dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-83cce351f7ce40fbbfb94ec6344ceae4 | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCN=C=S>>CCN(CC)CCCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C | C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C.C(C)N(CC)CCCN=C=S>>C(C)N(CCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC | [NH:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]([CH3:25])[CH3:26].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[S:11]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[S:11])[N:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[... | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCN=C=S | CCN(CC)CCCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thiourea | 16b9dd18807f693b1cdd004c800af858aba15692e46e0e83fca1718f8bcadabb | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | c1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9](-[C;D1;H3:10])-[C;D1;H3:11]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9](-[C;D1;H3:10])-[C;D1;H3:11])-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | 76.9 | [{"value": 76.9, "product": "C(C)N(CCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C(C)N(CCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1 | null | C(C)#N | null | null | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCN=C=S>C(C)#N>CCN(CC)CCCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-00fb66882c6644f8a3f0fc09bf6d44fa | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.S=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C | C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C.C(C)N(CCN)CC.C(=S)(N1C=NC=C1)N1C=NC=C1>>C(C)N(CCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC | [NH:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:23]([CH3:24])[CH3:25].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].c1cn([C:9](n2ccnc2)=[S:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[S:10])[N:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:1... | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.S=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8f6639d4c1d8e74fe1edd589fbd0e52f490ad6c8933b6e3ee8c7c59b99e2905a | ac8bed454cbd32bb2d251ac3f635c69390732f28930050cdce90686f9b13ad73 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[S;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C;H0;D3;+0:11](=[S;D1;H0:10])-[NH;D2;+0:3]-[C:2]-[C:1] | 72.5 | [{"value": 72.5, "product": "C(C)N(CCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "C(C)N(CCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=S)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2.78 g (0.024 mole) of N,N-diethylethylenediamine and 4.82 g (0.027 mole) of 1,1'-thiocarbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.00 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 100 ml of tetrahydrofuran was added, and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Thiocarbonyl | Thiourea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.S=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ef1535005443433a943b7d450a9fc636 | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCCN.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCCCNC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C | C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCCCN)CC>>C(C)N(CCCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC | [NH:13]([CH2:14][CH2:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH:25]([CH3:26])[CH3:27].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].c1cn([C:11](n2ccnc2)=[O:12])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[N:13]([CH2:... | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCCN.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCCCNC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:3]-[C:2]-[C:1] | 26.2 | [{"value": 26.2, "product": "C(C)N(CCCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.2, "product": "C(C)N(CCCCNC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4.40 g (0.0272 mole) of 1,1'-carbonyldiimidazole and 3.46 g (0.024 mole) of N,N-diethyl-1,4-butanediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.00 g (0.0220 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the so... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CCCCN.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCCCNC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-676a05e13ec14819a379f9e941d94caf | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CC(C)N.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CC(C)NC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C | C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CC(C)N)CC>>C(C)N(CC(C)NC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC | [NH:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]([CH3:25])[CH3:26].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH:7]([CH3:8])[NH2:9].c1cn([C:10](n2ccnc2)=[O:11])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH:7]([CH3:8])[NH:9][C:10](=[O:11])[N:12]([CH2:13][CH2:14][S:... | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CC(C)N.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CC(C)NC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C;H0;D3;+0:12](=[O;D1;H0:11])-[NH;D2;+0:4]-[C:2](-[C:1])-[C;D1;H3:3] | 59.5 | [{"value": 59.5, "product": "C(C)N(CC(C)NC(N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 12.15 g (0.075 mole) of 1,1'-carbonyl diimidazole and 7.50 g (0.0476 mole) of 1-diethylamino-2-propanamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 12.26 g (0.054 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the so... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | CC(C)NCCS(=O)(=O)c1ccccc1.CCN(CC)CC(C)N.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CC(C)NC(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f9350ef6ad3d4d59a6d8bded0cf293e3 | CC(C)NCCS(=O)(=O)c1ccccc1.NCCCN1CCCCC1.O=C(n1ccnc1)n1ccnc1>>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCCCC1 | C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.NCCCN1CCCCC1>>CC(C)N(C(=O)NCCCN1CCCCC1)CCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1.c1cn([C:16](n2ccnc2)=[O:17])cn1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][... | CC(C)NCCS(=O)(=O)c1ccccc1.NCCCN1CCCCC1.O=C(n1ccnc1)n1ccnc1 | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCCCC1 | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C(NCCCN1CCCCC1)NCCS(=O)(=O)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9] | 27.1 | [{"value": 27.1, "product": "CC(C)N(C(=O)NCCCN1CCCCC1)CCS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "CC(C)N(C(=O)NCCCN1CCCCC1)CCS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5.16 g (0.0319 mole) of 1,1'-carbonyldiimidazole and 4.16 g (0.029 mole) of N-(3-aminopropyl)piperidine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.13 g (0.027 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.C1CC[NH]CC1 | Other | O1CCCC1 | null | 1 | CC(C)NCCS(=O)(=O)c1ccccc1.NCCCN1CCCCC1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9fc3086f133b4cb882634b634e570ee1 | CC(C)NCCS(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=O)N(CCS(=O)c1ccccc1)C(C)C | C1(=CC=CC=C1)S(=O)CCNC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCN)CC>>C(C)N(CCNC(N(CCS(=O)C1=CC=CC=C1)C(C)C)=O)CC | [NH:11]([CH2:12][CH2:13][S:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH:22]([CH3:23])[CH3:24].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][S:14](=[O:15])[c:16]1[cH:17][... | CC(C)NCCS(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=O)N(CCS(=O)c1ccccc1)C(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:3]-[C:2]-[C:1] | 55.9 | [{"value": 55.9, "product": "C(C)N(CCNC(N(CCS(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "C(C)N(CCNC(N(CCS(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 4.70 g (0.029 mole) of 1,1'-carbonyldiimidazole- and 3.07 g (0.0265 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.00 g (0.0245 mole) of N-[2-(phenylsulfinyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | CC(C)NCCS(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCNC(=O)N(CCS(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b2b3cfe9a1a74be8888f94a8f751e180 | CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1.O=S(=O)(CCNCc1ccccc1)c1ccccc1>>CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccccc1)Cc1ccccc1 | C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCN)CC.C(C1=CC=CC=C1)NCCS(=O)(=O)C1=CC=CC=C1>>C(C)N(CCNC(N(CCS(=O)(=O)C1=CC=CC=C1)CC1=CC=CC=C1)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].c1cn([C:9](n2ccnc2)=[O:10])cn1.[NH:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH2:12][CH... | CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1.O=S(=O)(CCNCc1ccccc1)c1ccccc1 | CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccccc1)Cc1ccccc1 | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=S(=O)(CCNCc1ccccc1)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[c:8].[O;D1;H0:9]=[C;H0;D3;+0:10](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[c:8])-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:3]-[C:2]-[C:1] | 69.98 | [{"value": 69.98, "product": "C(C)N(CCNC(N(CCS(=O)(=O)C1=CC=CC=C1)CC1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3.89 (0.024 mole) of 1,1'-carbonyldiimidazole and 2.55 g (0.022 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.70 g (0.0183 mole) of N-benzyl-2-phenylsulfonylethanamine in 50 ml of tetrahydrofuran was added, and the mixture was ref... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 1 | CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1.O=S(=O)(CCNCc1ccccc1)c1ccccc1>O1CCCC1>CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccccc1)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-55f9bf21ef824a7cb9d80cb03f44809d | CCN(CC)CCNC(C)C.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCN(C(=O)NCCS(=O)(=O)c1ccccc1)C(C)C | C(C)N(CCNC(C)C)CC.C1(=CC=CC=C1)S(=O)(=O)CCN.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)N(CCN(C(=O)NCCS(=O)(=O)C1=CC=CC=C1)C(C)C)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][CH:23]([CH3:24])[CH3:25].[NH2:11][CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[NH:11][CH2:12][CH2:13][S:14](=[O:15])(=[O:16]... | CCN(CC)CCNC(C)C.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCN(C(=O)NCCS(=O)(=O)c1ccccc1)C(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | null | null | 1 | HOUR | A mixture of 6.96 g (0.0376 mole) of 2-phenylsulfonylethanamine and 6.64 g (0.041 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.16 g (0.039 mole) of N-[2-(diethylamino)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | CCN(CC)CCNC(C)C.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCN(C(=O)NCCS(=O)(=O)c1ccccc1)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-54b66e4802a3406cb2dc05cb341eaba1 | CC(C)NCCS(=O)(=O)c1ccccc1.CN1CCN(CCCN)CC1.O=C(n1ccnc1)n1ccnc1>>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCN(C)CC1 | NCCCN1CCN(CC1)C.C(=O)(N1C=NC=C1)N1C=NC=C1.C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)S(=O)(=O)CCNC(C)C>>C(\C=C/C(=O)O)(=O)O.CC(C)N(C(=O)NCCCN1CCN(CC1)C)CCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1.c1cn([C:16](n2ccnc2)=[O:17])cn1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13]... | CC(C)NCCS(=O)(=O)c1ccccc1.CN1CCN(CCCN)CC1.O=C(n1ccnc1)n1ccnc1 | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCN(C)CC1 | null | null | CO.O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C(NCCCN1CCNCC1)NCCS(=O)(=O)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9] | 68.8 | [{"value": 68.8, "product": "C(\\C=C/C(=O)O)(=O)O.CC(C)N(C(=O)NCCCN1CCN(CC1)C)CCS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 6.00 g (0.035 mole) of 1-(3-aminopropyl)-4-methylpiperazine and 6.97 g (0.043 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.17 g (0.036 mole) of N-(2-phenylsulfonylethyl)-2-propanamine in 100 ml of tetrahydrofuran was added, and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.C1C[NH]CC[NH]1 | Other | CO.O1CCCC1 | null | 1 | CC(C)NCCS(=O)(=O)c1ccccc1.CN1CCN(CCCN)CC1.O=C(n1ccnc1)n1ccnc1>CO.O1CCCC1>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCCN1CCN(C)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-696537874e0c4dd5a445f74308693ec2 | CC(C)NC(C)CS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=O)N(C(C)C)C(C)CS(=O)(=O)c1ccccc1.O | C(C)N(CCN)CC.C(=O)(N1C=NC=C1)N1C=NC=C1.CC(C)NC(CS(=O)(=O)C1=CC=CC=C1)C>>O.C(C)N(CCNC(N(C(CS(=O)(=O)C1=CC=CC=C1)C)C(C)C)=O)CC | [NH:11]([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:16])[CH2:17][S:18](=[O:19])([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)=[O:27].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH:12]([CH3:13])[CH3:14])[C... | CC(C)NC(C)CS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=O)N(C(C)C)C(C)CS(=O)(=O)c1ccccc1.O | null | null | O1CCCC1 | Acylation | OtherReaction | 790fd9b6942665d99bc38ff775379891b82637e44650212952f5cedda0ed0eb1 | 013dbbbfd9d5d2d5efa0ece1df2d405de29fafa80f1f880bc16f7f746e690bb0 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5](-[C;D1;H3:6])-[C:7]-[S;H0;D4;+0:8](=[O;D1;H0:9])(=[O;H0;D1;+0:10])-[c:11](:[c:12]):[c:13].[C:14]-[C:15]-[NH2;D1;+0:16].[O;D1;H0:17]=[C;H0;D3;+0:18](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:14]-[C:15]-[NH;D2;+0:16]-[C;H0;D3;+0:18](=[O;D1;H0:17])-[N;H0;D3;+0:4](-[C:2](-[C;D1;H3:1... | null | [] | null | null | null | null | A solution of 3.71 g (0.032 mole) of N,N-diethylethylenediamine and 5.83 (0.036 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.30 g (0.030 mole) of N-(2-propyl)-1-(phenylsulfonyl)-2-propanamine in 50 ml of tetrahydrofuran was added and the soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Sulfone | Urea.Sulfone | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)NC(C)CS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCNC(=O)N(C(C)C)C(C)CS(=O)(=O)c1ccccc1.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1bbdfdf4f42246edb2dbfdf161a6a0b2 | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)Cl.CCN(CC)CCNC>>CCN(CC)CCN(C)C(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C.O | C(C)N(CCNC)CC.C(C)N(CC)CC.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CC(C)N(C(=O)Cl)CCS(=O)(=O)C1=CC=CC=C1>>O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)N(CCN(C(=O)N(CCS(=O)(=O)C1=CC=CC=C1)C(C)C)C)CC | Cl[C:10](=[O:11])[N:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]([CH3:25])[CH3:26].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][CH3:9]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]([CH3:9])[C:10](=[O:11])[N:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:1... | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)Cl.CCN(CC)CCNC | CCN(CC)CCN(C)C(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C.O | null | null | CCOCC.CO.O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | 21141392b95d6b95cd118c7c0b595c90f08886f6a08d558238622ce18df3aa9b | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C:4]-[#7:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C:7]-[C:6] | null | [] | null | null | null | null | A mixture of 6.65 g (0.023 mole) of N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]carbamic chloride; 3.0 g (0.023 mole) of N,N-diethyl-N'-methylethylenediamine and triethylamine (2.7 g, 0.0267 mole) in 400 ml of tetrahydrofuran was stirred at room temperature for 10 hr. The solvent was removed in vacuo, and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | null | null | c1ccccc1 | null | CCOCC.CO.O1CCCC1 | null | null | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)Cl.CCN(CC)CCNC>CCOCC.CO.O1CCCC1>CCN(CC)CCN(C)C(=O)N(CCS(=O)(=O)c1ccccc1)C(C)C.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f4da05c15f66425caadd5d8639eb6bb2 | CC(C)NCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=O)N(CCCCS(=O)(=O)c1ccccc1)C(C)C.O | C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCN)CC.CC(C)NCCCCS(=O)(=O)C1=CC=CC=C1>>O.C(C)N(CCNC(N(CCCCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC | [NH:11]([CH2:12][CH2:13][CH2:14][CH2:15][S:16](=[O:17])([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)=[O:28])[CH:25]([CH3:26])[CH3:27].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:... | CC(C)NCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=O)N(CCCCS(=O)(=O)c1ccccc1)C(C)C.O | null | null | C(Cl)(Cl)Cl.O1CCCC1 | Acylation | OtherReaction | 790fd9b6942665d99bc38ff775379891b82637e44650212952f5cedda0ed0eb1 | 013dbbbfd9d5d2d5efa0ece1df2d405de29fafa80f1f880bc16f7f746e690bb0 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[C:6]-[C:7]-[C:8]-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14].[C:15]-[C:16]-[NH2;D1;+0:17].[O;D1;H0:18]=[C;H0;D3;+0:19](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:15]-[C:16]-[NH;D2;+0:17]-[C;H0;D3;+0:19](=[O;D1;H0:18])-[N;H0;D3;+0:4](-[C:5]-[C:6]-[C:7]-... | 69.8 | [{"value": 42.2, "product": "O.C(C)N(CCNC(N(CCCCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "O.C(C)N(CCNC(N(CCCCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1,1'-carbonyldiimidazole (6.00 g, 0.037 mole) and N,N-diethylethylenediamine (4.00 g, 0.034 mole) was stirred at room temperature for 2 hours in 200 ml of tetrahydrofuran. A solution of N-(1-methylethyl)-4-(phenylsulfonyl]-1-butylamine (free base 7.99 g, 0.0313 mole) in 100 ml of tetrahydrofuran was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Sulfone | Urea.Sulfone | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | C(Cl)(Cl)Cl.O1CCCC1 | null | null | CC(C)NCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.O=C(n1ccnc1)n1ccnc1>C(Cl)(Cl)Cl.O1CCCC1>CCN(CC)CCNC(=O)N(CCCCS(=O)(=O)c1ccccc1)C(C)C.