccc2c2c1ncn2Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-70af8be2728549008f36c1cf9792bfa8 | NCc1ccc(Cl)cc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCc1ccc(Cl)cc1 | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].ClC1=CC=C(CN)C=C1>>ClC1=CC=C(CNC2=C(C=NC3=CC=CC=C23)[N+](=O)[O-])C=C1 | [NH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1.Cl[c:13]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1 | NCc1ccc(Cl)cc1.O=[N+]([O-])c1cnc2ccccc2c1Cl | O=[N+]([O-])c1cnc2ccccc2c1NCc1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:10]-[C:11]-[c:12] | null | [] | null | null | null | null | Using the method of Example 1, 4-chloro-3-nitroquinoline was reacted with 4-chlorobenzylamine to provide yellow solid 4-(4-chlorobenzylamino)-3-nitroquinoline, the melting point of the crude product being 168°-173° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | NCc1ccc(Cl)cc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8ef73e706205480ba66a62dbc024f1f3 | NCCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCCc1ccccc1 | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].C1(=CC=CC=C1)CCN>>[N+](=O)([O-])C=1C=NC2=CC=CC=C2C1NCCC1=CC=CC=C1 | [NH2:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.Cl[c:13]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | NCCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl | O=[N+]([O-])c1cnc2ccccc2c1NCCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCNc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | null | [] | null | null | null | null | Using the method of Example 1, 4-chloro-3-nitroquinoline was reacted with 2-(phenyl)ethylamine to provide yellow solid 3-nitro-4-[2-(phenyl)ethylamino]quinoline, the melting point of the crude product being 174°-180° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | NCCc1ccccc1.O=[N+]([O-])c1cnc2ccccc2c1Cl>>O=[N+]([O-])c1cnc2ccccc2c1NCCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-88618bfd351a40df87e724b2284ff983 | Nc1cnc2ccccc2c1NCCc1ccccc1>>c1ccc(CCn2cnc3cnc4ccccc4c32)cc1 | NC=1C=NC2=CC=CC=C2C1NCCC1=CC=CC=C1.C(OCC)(OCC)OCC>>C1(=CC=CC=C1)CCN1C=NC=2C=NC=3C=CC=CC3C21 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][NH:7][c:19]2[c:10]([NH2:9])[cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][n:7]2[cH:8][n:9][c:10]3[cH:11][n:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[c:19]23)[cH:20][cH:21]1 | Nc1cnc2ccccc2c1NCCc1ccccc1 | c1ccc(CCn2cnc3cnc4ccccc4c32)cc1 | null | null | C(=O)O | Aromatic Heterocycle Formation | OtherReaction | 26779edfcc2b370e3e3dc285e0fedfbcf04e6b6c7fd46f2674bab3f061a7b270 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc(CCn2cnc3cnc4ccccc4c32)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[NH2;D1;+0:10]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:11]:[n;H0;D2;+0:10]:[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[c:4]:2:1 | null | [] | null | null | null | null | Using the method of Example 31, 3-amino-4-[2-(phenyl)ethylamino]quinoline was reacted with triethyl orthoformate and formic acid to provide 1-[2-(phenyl)ethyl]-1H-imidazo[4,5-c]quinoline, m.p. 105°-108° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccccc1.c1ccc2c(c1)ncc1nc[nH]c12 | Other | C(=O)O | null | null | Nc1cnc2ccccc2c1NCCc1ccccc1>C(=O)O>c1ccc(CCn2cnc3cnc4ccccc4c32)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2c24100fb43743379bf527993650331f | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCc1ccccc1>>Cc1nc2cnc3ccccc3c2n1Cc1ccccc1.O | NC=1C=NC2=CC=CC=C2C1NCC1=CC=CC=C1.C(C)(OCC)(OCC)OCC>>O.C(C1=CC=CC=C1)N1C(=NC=2C=NC=3C=CC=CC3C21)C | CCO[C:2](OCC)([CH3:1])[O:22]CC.[NH2:3][c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[c:13]2[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[OH2:22] | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCc1ccccc1 | Cc1nc2cnc3ccccc3c2n1Cc1ccccc1.O | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | af7d6de7ca5153ecd31a13d7075f2969261301df4b656bfec36bc67fd1ea176b | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(Cn2cnc3cnc4ccccc4c32)cc1 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-[O;H0;D2;+0:3]-C-C.[NH2;D1;+0:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[c:13]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:[n;H0;D3;+0:11]:1-[C:12]-[c:13].