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3bf903c0996240489547e5913b65a55e | CC(C)NCCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.CO.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=O)N(CCCCCS(=O)(=O)c1ccccc1)C(C)C.O | CO.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCN)CC.CC(C)NCCCCCS(=O)(=O)C1=CC=CC=C1>>O.C(C)N(CCNC(N(CCCCCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC | [NH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[CH:26]([CH3:27])[CH3:28].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].C[OH:29].c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH2... | CC(C)NCCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.CO.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=O)N(CCCCCS(=O)(=O)c1ccccc1)C(C)C.O | null | null | C(Cl)(Cl)Cl.O1CCCC1 | Acylation | OtherReaction | 3a9361bdbd95be6f6498be3f52a439bd7b3c42ac2343fcede959a771740be9b3 | 6079f211a2cccdac0f05b041613d4ae0d7c41f3cbc8e16635694efeef0e716e4 | c1ccccc1 | C-[OH;D1;+0:1].[C:2]-[C:3]-[NH2;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C;H0;D3;+0:12](=[O;D1;H0:11])-[NH;D2;+0:4]-[C:3]-[C:2].[OH2;D0;+0:1] | 66.6 | [{"value": 66.6, "product": "O.C(C)N(CCNC(N(CCCCCS(=O)(=O)C1=CC=CC=C1)C(C)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1,1'-carbonyldiimidazole (4.54 g, 0.028 mole) and N,N-diethylethylenediamine (2.90 g, 0.025 mole) in tetrahydrofuran was stirred for 1 hr at room temperature. A solution of N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine (6.74 g, 0.025 mole) in tetrahydrofuran (dried over 4 A molecular sieves) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Methanol | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | C(Cl)(Cl)Cl.O1CCCC1 | null | null | CC(C)NCCCCCS(=O)(=O)c1ccccc1.CCN(CC)CCN.CO.O=C(n1ccnc1)n1ccnc1>C(Cl)(Cl)Cl.O1CCCC1>CCN(CC)CCNC(=O)N(CCCCCS(=O)(=O)c1ccccc1)C(C)C.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-996cfb8dec7f4d15aaf706f5b8c366a3 | O=[N+]([O-])c1cc(Cl)c(NS(=O)(=O)c2ccccc2)cc1Cl>>Nc1cc(Cl)c([N+](=O)[O-])cc1Cl | ClC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C(=C1)[N+](=O)[O-])Cl>>ClC1=C(N)C=C(C(=C1)[N+](=O)[O-])Cl | O=S(=O)(c1ccccc1)[NH:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12]>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12] | O=[N+]([O-])c1cc(Cl)c(NS(=O)(=O)c2ccccc2)cc1Cl | Nc1cc(Cl)c([N+](=O)[O-])cc1Cl | null | null | S(O)(O)(=O)=O | Reduction | OtherReaction | 2e17a3c810032c9f14c9fec7e34afbbdc0ecfd09afc752c87a3897df8c7aa53a | a7ea9d81d4cfa76d8b5a506ce4b577cf1cb07ecc98efc32d6e49796f60cf3810 | c1ccccc1 | O=S(=O)(-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 24 | HOUR | 0.44 mole (154 g) of 2,5-dichloro-4-nitro-N-benzenesulphonylaniline prepared in the previous stage is suspended in 600 ml of concentrated sulphuric acid. After 24 hours' stirring at ambient temperature the reaction mixture is poured onto 5 kg of ice. The expected product precipitates. After filtering, washing to neutra... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 24 | O=[N+]([O-])c1cc(Cl)c(NS(=O)(=O)c2ccccc2)cc1Cl>S(O)(O)(=O)=O>Nc1cc(Cl)c([N+](=O)[O-])cc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-617bfdd769eb46abb48d202834543d87 | O=S(=O)(Nc1cc(Br)ccc1Br)c1ccccc1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br | C(C)(=O)O.N(=O)[O-].[Na+].BrC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C=C1)Br.[N+](=O)(O)[O-]>>BrC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C(=C1)[N+](=O)[O-])Br | [cH:4]1[cH:5][c:6]([Br:7])[c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[Br:21].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[Br:21] | O=S(=O)(Nc1cc(Br)ccc1Br)c1ccccc1.O=[N+]([O-])O | O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Br;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | 90 | CELSIUS | null | null | To 250 ml of acetic acid, diluted with 130 ml of water, are added: 1.5 g of sodium nitrite, 0.13 mole of 2,5-dibromo-N-benzenesulphonylaniline prepared in the previous stage and 0.78 mole (32.5 ml) of nitric acid (d=1.52). The reaction mixture is heated for 1 hour at 90° C. The reaction mixture, cooled beforehand, is p... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O | 90 | null | O=S(=O)(Nc1cc(Br)ccc1Br)c1ccccc1.O=[N+]([O-])O>O>O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dbe92f0c312a4853a6a2bebab89efc08 | O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br>>Nc1cc(Br)c([N+](=O)[O-])cc1Br | S(O)(O)(=O)=O.BrC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C(=C1)[N+](=O)[O-])Br>>BrC1=C(N)C=C(C(=C1)[N+](=O)[O-])Br | O=S(=O)(c1ccccc1)[NH:1][c:2]1[cH:3][c:4]([Br:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Br:12]>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Br:12] | O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br | Nc1cc(Br)c([N+](=O)[O-])cc1Br | null | null | O | Reduction | OtherReaction | 2e17a3c810032c9f14c9fec7e34afbbdc0ecfd09afc752c87a3897df8c7aa53a | a7ea9d81d4cfa76d8b5a506ce4b577cf1cb07ecc98efc32d6e49796f60cf3810 | c1ccccc1 | O=S(=O)(-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 15 ml of water are added, with due care, to 115 ml of concentrated sulphuric acid; the temperature rises to 70° C. 0.105 mole (46 g) of 2,5-dibromo-4-nitro-N-benzenesulphonylaniline are then added. The temperature is maintained at 70°-78° C. for 2 hours. The reaction mixture is poured into 1 kg of ice and water; the ex... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | O | null | null | O=[N+]([O-])c1cc(Br)c(NS(=O)(=O)c2ccccc2)cc1Br>O>Nc1cc(Br)c([N+](=O)[O-])cc1Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3dbdfcae709944628a41bf0158fca242 | Nc1cc(F)ccc1F.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1 | Cl.FC1=C(N)C=C(C=C1)F.N1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>FC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C=C1)F | [NH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[F:12].Cl[S:2](=[O:1])(=[O:3])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[S:2](=[O:3])([NH:4][c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[F:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Nc1cc(F)ccc1F.O=S(=O)(Cl)c1ccccc1 | O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1 | null | null | O | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | 40 | CELSIUS | null | null | 0.194 mole (25 g) of 2,5-difluoroaniline is added to 125 ml of pyridine. 0.2 mole (25.5 ml) of benzenesulphonyl chloride is added, while the temperature is between 35° C. and 45° C. The temperature is maintained at 40° C. for 1 hour after the addition is completed, and then the reaction mixture is poured onto 1 kg of i... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | O | 40 | null | Nc1cc(F)ccc1F.O=S(=O)(Cl)c1ccccc1>O>O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6690a163904649839ee51f83c59f74e3 | O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F | C(C)(=O)O.N(=O)[O-].[Na+].FC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C=C1)F.[N+](=O)(O)[O-]>>FC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C(=C1)[N+](=O)[O-])F | [cH:4]1[cH:5][c:6]([F:7])[c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[F:21].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[F:21] | O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1.O=[N+]([O-])O | O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[F;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | 96 | CELSIUS | null | null | To 310 ml of acetic acid diluted with 160 ml of water are added: 1.5 g of sodium nitrite, 0.16 mole (42 g) of 2,5-difluoro-N-benzenesulphonylaniline prepared in the previous stage and 0.94 mole (39 ml) of nitric acid (d=1.52). The reaction mixture is heated to 96° C. for 1 hour. After cooling it is poured onto 1 kg of ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O | 96 | null | O=S(=O)(Nc1cc(F)ccc1F)c1ccccc1.O=[N+]([O-])O>O>O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8734794de3904b748c5147f7f30b1fb2 | O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F>>Nc1cc(F)c([N+](=O)[O-])cc1F | S(O)(O)(=O)=O.FC1=C(NS(=O)(=O)C2=CC=CC=C2)C=C(C(=C1)[N+](=O)[O-])F>>FC1=C(N)C=C(C(=C1)[N+](=O)[O-])F | O=S(=O)(c1ccccc1)[NH:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[F:12]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[F:12] | O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F | Nc1cc(F)c([N+](=O)[O-])cc1F | null | null | O | Reduction | OtherReaction | 2e17a3c810032c9f14c9fec7e34afbbdc0ecfd09afc752c87a3897df8c7aa53a | a7ea9d81d4cfa76d8b5a506ce4b577cf1cb07ecc98efc32d6e49796f60cf3810 | c1ccccc1 | O=S(=O)(-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | null | null | 10 ml of water are added with due care to 75 ml of concentrated sulphuric acid; the temperature rises to 70° C. 0.105 mole (33 g) of 2,5-difluoro-4-nitro-N-benzenesulphonylaniline prepared in the previous stage is then added. The temperature is maintained at 70° C. for 2 hours. The reaction mixture is poured onto 1 kg ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | O | 70 | null | O=[N+]([O-])c1cc(F)c(NS(=O)(=O)c2ccccc2)cc1F>O>Nc1cc(F)c([N+](=O)[O-])cc1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b1ae56670021489c8b0a911be0cc61d1 | NCCO.Nc1cc(Cl)c(Cl)cc1[N+](=O)[O-]>>Nc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] | ClC1=CC(=C(N)C=C1Cl)[N+](=O)[O-].C(O)CN>>NC1=C(C=C(C(=C1)NCCO)Cl)[N+](=O)[O-] | [NH2:5][CH2:6][CH2:7][OH:8].Cl[c:4]1[cH:3][c:2]([NH2:1])[c:12]([N+:13](=[O:14])[O-:15])[cH:11][c:9]1[Cl:10]>>[NH2:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][OH:8])[c:9]([Cl:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15] | NCCO.Nc1cc(Cl)c(Cl)cc1[N+](=O)[O-] | Nc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | null | [] | null | null | null | null | 0.11 mole (22.8 g) of 4,5-dichloro-2-nitroaniline is added to a solution of 0.55 mole (33.3 ml) of ethanolamine in 70 ml of dioxane. The reaction mixture is heated for 6 hours in refluxing dioxane. After dilution with water and neutralization with concentrated hydrochloric acid, the expected product precipitates.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O1CCOCC1 | null | null | NCCO.Nc1cc(Cl)c(Cl)cc1[N+](=O)[O-]>O1CCOCC1>Nc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8234a4b6b1c4b76ac1f1dde36971aea | NCCN.O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl>>NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-] | ClC1=C(C=C(C(=C1)Cl)Cl)[N+](=O)[O-].C(CN)N.C(C)O>>ClC1=CC(=C(NCCN)C=C1Cl)[N+](=O)[O-] | [NH2:1][CH2:2][CH2:3][NH2:4].Cl[c:5]1[cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15] | NCCN.O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl | NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | 0.13 mole (30.6 g) of 2,4,5-trichloronitrobenzene is added to a solution of 78 g of ethylenediamine in 100 ml of 96° ethanol and 117 ml of water. After heating under reflux for 1 h 30 min, the reaction mixture is cooled. After dilution with iced water, the expected product precipitates. It melts as 84° C.-87° C.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O | null | null | NCCN.O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl>O>NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4c54e3751d4842d7a5094d5ea6aa2e59 | NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-].NCCO>>NCCNc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] | ClC1=CC(=C(NCCN)C=C1Cl)[N+](=O)[O-].C(O)CN>>ClC1=C(NCCO)C=C(C(=C1)[N+](=O)[O-])NCCN | Cl[c:7]1[cH:6][c:5]([NH:4][CH2:3][CH2:2][NH2:1])[c:15]([N+:16](=[O:17])[O-:18])[cH:14][c:12]1[Cl:13].[NH2:8][CH2:9][CH2:10][OH:11]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][c:7]([NH:8][CH2:9][CH2:10][OH:11])[c:12]([Cl:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-].NCCO | NCCNc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | null | [] | null | null | null | null | 0.04 mole (10 g) of 4,5-dichloro-2-nitro-N-β-aminoethylaniline prepared in the 1st stage is heated in 40 ml of monoethanolamine for 30 minutes to 100° C. The reaction mixture is diluted with 450 ml of iced water. An impurity is precipitated by adding hydrochloric acid and is removed by filtration. The filtrate is made ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O | null | null | NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-].NCCO>O>NCCNc1cc(NCCO)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-363bfb4003904efb8b5cf573bf65a281 | NCCO.Nc1cc(Br)c([N+](=O)[O-])cc1Br>>Nc1cc(NCCO)c([N+](=O)[O-])cc1Br | BrC1=C(N)C=C(C(=C1)[N+](=O)[O-])Br.BrC1=C(N)C=C(C(=C1)[N+](=O)[O-])Br.C(O)CN>>OCCNC1=C(C=C(C(=C1)N)Br)[N+](=O)[O-] | [NH2:5][CH2:6][CH2:7][OH:8].Br[c:4]1[cH:3][c:2]([NH2:1])[c:14]([Br:15])[cH:13][c:9]1[N+:10](=[O:11])[O-:12]>>[NH2:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[Br:15] | NCCO.Nc1cc(Br)c([N+](=O)[O-])cc1Br | Nc1cc(NCCO)c([N+](=O)[O-])cc1Br | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | 0.02 mole (5.92 g) of 2,5-dibromo-4-nitroaniline (compound B) is added to 15 ml of 96° ethanol to which 12 ml of ethanolamine have been added. The mixture is heated in refluxing alcohol for 6 h 30 min. After cooling and dilution of the reaction mixture with 100 ml of iced water, the expected product precipitates.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)O | null | null | NCCO.Nc1cc(Br)c([N+](=O)[O-])cc1Br>C(C)O>Nc1cc(NCCO)c([N+](=O)[O-])cc1Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4db7c84e1eb24c088f78a0ceb966e2c1 | CSCCO.O=[N+]([O-])c1ccccc1F>>CSCCOc1ccccc1[N+](=O)[O-] | OCCSC.[H-].[Na+].FC1=C(C=CC=C1)[N+](=O)[O-]>>CSCCOC1=C(C=CC=C1)[N+](=O)[O-] | [CH3:1][S:2][CH2:3][CH2:4][OH:5].F[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14] | CSCCO.O=[N+]([O-])c1ccccc1F | CSCCOc1ccccc1[N+](=O)[O-] | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | 40 | CELSIUS | 20 | MINUTE | 16.3 g of 2-hydroxyethylmethyl sulfide are added dropwise at 20°-25° C. to 8.5 g of a 55% NaH suspension in 150 ml of absolute tetrahydrofuran. The mixture is stirred for 1 hour at 20° C. and for 20 minutes at 40° C., and 25 g of 1-fluoro-2-nitrobenzene are subsequently added at 20° C. After the suspension has been sti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O1CCCC1 | 40 | 0.333333 | CSCCO.O=[N+]([O-])c1ccccc1F>O1CCCC1>CSCCOc1ccccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-242fffddb7bc46a48d2d17eb9c1eb71e | CSCCOc1ccccc1[N+](=O)[O-]>>CSCCOc1ccccc1N | CSCCOC1=C(C=CC=C1)[N+](=O)[O-].[H][H]>>CSCCOC1=C(N)C=CC=C1 | O=[N+:12]([O-])[c:11]1[c:6]([O:5][CH2:4][CH2:3][S:2][CH3:1])[cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12] | CSCCOc1ccccc1[N+](=O)[O-] | CSCCOc1ccccc1N | null | [Ni] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 33.9 g of he oil obtained under (a) are hydrogenated in 100 ml of absolute tetrahydrofuran, with the addition of 13.6 g of Raney nickel, under normal pressure (hydrogen absorption=10.6 liters). After the catalyst has been filtered off, the filtrate is concentrated by evaporation, and then purified by means of chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].O1CCCC1 | null | null | CSCCOc1ccccc1[N+](=O)[O-]>[Ni].O1CCCC1>CSCCOc1ccccc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8ff8d568cf1248518f7da91bcabe7759 | CSCCOc1ccccc1N>>CSCCOc1ccccc1NN | O.O.Cl[Sn]Cl.NC1=CC=CC=C1.CSCCOC1=C(N)C=CC=C1.[OH-].[Na+].N(=O)[O-].[Na+]>>CSCCOC1=C(C=CC=C1)NN | [CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][NH2:13] | CSCCOc1ccccc1N | CSCCOc1ccccc1NN | null | null | C(C)(=O)O.Cl.O.CCOCC | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | HOUR | 27.4 g of the aniline obtained under (b) are placed into 45 ml of glacial acetic acid and, with ice cooling, a mixture of 37 ml of concentrated HCl and 75 ml of H2O is added. The formed suspension is diazotised at 0°-5° C. with 10.3 g of NaNO2 in 22 ml of water. The diazonium solution is subsequently stirred at 0° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | C(C)(=O)O.Cl.O.CCOCC | null | 4 | CSCCOc1ccccc1N>C(C)(=O)O.Cl.O.CCOCC>CSCCOc1ccccc1NN |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e8648a916c7c4fcfb8175365162e18a3 | COC(=O)Cl.CSCCOc1ccccc1NN>>COC(=O)NNc1ccccc1OCCSC | COC(=O)Cl.CSCCOC1=C(C=CC=C1)NN.O>>COC(=O)NNC1=C(C=CC=C1)OCCSC | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH2:14][CH2:15][S:16][CH3:17]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][CH2:14][CH2:15][S:16][CH3:17] | COC(=O)Cl.CSCCOc1ccccc1NN | COC(=O)NNc1ccccc1OCCSC | null | null | C(C)N(C(C)C)C(C)C.O1CCCC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 5be28d87ebf4e99b19d55116b9ee6a2de77dfa39d592d5f1181884aff5e22c5f | 5fd6250903fa66c378faf3ffa4e2360187bf8e16b5a0c6900f15dfbc5082c0be | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[c:7] | null | [] | 20 | CELSIUS | 2 | HOUR | 5.6 ml of chloroformic acid methyl ester are added dropwise at 0° C. to 14.4 g of 2-(2-methylthioethoxy)-phenylhydrazine in 100 ml of tetrahydrofuran and 14 g of N-ethyldiisopropylamine. The reaction mixture is stirred at 20° C. for 2 hours; H2O is then added, and the mixture is repeatedly extracted with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Acylhydrazine | null | null | c1ccccc1 | HCl | C(C)N(C(C)C)C(C)C.O1CCCC1 | 20 | 2 | COC(=O)Cl.CSCCOc1ccccc1NN>C(C)N(C(C)C)C(C)C.O1CCCC1>COC(=O)NNc1ccccc1OCCSC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f06ba04cb6474d75ba73dea89e898e68 | COC(=O)NNc1ccccc1OCCSC.O=C(Cl)Cl>>COC(=O)NN(C(=O)Cl)c1ccccc1OCCSC | C(=O)(Cl)Cl.COC(=O)NNC1=C(C=CC=C1)OCCSC>>COC(=O)NN(C1=C(C=CC=C1)OCCSC)C(=O)Cl | [CH3:1][O:2][C:3](=[O:4])[NH:5][NH:6][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][S:19][CH3:20].Cl[C:7](=[O:8])[Cl:9]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][N:6]([C:7](=[O:8])[Cl:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][S:19][CH3:20] | COC(=O)NNc1ccccc1OCCSC.O=C(Cl)Cl | COC(=O)NN(C(=O)Cl)c1ccccc1OCCSC | null | null | C1(=CC=CC=C1)C | Acylation | N-alkylation of secondary amines with alkyl halides | db2f2d9badbb4cb36546ceda2ff379720def5866cf636a6d826453d7aa31a0ea | bfae58b08a51df04e7066f096095322c7298aefc6db308d508a4f7157775bd3b | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3])-[c:10](:[c:11]):[c:12] | null | [] | 90 | CELSIUS | null | null | 80 ml of a 20% solution of phosgene in toluene are added at 20° C. to 14.1 g of 2-[2-(2-methylthioethoxy)-phenyl]-hydrazinecarboxylic acid methyl ester in 130 ml of toluene. The reaction mixture is subsequently heated for 3 hours at 90° C., and the solvent is then removed. Recrystallisation of the residue in ethyl alco... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Acylhydrazine | Acyl halide.Acylhydrazine | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | 90 | null | COC(=O)NNc1ccccc1OCCSC.O=C(Cl)Cl>C1(=CC=CC=C1)C>COC(=O)NN(C(=O)Cl)c1ccccc1OCCSC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f5275a19c7a34928b700f9075a50c3db | CC(=O)CC(C)=O.N#CNC(=N)N>>Cc1cc(C)nc(NC#N)n1 | C(#N)NC(=N)N.CC(CC(C)=O)=O.Cl>>C(#N)NC1=NC(=CC(=N1)C)C | O=[C:2]([CH3:1])[CH2:3][C:4](=O)[CH3:5].[NH:6]=[C:7]([NH:8][C:9]#[N:10])[NH2:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9]#[N:10])[n:11]1 | CC(=O)CC(C)=O.N#CNC(=N)N | Cc1cc(C)nc(NC#N)n1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 13c4f8274b8a1498bbf21922aa6710f05b644e60bec8d6f0e0485988f777d70e | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1cncnc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[N;D1;H0:6]#[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[n;H0;D2;+0:11]:[c;H0;D3;+0:9](-[#7:8]-[C:7]#[N;D1;H0:6]):[n;H0;D2;+0:10]:1 | 70 | [{"value": 70.0, "product": "C(#N)NC1=NC(=CC(=N1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "C(#N)NC1=NC(=CC(=N1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 42 g (0.5 mol) of cyanoguanidine ("dicyanodiamide") and 50 g (0.5 mol) of 2,4-pentanedione ("acetylacetone") is heated to 120° C. for 15 hours. The reaction mixture is then cooled, after which 500 ml of water are added and the solution is acidified with hydrochloric acid at 0° C. to 10° C. The product obta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cncnc1 | c1cncnc1 | HO- | O | 120 | null | CC(=O)CC(C)=O.N#CNC(=N)N>O>Cc1cc(C)nc(NC#N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-337e60123b3b4db0a8dbe09ecff88ae9 | CC(=O)CC(C)=O.N#CNC(=N)N>>Cc1cc(C)nc(NC#N)n1 | C(#N)NC(=N)N.CC(CC(C)=O)=O.Cl>>C(#N)NC1=NC(=CC(=N1)C)C | O=[C:2]([CH3:1])[CH2:3][C:4](=O)[CH3:5].[NH:6]=[C:7]([NH:8][C:9]#[N:10])[NH2:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9]#[N:10])[n:11]1 | CC(=O)CC(C)=O.N#CNC(=N)N | Cc1cc(C)nc(NC#N)n1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 13c4f8274b8a1498bbf21922aa6710f05b644e60bec8d6f0e0485988f777d70e | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1cncnc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[N;D1;H0:6]#[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[n;H0;D2;+0:11]:[c;H0;D3;+0:9](-[#7:8]-[C:7]#[N;D1;H0:6]):[n;H0;D2;+0:10]:1 | 70 | [{"value": 70.0, "product": "C(#N)NC1=NC(=CC(=N1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "C(#N)NC1=NC(=CC(=N1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 42 g (0.5 mol) of cyanoguanidine ("dicyanodiamide") and 50 g (0.5 mol) of 2,4-pentanedione ("acetylacetone") is heated to 120° C. for 15 hours. The reaction mixture is then cooled, after which 500 ml of water are added and the solution is acidified with hydrochloric acid at 0° C. to 10° C. The product obta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cncnc1 | c1cncnc1 | HO- | O | 120 | null | CC(=O)CC(C)=O.N#CNC(=N)N>O>Cc1cc(C)nc(NC#N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6d3bb0315e504c3db3692c33e7836381 | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O>>OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O)O.[H][H]>>C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O | [OH:1][CH2:2][C@H:3]1[O:4][C@@H:22]([OH:23])[C@H:20]([OH:21])[C@@H:18]([OH:19])[C@@H:5]1[O:6][C@H:7]1[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]1[OH:17]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:5]([O:6][C@H:7]1[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]1[OH:17])[C@H:... | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O | OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | null | [Ni] | null | Reduction | OtherReaction | 93bad9e1481d9297027cc2205dbf9942d4ce365c281baf2a9085a614009c66b8 | 81b1ad4a7cad3c1b76b9a651363a849ef67dca7066b2c65cf8c797861273206f | C1CCOCC1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5](-[O;D1;H1:6])-[C@H;D3;+0:7](-[O;D1;H1:8])-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[OH;D1;+0:9])-[C:3]-[C:4]-[C:5](-[O;D1;H1:6])-[CH2;D2;+0:7]-[O;D1;H1:8] | null | [] | null | null | null | null | A 50% aqueous solution of the highly-purified maltose was placed in an autoclave, and added with Raney nickel catalyst in an amount of 10%. Thereafter, the content was heated to 90°-125° C., and hydrogenation was effected at the temperature and a hydrogen pressure of 20-100 kg/cm2. After completion of the hydrogenation... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol.Secondary alcohol | C1CCOCC1 | null | C1CCOCC1 | null | [Ni] | null | null | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O>[Ni]>OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-876c8ad5813343f88cacf0ee9c0dee04 | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O>>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](... | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O)O>>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C... | [OH:1][C@H:2]1[C@H:42]([OH:4])[O:43][C@H:21]([CH2:22][OH:23])[C@@H:47]([O:48][C@H:49]2[O:50][C@H:51]([CH2:52][OH:53])[C@@H:54]([OH:55])[C@H:56]([OH:57])[C@H:58]2[OH:59])[C@@H:60]1[OH:61]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]([OH:10])[CH2:11][OH:12].[OH:13][CH2:14][C@@H:15]([OH:16])[C@@H:... | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | null | [Ni] | null | Heteroatom Alkylation and Arylation | OtherReaction | d3a1656cd59da9f3f895c4de466f4ef60e84b8de5788edbd62c4fda36ca8a4d0 | 515bdaf89df1395d99a4348c18f1eae4dce256da814e2bf511d567890d844f9b | C1CCOCC1.C1CC[C@@H](O[C@H]2CCCOC2)OC1 | [#8:1]-[C:2]-[#8:3]-[C@@H;D3;+0:4]1-[C@@H;D3;+0:5](-[C:6]-[O;D1;H1:7])-[O;H0;D2;+0:8]-[C@@H;D3;+0:9](-[OH;D1;+0:10])-[C@H;D3;+0:11](-[O;D1;H1:12])-[C@H;D3;+0:13]-1-[O;D1;H1:14]>>[#8:1]-[C:2]-[#8:3]-[C@@H;D3;+0:4]1-[C:15](-[C:16])-[O;H0;D2;+0:8]-[C@H;D3;+0:9](-[#8:17]-[C:18])-[C:19](-[O;D1;H1:20])-[C@H;D3;+0:13]-1-[O;D1... | null | [] | null | null | null | null | After adjusting the concentration of the maltose solution to 50%, to the concentrate was added Raney nickel catalyst in an amount of 10%, and the admixture was then heated to 90°-125° C. under stirring conditions, and hydrogenated at this temperature under a hydrogen pressure of 20-100 kg/cm2. After completion of the h... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol.Secondary alcohol | Ether.Ether.Ether.Ether.Ether.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcoho... | C1CCOCC1 | C1CCOCC1.C1CCOCC1 | C1CCOCC1.C1CCOCC1.C1CCOCC1 | Other | [Ni] | null | null | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O>[Ni]>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO.OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)[C@... |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fc92f46fd2df4e82ac255cb55bc6c991 | Cc1ccccc1-n1[nH]c(C(N)=O)cc1=O>>Cc1ccccc1-n1[nH]c(C#N)cc1=O | P(=O)(Cl)(Cl)Cl.C(N)(=O)C=1NN(C(C1)=O)C1=C(C=CC=C1)C.C(C)#N>>C(#N)C=1NN(C(C1)=O)C1=C(C=CC=C1)C | O=[C:11]([c:10]1[nH:9][n:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)[c:14](=[O:15])[cH:13]1)[NH2:12]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[nH:9][c:10]([C:11]#[N:12])[cH:13][c:14]1=[O:15] | Cc1ccccc1-n1[nH]c(C(N)=O)cc1=O | Cc1ccccc1-n1[nH]c(C#N)cc1=O | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=c1cc[nH]n1-c1ccccc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | null | [] | null | null | null | null | 22.5 g of 3-carbamoyl-1-(2-methylphenyl)-5-pyrazolone and 150 ml of acetonitrile were put into a 300 ml three-necked flask. A mixture solution of 35 ml of phosphorus oxychloride and 100 ml of N,N-dimethylformamide was added dropwise thereto at a temperature of 15° C. or below. After completion of the dropwise addition,... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1cn[nH]c1 | HO- | CN(C=O)C | null | null | Cc1ccccc1-n1[nH]c(C(N)=O)cc1=O>CN(C=O)C>Cc1ccccc1-n1[nH]c(C#N)cc1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b37197377f3049a1b8bb4c506a8c3f2c | Cc1cc(S(=O)(=O)O)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O.O=P(Cl)(Cl)Cl>>Cc1cc(S(=O)(=O)Cl)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O | C(#N)C=1NN(C(C1N=NC1=C(C=C(C(=C1)C)S(=O)(=O)O)C)=O)C1=C(C=CC=C1)C.C(C)#N.P(=O)(Cl)(Cl)Cl>>ClS(=O)(=O)C1=CC(=C(C=C1C)N=NC1=C(NN(C1=O)C1=C(C=CC=C1)C)C#N)C | O[S:5]([c:4]1[cH:3][c:2]([CH3:1])[c:12]([N:13]=[N:14][c:15]2[c:16]([C:17]#[N:18])[nH:19][n:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[CH3:27])[c:28]2=[O:29])[cH:11][c:9]1[CH3:10])(=[O:6])=[O:7].O=P(Cl)(Cl)[Cl:8]>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[Cl:8])[c:9]([CH3:10])[cH:11][c:12]1[N:13]=[N:14][c:15]1... | Cc1cc(S(=O)(=O)O)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O.O=P(Cl)(Cl)Cl | Cc1cc(S(=O)(=O)Cl)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O | null | null | CN(C(C)=O)C | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | O=c1c(N=Nc2ccccc2)c[nH]n1-c1ccccc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 30 | MINUTE | 8.6 g of the azo obtained in step (2) above, 35 ml of acetonitrile, and 8.6 ml of N,N-dimethylacetamide were put into a 100 ml three-necked flask and 8.6 ml of phosphorus oxychloride was added dropwise to the mixture at a temperature of 50° C. or below. After completion of the dropwise addition, the mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccccc1.c1cn[nH]c1.c1ccccc1 | HCl | CN(C(C)=O)C | null | 0.5 | Cc1cc(S(=O)(=O)O)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O.O=P(Cl)(Cl)Cl>CN(C(C)=O)C>Cc1cc(S(=O)(=O)Cl)c(C)cc1N=Nc1c(C#N)[nH]n(-c2ccccc2C)c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-10a5e567c3634c778989865c564fb6c3 | COc1ccc(C)c(N)c1.NS(=O)(=O)O>>COc1cc(N)c(C)cc1S(=O)(=O)O | COC=1C=C(N)C(=CC1)C.S(N)(O)(=O)=O>>COC1=C(S(=O)(=O)O)C=C(C(=C1)N)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH3:8])[cH:9][cH:10]1.N[S:11](=[O:12])(=[O:13])[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH3:8])[cH:9][c:10]1[S:11](=[O:12])(=[O:13])[OH:14] | COc1ccc(C)c(N)c1.NS(=O)(=O)O | COc1cc(N)c(C)cc1S(=O)(=O)O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 1bd69bda1d4654ef7571835d484654e43991922743754be44c6c12fd5f0fb8d1 | ad1e84ed1c8a6e8f7849804ad9b2e13754d927e4c3c238c80d1249ced51d5be8 | c1ccccc1 | N-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4].[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4]):[c:9]:[c:10] | null | [] | null | null | 2 | HOUR | 23.1 g of 3-methoxy-6-methylaniline and 16.4 g of sulfamic acid were put into a 100 ml egg-plant type flask and the mixture was heated to temperature of from 150° to 160° C. and maintained thereat for 2 hours. Acetonitrile was added to the reaction mixture and the crystals thus deposited were collected. The crystals we... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)#N | null | 2 | COc1ccc(C)c(N)c1.NS(=O)(=O)O>C(C)#N>COc1cc(N)c(C)cc1S(=O)(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c6d9edc5bfb342979086cd16e1aa58ad | Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1 | P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)N=C(N)C=C1)O.P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC=2C(=O)NC(N)=NC12)O.OP(OP(O)(OP(O)(O)=O)=O)(OC[C@@H]1[C@@H](O)C[C@H](N2C(NC(C(C)=C2)=O)=O)O1)=O>>C1=NC(=C2C(=N1)N(C=N2)[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)N | O=[c:2]1[nH:3][c:4]([NH2:1])[n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H:15]([CH2:16][O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([OH:24])[O:25][P:26](=[O:27])([OH:28])[OH:29])[O:30]1>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H... | Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1 | Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1 | null | null | null | Miscellaneous | OtherReaction | c51652fc80ac6d86c1af8f05954073530c62ebdbfbe33195e3f5b1ae43447cd0 | c42d4a51b8decce845f4dd55a8ddb5af4c9af9d71e89c8422599c828a2d398e9 | c1ncc2ncn([C@H]3CCCO3)c2n1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]-[#8:9]):[c:10]:[#7;a:11]:[c:12]:2:1>>[#8:9]-[C:8]-[#7;a:7]1:[c:10]:[#7;a:11]:[c:12]2:[c:6]:1:[#7;a:5]:[cH;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:4] | null | [] | null | null | null | null | 3.75 microliter 6.6 mM mix of dCTP, dGTP and dTTP
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ncc2[nH]cnc2n1 | c1ncnc2nc[nH]c12 | c1ncnc2nc[nH]c12.C1CCOC1 | Other | null | null | null | Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ca4ebe883a8d4c61a09a581b5deadc24 | O=S(=O)([O-])CC(S)CS>>O=S(=O)([O-])CC(S)CS | [S].CSSC.CSSC.C(C(CS(=O)(=O)[O-])S)S.[Na+]>>CSSC.C(C(CS(=O)(=O)[O-])S)S.[Na+] | [O:5]=[S:6](=[O:7])([O-:8])[CH2:9][CH:10]([SH:11])[CH2:12][SH:13]>>[O:5]=[S:6](=[O:7])([O-:8])[CH2:9][CH:10]([SH:11])[CH2:12][SH:13] | O=S(=O)([O-])CC(S)CS | O=S(=O)([O-])CC(S)CS | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | The procedure shown for DMDS above was repeated except that a 1:1 weight blend of DMDS and DMPS was used as the presulfiding agent and 55 g of the 1:1 blend was dissolved in 3905 g of diesel oil to give a solution containing 1.0 wt % sulfur contributed by the blend. The results are given in Table 1 below.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | O=S(=O)([O-])CC(S)CS>>O=S(=O)([O-])CC(S)CS |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5281eca835b24f4999f7ce801feb6dce | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C>>C=CC(O)[C@H](CC(C)C)NC(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)N[C@@H](CC(C)C)C=O.C(=C)[Mg]Br>>C(C)(C)(C)OC(=O)N[C@H](C(C=C)O)CC(C)C | [CH:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH2:1]=[CH:2][CH:3]([OH:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C | C=CC(O)[C@H](CC(C)C)NC(=O)OC(C)(C)C | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 7c95c9d475b3e4739c4b4bffdb557ccc0332365664dc5f751958e7bb4139acbc | 1cfdacde78204b273e664dc0eb50ffc4dc70522ea435514fcadd01e492b9b547 | null | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D3;+0:11](-[OH;D1;+0:12])-[C:13]=[C;D1;H2:14] | 65 | [{"value": 65.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C(C=C)O)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry tetrahydrofuran (THF) (70 ml) was added vinyl magnesium bromide (35 ml of a 1.0M solution in THF). After 5 hours, the mixture was quenched with 1.0M NH4Cl (50 ml). Most of the THF was evaporated in vacuo and the residue was extracted with ether seve... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Vinyl | null | null | null | Other | O1CCCC1 | null | 5 | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C>O1CCCC1>C=CC(O)[C@H](CC(C)C)NC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8c1f3451869a4ee29ada0d2769e0ba54 | CC(C)C[CH2][Mg][Br].Cc1ccc(S(=O)(=O)N[C@@H](CC(C)C)C(=O)O)cc1>>Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C | C(CC(C)C)[Mg]Br.Cl.N([C@@H](CC(C)C)C(=O)O)S(=O)(=O)C1=CC=C(C)C=C1.C(CCC)[Li]>>CC(C)C[C@@H](C(CCC(C)C)=O)NS(=O)(=O)C=1C(=CC=CC1)C | [Br][Mg][CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23].O[C:17]([C@@H:12]([NH:11][S:8]([c:7]1[cH:4][cH:3][c:2]([CH3:1])[cH:5][cH:6]1)(=[O:9])=[O:10])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:18]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH:11][C@@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[CH... | CC(C)C[CH2][Mg][Br].Cc1ccc(S(=O)(=O)N[C@@H](CC(C)C)C(=O)O)cc1 | Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C | null | null | C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | d940fd70b89cc2cc4be47412d1f6d0fafa3926c675fc36f0a31d78a298f1ecc6 | 640cebf51e15100e78116250be2508b04a71dccc1a9f5ef1e1c6773bcd660eb7 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[C;D1;H3:13]):[c:14]:[cH;D2;+0:15]:1.[Br]-[Mg]-[CH2;D2;+0:16]-[C:17]-[C:18]>>[C:4]-[C:3](-[#7:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+... | 41 | [{"value": 41.0, "product": "CC(C)C[C@@H](C(CCC(C)C)=O)NS(=O)(=O)C=1C(=CC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred -78° C. solution of Ts-Leu (15 g, 53 mmol) in dry THF (240 ml) was added n-butyl lithium (57.8 ml of a 0.91M solution in hexane) followed 15 minutes later by isopentyl magnesium bromide (185 ml of a 0.8M solution in THF). The mixture was heated at reflux for 3 days, then cooled and poured into 0° C. 1M HCl... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tosylate.Carboxylic acid | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Mg | C1CCOC1.CCCCCC | null | null | CC(C)C[CH2][Mg][Br].Cc1ccc(S(=O)(=O)N[C@@H](CC(C)C)C(=O)O)cc1>C1CCOC1.CCCCCC>Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-558929a71aa1437ba847c6cb70cee4f2 | Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C>>C=CC(O)(CCC(C)C)[C@H](CC(C)C)NS(=O)(=O)c1ccccc1C | CC(C)C[C@@H](C(CCC(C)C)=O)NS(=O)(=O)C=1C(=CC=CC1)C.C(=C)[Mg]Br>>CC(C)C[C@@H](C(CCC(C)C)(C=C)O)NS(=O)(=O)C=1C(=CC=CC1)C | [C:3](=[O:4])([CH2:5][CH2:6][CH:7]([CH3:8])[CH3:9])[C@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[NH:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[CH3:25]>>[CH2:1]=[CH:2][C:3]([OH:4])([CH2:5][CH2:6][CH:7]([CH3:8])[CH3:9])[C@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[NH:15][S:16](=[O:17])(=[O:18])[c:1... | Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C | C=CC(O)(CCC(C)C)[C@H](CC(C)C)NS(=O)(=O)c1ccccc1C | null | null | C1CCOC1 | Miscellaneous | OtherReaction | e4a1e0cd9d6dfd9db238e7c2c1de7c3e0737df0f5a991ca26c06602eed667e3f | 2ce956c609b76ee2dc626ad09e785d954b7df9a7379fec6f4a0d038e8e2d1b2b | c1ccccc1 | [#7:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C:7]>>[#7:1]-[C:2](-[C:3])-[C;H0;D4;+0:4](-[OH;D1;+0:5])(-[C:8]=[C;D1;H2:9])-[C:6]-[C:7] | 95 | [{"value": 95.0, "product": "CC(C)C[C@@H](C(CCC(C)C)(C=C)O)NS(=O)(=O)C=1C(=CC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred 0° C. solution of the resultant compound of Example 5 (79 mg, 0.23 mmol) in dry THF (8 ml) was added vinyl magnesium bromide (1.5 ml of a 1.0M solution in THF) dropwise. The mixture was warmed (room temperature, 10 hours), quenched (8 ml H2O+2 ml brine), acidified with 0.1M H3PO4 (pH=7), and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Vinyl | null | null | c1ccccc1 | Other | C1CCOC1 | null | null | Cc1ccccc1S(=O)(=O)N[C@@H](CC(C)C)C(=O)CCC(C)C>C1CCOC1>C=CC(O)(CCC(C)C)[C@H](CC(C)C)NS(=O)(=O)c1ccccc1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8bab05ee85f7428ab7f581565106fcda | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C>>C=CC(O)C(CC(C)C)NC(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)N[C@@H](CC(C)C)C=O.C(=C)[Mg]Br>>C(C)(C)(C)OC(=O)NC(C(C=C)O)CC(C)C | [CH:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH2:1]=[CH:2][CH:3]([OH:4])[CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C | C=CC(O)C(CC(C)C)NC(=O)OC(C)(C)C | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 7c95c9d475b3e4739c4b4bffdb557ccc0332365664dc5f751958e7bb4139acbc | 1cfdacde78204b273e664dc0eb50ffc4dc70522ea435514fcadd01e492b9b547 | null | [C:1]-[C:2]-[C@H;D3;+0:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH;D2;+0:12]=[O;H0;D1;+0:13]>>[C:1]-[C:2]-[CH;D3;+0:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:14]=[C;D1;H2:15] | null | [] | null | null | 5 | HOUR | To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry THF (70 ml) was added vinyl magnesium bromide (35 ml of a 1.0M solution in THF). After 5 hours, the mixture was quenched with 1.0M NH4Cl (50 ml). Most of the THF was evaporated in vacuo and the residue was extracted with ether several times. The com... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Vinyl | null | null | null | Other | C1CCOC1 | null | 5 | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C>C1CCOC1>C=CC(O)C(CC(C)C)NC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-44f5f31ec6e3435b87b6de372f03caf8 | CC(C)CC(=O)OC(I)C(C)C.CN(C)CCn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.Cl>>CC(C)CC(=O)OC(OC(=O)C1=C(CSc2nnnn2CCN(C)C)CS[C@@H]2[C@H](N)C(=O)N12)C(C)C.Cl | Cl.C(C)(=O)[O-].[K+].Cl.Cl.N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CCN(C)C)C(=O)O)C1=O.CC(CC(=O)OC(C(C)C)I)C>>Cl.Cl.N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CCN(C)C)C(=O)OC(C(C)C)OC(CC(C)C)=O)C1=O | I[CH:8]([O:7][C:5]([CH2:4][CH:2]([CH3:1])[CH3:3])=[O:6])[CH:34]([CH3:35])[CH3:36].[OH:9][C:10](=[O:11])[C:12]1=[C:13]([CH2:14][S:15][c:16]2[n:17][n:18][n:19][n:20]2[CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[CH2:26][S:27][C@@H:28]2[C@H:29]([NH2:30])[C:31](=[O:32])[N:33]12.[ClH:38]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5](=[O:... | CC(C)CC(=O)OC(I)C(C)C.CN(C)CCn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.Cl | CC(C)CC(=O)OC(OC(=O)C1=C(CSc2nnnn2CCN(C)C)CS[C@@H]2[C@H](N)C(=O)N12)C(C)C.Cl | null | null | CN(C=O)C.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 77b141d26ed5a7bde59d3b5f7a91610561531c64abebd7939b6101e4e6702cce | e0de5d8944748c8a8ff1e66140ca54f4b21d5de4aadb39226f32b2358b79ca36 | O=C1C[C@H]2SCC(CSc3nnn[nH]3)=CN12 | I-[CH;D3;+0:1](-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](-[C;D1;H3:7])-[C;D1;H3:8].[#16:9]-[C:10]-[C:11](-[C:12])=[C:13](-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16])-[#7:17]-[C:18]=[O;D1;H0:19]>>[#16:9]-[C:10]-[C:11](-[C:12])=[C:13](-[C:14](=[O;D1;H0:15])-[O;H0;D2;+0:16]-[CH;D3;+0:1](-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](-[... | 106 | [{"value": 106.0, "product": "Cl.Cl.N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CCN(C)C)C(=O)OC(C(C)C)OC(CC(C)C)=O)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To 60 ml of dimethylformamide solution containing 4.22 g of 7β-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid dihydrochloride is added 1.67 g of potassium acetate. The mixture is cooled to 0° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwis... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester.Ester | null | null | c1nnn[nH]1.C1=CN2CC[C@H]2SC1 | HI | CN(C=O)C.C(Cl)Cl | 0 | null | CC(C)CC(=O)OC(I)C(C)C.CN(C)CCn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.Cl>CN(C=O)C.C(Cl)Cl>CC(C)CC(=O)OC(OC(=O)C1=C(CSc2nnnn2CCN(C)C)CS[C@@H]2[C@H](N)C(=O)N12)C(C)C.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-14d0b639897e4843a7bf6d6a18bfd472 | CC(=O)CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.CC(C)CC(=O)OC(I)C(C)C>>CC(=O)CC(=O)OCC1=C(C(=O)OC(OC(=O)CC(C)C)C(C)C)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1 | NC=1SC=C(N1)CC(=O)N[C@H]1[C@@H]2N(C(=C(CS2)COC(CC(=O)C)=O)C(=O)[O-])C1=O.[Na+].CC(CC(=O)OC(C(C)C)I)C>>NC=1SC=C(N1)CC(=O)N[C@H]1[C@@H]2N(C(=C(CS2)COC(CC(=O)C)=O)C(=O)OC(C(C)C)OC(CC(C)C)=O)C1=O | [CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[O:7][CH2:8][C:9]1=[C:10]([C:11](=[O:12])[O-:13])[N:25]2[C:26](=[O:27])[C@@H:28]([NH:29][C:30](=[O:31])[CH2:32][c:33]3[cH:34][s:35][c:36]([NH2:37])[n:38]3)[C@H:39]2[S:40][CH2:41]1.I[CH:14]([O:15][C:16](=[O:17])[CH2:18][CH:19]([CH3:20])[CH3:21])[CH:22]([CH3:23])[CH3:24]>>[CH3:1][C... | CC(=O)CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.CC(C)CC(=O)OC(I)C(C)C | CC(=O)CC(=O)OCC1=C(C(=O)OC(OC(=O)CC(C)C)C(C)C)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ad601d2996b206a686c37882a286cf985a715f8c54c0bc9146c1f2c2ac0eb520 | 35ea08e89ab24be5344101bc972eb4bf72e9ff1d48154cb4bcd2eca6eda7c194 | O=C(Cc1cscn1)N[C@@H]1C(=O)N2C=CCS[C@H]12 | I-[CH;D3;+0:1](-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](-[C;D1;H3:7])-[C;D1;H3:8].[#16:9]-[C:10]-[C:11](-[C:12])=[C:13](-[C:14](-[O-;H0;D1:15])=[O;D1;H0:16])-[#7:17]-[C:18]=[O;D1;H0:19]>>[#16:9]-[C:10]-[C:11](-[C:12])=[C:13](-[C:14](=[O;D1;H0:16])-[O;H0;D2;+0:15]-[CH;D3;+0:1](-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](-[... | 41 | [{"value": 41.0, "product": "NC=1SC=C(N1)CC(=O)N[C@H]1[C@@H]2N(C(=C(CS2)COC(CC(=O)C)=O)C(=O)OC(C(C)C)OC(CC(C)C)=O)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | In 30 ml of N,N-dimethylformamide is dissolved 4.76 g of sodium 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate and the solution is cooled to -5° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwise, followed by stirring for further 5 minutes. Thereafter... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester.Ester | null | null | C1=CN2CC[C@H]2SC1.c1cscn1 | I- | CN(C=O)C | -5 | null | CC(=O)CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.CC(C)CC(=O)OC(I)C(C)C>CN(C=O)C>CC(=O)CC(=O)OCC1=C(C(=O)OC(OC(=O)CC(C)C)C(C)C)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d2b7c2cbd73f4fd7b71a3e7b4b6f8592 | O=C(O)c1cc(F)c(F)c(Cl)c1F.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)c(Cl)c1F | FC1=C(C(=O)O)C=C(C(=C1)F)F.ClC=1C(=C(C(=O)O)C=C(C1F)F)F.S(=O)(Cl)Cl>>ClC=1C(=C(C(=O)Cl)C=C(C1F)F)F | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([Cl:11])[c:12]1[F:13].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([Cl:11])[c:12]1[F:13] | O=C(O)c1cc(F)c(F)c(Cl)c1F.O=S(Cl)Cl | O=C(Cl)c1cc(F)c(F)c(Cl)c1F | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Chlorination of 2,4,5-trifluorobenzoic acid in chlorosulphonic acid leads to 3-chloro-2,4,5-trifluorobenzoic acid, which is reacted as a crude product with thionyl chloride to give 3-chloro-2,4,5-trifluorobenzoyl chloride (boiling point 94°/18 mbar; nD20 =1.5164): ##STR10##
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | O=C(O)c1cc(F)c(F)c(Cl)c1F.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)c(Cl)c1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fa8aee38ba2a46708a7c9d020ef29ebe | O=C(O)c1cc(F)c(Cl)cc1Cl.O=[N+]([O-])O>>O=C(O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | [N+](=O)(O)[O-].S(O)(O)(=O)=O.ClC1=C(C(=O)O)C=C(C(=C1)Cl)F>>ClC1=C(C(=O)O)C=C(C(=C1[N+](=O)[O-])Cl)F | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10][c:14]1[Cl:15].O[N+:11](=[O:12])[O-:13]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Cl:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]1[Cl:15] | O=C(O)c1cc(F)c(Cl)cc1Cl.O=[N+]([O-])O | O=C(O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[cH;D2;+0:10]:[c:11](-[Cl;D1;H0:12]):[c:13]>>[Cl;D1;H0:4]-[c:5](:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c;H0;D3;+0:10](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:11](-[Cl;D1;H0:12]):[c:13] | null | [] | null | null | null | null | 40 ml of concentrated nitric acid are added dropwise to 34 ml of concentrated sulphuric acid, while cooling with ice and stirring. 20.9 g of 2,4-dichloro-5-fluorobenzoic acid are introduced in portions into this nitration mixture, whereupon the temperature rises to 45°-50° C. The mixture is then heated at 90°-100° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | O=C(O)c1cc(F)c(Cl)cc1Cl.O=[N+]([O-])O>>O=C(O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-649c77e7ea1f4e54aff363d399cc7db7 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl>>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | C(CC(=O)OCC)(=O)OCC.[Mg].ClC1=C(C(=O)Cl)C=C(C(=C1[N+](=O)[O-])Cl)F.[H][H].S(O)(O)(=O)=O>>ClC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1[N+](=O)[O-])Cl)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([Cl:19])[c:20]([N+:21](=[O:22])[O-:23])[c:24]1[Cl:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([Cl:19])[c:20](... | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | null | C(Cl)(Cl)(Cl)Cl | C(C)O.C1(=CC=CC=C1)C.O | C-C Coupling | OtherReaction | 872dd4ea89053916cf9ee557745988425973a0fb6c3fde7e681bde82864a0018 | a7050091370b27e4945622bf444949c46249e49bd26e357ae44671cc72030a02 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "ClC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1[N+](=O)[O-])Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2.1 g of carbon tetrachloride are added to 10.1 g of magnesium filings in 21 ml of ethanol and, when the evolution of hydrogen has started, a mixture of 66.6 g of diethyl malonate, 40 ml of ethanol and 150 ml of toluene is added dropwise at 50°-60° C. The mixture is subsequently stirred at this temperature for 1 hour a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone | null | null | c1ccccc1 | HCl | C(Cl)(Cl)(Cl)Cl.C(C)O.C1(=CC=CC=C1)C.O | null | 1 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl>C(Cl)(Cl)(Cl)Cl.C(C)O.C1(=CC=CC=C1)C.O>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cc19d9ec45394266839c589e505a7929 | CCOC(=O)CC(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | ClC1=C(C(=O)CC(=O)OCC)C=C(C(=C1[N+](=O)[O-])Cl)F.C(OCC)(OCC)OCC.C(C)(=O)OC(C)=O>>ClC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1[N+](=O)[O-])Cl)F | [CH2:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([Cl:18])[c:19]([N+:20](=[O:21])[O-:22])[c:23]1[Cl:24].CCO[CH:4](OCC)[O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([Cl:18])[c:19]([N+:20](... | CCOC(=O)CC(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl.CCOC(OCC)OCC | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl | null | null | null | C-C Coupling | OtherReaction | 7cfff3053680512afd8f3daf149645dfb2cfa4c9c32bf9b885b72097190aacf2 | 9164ecc9bc41a60ea056ee2b5a56d6c3899e2ff7c236ad9974338a128257f79c | c1ccccc1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[#8:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:3]-[#8:2]-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | null | [] | null | null | null | null | 244.8 g of ethyl (2,4-dichloro-5-fluoro-3-nitrobenzoyl)-acetate are heated at 150°-160° C. with 166 g of triethyl orthoformate and 185 g of acetic anhydride for 3 hours. The mixture is then concentrated in vacuo and 270 g of ethyl benzoyl-ethoxy-acrylate are obtained as an oily residue.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Ether | Ketone.Ester.Ether | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)CC(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6c47ed8b0d894cfb943cb4f2702a1e21 | CC(=O)OC(C)=O.N#CCC(=O)c1cc(F)c(F)c(F)c1F>>COC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)CC#N)C=C(C(=C1F)F)F.C(C)(=O)OC(C)=O>>FC1=C(C(=O)C(C#N)=COC)C=C(C(=C1F)F)F | CC(=O)O[C:3]([CH3:1])=[O:2].[CH2:4]([C:5]#[N:6])[C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18]>>[CH3:1][O:2][CH:3]=[C:4]([C:5]#[N:6])[C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18] | CC(=O)OC(C)=O.N#CCC(=O)c1cc(F)c(F)c(F)c1F | COC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 22ff39feb71b498e65b9013c0acd77555446adc9e81686fa9880967369d0b854 | 4adcb9ae66fe3dc60ef78becfc80a25c7cd5002548129eda6bd7322d22f759a3 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;H0;D1;+0:3].[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[CH3;D1;+0:2]-[O;H0;D2;+0:3]-[CH;D2;+0:1]=[C;H0;D3;+0:6](-[C:5]#[N;D1;H0:4])-[C:7](=[O;D1;H0:8])-[c:9] | 95.3 | [{"value": 95.3, "product": "FC1=C(C(=O)C(C#N)=COC)C=C(C(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 16 g of 2,3,4,5-tetrafluorobenzoyl-acetonitrile, 15.6 g of trimethyl o-formate and 18.8 g of acetic anhydride is heated at 150° C. (bath temperature) for 3 hours. The solvent mixture is distilled off completely under a waterpump vacuum and finally under a high vacuum, at a bath temperature of 120° C. 18.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ketone | Ketone.Ether | null | null | c1ccccc1 | HO- | null | 150 | null | CC(=O)OC(C)=O.N#CCC(=O)c1cc(F)c(F)c(F)c1F>>COC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-87003c6c45064e96a5879078c6f45037 | O=C1c2cccnc2N(c2ccccc2)C2=NCCN12>>O=C1C2=C(NCCC2)N(c2ccccc2)C2=NCCN12 | C1(=CC=CC=C1)N1C=2N(C(C3=C1N=CC=C3)=O)CCN2>>C1(=CC=CC=C1)N1C=2N(C(C3=C1NCCC3)=O)CCN2 | [O:1]=[C:2]1[c:3]2[c:4]([n:5][cH:6][cH:7][cH:8]2)[N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[C:16]2=[N:17][CH2:18][CH2:19][N:20]12>>[O:1]=[C:2]1[C:3]2=[C:4]([NH:5][CH2:6][CH2:7][CH2:8]2)[N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[C:16]2=[N:17][CH2:18][CH2:19][N:20]12 | O=C1c2cccnc2N(c2ccccc2)C2=NCCN12 | O=C1C2=C(NCCC2)N(c2ccccc2)C2=NCCN12 | null | [Pd] | C(C)(=O)O | Miscellaneous | OtherReaction | 7fb15d0b3e0ba1f4ffb65b4c5bfa4220018fa4efb1003cbd41d7d701e4bbbf8d | 202737ae2b4699d92d2248429bad18cbcc9b0d9df13a8e6ccc41e4e185dac3e3 | O=C1C2=C(NCCC2)N(c2ccccc2)C2=NCCN12 | [#7:1]=[C:2]1-[#7:3](-[C:4])-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:2-[#7:13]-1-[c:14]>>[#7:1]=[C:2]1-[#7:3](-[C:4])-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7]2=[C;H0;D3;+0:12](-[NH;D2;+0:11]-[CH2;D2;+0:10]-[CH2;D2;+0:9]-[CH2;D2;+0:8]-2)-[#7:13]-1-[c:14] | null | [] | null | null | null | null | Hydrogenate a mixture of 10% Pd/C (2.5 g), 10-phenyl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-one (5 g) and glacial acetic acid (125 ml) at 60 psi in a Paar apparatus for 24 hrs. at 25° C. Filter the mixture and evaporate the solvent of the filtrate. Dissolve the residue in 1N NaHCO3 (50 ml), neutralize w... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine.Enamine | c1cnc2c(c1)CN1CCN=C1[NH]2 | C1CNC2=C(C1)CN1CCN=C1[NH]2 | c1ccccc1.C1CNC2=C(C1)CN1CCN=C1[NH]2 | null | [Pd].C(C)(=O)O | null | null | O=C1c2cccnc2N(c2ccccc2)C2=NCCN12>[Pd].C(C)(=O)O>O=C1C2=C(NCCC2)N(c2ccccc2)C2=NCCN12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1c1a49e7765a4431bc8ffdded835f413 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Cl)c(Cl)sc12>>COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | N1=CN=CC2=C1C=CS2=O.ClC1=C(C=2N=CNC(C2S1)=O)Cl.C[O-].