[OH2;D0;+0:3] | null | [] | null | null | null | null | Using the method of Example 31, 3-amino-4-(benzylamino)quinoline (from Example 124, Part B) was reacted with triethyl orthoacetate and acetic acid to provide 1-benzyl-2-methyl-1H-imidazo[4,5-c]quinoline hydrate, m.p. 145°-147° C. Analysis: Calculated for C18H15N3 ·2.25H2O: % C, 68.9; % H, 6.3; % N, 13.4; Found: % C, 69... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | HO- | C(C)(=O)O | null | null | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCc1ccccc1>C(C)(=O)O>Cc1nc2cnc3ccccc3c2n1Cc1ccccc1.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb431508c7dd457ab6337acbc87ef42d | N.OCCn1cnc2c(Cl)nc3ccccc3c21>>Nc1nc2ccccc2c2c1ncn2CCO | ClC1=NC=2C=CC=CC2C2=C1N=CN2CCO.N>>OCCN1C=NC=2C(=NC=3C=CC=CC3C21)N | [NH3:1].Cl[c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[c:11]1[n:12][cH:13][n:14]2[CH2:15][CH2:16][OH:17]>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[c:11]1[n:12][cH:13][n:14]2[CH2:15][CH2:16][OH:17] | N.OCCn1cnc2c(Cl)nc3ccccc3c21 | Nc1nc2ccccc2c2c1ncn2CCO | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a67570e0a22d637a1d2a31207671ab3b6e569ccedb0b9b67428b6008b9e1da93 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | A mixture of 4.0 g (0.016 mole) of 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline (from Example 118) and 30 ml of 10% ammonia in methanol was heated in a steel bomb for 12 hours at 150° C. The resulting solid was separated from the cooled mixture by filtration, and was washed sequentially with water and methano... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2nc[nH]c12 | HCl | CO | null | null | N.OCCn1cnc2c(Cl)nc3ccccc3c21>CO>Nc1nc2ccccc2c2c1ncn2CCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-97b456bb57504bd59428925f2a296995 | CN.O=[N+]([O-])c1cnc2ccccc2c1O>>CNc1c([N+](=O)[O-])cnc2ccccc12 | CN.OC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].P(=O)(Cl)(Cl)Cl>>CNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [CH3:1][NH2:2].O[c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[CH3:1][NH:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | CN.O=[N+]([O-])c1cnc2ccccc2c1O | CNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | O.CN(C=O)C | Functional Group Addition | Reductive amination with alcohol | 323be3a29db03987af5437147ca38f381a61d3758dc3e1e15c9bfbbe48d7afab | 48d1b7679391da0e4d23024ff9a58734100ee909371b4065e4b5a1e4d85a7201 | c1ccc2ncccc2c1 | O-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[C;D1;H3:10] | null | [] | null | null | null | null | To a solution of 5.7 g (0.030 mole) of 4-hydroxy-3-nitroquinoline in 50 ml of N,N-dimethylformamide was added 9.3 g (0.060 mole) of phosphorous oxychloride. The solution was heated on a steam bath for 5 minutes, then poured with stirring into 200 ml of 40% aqueous methylamine. The mixture was heated on a steam bath for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | O.CN(C=O)C | null | null | CN.O=[N+]([O-])c1cnc2ccccc2c1O>O.CN(C=O)C>CNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b0d95afb09d243d89f5ffbf0df4d6ca8 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl.[OH-]>>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.O | [OH-].[NH4+].P(=O)(Cl)(Cl)Cl.C(C(C)C)N1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-]>>O.ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C | [O-][n+:11]1[cH:9][c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2.O=P(Cl)(Cl)[Cl:10].[OH-:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([Cl:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12.[OH2:19] | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl.[OH-] | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.O | null | null | CN(C=O)C | Miscellaneous | OtherReaction | c5cfc3e69c2d1a66a8560034fe025f449600689a18546e68a564dc97632a28be | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[n+;H0;D3:8](-[O-]):[c:9](:[c:10]):[c:11]:[c:12]:1:2.[OH-;D0:13]>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[c:12]:1:[c:11]:[c:9](:[c:10]):[n;H0;D2;+0:8]:[c;H0;D3;+0:7]:2-[Cl;H0;D1;+0:1].[OH2;D0;+0:13] | null | [] | 20 | CELSIUS | 15 | MINUTE | To a solution of 4.8 g (0.0311 mole) of phosphorus oxychloride in 20 ml of N,N-dimethylformamide was added in small portions 5.0 g (0.0207 mole) of 1-isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide. The solution was stirred for 15 minutes at 20° C., then heated on a steam bath for 15 minutes. The solution was cooled to 20° ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)[n+]cc1[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | Other | CN(C=O)C | 20 | 0.25 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl.[OH-]>CN(C=O)C>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d6af7c98dd194e5db7be6f74241761d1 | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCCc1ccccc1>>Cc1nc2cnc3ccccc3c2n1CCc1ccccc1 | NC=1C=NC2=CC=CC=C2C1NCCC1=CC=CC=C1.C(C)(OCC)(OCC)OCC>>CC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCC1=CC=CC=C1 | CCO[C:2](OCC)(OCC)[CH3:1].[NH2:3][c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[c:13]2[n:14]1[CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCCc1ccccc1 | Cc1nc2cnc3ccccc3c2n1CCc1ccccc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | af7d6de7ca5153ecd31a13d7075f2969261301df4b656bfec36bc67fd1ea176b | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(CCn2cnc3cnc4ccccc4c32)cc1 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-O-C-C.[C:3]-[C:4]-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:3]-[C:4]-[n;H0;D3;+0:5]1:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[C;D1;H3:2] | null | [] | null | null | null | null | Using the method of Example 31, 3-amino-4-[2-(phenyl)ethylamino]quinoline (from Example 130, Part A) was reacted with triethyl orthoacetate and acetic acid to provide 2-methyl-1-[2-(phenyl)ethyl]-1H-imidazo[4,5-c]-quinoline.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | HO- | C(C)(=O)O | null | null | CCOC(C)(OCC)OCC.Nc1cnc2ccccc2c1NCCc1ccccc1>C(C)(=O)O>Cc1nc2cnc3ccccc3c2n1CCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40c5db691dac434a8e856094f8e30b26 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N>>CC(C)Cn1cnc2c(N)nc3ccccc3c21 | ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C.N>>C(C(C)C)N1C=NC=2C(=NC=3C=CC=CC3C21)N | Cl[c:9]1[c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]([n:11]1)[cH:13][cH:14][cH:15][cH:16]2.[NH3:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N | CC(C)Cn1cnc2c(N)nc3ccccc3c21 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c28f0ec61c908136ffb0a30dd77edf081d280d13023b48fbaccc360a51826dd0 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | A mixture of 6.0 g (0.023 mole) of 4-chloro-1-isobuty-I-1H-imidazo[4,5-c]quinoline (from Example 77) and 30 ml of 20% ammonia in methanol was heated in a steel bomb for 18 hours at 150° C. The bomb was cooled, and the solid was separated by filtration, washed with methanol and recrystallized from N,N-dimethylformamide ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | CO | null | null | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N>CO>CC(C)Cn1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b76c5bba7f784ca49f6ef483068d4e3f | CCCCCCNc1c([N+](=O)[O-])cnc2ccccc12>>CCCCCCNc1c(N)cnc2ccccc12 | C(CCCCC)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>NC=1C=NC2=CC=CC=C2C1NCCCCCC | O=[N+:10]([O-])[c:9]1[c:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:18]2[c:13]([n:12][cH:11]1)[cH:14][cH:15][cH:16][cH:17]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[c:9]([NH2:10])[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CCCCCCNc1c([N+](=O)[O-])cnc2ccccc12 | CCCCCCNc1c(N)cnc2ccccc12 | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 1.5 | HOUR | To a solution of 22.5 g (0.0823 mole) of 4-(n-hexyl)amino-3-nitroquinoline in 300 ml of toluene was added about 1.0 g of 5% platinum on charcoal and the mixture was hydrogenated on a Paar apparatus for 1.5 hours. Filtration followed by evaporation in vacuo provided a residue of 3-amino-4-(n-hexyl)aminoquinoline as an o... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C1(=CC=CC=C1)C | null | 1.5 | CCCCCCNc1c([N+](=O)[O-])cnc2ccccc12>[Pt].C1(=CC=CC=C1)C>CCCCCCNc1c(N)cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d731061a926a478b9b411d4d4b43e710 | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1O>>CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 | C(C(C)C)N.Cl.C(C)N(CC)CC.P(=O)(Cl)(Cl)Cl.C(C(C)C)N.OC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>C(C(C)C)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1O | CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | CN(C=O)C | Functional Group Addition | Reductive amination with alcohol | 323be3a29db03987af5437147ca38f381a61d3758dc3e1e15c9bfbbe48d7afab | 48d1b7679391da0e4d23024ff9a58734100ee909371b4065e4b5a1e4d85a7201 | c1ccc2ncccc2c1 | O-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 111.2 | [{"value": 111.2, "product": "C(C(C)C)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 50.0 g (0.269 mole) of 4-hydroxy-3-nitroquinoline in 300 ml of N,N-dimethylformamide in a 500 ml erlenmeyer flask was added, gradually, 44.3 g (0.2892 mole) of phosphorus oxychloride. The resulting mixture was heated on a steam bath for about 15 minutes, and was then poured onto ice with stirring. After neutralizati... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CN(C=O)C | null | null | CC(C)CN.O=[N+]([O-])c1cnc2ccccc2c1O>CN(C=O)C>CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-32844ea9b2634382ab9882881a5458d7 | CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12>>CC(C)CNc1c(N)cnc2ccccc12 | C(C(C)C)NC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>NC=1C=NC2=CC=CC=C2C1NCC(C)C | O=[N+:8]([O-])[c:7]1[c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:16]2[c:11]([n:10][cH:9]1)[cH:12][cH:13][cH:14][cH:15]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([NH2:8])[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12 | CC(C)CNc1c(N)cnc2ccccc12 | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 100.6 | [{"value": 100.6, "product": "NC=1C=NC2=CC=CC=C2C1NCC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Isobutylamino-3-nitroquinoline (31.5 g, 0.1284 moles) from Step (A) above, was dissolved in 300 ml of toluene, and about one g of platinum on charcoal was added thereto. The resulting mixture was hydrogenated on a Parr apparatus for one and one-half hours. The mixture was then heated and filtered. Toluene was removed... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C1(=CC=CC=C1)C | null | null | CC(C)CNc1c([N+](=O)[O-])cnc2ccccc12>[Pt].C1(=CC=CC=C1)C>CC(C)CNc1c(N)cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-77406bcb46cf4afa95cd7512a1662d08 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl>>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 | C(C(C)C)N1C=NC=2C=[N+](C=3C=CC=CC3C21)[O-].P(=O)(Cl)(Cl)Cl.[OH-].[NH4+]>>ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C | [O-][n+:11]1[cH:9][c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([Cl:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | c5cfc3e69c2d1a66a8560034fe025f449600689a18546e68a564dc97632a28be | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[n+;H0;D3:8](-[O-]):[c:9](:[c:10]):[c:11]:[c:12]:1:2>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[c:12]:1:[c:11]:[c:9](:[c:10]):[n;H0;D2;+0:8]:[c;H0;D3;+0:7]:2-[Cl;H0;D1;+0:1] | 89.9 | [{"value": 89.9, "product": "ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 30 | MINUTE | To 40 ml of cold N,N-dimethylformamide (10°-20° C.) was added slowly 5.9 g (0.0385 mole) of phosphorus oxychloride with swirling, the temperature of the mixture being maintained at 10-20° C. 1-Isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide (6.2 g; 0.0257 mole) from Step (C) above was added gradually with swirling and cooli... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)[n+]cc1[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | CN(C=O)C | 15 | 0.5 | CC(C)Cn1cnc2c[n+]([O-])c3ccccc3c21.O=P(Cl)(Cl)Cl>CN(C=O)C>CC(C)Cn1cnc2c(Cl)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9f8211210c6d4dbf81d1600cda775b83 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N>>CC(C)Cn1cnc2c(N)nc3ccccc3c21 | ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)C.N>>C(C(C)C)N1C=NC=2C(=NC=3C=CC=CC3C21)N | Cl[c:9]1[c:8]2[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]2[c:17]2[c:12]([n:11]1)[cH:13][cH:14][cH:15][cH:16]2.