[Na+].CO[C@H]1[C@@H](N(CCC1)C(=O)OC)CC(CBr)=O>>ClC1=C(C=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1OC)C(=O)OC)=O)Cl | Br[CH2:16][C:14]([CH2:13][C@@H:12]1[N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8][C@H:9]1[O:10][CH3:11])=[O:15].[nH:17]1[cH:18][n:19][c:20]2[c:21]([Cl:22])[c:23]([Cl:24])[s:25][c:26]2[c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([O:10][CH3:11])[C@@H:12]1[CH2:13][C:14](=[O:15])[CH2:... | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Cl)c(Cl)sc12 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | defcff97999181c881fe745fb7edf5f37965e4b434cb8b35499ced30efce9e33 | 0844e813fd6aa8a6f803ffd9d05cd5ff5272ddf69396b8c87d384d86e0562add | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[c:6]1:[nH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1:[#16;a:12]:[c:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](:[#16;a:12]:[c:13]):[c:6]:1=[O;D1;H0:5] | null | [] | null | null | 2 | HOUR | Under nitrogen in a flame dried round bottom flask with magnetic stirring, a solution of 0.440 g (0.002 moles) of 6,7-dichlorothieno[3,2-d]pyrimidin-4(3H)-one [M. Robba, J- M. Lecomte, and M. Cugnon de Sevricourt, Bull. soc. chim. France, 1970, 3630-3636], 5 ml of methanol, and 2.0 ml of 1.0N sodium methoxide in methan... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | c1cc2ncncc2s1 | c1ncc2sccc2n1 | C1CC[NH]CC1.c1ncc2sccc2n1 | HBr | CO | null | 2 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Cl)c(Cl)sc12>CO>COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bdb9779579ef468e9f8a5572939fe3c5 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O>>COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | ClC1=C(C=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1OC)C(=O)OC)=O)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>>ClC1=C(C=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1O)C(=O)OC)=O)Cl | C[O:10][C@@H:9]1[CH2:8][CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[C@H:11]1[CH2:12][C:13](=[O:14])[CH2:15][n:16]1[cH:17][n:18][c:19]2[c:20]([Cl:21])[c:22]([Cl:23])[s:24][c:25]2[c:26]1=[O:27]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([OH:10])[C@@H:11]1[CH2:12][C:13](=[O:14])[CH2:15][n:16]1[cH:17][... | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | dcaefb482d0d4070854ae2f21edb78f004963f26f985f41a9781ad20aca44e4e | 32e9a9ca3191eb6608eee26da72fef0d2c2afd087eefdbcc65ce4c46772064f8 | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[OH;D1;+0:1])-[C:3] | null | [] | null | null | 10 | MINUTE | A 35 ml single neck round bottom flask equipped with a magnetic stirring bar was flame dried and then stoppered with a serum cap. Through a syringe needle the flask was evacuated and filled with dry nitrogen four times. A solution of 0.270 g (0.0006 mole) of methyl trans-2-[3-(6,7-dichloro-3,4-dihydro-4-oxothieno[3,2-d... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | null | null | C1CC[NH]CC1.c1ncc2sccc2n1 | Other | ClCCl | null | 0.166667 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O>ClCCl>COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-303909f3f84f4a05bac9039b7243a17c | COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O>>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | ClC1=C(C=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1O)C(=O)OC)=O)Cl.Br>>Br.Br.ClC1=C(C=2N=CN(C(C2S1)=O)CC(C[C@@H]1NCCC[C@H]1O)=O)Cl | COC(=O)[N:7]1[C@@H:6]([CH2:5][C:4](=[O:3])[CH2:13][n:14]2[cH:15][n:16][c:17]3[c:18]([Cl:19])[c:20]([Cl:21])[s:22][c:23]3[c:24]2=[O:25])[C@H:11]([OH:12])[CH2:10][CH2:9][CH2:8]1>>[BrH:2].[O:3]=[C:4]([CH2:5][C@@H:6]1[NH:7][CH2:8][CH2:9][CH2:10][C@H:11]1[OH:12])[CH2:13][n:14]1[cH:15][n:16][c:17]2[c:18]([Cl:19])[c:20]([Cl:2... | COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(Cl)c(Cl)sc2c1=O | null | null | C(C)O | Miscellaneous | Hydrogenolysis of tertiary amines | 393e5d874f317ec1155203f17eea0a123929a5fcf273863e84fbd79bfa0739cd | ce1d20ece0ee3db84a8954171912e0cc035fe478f2082f416fe209b2e3984b26 | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C:5]-[C:6]=[O;D1;H0:7])-[C:8]>>[C:8]-[C:4](-[C:5]-[C:6]=[O;D1;H0:7])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 3 | MINUTE | In a 15 ml single-neck round bottom flask equipped with a reflux condenser, a solution of 0.190 g (0.00044 mole) of methyl trans-2-[3-(6,7-dichloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate and 6.2 ml of 48% aqueous hydrobromic acid was immersed in an oil bath preheate... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ncc2sccc2n1 | HO- | C(C)O | null | 0.05 | COC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2c(Cl)c(Cl)sc2c1=O>C(C)O>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(Cl)c(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-28268398841145ef80593572bb765ce9 | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2cc(Cl)sc12>>C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O | ClC1=CC=2N=CNC(C2S1)=O.C[O-].[Na+].CO[C@H]1[C@@H](N(CCC1)C(=O)OCC=C)CC(CBr)=O>>ClC1=CC=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1OC)C(=O)OCC=C)=O | Br[CH2:18][C:16]([CH2:15][C@@H:14]1[N:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:8][CH2:9][CH2:10][C@H:11]1[O:12][CH3:13])=[O:17].[nH:19]1[cH:20][n:21][c:22]2[cH:23][c:24]([Cl:25])[s:26][c:27]2[c:28]1=[O:29]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][C@@H:11]([O:12][CH3:13])[C@@H:14]1[CH2... | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2cc(Cl)sc12 | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | defcff97999181c881fe745fb7edf5f37965e4b434cb8b35499ced30efce9e33 | 0844e813fd6aa8a6f803ffd9d05cd5ff5272ddf69396b8c87d384d86e0562add | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[c:6]1:[nH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1:[#16;a:12]:[c:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](:[#16;a:12]:[c:13]):[c:6]:1=[O;D1;H0:5] | null | [] | null | null | 8 | HOUR | Under a nitrogen atmosphere in a flame dried flask and with magnetic stirring, a solution of 0.80 g (0.0043 mole) of 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one, 3.52 ml of 1.22N sodium methoxide in methanol, and 20 ml of methanol was treated with 1.86 g (0.0056 mole) of allyl trans-3-methoxy-2-(3-bromo-2-oxopropyl)-1-pip... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | c1cc2ncncc2s1 | c1ncc2sccc2n1 | C1CC[NH]CC1.c1ncc2sccc2n1 | HBr | CO | null | 8 | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2cc(Cl)sc12>CO>C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0a4cb4e545e64cc5b3c6911886f99a0d | C=CCOC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O>>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2cc(Cl)sc2c1=O | ClC1=CC=2N=CN(C(C2S1)=O)CC(C[C@@H]1N(CCC[C@H]1O)C(=O)OCC=C)=O.Br>>Br.Br.ClC1=CC=2N=CN(C(C2S1)=O)CC(C[C@@H]1NCCC[C@H]1O)=O | C=CCOC(=O)[N:7]1[C@@H:6]([CH2:5][C:4](=[O:3])[CH2:13][n:14]2[cH:15][n:16][c:17]3[cH:18][c:19]([Cl:20])[s:21][c:22]3[c:23]2=[O:24])[C@H:11]([OH:12])[CH2:10][CH2:9][CH2:8]1>>[BrH:2].[O:3]=[C:4]([CH2:5][C@@H:6]1[NH:7][CH2:8][CH2:9][CH2:10][C@H:11]1[OH:12])[CH2:13][n:14]1[cH:15][n:16][c:17]2[cH:18][c:19]([Cl:20])[s:21][c:2... | C=CCOC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O | Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2cc(Cl)sc2c1=O | null | null | null | Miscellaneous | Hydrogenolysis of tertiary amines | 5ff8911a6b43572b9beb59978ab6f79b27754a7f46f3374df3680f737ecfb56e | dc79cadbf5b0b7e63ff6b048e333711cda1fe9e54b6e666841c0c26e8bed1f97 | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | C=C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C:5]-[C:6]=[O;D1;H0:7])-[C:8]>>[C:8]-[C:4](-[C:5]-[C:6]=[O;D1;H0:7])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 7 | MINUTE | In a 15 ml single-neck round bottom flask equipped with a reflux condenser, a solution of 0.69 g (0.00162 mole) of allyl trans-2-[3-(6-chloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate and 6 ml of 48% aqueous hydrobromic acid was immersed in an oil bath preheated to 100... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Allyl | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ncc2sccc2n1 | HO- | null | null | 0.116667 | C=CCOC(=O)N1CCC[C@@H](O)[C@@H]1CC(=O)Cn1cnc2cc(Cl)sc2c1=O>>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2cc(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7e66be7c0e9d4c90b088462789db9336 | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Br)c(Cl)sc12>>C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Br)c(Cl)sc2c1=O | BrC1=C(SC2=C1N=CNC2=O)Cl.CO[C@H]1[C@@H](N(CCC1)C(=O)OCC=C)CC(CBr)=O>>BrC1=C(SC2=C1N=CN(C2=O)CC(C[C@@H]2N(CCC[C@H]2OC)C(=O)OCC=C)=O)Cl | Br[CH2:18][C:16]([CH2:15][C@@H:14]1[N:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:8][CH2:9][CH2:10][C@H:11]1[O:12][CH3:13])=[O:17].[nH:19]1[cH:20][n:21][c:22]2[c:23]([Br:24])[c:25]([Cl:26])[s:27][c:28]2[c:29]1=[O:30]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][C@@H:11]([O:12][CH3:13])[C@@H:... | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Br)c(Cl)sc12 | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Br)c(Cl)sc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | defcff97999181c881fe745fb7edf5f37965e4b434cb8b35499ced30efce9e33 | 0844e813fd6aa8a6f803ffd9d05cd5ff5272ddf69396b8c87d384d86e0562add | O=C(C[C@H]1CCCCN1)Cn1cnc2ccsc2c1=O | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[c:6]1:[nH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1:[#16;a:12]:[c:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](:[#16;a:12]:[c:13]):[c:6]:1=[O;D1;H0:5] | null | [] | null | null | null | null | According to the method of Example 4, 0.662 g (0.0025 mole) of 7-bromo-6-chlorothieno[3,2-d]pyrimidin-4(3H)-one and 1.24 g (0.0037 mole) of allyl trans-3-methoxy-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate were combined to give the title compound: yield 0.90 g (69%); 1H-nmr (CDCl3) delta 1.3-2.1 ppm (multiplet, 4H,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | c1cc2ncncc2s1 | c1ncc2sccc2n1 | C1CC[NH]CC1.c1ncc2sccc2n1 | HBr | null | null | null | C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c(Br)c(Cl)sc12>>C=CCOC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(Br)c(Cl)sc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0dbed953e7ea41bf9d9c0da06739cec1 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c1oc1ccccc12>>COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O | N1=CNC(C2=C1C1=C(O2)C=CC=C1)=O.CO[C@H]1[C@@H](N(CCC1)C(=O)OC)CC(CBr)=O>>O=C1C2=C(N=CN1CC(C[C@@H]1N(CCC[C@H]1OC)C(=O)OC)=O)C1=C(O2)C=CC=C1 | Br[CH2:16][C:14]([CH2:13][C@@H:12]1[N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8][C@H:9]1[O:10][CH3:11])=[O:15].[nH:17]1[cH:18][n:19][c:20]2[c:21]([o:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]23)[c:29]1=[O:30]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([O:10][CH3:11])[C@@H:12]1[CH2:13][C:14]... | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c1oc1ccccc12 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 18cb901ea1a7041f60b07e0a7eb806cc3ad6eb5b85db9f97a2701be9b90609a8 | 0844e813fd6aa8a6f803ffd9d05cd5ff5272ddf69396b8c87d384d86e0562add | O=C(C[C@H]1CCCCN1)Cn1cnc2c(oc3ccccc32)c1=O | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[c:6]1:[nH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1:[#8;a:12]:[c:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](:[#8;a:12]:[c:13]):[c:6]:1=[O;D1;H0:5] | null | [] | null | null | null | null | According to the method of Example 1, 1.22 g (0.0066 mole) of benzofuro[3,2-d]pyrimidin-4(3H)-one [S. S. Sangapure and Y. S. Agasimundin, Indian J. Chem., 14B, 688-691 (1976)] and 0.0066 moles of methyl trans-3-methoxy-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate were combined to give the title compound: yield 0.627... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | c1ncnc2c1oc1ccccc12 | c1ccc2c(c1)oc1cncnc12 | C1CC[NH]CC1.c1ccc2c(c1)oc1cncnc12 | HBr | null | null | null | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)CBr.O=c1[nH]cnc2c1oc1ccccc12>>COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e73b22e82350428eb477a670f319f5f9 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O>>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(oc3ccccc32)c1=O | O=C1C2=C(N=CN1CC(C[C@@H]1N(CCC[C@H]1OC)C(=O)OC)=O)C1=C(O2)C=CC=C1.Br>>Br.Br.O[C@H]1[C@@H](NCCC1)CC(CN1C=NC2=C(C1=O)OC1=C2C=CC=C1)=O | COC(=O)[N:7]1[C@@H:6]([CH2:5][C:4](=[O:3])[CH2:13][n:14]2[cH:15][n:16][c:17]3[c:18]([o:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]34)[c:26]2=[O:27])[C@H:11]([O:12]C)[CH2:10][CH2:9][CH2:8]1>>[BrH:2].[O:3]=[C:4]([CH2:5][C@@H:6]1[NH:7][CH2:8][CH2:9][CH2:10][C@H:11]1[OH:12])[CH2:13][n:14]1[cH:15][n:16][c:17]2[c:18]([o:19]... | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O | Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(oc3ccccc32)c1=O | null | null | C(C)O | Miscellaneous | OtherReaction | f876fc69bce4686ec83597e83d01503a38ea8758fb4ebd928b1eeaac3eab6dff | dfd47adcccbf1a90279005b45b2f6771d2817194b0ad76c2f3a09e6a22d954eb | O=C(C[C@H]1CCCCN1)Cn1cnc2c(oc3ccccc32)c1=O | C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5](-[O;H0;D2;+0:6]-C)-[C:7]-1-[C:8]-[C:9]=[O;D1;H0:10]>>[O;D1;H0:10]=[C:9]-[C:8]-[C:7]1-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-1-[OH;D1;+0:6] | null | [] | null | null | 12 | MINUTE | A solution of 0.600 g (0.00145 mole) of methyl trans-2-[3-(3,4-dihydro-4-oxobenzofuro[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate and 30 ml of 48% hydrobromic acid in a 100 ml round bottom flask was immersed in a bath preheated to 150° C. and held there for 12 minutes. Upon cooling to room temp... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether | Secondary alcohol.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2c(c1)oc1cncnc12 | HO- | C(C)O | null | 0.2 | COC(=O)N1CCC[C@@H](OC)[C@@H]1CC(=O)Cn1cnc2c(oc3ccccc32)c1=O>C(C)O>Br.O=C(C[C@@H]1NCCC[C@H]1O)Cn1cnc2c(oc3ccccc32)c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9620239eddff4d22a6ab98be1c6bb71f | C=COCC.CC(=O)C(CCl)=NO>>CCOC1CCC(C(C)=O)=NO1 | C([O-])([O-])=O.[Na+].[Na+].C(=C)OCC.ClCC(C(C)=O)=NO>>C(C)OC1CCC(=NO1)C(C)=O | [CH3:1][CH2:2][O:3][CH:4]=[CH2:5].Cl[CH2:6][C:7]([C:8]([CH3:9])=[O:10])=[N:11][OH:12]>>[CH3:1][CH2:2][O:3][CH:4]1[CH2:5][CH2:6][C:7]([C:8]([CH3:9])=[O:10])=[N:11][O:12]1 | C=COCC.CC(=O)C(CCl)=NO | CCOC1CCC(C(C)=O)=NO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 734e6f2cdfe6a0dff13fac705e648d41fd9cf21a751c1bba66a3fc5458ee449a | 5604d9e685f8090034f972d4694e4198c7a13624f8e6d7666087c9f4e12ace64 | C1=NOCCC1 | Cl-[CH2;D2;+0:1]-[C:2](=[#7:3]-[OH;D1;+0:4])-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[C:8]-[#8:9]-[CH;D2;+0:10]=[CH2;D1;+0:11]>>[C:8]-[#8:9]-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])=[#7:3]-[O;H0;D2;+0:4]-1 | 98 | [{"value": 98.0, "product": "C(C)OC1CCC(=NO1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "C(C)OC1CCC(=NO1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 21 | HOUR | A 1000 ml three-neck flask equipped with a mechanical stirrer, a reflux condenser, and a nitrogen inlet adapter was heat dried and charged with nitrogen. When the flask was at room temperature, it was loaded in order: 39.5 g (0.37 mole) of anhydrous sodium carbonate; (with stirring) 132 g (1.83 mole) of ethyl vinyl eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Vinyl.Oxime | Ether | null | C1=NOCCC1 | C1=NOCCC1 | HCl | null | null | 21 | C=COCC.CC(=O)C(CCl)=NO>>CCOC1CCC(C(C)=O)=NO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8c00c59e6a604b8aaf1f1980523d636b | COc1ccc[n+]([O-])c1C>>COc1cccnc1C | [OH-].[Na+].[OH-].[Na+].COC=1C(=[N+](C=CC1)[O-])C.C(Cl)(Cl)Cl.P(Cl)(Cl)Cl.C(Cl)(Cl)Cl>>COC=1C(=NC=CC1)C | [O-][n+:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]1[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9] | COc1ccc[n+]([O-])c1C | COc1cccnc1C | null | null | O | Functional Group Interconversion | OtherReaction | 8660dc08f9c4d3b8c6814ee1b12714454b2bd6ddbe4d55cbaaeb274a83637cea | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccncc1 | [C;D1;H3:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-]):[c:5]:[c:6]>>[C;D1;H3:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6] | null | [] | null | null | 20 | MINUTE | Under a nitrogen atmosphere, a magnetically stirred solution of 25.8 g (0.185 mole) of 3-methoxy-2-methylpyridine 1-oxide and 200 ml of chloroform cooled to 0° C. was treated dropwise a solution of 75.6 g (0.556 mole) of phosphorus trichloride and 50 ml of chloroform. The temperature was maintained at <10° C. during th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | Other | O | null | 0.333333 | COc1ccc[n+]([O-])c1C>O>COc1cccnc1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6e4b65d842a24b1fb016b47316612e80 | COC(=O)CS.N#CC=C(Cl)Cl>>COC(=O)c1sc(Cl)cc1N | C(CS)(=O)OC.[Na].ClC(=CC#N)Cl>>NC1=C(SC(=C1)Cl)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][SH:6].Cl[C:7]([Cl:8])=[CH:9][C:10]#[N:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([Cl:8])[cH:9][c:10]1[NH2:11] | COC(=O)CS.N#CC=C(Cl)Cl | COC(=O)c1sc(Cl)cc1N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 572f3af6ed732dd565c44e5540bbf9696e221e49e641738804d0125b2ba60245 | c6e202d7ab98aff5fe00b144ad3e840d360bb1662b4e877c3dc15d79ccfaa037 | c1ccsc1 | Cl-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[CH;D2;+0:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[SH;D1;+0:11]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[s;H0;D2;+0:11]:[c;H0;D3;+0:1](-[Cl;D1;H0:2]):[cH;D2;+0:3]:[c;H0;D3;+0:4]:1-[NH2;D1;+0:5] | null | [] | null | null | null | null | In a flame dried flask under a nitrogen atmosphere, and with mechanical stirring, a solution of about 1.2 g (0.05 mole) of sodium metal dissolved in 30 ml of dry methanol was treated dropwise with 2.35 g (1.98 ml, 0.022 mole) of methyl thioglycolate while maintaining the temperature below 25° C. A solution of 2.70 g (0... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Ester.Nitrile.Aliphatic thiol | Aromatic halide.Ester.Primary amine | null | c1ccsc1 | c1ccsc1 | HCl | CO | null | null | COC(=O)CS.N#CC=C(Cl)Cl>CO>COC(=O)c1sc(Cl)cc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cfc067ec972b42689c43ec1a5ef3a03e | BrBr.O=c1[nH]cnc2cc(Cl)sc12>>O=c1[nH]cnc2c(Br)c(Cl)sc12 | ClC1=CC=2N=CNC(C2S1)=O.BrBr>>BrC1=C(SC2=C1N=CNC2=O)Cl | Br[Br:8].[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:9]([Cl:10])[s:11][c:12]12>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[c:7]([Br:8])[c:9]([Cl:10])[s:11][c:12]12 | BrBr.O=c1[nH]cnc2cc(Cl)sc12 | O=c1[nH]cnc2c(Br)c(Cl)sc12 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 8d37b11a43d310b2ffdc4474e084c26188cb26c3957270a92d4c5d02a0646cc0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1[nH]cnc2ccsc12 | Br-[Br;H0;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[#16;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:[cH;D2;+0:11]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:10]2:[#7;a:9]:[c:8]:[#7;a:7]:[c:6]:[c:5]:2:[#16;a:4]:[c:3]:1-[Cl;D1;H0:2] | 44 | [{"value": 44.0, "product": "BrC1=C(SC2=C1N=CNC2=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "BrC1=C(SC2=C1N=CNC2=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A solution of 1.12 g (0.006 mole) of 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one and 15 ml of acetic acid at 80° C. was treated with 2.88 g (0.92 ml, 0.018 mole) of bromine. Heating was continued for 2.5 hours during which time solids precipitated. After cooling to room temperature, the mixture was filtered and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2ncncc2s1 | c1cc2ncncc2s1 | c1cc2ncncc2s1 | HBr | C(C)(=O)O | null | 2.5 | BrBr.O=c1[nH]cnc2cc(Cl)sc12>C(C)(=O)O>O=c1[nH]cnc2c(Br)c(Cl)sc12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-06fbe5b3f1e34d95a302135ea4df5b48 | COc1cccc(CC(=O)O)c1.ClI>>COc1ccc(I)c(CC(=O)O)c1 | COC=1C=C(C=CC1)CC(=O)O.ICl.O>>IC1=C(C=C(C=C1)OC)CC(=O)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:8]([CH2:9][C:10](=[O:11])[OH:12])[cH:13]1.Cl[I:7]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([I:7])[c:8]([CH2:9][C:10](=[O:11])[OH:12])[cH:13]1 | COc1cccc(CC(=O)O)c1.ClI | COc1ccc(I)c(CC(=O)O)c1 | null | II | C(C)(=O)O | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-[I;H0;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[C:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[C:5]-[C:3](=[O;D1;H0:2])-[O;D1;H1:4]):[c:7] | 65 | [{"value": 65.0, "product": "IC1=C(C=C(C=C1)OC)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "IC1=C(C=C(C=C1)OC)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 45 g (0.27 mole) of 3-methoxybenzeneacetic acid, 52.6 g (0.32 mole) of iodine monochloride and 1 g of iodine was allowed to stand in 500 ml of glacial acetic acid for six days at room temperature. The reaction was poured into water and the solid collected. It was recrystallized from toluene to give 51 g o... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | II.C(C)(=O)O | null | null | COc1cccc(CC(=O)O)c1.ClI>II.C(C)(=O)O>COc1ccc(I)c(CC(=O)O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-986aa5b3e849477ab861a73561ebea06 | COc1cccc(CCC(C)=O)c1.II>>COc1ccc(I)c(CCC(C)=O)c1 | II.COC=1C=C(C=CC1)CCC(C)=O>>IC1=C(C=C(C=C1)OC)CCC(C)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:8]([CH2:9][CH2:10][C:11]([CH3:12])=[O:13])[cH:14]1.I[I:7]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([I:7])[c:8]([CH2:9][CH2:10][C:11]([CH3:12])=[O:13])[cH:14]1 | COc1cccc(CCC(C)=O)c1.II | COc1ccc(I)c(CCC(C)=O)c1 | null | C(C)(=O)[O-].[Ag+] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[C:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[C:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6]:[c:7] | 82.3 | [{"value": 82.0, "product": "IC1=C(C=C(C=C1)OC)CCC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "IC1=C(C=C(C=C1)OC)CCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Samples of iodine (42.4 g, 0.167 mole) and silver acetate (27.87 g, 0.167 mole) were added in portions to a solution of 29.8 g (0.167 mole) of 1-(3-methoxyphenyl)butane-3-one in 167 ml of glacial acetic acid. The mixture was stirred one hour. The silver iodide was removed by filtration and washed with acetic acid. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | C(C)(=O)[O-].[Ag+].C(C)(=O)O | null | 1 | COc1cccc(CCC(C)=O)c1.II>C(C)(=O)[O-].[Ag+].C(C)(=O)O>COc1ccc(I)c(CCC(C)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-376b3b80298747838d4894a89b3c46a4 | CNC.COc1ccc(I)c(CC(=O)O)c1>>COc1ccc(I)c(CC(=O)N(C)C)c1 | C(Cl)Cl.C(C(=O)Cl)(=O)Cl.IC1=C(C=C(C=C1)OC)CC(=O)O.CNC>>CN(C(CC1=C(C=CC(=C1)OC)I)=O)C | [NH:12]([CH3:13])[CH3:14].O[C:10]([CH2:9][c:8]1[c:6]([I:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([I:7])[c:8]([CH2:9][C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[cH:15]1 | CNC.COc1ccc(I)c(CC(=O)O)c1 | COc1ccc(I)c(CC(=O)N(C)C)c1 | null | null | CN(C)C=O.C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | 16 | HOUR | A 16.7 g (0.19 mole) sample of oxalyl chloride was added dropwise at 0° C. to a solution of 50.0 g (0.17 mole) of 2-iodo-5-methoxybenzeneacetic acid in 310 ml dry toluene and 31.7 ml of DMF. The mixture was allowed to warm to room temperature and stir for 16 hours. The solution was cooled to 0° C. and dimethylamine gas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | CN(C)C=O.C1(=CC=CC=C1)C | null | 16 | CNC.COc1ccc(I)c(CC(=O)O)c1>CN(C)C=O.C1(=CC=CC=C1)C>COc1ccc(I)c(CC(=O)N(C)C)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-214ecc35b1464ace9fcae69c7d4277a7 | COc1cccc(C=CC(C)=O)c1>>COc1cccc(CCC(C)=O)c1 | COC=1C=C(C=CC1)C=CC(C)=O>>COC=1C=C(C=CC1)CCC(C)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[CH:9][C:10]([CH3:11])=[O:12])[cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][C:10]([CH3:11])=[O:12])[cH:13]1 | COc1cccc(C=CC(C)=O)c1 | COc1cccc(CCC(C)=O)c1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 6556ac5f7a00160b061cac263043ece7ea2394a4006031c4a0b899c0ea4ccfef | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 99.2 | [{"value": 99.2, "product": "COC=1C=C(C=CC1)CCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 30.1 g of 4-(3-methoxyphenyl)-3-buten-2-one in 200 ml of MeOH was hydrogenated over 200 mg of 10% palladium on carbon for two hours. The catalyst was filtered and the solvent evaporated in vacuo to give 30.2 g of yellow oily 4-(3-methoxyphenyl)-2-butanone.
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | null | null | c1ccccc1 | null | [Pd].CO | null | null | COc1cccc(C=CC(C)=O)c1>[Pd].CO>COc1cccc(CCC(C)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7271bcbdc29044d1993bceb145ad2cb2 | CCCCCC(=O)C=Cc1cccc(OC)c1>>CCCCCC(=O)CCc1cccc(OC)c1 | COC=1C=C(C=CC1)C=CC(CCCCC)=O.COC=1C=C(C=CC1)C=CC(C)=O>>COC=1C=C(C=CC1)CCC(CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17]1 | CCCCCC(=O)C=Cc1cccc(OC)c1 | CCCCCC(=O)CCc1cccc(OC)c1 | null | null | null | Reduction | Hydrogenation (double to single) | 6556ac5f7a00160b061cac263043ece7ea2394a4006031c4a0b899c0ea4ccfef | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | Following the procedure of Example 15 and substituting an equivalent quantity of 1-(3-methoxyphenyl)-1-octen-3-one for 4-(3-methoxyphenyl)-3-buten-2-one there was obtained as the product 1-(3-methoxyphenyl)octan-3-one as a colorless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | null | null | c1ccccc1 | null | null | null | null | CCCCCC(=O)C=Cc1cccc(OC)c1>>CCCCCC(=O)CCc1cccc(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4b5a38fe3955401aa0ddf3e185732936 | CCCCCC(=O)Cc1cc(OC)ccc1I.CNC.CNC>>CCCCCC(CCc1cc(OC)ccc1I)N(C)C | IC1=C(C=C(C=C1)OC)CC(CCCCC)=O.CNC.Cl.CNC.C(#N)[BH3-].[Na+].Cl>>Cl.IC1=C(C=C(C=C1)OC)CCC(N(C)C)CCCCC | O=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH3:2])[CH2:8][c:9]1[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]1[I:17].[NH:18]([CH3:19])[CH3:20].CN[CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][c:9]1[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]1[I:17])[N:18]([CH3:19])[CH3:20] | CCCCCC(=O)Cc1cc(OC)ccc1I.CNC.CNC | CCCCCC(CCc1cc(OC)ccc1I)N(C)C | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | ef7c79135e297dfd2538d1b5aff73e623d0318673162ff6faa0976fc32092ae3 | 392f4bf36c5dce5fac128c91895ac6331ef01e9645f5108b22ed0b00d3833c53 | c1ccccc1 | C-N-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[C:3]-[c:4])-[CH2;D2;+0:5]-[C:6]-[C:7]-[C:8]-[CH3;D1;+0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[CH;D3;+0:5](-[C:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-[CH3;D1;+0:1])-[CH2;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | 8 | HOUR | A mixture of 13.0 g (0.036 mole) of 1-(2-iodo-5-methoxyphenyl)heptan-2-one, 46.6 ml (0.18 mole) of a solution of 3.86 M dimethylamine in methanol, 8.24 g (0.101 mole) of dimethylamine hydrochloride, 100 ml of methanol and 1.82 g (0.029 mole) of sodium cyanoborohydride was stirred overnight under an atmosphere of nitrog... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine.Secondary amine | Tertiary amine | null | null | c1ccccc1 | HO- | CO | null | 8 | CCCCCC(=O)Cc1cc(OC)ccc1I.CNC.CNC>CO>CCCCCC(CCc1cc(OC)ccc1I)N(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c233d3f7474f4b86a95a4c7f7873d8ec | C#CCCCC.COc1ccc(I)c(CCN(C)C)c1>>CCCCC#Cc1ccc(OC)cc1CCN(C)C | Cl.[Li]CCCC.IC1=C(C=C(C=C1)OC)CCN(C)C.C#CCCCC>>Cl.C(#CCCCC)C1=C(C=C(C=C1)OC)CCN(C)C | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6].I[c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH3:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH3:19] | C#CCCCC.COc1ccc(I)c(CCN(C)C)c1 | CCCCC#Cc1ccc(OC)cc1CCN(C)C | null | [Cl-].[Zn+2].[Cl-].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.O1CCCC1 | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:8]-[C:7]):[c:2]:[c:3] | 27 | [{"value": 27.0, "product": "Cl.C(#CCCCC)C1=C(C=C(C=C1)OC)CCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A solution of 2.7 ml (0.027 mole) 1-hexyne in 10 ml dry (4 A sieves) tetrahydrofuran was cooled to 0° C. in an ice bath. Argon was passed over the solution 10.4 ml (0.027 mole) 2.69 M n-BuLi was added slowly via syringe through a serum cap. The resulting solution was stirred 20 minutes under argon. During this time, a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cl-].[Zn+2].[Cl-].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.O1CCCC1 | 0 | 0.333333 | C#CCCCC.COc1ccc(I)c(CCN(C)C)c1>[Cl-].[Zn+2].[Cl-].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.O1CCCC1>CCCCC#Cc1ccc(OC)cc1CCN(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5738c90848c14330a8109484a074deed | O=C(O)C=Cc1cccc([N+](=O)[O-])c1>>Nc1cccc(CCC(=O)O)c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)O)C=CC1.[H][H]>>NC=1C=C(C=CC1)CCC(=O)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]=[CH:8][C:9](=[O:10])[OH:11])[cH:12]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH2:8][C:9](=[O:10])[OH:11])[cH:12]1 | O=C(O)C=Cc1cccc([N+](=O)[O-])c1 | Nc1cccc(CCC(=O)O)c1 | null | [Pd] | C(C)(=O)O.CO | Reduction | OtherReaction | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5](-[CH;D2;+0:6]=[CH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:11]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:11] | null | [] | null | null | null | null | A suspension of 100 g (0.52 moles) of 3-nitrocinnamic acid in 800 ml glacial acetic acid and 100 ml of methanol was hydrogenated at 50 pounds per square inch over 2.5 g 10% palladium on carbon until four equivalents of hydrogen were absorbed. The catalyst was filtered off, the filtrates combined and the solvent was con... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)O.CO | null | null | O=C(O)C=Cc1cccc([N+](=O)[O-])c1>[Pd].C(C)(=O)O.CO>Nc1cccc(CCC(=O)O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cd3f0cac90124ff0adb84e6417ad574b | C#CCC(O)C(C)=O.Cc1ccc(S(=O)(=O)Cl)cc1>>C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O | S(=O)(=O)(C1=CC=C(C)C=C1)Cl.OC(C(C)=O)CC#C.C(C)N(CC)CC>>S(=O)(=O)(C1=CC=C(C)C=C1)OC(C(C)=O)CC#C | [CH:1]#[C:2][CH2:3][CH:4]([OH:5])[C:16]([CH3:17])=[O:18].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1>>[CH:1]#[C:2][CH2:3][CH:4]([O:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1)[C:16]([CH3:17])=[O:18] | C#CCC(O)C(C)=O.Cc1ccc(S(=O)(=O)Cl)cc1 | C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | ad3deb6f5d4dc7823aa3ad2bfe24985be1f3e6860ff8cc0ba215d7624074ef69 | ec645297cfd3107bffb1a4753ac125e48856598e58005e939bb2f0e91bf5e57c | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H1:7]#[C:8]-[C:9]-[C:10](-[OH;D1;+0:11])-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]>>[C;D1;H1:7]#[C:8]-[C:9]-[C:10](-[O;H0;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:12](-[C;D1;H3:13])=[O;D1;H0:14] | 55.3 | [{"value": 55.3, "product": "S(=O)(=O)(C1=CC=C(C)C=C1)OC(C(C)=O)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Tosyl chloride (3.81 g) was added to a solution of 3-hydroxy-5-hexyn-2-one (2.24 g) and triethylamine (2.424 g) in methylene chloride (20 ml) under ice-cooling. After being stirred for 2.5 hours, the mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by co... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 2.5 | C#CCC(O)C(C)=O.Cc1ccc(S(=O)(=O)Cl)cc1>C(Cl)Cl>C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fb1b8a9a3abb43df9bafa1d48884824e | C#CCC(O)C(=C)OC.CS(=O)(=O)Cl>>C#CCC(OS(C)(=O)=O)C(=C)OC | S(=O)(=O)(C)Cl.OC(C(=C)OC)CC#C.C(C)N(CC)CC>>S(=O)(=O)(C)OC(C(=C)OC)CC#C | [CH:1]#[C:2][CH2:3][CH:4]([OH:5])[C:10](=[CH2:11])[O:12][CH3:13].Cl[S:6]([CH3:7])(=[O:8])=[O:9]>>[CH:1]#[C:2][CH2:3][CH:4]([O:5][S:6]([CH3:7])(=[O:8])=[O:9])[C:10](=[CH2:11])[O:12][CH3:13] | C#CCC(O)C(=C)OC.CS(=O)(=O)Cl | C#CCC(OS(C)(=O)=O)C(=C)OC | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[C;D1;H2:7])-[C:8](-[OH;D1;+0:9])-[C:10]-[C:11]#[C;D1;H1:12]>>[#8:5]-[C:6](=[C;D1;H2:7])-[C:8](-[C:10]-[C:11]#[C;D1;H1:12])-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 48 | HOUR | Mesyl chloride (1.73 ml) was added dropwise to a solution of 3-hydroxy-2-methoxy-1-hexen-5-yne (2 g) and triethylamine (3.32 ml) in methylene chloride (20 ml) under ice-cooling over a period of 10 minutes. After being stirred for 48 hours at room temperature the mixture was washed successively with water, aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(Cl)Cl | null | 48 | C#CCC(O)C(=C)OC.CS(=O)(=O)Cl>C(Cl)Cl>C#CCC(OS(C)(=O)=O)C(=C)OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8f160543fa44baea176707de4dac95e | C#CCC(OS(C)(=O)=O)C(=C)OC>>C#CCC(OS(C)(=O)=O)C(C)=O | S(=O)(=O)(C)OC(C(=C)OC)CC#C.S(O)(O)(=O)=O>>S(=O)(=O)(C)OC(C(C)=O)CC#C | C[O:12][C:10]([CH:4]([CH2:3][C:2]#[CH:1])[O:5][S:6]([CH3:7])(=[O:8])=[O:9])=[CH2:11]>>[CH:1]#[C:2][CH2:3][CH:4]([O:5][S:6]([CH3:7])(=[O:8])=[O:9])[C:10]([CH3:11])=[O:12] | C#CCC(OS(C)(=O)=O)C(=C)OC | C#CCC(OS(C)(=O)=O)C(C)=O | null | null | CC(=O)C | Miscellaneous | OtherReaction | 3e02cda7ca3208f28d8355e2c059d63c9e4eb2c7eba0cae088d693f3c74db23e | 215582e9637166736070a53bb588f4e45b0dfc6c974d1df4c97ac5a98451627c | null | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[C:4](-[#8:5])-[C:6]-[C:7]#[C;D1;H1:8]>>[#8:5]-[C:4](-[C:6]-[C:7]#[C;D1;H1:8])-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:1] | 88 | [{"value": 88.0, "product": "S(=O)(=O)(C)OC(C(C)=O)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 3-mesyloxy-2-methoxy-1-hexen-5-yne (0.5 g) in acetone (1.5 ml) was added 20% sulfuric acid (1.5 ml) under ice-cooling and the mixture was stirred for 1.5 hours under the same conditions and then for 1.5 hours at room temperature. Acetone was evaporated in vacuo and the residue was extracted with methyl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl | Ketone | null | null | null | Other | CC(=O)C | null | 1.5 | C#CCC(OS(C)(=O)=O)C(=C)OC>CC(=O)C>C#CCC(OS(C)(=O)=O)C(C)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4a0ab28d099d4c989edf76e5c61389c1 | Cc1ccccc1CCl.Nc1ncccc1O>>Cc1ccccc1COc1cccnc1N | NC1=NC=CC=C1O.CC1=C(CCl)C=CC=C1>>NC1=NC=CC=C1OCC1=C(C=CC=C1)C | Cl[CH2:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][n:14][c:15]1[NH2:16] | Cc1ccccc1CCl.Nc1ncccc1O | Cc1ccccc1COc1cccnc1N | null | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-] | [OH-].[Na+].C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cccnc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | null | [] | null | null | 24 | HOUR | To a mixture of 2-amino-3-hydroxypyridine (7 g) and Adogen 464 (Trademark: prepared by Aldrich Chemical Co.) (0.4 g) in 40% aqueous sodium hydroxide (32 ml) and methylene chloride (32 ml) was added 2-methylbenzyl chloride (8.42 ml) at ambient temperature. After being stirred for 24 hours, the organic layer was separate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccncc1 | HCl | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].