[NH3:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N | CC(C)Cn1cnc2c(N)nc3ccccc3c21 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c28f0ec61c908136ffb0a30dd77edf081d280d13023b48fbaccc360a51826dd0 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | 8 | HOUR | A mixture of 6.0 g (0.0231 mole) of 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline from Step (D) above and 30 ml of 20% ammonia in methanol was heated in a steel bomb for about 8 hours at about 145° C. The bomb was allowed to stand overnight at room temperature. The bomb was then cooled in an ice bath, and the solid th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | CO | null | 8 | CC(C)Cn1cnc2c(Cl)nc3ccccc3c21.N>CO>CC(C)Cn1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-79e71bee98e74baf9f6c9abcace69231 | CC(C)(O)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12 | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].OC(CN)(C)C>>OC(CNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-])(C)C | [CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH2:6].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH:6][c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CC(C)(O)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl | CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | null | [] | null | null | null | null | Using the method of Example 1, 4-chloro-3-nitroquinoline was reacted with 2-hydroxy-2-methylpropylamine to provide 4-(2-hydroxy-2-methylpropylamino)3-nitroquinoline, m.p. 234°-244° C. (dec.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | CC(C)(O)CN.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-688336cc55214556ac93ccfe0ea98ef2 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12>>CC(C)(O)CNc1c(N)cnc2ccccc12 | OC(CNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-])(C)C.C1(=CC=CC=C1)C>>NC=1C=NC2=CC=CC=C2C1NCC(C)(C)O | O=[N+:9]([O-])[c:8]1[c:7]([NH:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[c:17]2[c:12]([n:11][cH:10]1)[cH:13][cH:14][cH:15][cH:16]2>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH:6][c:7]1[c:8]([NH2:9])[cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12 | CC(C)(O)CNc1c(N)cnc2ccccc12 | null | [Pt] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the method of Example 16, 7.0 g (0.027 mole) of 4-(2-hydroxy-2-methylpropylamino)-3-nitroquinoline, 1 g of platinum on charcoal, 200 ml of toluene and 150 ml of ethanol was hydrogenated on a Paar apparatus. The solution was filtered, then evaporated to dryness to provide 3-amino-4-(2-hydroxy-2-methylpropylamino)q... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C(C)O | null | null | CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccccc12>[Pt].C(C)O>CC(C)(O)CNc1c(N)cnc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-37ae88eabedd477fbfe382c31767cfc2 | CC(C)(O)Cn1cnc2c(Cl)nc3ccccc3c21.N>>CC(C)(O)Cn1cnc2c(N)nc3ccccc3c21 | ClC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)(C)O.N>>NC1=NC=2C=CC=CC2C2=C1N=CN2CC(C)(C)O | Cl[c:10]1[c:9]2[n:8][cH:7][n:6]([CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[c:19]2[c:18]2[c:13]([n:12]1)[cH:14][cH:15][cH:16][cH:17]2.[NH3:11]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]([NH2:11])[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]12 | CC(C)(O)Cn1cnc2c(Cl)nc3ccccc3c21.N | CC(C)(O)Cn1cnc2c(N)nc3ccccc3c21 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c28f0ec61c908136ffb0a30dd77edf081d280d13023b48fbaccc360a51826dd0 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | A mixture of 1.1 g (0.004 mole) of 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline and 30 ml of 15 to 20% ammonia in methanol was heated at 150° to 160° C. for five hours in a bomb reactor. The mixture was filtered and the solid washed sequentially with methanol, ethyl acetate, water, and methanol then... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1nc2ccccc2c2nc[nH]c12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HCl | CO | null | null | CC(C)(O)Cn1cnc2c(Cl)nc3ccccc3c21.N>CO>CC(C)(O)Cn1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ccd81c7a01fc41eea9e96fd7b3fd7c67 | CC(C)Cn1c(-c2ccccc2)nc2c(Cl)nc3ccccc3c21.CO.N>>CC(C)Cn1c(-c2ccccc2)nc2c(N)nc3ccccc3c21.O | ClC1=NC=2C=CC=CC2C2=C1N=C(N2CC(C)C)C2=CC=CC=C2.N.CO>>O.C(C(C)C)N1C(=NC=2C(=NC=3C=CC=CC3C21)N)C2=CC=CC=C2 | Cl[c:15]1[c:14]2[n:13][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:24]2[c:23]2[c:18]([n:17]1)[cH:19][cH:20][cH:21][cH:22]2.C[OH:25].[NH3:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]2[c:15]([NH2:16])[n:17][c:18]3[cH:19][cH:... | CC(C)Cn1c(-c2ccccc2)nc2c(Cl)nc3ccccc3c21.CO.N | CC(C)Cn1c(-c2ccccc2)nc2c(N)nc3ccccc3c21.O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8c8a5c893d886f8e242b67f9a3ad5148e87067796ba94f9095249c16bdc94ad8 | 152de3e76630e7985ec8784a0546cb68833650aaca34ad49d4293f11c3fa6912 | c1ccc(-c2nc3cnc4ccccc4c3[nH]2)cc1 | C-[OH;D1;+0:1].Cl-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]2:[#7;a:7](-[C:8]):[c:9]:[#7;a:10]:[c:11]:2:1.[NH3;D0;+0:12]>>[C:8]-[#7;a:7]1:[c:9]:[#7;a:10]:[c:11]2:[c:6]:1:[c:5]:[c:4]:[#7;a:3]:[c;H0;D3;+0:2]:2-[NH2;D1;+0:12].[OH2;D0;+0:1] | null | [] | null | null | null | null | A mixture of 5.6 g (0.016 mole) of 4-chloro-1-isobutyl-2-phenyl-1H-imidazo[4,5-c]quinoline and 30 ml of a 20% mixture of ammonia in methanol was placed in a metal bomb and heated at 145°-150° C. for about 6 hours. After cooling, the solid was separated by filtration, washed with methanol and dried to provide 3.8 g of c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Primary amine | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2cnc3ccccc3c2[nH]1 | c1ccccc1.c1nc2cnc3ccccc3c2[nH]1 | HCl | null | null | null | CC(C)Cn1c(-c2ccccc2)nc2c(Cl)nc3ccccc3c21.CO.N>>CC(C)Cn1c(-c2ccccc2)nc2c(N)nc3ccccc3c21.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4558a0d0ae84408dbd0ef2b8670238d8 | CNc1c(N)cnc2ccccc12.O=Cc1ccccc1>>Cn1c(-c2ccccc2)nc2cnc3ccccc3c21 | NC=1C=NC2=CC=CC=C2C1NC.C(C1=CC=CC=C1)=O>>CN1C(=NC=2C=NC=3C=CC=CC3C21)C2=CC=CC=C2 | [CH3:1][NH:2][c:20]1[c:11]([NH2:10])[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21.O=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[n:10][c:11]2[cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[c:20]12 | CNc1c(N)cnc2ccccc12.O=Cc1ccccc1 | Cn1c(-c2ccccc2)nc2cnc3ccccc3c21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 46c093c164e38091133c376b7b402743704aca08af9e6ec3245496a8ac99dc6d | 102dc8cc7684c6225e704279ada61418fcb470f382f53c7127f5c8ad00fc07fc | c1ccc(-c2nc3cnc4ccccc4c3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1-[NH2;D1;+0:15]>>[C;D1;H3:7]-[n;H0;D3;+0:8]1:[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:2:[n;H0;D2;+0:15]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | null | [] | null | null | null | null | Following the general method of Example 195, Step B, 3-amino-4-(methylamino)quinoline was reacted with benzaldehyde to provide 1-methyl-2-phenyl-1H-imidazo[4,5-c]quinoline, melting point 168-170° C. Analysis: Calculated for C17H13N3 : % C, 78.7; % H, 5.1; % N, 16.2. Found: % C, 78.9; % H, 5.0; % N, 16.1.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2cnc3ccccc3c2[nH]1 | c1ccccc1.c1nc2cnc3ccccc3c2[nH]1 | HO- | null | null | null | CNc1c(N)cnc2ccccc12.O=Cc1ccccc1>>Cn1c(-c2ccccc2)nc2cnc3ccccc3c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-34c8435756eb44168d336df0c543e20d | CC(C)CNc1c(N)cnc2ccccc12.COc1ccc(C=O)cc1OC>>COc1ccc(-c2nc3cnc4ccccc4c3n2CC(C)C)cc1OC | NC=1C=NC2=CC=CC=C2C1NCC(C)C.C(C1=CC(OC)=C(OC)C=C1)=O>>COC=1C=C(C=CC1OC)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CC(C)C | [NH2:8][c:9]1[cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1[NH:19][CH2:20][CH:21]([CH3:22])[CH3:23].O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][n:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[c:18]3[n:19]2[CH2... | CC(C)CNc1c(N)cnc2ccccc12.COc1ccc(C=O)cc1OC | COc1ccc(-c2nc3cnc4ccccc4c3n2CC(C)C)cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 93bb1b44f1d1432768c071e289ea08e6380da40bcdeccf4285629e70068050c1 | 102dc8cc7684c6225e704279ada61418fcb470f382f53c7127f5c8ad00fc07fc | c1ccc(-c2nc3cnc4ccccc4c3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1-[NH2;D1;+0:16]>>[C:7]-[C:8]-[n;H0;D3;+0:9]1:[c:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2:[n;H0;D2;+0:16]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | null | [] | null | null | null | null | Following the general method of Example 195, Step B, 3-amino-4-(isobutylamino)quinoline was reacted with veratraldehyde to provide 2-(3,4-dimethoxyphenyl)-1-isobutyl-1H-imidazo[4,5-c]quinoline, melting point 192°-199° C. Analysis: Calculated for C20H23N3O2 : % C, 73.1; % H, 6.4; % N, 11.6. Found: % C, 72.7; % H, 6.3; %... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1ccccc1.c1nc2c(cnc3ccccc32)[nH]1 | HO- | null | null | null | CC(C)CNc1c(N)cnc2ccccc12.COc1ccc(C=O)cc1OC>>COc1ccc(-c2nc3cnc4ccccc4c3n2CC(C)C)cc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1c55745b770e48968de56de9887cde31 | CC(=O)Nc1ccc(CCCCOC(C)=O)cc1>>CC(=O)Nc1ccc(CCCCO)cc1 | C(C)(=O)OCCCCC1=CC=C(C=C1)NC(C)=O.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)NC1=CC=C(C=C1)CCCCO | CC(=O)[O:13][CH2:12][CH2:11][CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:15][cH:14]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[cH:14][cH:15]1 | CC(=O)Nc1ccc(CCCCOC(C)=O)cc1 | CC(=O)Nc1ccc(CCCCO)cc1 | null | null | O.C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | 55 | CELSIUS | null | null | To a solution of 19.3 g (0.077 mole) of acetic acid, 4-[4-(acetylamino)phenyl]butyl ester in 300 ml of ethanol, add a solution of 21 g potassium carbonate in 300 ml of water. Heat the resulting solution at 55° C. for 4 hrs. following the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | O.C(C)O | 55 | null | CC(=O)Nc1ccc(CCCCOC(C)=O)cc1>O.C(C)O>CC(=O)Nc1ccc(CCCCO)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0333de16236342b8b20d9c4d91eee625 | CCCCCCCBr.Cc1nc(C)c(C)[nH]1>>CCCCCCCn1c(C)nc(C)c1C | O.[H-].[Na+].Cl.CC=1NC(=C(N1)C)C.C(CCCCCC)Br>>C(CCCCCC)N1C(=NC(=C1C)C)C | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[nH:8]1[c:9]([CH3:10])[n:11][c:12]([CH3:13])[c:14]1[CH3:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9]([CH3:10])[n:11][c:12]([CH3:13])[c:14]1[CH3:15] | CCCCCCCBr.Cc1nc(C)c(C)[nH]1 | CCCCCCCn1c(C)nc(C)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7](-[C;D1;H3:8]):[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:9](-[C;D1;H3:10]):[c:7](-[C;D1;H3:8]):[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | 0 | CELSIUS | 30 | MINUTE | Dissolve 16.0 g (0.019 mole) of 2,4,5-trimethyl-1H-imidazole hydrochloride in 125 ml dry N,N-dimethylformamide and cool to 0° C. Add 8.75 g (0.218 mole) of sodium hydride (60%), stir at 0° C. for 30 minutes and then heat reaction mixture to 100° C. for one hour. Cool to 0° C. and then add 18.0 ml (0.114 mole) of n-hept... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HBr | CN(C=O)C | 0 | 0.5 | CCCCCCCBr.Cc1nc(C)c(C)[nH]1>CN(C=O)C>CCCCCCCn1c(C)nc(C)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-57b944a444a247edb173341c73d19415 | BrC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(Cl)cc1>>C#Cc1ccc(Cl)cc1 | CC(C)([O-])C.[K+].[Cl-].[NH4+].[Br-].BrC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[K+].ClC1=CC=C(C=O)C=C1>>ClC1=CC=C(C=C1)C#C | Br[CH2:1][P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=[CH:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1 | BrC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(Cl)cc1 | C#Cc1ccc(Cl)cc1 | null | null | O.C1CCOC1 | Miscellaneous | OtherReaction | b5e69f6284ae9f6c52b1911e39a0a898004174961d6025d7bb8cb77cbd850106 | 308ec825ff187ec0e11eceb565511738e2dacb42c714ffa84b499d992753cbd1 | c1ccccc1 | Br-[CH2;D2;+0:1]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 2 | HOUR | Dissolve 276.5 g (0.634 mole) of bromomethyltriphenyl phosphonium bromide in 1800 ml THF and cool to -78° C. Add 67.6 g (0.062 mole) potassium tert.-butoxide and stir at -78° C. for 2 hours. Add 89.12 g p-chlorobenzaldehyde in 200 ml THF to cold reaction mixture and stir for 30 minutes. Add 142.3 g potassium tert.-buto... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Alkyne | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HBr | O.C1CCOC1 | -78 | 2 | BrC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(Cl)cc1>O.C1CCOC1>C#Cc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bdc533e715184965bbc0536d30ee978f | C#Cc1ccc(Cl)cc1.C1CO1>>OCCC#Cc1ccc(Cl)cc1 | [Cl-].[NH4+].C(CCC)[Li].ClC1=CC=C(C=C1)C#C.C1CO1>>ClC1=CC=C(C=C1)C#CCCO | [CH:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[O:1]1[CH2:2][CH2:3]1>>[OH:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | C#Cc1ccc(Cl)cc1.C1CO1 | OCCC#Cc1ccc(Cl)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 74881f120d30039dded129c43f3931fc5b61be5ec7ff7e68b1ee41afe1e0a524 | 47c0afae0bab7143ec21638567c860dc3df06c531350cee5b2c3bb02fce1440c | c1ccccc1 | [CH;D1;+0:1]#[C:2]-[c:3].[C:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-1>>[OH;D1;+0:6]-[C:4]-[CH2;D2;+0:5]-[C;H0;D2;+0:1]#[C:2]-[c:3] | null | [] | -78 | CELSIUS | 2 | HOUR | Dissolve 14.2 g (0.104 mole) of 1-chloro-4-ethynylbenzene in 35 ml dry THF and cool to -78° C. Add 49 ml butyl lithium to cold reaction mixture and allow to warm to room temperature for 2 hours. After 2 hours, cool to -78° C. and the add 5.8 ml (0.114 mole) ethylene oxide in 20 ml THF. Allow to warm to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Alkyne | Primary alcohol.Alkyne | C1CO1 | null | c1ccccc1 | null | C1CCOC1 | -78 | 2 | C#Cc1ccc(Cl)cc1.C1CO1>C1CCOC1>OCCC#Cc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1c4e4b4ca92940e9b18a794c32368b52 | Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)[O-])cc1 | ClC1=CC=C(C=C1)C#CCCO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)OCC>>ClC1=CC=C(C=C1)C#CCCO.CC1=CC=C(C=C1)S(=O)(=O)[O-] | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:11][cH:10]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O-:9])[cH:10][cH:11]1 | Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)[O-])cc1 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 0cd2ed4c6a94f21490c2adf2b68d468bae5848a2a7182f1ca312bdc9820ddd3f | fcd366d2a12b9f2b1304281b4b55e60873460be0844fd3f482f05b099eb21cf7 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[O;-;D1;H0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | 1 | HOUR | Dissolve 13.3 g (0.0736 mole) of 4-(4-chlorophenyl)-3-butyn-1-ol in 70 ml pyridine and cool to 0° C. Add 16 g (0.0837 mole) of p-toluenesulfonyl chloride and stir in ice bath for one hour. Store in freezer over night. Add 200 ml diethyl ether and then wash with 3×150 ml 1N hydrochloric acid. The organic layer is then w... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | null | N1=CC=CC=C1 | 0 | 1 | Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e58ccd8a18b34601959a020e8d497689 | CS(=O)(=O)Cl.CS(=O)(=O)Cl.Nc1ccc(CCCCO)cc1>>CS(=O)(=O)Nc1ccc(CCCCOS(C)(=O)=O)cc1 | CS(=O)(=O)Cl.NC1=CC=C(C=C1)CCCCO.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCC1=CC=C(C=C1)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].Cl[S:15]([CH3:16])(=[O:17])=[O:18].[NH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[cH:19][cH:20]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][cH:20]1 | CS(=O)(=O)Cl.CS(=O)(=O)Cl.Nc1ccc(CCCCO)cc1 | CS(=O)(=O)Nc1ccc(CCCCOS(C)(=O)=O)cc1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | b2bf6220584234f1bd19047ee82945b25f43600c7ad23e864d53425aab806ad7 | 6c124ade914d189e6ed09bfe0a6c1651505ee2fd7e35365d194d1b93a5b77eb7 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].Cl-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8].[C:9]-[C:10]-[OH;D1;+0:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15].[C:9]-[C:10]-[O;H0;D2;+0:11]-[S;H0;D4;+0:5](-[... | null | [] | -10 | CELSIUS | 2 | DAY | 9.25 g (0.056 mole) 4-aminobenzenebutanol is dissolved in 100 ml pyridine and the solution is cooled to ca. -10° C. 17.33 ml (25.65 g) (0.244 mole) methanesulfonyl chloride is added dropwise with vigorous stirring at a rate such that the methanesulfonyl chloride is added, the reaction mixture is left in the freezer for... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine.Sulfonyl halide.Sulfonyl halide | Sulfonamide.Mesylate | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | -10 | 48 | CS(=O)(=O)Cl.CS(=O)(=O)Cl.Nc1ccc(CCCCO)cc1>N1=CC=CC=C1>CS(=O)(=O)Nc1ccc(CCCCOS(C)(=O)=O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eb0e73cb164b48d4ba41188c18c754fc | Cl.Nc1cccc(Cl)c1Cl>>N#[N+]c1cccc(Cl)c1Cl.[Cl-] | N(=O)[O-].[Na+].ClC1=C(N)C=CC=C1Cl.Cl>>[Cl-].ClC1=C(C=CC=C1Cl)[N+]#N | [ClH:11].[NH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1[Cl:10]>>[N:1]#[N+:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1[Cl:10].[Cl-:11] | Cl.Nc1cccc(Cl)c1Cl | N#[N+]c1cccc(Cl)c1Cl.[Cl-] | null | null | 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 | [] | null | null | 5 | MINUTE | To a suspension of 25 g (0.15 mole) 2,3-dichloroaniline in 16 ml H2O, add 39 ml (0.46 mole) concentrated HCl. Stir the mixture at room temperature for about five minutes. Cool the mixture to -5° to 0° C. and add dropwise a solution of 11 g (0.16 mole) NaNO2 in 30 ml H2O. Stir the resulting solution at -5° to 0° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | null | c1ccccc1 | null | O | null | 0.083333 | Cl.Nc1cccc(Cl)c1Cl>O>N#[N+]c1cccc(Cl)c1Cl.[Cl-] |
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