[OH-].[Na+].C(Cl)Cl | null | 24 | Cc1ccccc1CCl.Nc1ncccc1O>CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].[OH-].[Na+].C(Cl)Cl>Cc1ccccc1COc1cccnc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8afe18d01bb54bda9ec3d89b8bd7890e | Cc1ccccc1C=O.Nc1cccnc1N>>Cc1ccccc1CNc1cccnc1N | C([O-])(O)=O.[Na+].NC1=NC=CC=C1N.CC1=C(C=O)C=CC=C1.C(#N)[BH3-].[Na+]>>NC1=NC=CC=C1NCC1=C(C=CC=C1)C | O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][c:10]1[cH:11][cH:12][cH:13][n:14][c:15]1[NH2:16] | Cc1ccccc1C=O.Nc1cccnc1N | Cc1ccccc1CNc1cccnc1N | null | null | C(C)(=O)O.CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2cccnc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | 34.4 | [{"value": 34.4, "product": "NC1=NC=CC=C1NCC1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | Molecular Sieves (16 g) was added to a solution of 2,3-diaminopyridine (8 g), 2-methylbenzaldehyde (8.81 g), and acetic acid (4.2 ml) in methanol (160 ml) and the mixture was stirred for 96 hours at room temperature. Sodium cyanoborohydride (4.61 g) was added portionwise to the mixture with stirring under ice-cooling o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1 | Other | C(C)(=O)O.CO | null | 96 | Cc1ccccc1C=O.Nc1cccnc1N>C(C)(=O)O.CO>Cc1ccccc1CNc1cccnc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-163ac3e349334314939c73ed51b57929 | Cc1ccccc1CO.Nc1nccnc1Cl>>Cc1ccccc1COc1nccnc1N | NC1=NC=CN=C1Cl.CC1=C(CO)C=CC=C1.[H-].[Na+]>>NC1=NC=CN=C1OCC1=C(C=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:9].Cl[c:10]1[n:11][cH:12][cH:13][n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][O:9][c:10]1[n:11][cH:12][cH:13][n:14][c:15]1[NH2:16] | Cc1ccccc1CO.Nc1nccnc1Cl | Cc1ccccc1COc1nccnc1N | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[N;D1;H2:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[N;D1;H2:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:8]-[C:9]-[c:10] | 41.5 | [{"value": 41.5, "product": "NC1=NC=CN=C1OCC1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 30 | MINUTE | To a solution of 2-methylbenzyl alcohol (0.985 g) in N,N-dimethylformamide (10 ml) was added 62.8% sodium hydride (0.308 g) under a nitrogen atmosphere and then stirred for 30 minutes. 2-Amino-3-chloropyrazine (0.87 g) was added to the solution and the mixture was heated at 65° C. for 2 hours and poured onto crushed ic... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1 | HCl | CN(C=O)C | 65 | 0.5 | Cc1ccccc1CO.Nc1nccnc1Cl>CN(C=O)C>Cc1ccccc1COc1nccnc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d28aa19805e4a3182693ceb169ad3c2 | Cc1ccccc1CN.Nc1nccnc1Cl>>Cc1ccccc1CNc1nccnc1N | NC1=NC=CN=C1Cl.CC1=C(CN)C=CC=C1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>NC1=NC=CN=C1NCC1=C(C=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9].Cl[c:10]1[n:11][cH:12][cH:13][n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][c:10]1[n:11][cH:12][cH:13][n:14][c:15]1[NH2:16] | Cc1ccccc1CN.Nc1nccnc1Cl | Cc1ccccc1CNc1nccnc1N | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[N;D1;H2:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[N;D1;H2:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[C:9]-[c:10] | 19.7 | [{"value": 19.7, "product": "NC1=NC=CN=C1NCC1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-3-chloropyrazine (4.3 g), 2-methylbenzylamine (4.6 g), potassium carbonate (5.5 g), and potassium iodide (0.4 g) in N,N-dimethylformamide (43 ml) was refluxed for 24 hours under a nitrogen atmosphere and allowed to stand at room temperature. The mixture was poured into water and extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1 | HCl | CN(C=O)C.O | null | null | Cc1ccccc1CN.Nc1nccnc1Cl>CN(C=O)C.O>Cc1ccccc1CNc1nccnc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d1e537d445bf410db0fd0a5741375d9f | Cc1cn2cccc(O)c2n1.ClCc1ccccc1Cl>>Cc1cn2cccc(OCc3ccccc3Cl)c2n1 | ClC1=C(CCl)C=CC=C1.O.[H-].[Na+].OC=1C=2N(C=CC1)C=C(N2)C>>ClC1=C(COC=2C=3N(C=CC2)C=C(N3)C)C=CC=C1 | [CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][cH:7][c:8]([OH:9])[c:18]2[n:19]1.Cl[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[Cl:17]>>[CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18]2[n:19]1 | Cc1cn2cccc(O)c2n1.ClCc1ccccc1Cl | Cc1cn2cccc(OCc3ccccc3Cl)c2n1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cccn3ccnc23)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:1:[c:13]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:1:[c:13]):[c:4] | 66.8 | [{"value": 66.8, "product": "ClC1=C(COC=2C=3N(C=CC2)C=C(N3)C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A 60% dispersion of sodium hydride in mineral oil (1.87 g) was added portionwise to a suspension of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (6.3 g) in dimethyl sulfoxide (63 ml) at room temperature over a period of 15 minutes. After being stirred for 30 minutes, 2-chlorobenzyl chloride (7.54 g) was added in one portio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | CS(=O)C | null | 0.5 | Cc1cn2cccc(O)c2n1.ClCc1ccccc1Cl>CS(=O)C>Cc1cn2cccc(OCc3ccccc3Cl)c2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-022e022fa6a34c4ca3ba0dec5c804a5d | CC(=O)CCl.Cc1ccccc1CNc1cccnc1N>>Cc1cn2cccc(NCc3ccccc3C)c2n1 | NC1=NC=CC=C1NCC1=C(C=CC=C1)C.ClCC(C)=O>>CC1=C(CNC=2C=3N(C=CC2)C=C(N3)C)C=CC=C1 | O=[C:2]([CH3:1])[CH2:3]Cl.[n:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH3:17])[c:18]1[NH2:19]>>[CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH3:17])[c:18]2[n:19]1 | CC(=O)CCl.Cc1ccccc1CNc1cccnc1N | Cc1cn2cccc(NCc3ccccc3C)c2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(CNc2cccn3ccnc23)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6]):[n;H0;D2;+0:4]:1 | null | [] | null | null | null | null | A solution of 2-amino-3-(2-methylbenzylamino)pyridine (3.25 g) and chloroacetone (1.26 ml) in ethanol (65 ml) was refluxed for 18 hours and then evaporated in vacuo. To the residue was added aqueous sodium bicarbonate solution and the mixture was extracted with methylene chloride. The extract was washed with brine, dri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(C)O | null | null | CC(=O)CCl.Cc1ccccc1CNc1cccnc1N>C(C)O>Cc1cn2cccc(NCc3ccccc3C)c2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-92e60f8984b44a1db9d8ae0442b210af | C=O.CNC.Cc1cn2cccc(OCc3ccccc3Cl)c2n1>>Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C | ClC1=C(COC=2C=3N(C=CC2)C=C(N3)C)C=CC=C1.C=O.CNC>>ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)CN(C)C)C=CC=C1 | O=[CH2:23].[CH3:20][NH:21][CH3:22].[CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][n:18]2[cH:19]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][n:18]2[c:19]1[CH2:20][N:21]([CH3:22])[CH3:23] | C=O.CNC.Cc1cn2cccc(OCc3ccccc3Cl)c2n1 | Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 991ddcf1933c85b5de89c8220fc08fceb03a8dd4087543d85e8a78c13bfec399 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(COc2cccn3ccnc23)cc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[CH3;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[#7;a:10](:[c:11]):[cH;D2;+0:12]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[#7;a:10](:[c:11]):[c;H0;D3;+0:12]:1-[CH2;D2;+0:4]-[N;H0;D3;+0:3](-[C;D1;H3:2])-[CH3;D1;+0:1] | 85.4 | [{"value": 85.4, "product": "ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)CN(C)C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 37% aqueous formaldehyde (2.38 g) in acetic acid (38 ml) was added dropwise 50% aqueous dimethylamine (2.63 g) with ice-cooling over a period of 10 minutes and the mixture was stirred for an additional 10 minutes. The mixture was heated at 50°-55° C. for 2 hours after an addition of 8-(2-chlorobenzylox... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HO- | C(C)(=O)O | null | 0.166667 | C=O.CNC.Cc1cn2cccc(OCc3ccccc3Cl)c2n1>C(C)(=O)O>Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-91c2eee7c15b45b0a59d06a37df37e76 | CI.Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C>>Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C.[I-] | CI.ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)CN(C)C)C=CC=C1>>[I-].ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C[N+](C)(C)C)C=CC=C1 | [CH3:22][I:25].[CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][n:18]2[c:19]1[CH2:20][N:21]([CH3:23])[CH3:24]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][n:18]2[c:19]1[CH2:20][N+:21]([CH3:... | CI.Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C | Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C.[I-] | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | c1c361ee4cbadaf5c6784ce94893dc199b85d8bd1f54519979f4b44d8dfd8b3e | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(COc2cccn3ccnc23)cc1 | [#7;a:1]:[c:2](-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6]):[c:7]:[#7;a:8].[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[#7;a:1]:[c:2](-[C:3]-[N+;H0;D4:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:9]):[c:7]:[#7;a:8].[I-;H0;D0:10] | 101.7 | [{"value": 101.7, "product": "[I-].ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C[N+](C)(C)C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Methyl iodide (3.48 g) was added dropwise to a solution of 8-(2-chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine (7.8 g) in acetone (100 ml) at room temperature and the mixture was stirred for 24 hours. The resulting precipitate was collected by filtration, washed with acetone, and dried in a desic... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | null | null | c1ccccc1.c1ccn2ccnc2c1 | null | CC(=O)C | null | 24 | CI.Cc1nc2c(OCc3ccccc3Cl)cccn2c1CN(C)C>CC(=O)C>Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C.[I-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-185e83baf0c3403dab14950827063d22 | C=CCC(Cl)C(C)=O.Nc1ncccc1OCc1ccccc1>>C=CCc1c(C)nc2c(OCc3ccccc3)cccn12 | NC1=NC=CC=C1OCC1=CC=CC=C1.ClC(C(C)=O)CC=C>>C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC=C | O=[C:5]([CH:4](Cl)[CH2:3][CH:2]=[CH2:1])[CH3:6].[NH2:7][c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19][cH:20][n:21]1>>[CH2:1]=[CH:2][CH2:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][n:21]12 | C=CCC(Cl)C(C)=O.Nc1ncccc1OCc1ccccc1 | C=CCc1c(C)nc2c(OCc3ccccc3)cccn12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 68f76555483972bc3db5d3d4b5e479a66c1f89ab1b71b2a0fb941126aa9c191a | 235fd48cd394ba1137abde2ba7484c051be6ffcae187060d6065fe5adf0e90a3 | c1ccc(COc2cccn3ccnc23)cc1 | Cl-[CH;D3;+0:1](-[C:2]-[C:3]=[C;D1;H2:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H2:4]=[C:3]-[C:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:5](-[C;D1;H3:6]):[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | 7.4 | [{"value": 7.4, "product": "C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-3-benzyloxypyridine (3 g) and 3-chloro-5-hexen-2-one (2.981 g) in ethanol (15 ml) was stirred and refluxed for 45 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HCl | C(C)O | null | null | C=CCC(Cl)C(C)=O.Nc1ncccc1OCc1ccccc1>C(C)O>C=CCc1c(C)nc2c(OCc3ccccc3)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-30e0a8c847e3408db73ba26ed7bed814 | C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O.Nc1ncccc1OCc1ccccc1>>C#CCc1c(C)nc2c(OCc3ccccc3)cccn12 | NC1=NC=CC=C1OCC1=CC=CC=C1.S(=O)(=O)(C1=CC=C(C)C=C1)OC(C(C)=O)CC#C>>C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC#C | Cc1ccc(S(=O)(=O)O[CH:4]([CH2:3][C:2]#[CH:1])[C:5](=O)[CH3:6])cc1.[NH2:7][c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19][cH:20][n:21]1>>[CH:1]#[C:2][CH2:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][n:21]12 | C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O.Nc1ncccc1OCc1ccccc1 | C#CCc1c(C)nc2c(OCc3ccccc3)cccn12 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 05c332a02d21c1a0dc368986a4cd1766ba670505a7c33ce9a4e6613de9ab3a70 | b3fe639a14cda8cf395bb492e10e6f982c6df5a0f3702dac7bbaa7704cd5b4d9 | c1ccc(COc2cccn3ccnc23)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3]#[C;D1;H1:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6]):c:c:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H1:4]#[C:3]-[C:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:5](-[C;D1;H3:6]):[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | 31 | [{"value": 31.0, "product": "C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-3-benzyloxypyridine (2 g) and 3-tosyloxy-5-hexyn-2-one (2.66 g) in ethanol (15 ml) was stirred and refluxed for 24 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Primary amine | null | c1ccccc1.c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | TsOH.HO- | C(C)O | null | null | C#CCC(OS(=O)(=O)c1ccc(C)cc1)C(C)=O.Nc1ncccc1OCc1ccccc1>C(C)O>C#CCc1c(C)nc2c(OCc3ccccc3)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-02f0036534674dbdbf7bb937e43757ec | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1CNc1cccnc1N>>C#CCc1c(C)nc2c(NCc3ccccc3C)cccn12 | NC1=NC=CC=C1NCC1=C(C=CC=C1)C.S(=O)(=O)(C)OC(C(C)=O)CC#C>>CC1=C(CNC=2C=3N(C=CC2)C(=C(N3)C)CC#C)C=CC=C1 | CS(=O)(=O)O[CH:4]([CH2:3][C:2]#[CH:1])[C:5](=O)[CH3:6].[NH2:7][c:8]1[c:9]([NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH3:18])[cH:19][cH:20][cH:21][n:22]1>>[CH:1]#[C:2][CH2:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([NH:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[cH:19][cH:20][cH:21][n:22]1... | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1CNc1cccnc1N | C#CCc1c(C)nc2c(NCc3ccccc3C)cccn12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 77a56b54cbecae5bd21ceb645c55e500764965636e673cfcf991bf32c16bcf53 | bd0bab184c57def941fa6a922e349010f6f49341eb09c2fb9a172d2e8e4d8443 | c1ccc(CNc2cccn3ccnc23)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3]#[C;D1;H1:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H1:4]#[C:3]-[C:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:5](-[C;D1;H3:6]):[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | 30.3 | [{"value": 30.3, "product": "CC1=C(CNC=2C=3N(C=CC2)C(=C(N3)C)CC#C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-3-(2-methylbenzylamino)pyridine (2 g) and 3-mesyloxy-5-hexyn-2-one (1.78 g) in ethanol (40 ml) was refluxed for 31.5 hours and then evaporated in vacuo. The residue was treated with aqueous sodium bicarbonate solution and extracted with methylene chloride. The extract was washed with water, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | MsOH.HO- | C(C)O | null | null | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1CNc1cccnc1N>C(C)O>C#CCc1c(C)nc2c(NCc3ccccc3C)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5a47df5726014329923daab875341450 | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1COc1nccnc1N>>C#CCc1c(C)nc2c(OCc3ccccc3C)nccn12 | C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].NC1=NC=CN=C1OCC1=C(C=CC=C1)C.S(=O)(=O)(C)OC(C(C)=O)CC#C>>CC1=C(COC=2C=3N(C=CN2)C(=C(N3)C)CC#C)C=CC=C1 | CS(=O)(=O)O[CH:4]([CH2:3][C:2]#[CH:1])[C:5](=O)[CH3:6].[NH2:7][c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH3:18])[n:19][cH:20][cH:21][n:22]1>>[CH:1]#[C:2][CH2:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[n:19][cH:20][cH:21][n:22]12 | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1COc1nccnc1N | C#CCc1c(C)nc2c(OCc3ccccc3C)nccn12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 0b4115faa1b55129bb90c6c55ba81741c5593609c021552a032b4f0dd0725876 | bd0bab184c57def941fa6a922e349010f6f49341eb09c2fb9a172d2e8e4d8443 | c1ccc(COc2nccn3ccnc23)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3]#[C;D1;H1:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[#8:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[n;H0;D2;+0:12]:[c:13]:1-[NH2;D1;+0:14]>>[#8:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]2:[c:13]:1:[n;H0;D2;+0:14]:[c;H0;D3;+0:5](-[C;D1;H3:6]):[c;H0;D3;+0:1]:2-[C:2]-[C:3]#[C;D1;H1:4] | 3.8 | [{"value": 3.8, "product": "CC1=C(COC=2C=3N(C=CN2)C(=C(N3)C)CC#C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium bicarbonate (2.73 g) was added to a solution of 2-amino-3-(2-methylbenzyloxy)pyrazine (3.5 g) and 3-mesyloxy-5-hexyn-2-one (6.18 g) in ethanol (35 ml) and the mixture was refluxed for 12 hours. The mixture was poured into an aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was wa... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ketone.Primary amine | null | c1cnccn1 | c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | MsOH.HO- | C(C)O | null | null | C#CCC(OS(C)(=O)=O)C(C)=O.Cc1ccccc1COc1nccnc1N>C(C)O>C#CCc1c(C)nc2c(OCc3ccccc3C)nccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ebc91131d5f547cb8a0bb15bdb77240c | C#CCc1c(C)nc2c(OCc3ccccc3C)cccn12>>C=C=Cc1c(C)nc2c(OCc3ccccc3C)cccn12 | CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)CC#C)C=CC=C1.[OH-].[Na+]>>CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C=C=C)C=CC=C1 | [CH:1]#[C:2][CH2:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[cH:19][cH:20][cH:21][n:22]12>>[CH2:1]=[C:2]=[CH:3][c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[cH:19][cH:20][cH:21][n:22]12 | C#CCc1c(C)nc2c(OCc3ccccc3C)cccn12 | C=C=Cc1c(C)nc2c(OCc3ccccc3C)cccn12 | null | null | CO | Miscellaneous | OtherReaction | 2f13f6ad84546451f3d01481775a52c4098398348b523c935b8104d01b87fd5f | a396e5546fe76b7265b1c53702233ee449ddd085280941b2992883e25d48851e | c1ccc(COc2cccn3ccnc23)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5](:[c:6]):[c:7]:1-[CH2;D2;+0:8]-[C;H0;D2;+0:9]#[CH;D1;+0:10]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5](:[c:6]):[c:7]:1-[CH;D2;+0:8]=[C;H0;D2;+0:9]=[CH2;D1;+0:10] | 27.3 | [{"value": 27.3, "product": "CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C=C=C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.99 g) and 1N-sodium hydroxide solution (5.65 ml) in methanol (50 ml) was stirred for 72 hours at room temperature. The mixture was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with brine, dri... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Allene | null | null | c1ccccc1.c1ccn2ccnc2c1 | null | CO | null | null | C#CCc1c(C)nc2c(OCc3ccccc3C)cccn12>CO>C=C=Cc1c(C)nc2c(OCc3ccccc3C)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ff349a1b204b4c2aab891a575c293bf5 | Cc1ccccc1COc1cccn2c(C[N+](C)(C)C)c(C)nc12>>C#CCOCc1c(C)nc2c(OCc3ccccc3C)cccn12 | [H-].[Na+].[I-].CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C[N+](C)(C)C)C=CC=C1>>CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)COCC#C)C=CC=C1 | [N+]([CH3:1])([CH3:2])([CH3:3])[CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:4][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[CH3:20])[cH:21][cH:22][cH:23][n:24]12>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[CH3:20])[cH:21][cH:22... | Cc1ccccc1COc1cccn2c(C[N+](C)(C)C)c(C)nc12 | C#CCOCc1c(C)nc2c(OCc3ccccc3C)cccn12 | null | null | C(C#C)O | Functional Group Interconversion | OtherReaction | 482318f577acf49c86cbbb7e098cb729667daafa70f29010a70e72298356abb3 | 5c0da6dbcd390e2c3349103c81f82cc550c05f4a0fd872aee3b671caf307c53d | c1ccc(COc2cccn3ccnc23)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:15]:1-[CH2;D2;+0:16]-[N+](-[CH3;D1;+0:17])(-[CH3;D1;+0:18])-[CH3;D1;+0:19]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2-[#8:20]-[CH2;D2;+0:11]-[c:... | 110.8 | [{"value": 110.8, "product": "CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)COCC#C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of sodium hydride (63.6% in mineral oil dispersion, 0.285 g) in 2-propynyl alcohol (12 ml) was added 8-(2-methylbenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (3 g) and the mixture was heated at 85°-100° C. for 1.5 hours. After being cooled, the mixture was poured into ice-water... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Ether.Alkyne | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | null | C(C#C)O | null | null | Cc1ccccc1COc1cccn2c(C[N+](C)(C)C)c(C)nc12>C(C#C)O>C#CCOCc1c(C)nc2c(OCc3ccccc3C)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b00092430ac54cc19a9bd1a0f1697fff | Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C>>C#CCOCc1c(C)nc2c(OCc3ccccc3Cl)cccn12 | [H-].[Na+].[I-].ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C[N+](C)(C)C)C=CC=C1>>ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)COCC#C)C=CC=C1 | [N+]([CH3:1])([CH3:2])([CH3:3])[CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:4][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[Cl:20])[cH:21][cH:22][cH:23][n:24]12>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[Cl:20])[cH:21][cH:22][... | Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C | C#CCOCc1c(C)nc2c(OCc3ccccc3Cl)cccn12 | null | null | C(C#C)O | Functional Group Interconversion | OtherReaction | 482318f577acf49c86cbbb7e098cb729667daafa70f29010a70e72298356abb3 | 5c0da6dbcd390e2c3349103c81f82cc550c05f4a0fd872aee3b671caf307c53d | c1ccc(COc2cccn3ccnc23)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:15]:1-[CH2;D2;+0:16]-[N+](-[CH3;D1;+0:17])(-[CH3;D1;+0:18])-[CH3;D1;+0:19]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2-[#8:20]-[CH2;D2;+0:11]-[c:... | 124.6 | [{"value": 124.6, "product": "ClC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)COCC#C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of sodium hydride (60% in mineral oil dispersion, 0.186 g) in 2-propynyl alcohol (8 ml) was added 8-(2-chlorobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (2 g) and the mixture was heated at 90°-95° C. with stirring for 1 hour. After being cooled, the mixture was poured into ic... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Ether.Alkyne | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | null | C(C#C)O | null | 1 | Cc1nc2c(OCc3ccccc3Cl)cccn2c1C[N+](C)(C)C>C(C#C)O>C#CCOCc1c(C)nc2c(OCc3ccccc3Cl)cccn12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3372c0ca9f334c538c916228292e2cfe | C#CCOCc1c(C)nc2c(OCc3ccccc3)cccn12.O=C=O>>Cc1nc2c(OCc3ccccc3)cccn2c1COCC#CC(=O)O | C(=O)=O.C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)COCC#C.C(CCC)[Li].C(C)(=O)O>>C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)COCC#CC(=O)O | [CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15][cH:16][n:17]2[c:18]1[CH2:19][O:20][CH2:21][C:22]#[CH:23].[C:24](=[O:25])=[O:26]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15][cH:16][n:17]2[c:18]1[CH2:19][O:20][CH2:21... | C#CCOCc1c(C)nc2c(OCc3ccccc3)cccn12.O=C=O | Cc1nc2c(OCc3ccccc3)cccn2c1COCC#CC(=O)O | null | null | CCCCCC.O1CCCC1 | Acylation | OtherReaction | 79750b25e2e891222a6213659b9b96213d6cfd615f193dc07d015f66fa42c61b | d91f4325df4c0a97d921e50d724781c1eb02533a0e976122bbd0b1dc69cfd2e7 | c1ccc(COc2cccn3ccnc23)cc1 | [C:1]-[C:2]#[CH;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[O;H0;D1;+0:6]>>[C:1]-[C:2]#[C;H0;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[OH;D1;+0:6] | 58.6 | [{"value": 58.6, "product": "C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)COCC#CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (1 g) in tetrahydrofuran (10 ml) was added dropwise 10% solution of n-butyllithium in n-hexane (2.09 ml) at -60° C. under a nitrogen atmosphere. After being stirred for 10 minutes the solution was treated with dry ice (1.4 g), allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Carbon dioxide | Carboxylic acid.Alkyne | null | null | c1ccccc1.c1ccn2ccnc2c1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | C#CCOCc1c(C)nc2c(OCc3ccccc3)cccn12.O=C=O>CCCCCC.O1CCCC1>Cc1nc2c(OCc3ccccc3)cccn2c1COCC#CC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-374e80436b6f4dea998738769e836db4 | O=C(Cn1c(S)nc2ccccc21)c1ccccn1>>c1ccc(-c2cn3c(nc4ccccc43)s2)nc1 | SC1=NC2=C(N1CC(C1=NC=CC=C1)=O)C=CC=C2.C(=O)([O-])[O-].[Na+].[Na+]>>N1=C(C=CC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1 | O=[C:5]([c:4]1[cH:3][cH:2][cH:1][cH:18][n:17]1)[CH2:6][n:7]1[c:8]([SH:16])[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][n:7]3[c:8]([n:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]34)[s:16]2)[n:17][cH:18]1 | O=C(Cn1c(S)nc2ccccc21)c1ccccn1 | c1ccc(-c2cn3c(nc4ccccc43)s2)nc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9d1596ab3913372e735f11645b8fe1732fad7a35a5ee22cad45f2cb93f68875c | 7015f9bd646bfe69b891dc9cb85114e2d8c209a7ff8bee5e1ff5903b86ef8580 | c1ccc(-c2cn3c(nc4ccccc43)s2)nc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[#7;a:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1-[SH;D1;+0:8])-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12]:[c:13]>>[c:11]:[#7;a:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[s;H0;D2;+0:8]:1):[c:12]:[c:13] | 37.5 | [{"value": 37.5, "product": "N1=C(C=CC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-mercapto-1-[2-oxo-2-(2-pyridyl)ethyl]benzimidazole (1 g.) in polyphosphoric acid was heated at 140° C. for 1 hour. The solution was neutralised with Na2CO3 solution and extracted into EtOAc (700 ml). The extracts were dried (MgSO4) and evaporated to give a solid which was recrystallised from EtOAc/EtOH ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol | null | c1nc2ccccc2[nH]1 | c1ccc2c(c1)nc1sccn12 | c1ccncc1.c1ccc2c(c1)nc1sccn12 | HO- | null | null | null | O=C(Cn1c(S)nc2ccccc21)c1ccccn1>>c1ccc(-c2cn3c(nc4ccccc43)s2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e54381d6a37d4ac89c8f8f5dc9dbc8ea | COc1ccnc(C(=O)CBr)c1>>CC(C)O.CC(C)OC(C)C | C(=O)([O-])[O-].[K+].[K+].BrCC(=O)C1=NC=CC(=C1)OC.ClC=1NC2=C(N1)C=CC=C2.O>>CC(C)O.C(C)(C)OC(C)C | O=[C:5]([c:6]1nc[cH:1][c:2]([O:4][CH3:7])[cH:3]1)[CH2:11]Br>>[CH3:1][CH:2]([CH3:3])[OH:4].[CH3:5][CH:6]([CH3:7])[O:8][CH:9]([CH3:10])[CH3:11] | COc1ccnc(C(=O)CBr)c1 | CC(C)O.CC(C)OC(C)C | null | null | CN(C=O)C | Miscellaneous | OtherReaction | f35c709fea588031a645ddcbbe2fffed2ee75bd6c97ae4d6538342ad677e37bc | 97ee76a97823cae0ae8db273bb9cacc344d3c41821358baf271f1fb7c5df9370 | null | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[CH3;D1;+0:7]):[cH;D2;+0:8]:c:n:1>>[C;D1;H3:9]-[C:10](-[CH3;D1;+0:1])-[#8:11]-[CH;D3;+0:3](-[CH3;D1;+0:2])-[CH3;D1;+0:7].[CH3;D1;+0:8]-[CH;D3;+0:5](-[CH3;D1;+0:4])-[OH;D1;+0:6] | null | [] | 2 | CELSIUS | 0.5 | HOUR | 2-Bromoacetyl-4-methoxypyridine (11.5 g, 0.05) and 2-chlorobenzimidazole (7.5 g, 0.05 mole) were dissolved in dimethylformamide (75 ml) and cooled to 2° C. K2CO3 (12 g, 0.08 mole) was added and the temperature rose to 9° C. as the suspension was stirred for 1/2 hour. The mixture was added to H2O (200 ml) giving a solid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether | Ether.Secondary alcohol | c1ccncc1 | null | null | Br- | CN(C=O)C | 2 | 0.5 | COc1ccnc(C(=O)CBr)c1>CN(C=O)C>CC(C)O.CC(C)OC(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-39008d9572cc46a1a61451fb05242526 | Clc1nc2ccccc2[nH]1>>c1ccc2[nH]cnc2c1 | ClC=1NC2=C(N1)C=CC=C2.BrCC(=O)C1=NC=CC(=C1C)SCC.C(=O)([O-])[O-].[K+].[K+]>>N1=CNC2=C1C=CC=C2 | Cl[c:6]1[nH:5][c:4]2[cH:3][cH:2][cH:1][cH:9][c:8]2[n:7]1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | Clc1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | ca1ff206ba5e3245a070477a37dade787c5ff5e118fea1cc6b950980a4e5b17a | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2[nH]cnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1>>[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | 2-Chlorobenzimidazole is reacted with 2-bromoacetyl-4-ethylthio-3-methylpyridine in the presence of K2CO3 to give 2-chloro-1-[2-[4-ethylthio-3-methylpyridyl])-2-oxoethyl]benzimidazole. This is reacted with thiourea and treated with NH4OH to give 2-mercapto-1-(2-(2-(4-ethylthio-3-methylpyridyl))-2-oxoethyl)benzimidazole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | null | null | null | Clc1nc2ccccc2[nH]1>>c1ccc2[nH]cnc2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a0df9816cf51486da9d534d6342d0836 | CCSc1ccnc(-c2cn3c(nc4ccccc43)s2)c1C.O=C(OO)c1cccc(Cl)c1>>CCSc1ccnc(C2=Cn3c(nc4ccccc43)S2=O)c1C | C(C)SC1=C(C(=NC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1)C.ClC=1C=C(C(=O)OO)C=CC1>>C(C)SC1=C(C(=NC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1=O)C | [CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][n:7][c:8](-[c:9]2[cH:10][n:11]3[c:12]([n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]34)[s:20]2)[c:22]1[CH3:23].O=C(O[OH:21])c1cccc(Cl)c1>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][n:7][c:8]([C:9]2=[CH:10][n:11]3[c:12]([n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]34)[S:20]2=[O:21])[c... | CCSc1ccnc(-c2cn3c(nc4ccccc43)s2)c1C.O=C(OO)c1cccc(Cl)c1 | CCSc1ccnc(C2=Cn3c(nc4ccccc43)S2=O)c1C | null | null | C(Cl)Cl | Oxidation | OtherReaction | 3af9ed32602f5852fad4d7bddcb7110cf8597d7ff387aa22f73409d6e758b38e | 081bebe60ef12ca80072327af69d872c987a74a66ca947b1bdb982ac71fd1052 | O=S1C(c2ccccn2)=Cn2c1nc1ccccc12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[#7;a:8]2:[c:9]:[c:10]:[#7;a:11]:[c:12]:2:[s;H0;D2;+0:13]:1):[#7;a:14]:[c:15]>>[C;D1;H3:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[#7;a:8]2:[c:9]:[c:10]:[#7;a:11]:[c:12]:2-[S;H0;D3;+0:13]-... | null | [] | null | null | null | null | A solution of 2-(4-ethylthio-3-methylpyrid-2-yl)-thiazolo[3,2-a]benzimidazole (0.01 mole) is dissolved in CH2Cl2 solution (100 ml) at 0° C. and treated with m-chloroperoxybenzoic acid (0.01 mole) for 0.5 hours. The solution is then washed with sodium carbonate solution and dried (MgSO4). Purification by chromatography ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Sulfoxide | c1ccc2c(c1)nc1sccn12.c1ccccc1 | c1ccc2c(c1)nc1sccn12 | c1ccncc1.c1ccc2c(c1)nc1sccn12 | HCl | C(Cl)Cl | null | null | CCSc1ccnc(-c2cn3c(nc4ccccc43)s2)c1C.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCSc1ccnc(C2=Cn3c(nc4ccccc43)S2=O)c1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-adafda2f10aa459986df317fa2d32be6 | COc1ccc2[nH]ccc2c1.N#CCCl.NC(N)=S>>COc1ccc2[nH]cc(SCC#N)c2c1 | ClCC#N.COC=1C=C2C=CNC2=CC1.NC(=S)N.II>>COC=1C=C2C(=CNC2=CC1)SCC#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:14]2[cH:15]1.Cl[CH2:11][C:12]#[N:13].NC(N)=[S:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([S:10][CH2:11][C:12]#[N:13])[c:14]2[cH:15]1 | COc1ccc2[nH]ccc2c1.N#CCCl.NC(N)=S | COc1ccc2[nH]cc(SCC#N)c2c1 | null | null | CO.O.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 6eca71f48de78b8f1122f33a4f563f3ae4d8df6bf08c897e78e7ec4233dc53a4 | 304c94f4367e24c71f550ef55805048586c03c416bc00e3c48114269d0abdd01 | c1ccc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].N-C(-N)=[S;H0;D1;+0:4].[c:5]:[c:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:1:[c:11]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:6]:1:[c:5] | 42 | [{"value": 42.0, "product": "COC=1C=C2C(=CNC2=CC1)SCC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 50 g (0.34 mole) of 5-methoxyindole and 25.8 (0.34 mole) of thiourea in 1700 ml of 50% aqueous methanol was added 340 ml of KI/I2 in water over a 5 minute period and the reaction mixture was allowed to stir at room temperature for 3 hours. The reaction mixture was then evaporated in vacuo to about 1100... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | CO.O.C(C)OCC | null | 3 | COc1ccc2[nH]ccc2c1.N#CCCl.NC(N)=S>CO.O.C(C)OCC>COc1ccc2[nH]cc(SCC#N)c2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e1d5c8532bfa4e83949fd6e9d0c8900e | Cc1cccc2c(SCC#N)c[nH]c12>>Cc1cccc2c(SCCN)c[nH]c12 | CC=1C=CC=C2C(=CNC12)SCC#N.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Al+3].[Cl-].[Cl-].[Cl-]>>NCCSC1=CNC2=C(C=CC=C12)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([S:8][CH2:9][C:10]#[N:11])[cH:12][nH:13][c:14]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([S:8][CH2:9][CH2:10][NH2:11])[cH:12][nH:13][c:14]12 | Cc1cccc2c(SCC#N)c[nH]c12 | Cc1cccc2c(SCCN)c[nH]c12 | null | null | CCOCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2[nH]ccc2c1 | [#16:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#16:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | null | null | The ether solution was separated and dried over MgSO4. The filtered solution was evaporated in vacuo to give 24.4 g (66%) of 7-methylindol-3-ylthioacetonitrile as a tan solid. An ether solution of 14.1 g (70 mmole) of the nitrile was treated with 2.7 g (70 mmole) of lithium aluminum hydride and 9.5 g (70 mmole) of AlCl... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2[nH]ccc2c1 | null | CCOCC | null | null | Cc1cccc2c(SCC#N)c[nH]c12>CCOCC>Cc1cccc2c(SCCN)c[nH]c12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3ac68fcac968481094ca4e6ef976f341 | C1CNCCN1.Fc1ccc(CCl)cc1>>Fc1ccc(CN2CCNCC2)cc1 | FC1=CC=C(CCl)C=C1.C(C)O.N1CCNCC1.C(C)O>>FC1=CC=C(CN2CCNCC2)C=C1 | [NH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1.Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:14][cH:13]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[cH:13][cH:14]1 | C1CNCCN1.Fc1ccc(CCl)cc1 | Fc1ccc(CN2CCNCC2)cc1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 55.7 | [{"value": 55.7, "product": "FC1=CC=C(CN2CCNCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | A solution of 29 g of p-fluorobenzyl chloride in 50 g of reagent ethanol was added dropwise to a stirred solution of 34.5 g of piperazine in 150 g of reagent ethanol. A cold water bath was used to maintain the reaction temperature at 20° C. during the addition. The reaction mixture was stirred for an additional 11/2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HCl | CCOCC | 20 | 2 | C1CNCCN1.Fc1ccc(CCl)cc1>CCOCC>Fc1ccc(CN2CCNCC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9e8e1e68cd8c457689d598080df4296f | ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.O=C(CN1CCNCC1)c1ccccc1>>O=C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 | C(C(=O)C1=CC=CC=C1)N1CCNCC1.ClCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.C(C)N(CC)CC>>ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(=O)C2=CC=CC=C2)C=C1 | Cl[CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[CH2:23][CH2:24]1.[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:25][CH2:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:1... | ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.O=C(CN1CCNCC1)c1ccccc1 | O=C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCN(CCCN2CCN(Cc3ccccc3)CC2)CC1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 77.5 | [{"value": 50.0, "product": "ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(=O)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(=O)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.1 g of 1-phenacylpiperazine, 5.7 g of 1-chloro-3-[4-(4-chlorobenzyl)-1-piperazinyl]propane, 2.6 g of triethylamine and 35 ml of reagent ethanol was refluxed for 5 hours. The solvent was removed by rotary evaporation, 150 ml of water were added, and the mixture was extracted with ether (3×150 ml). The eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | C(C)O | null | null | ClCCCN1CCN(Cc2ccc(Cl)cc2)CC1.O=C(CN1CCNCC1)c1ccccc1>C(C)O>O=C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5fbf8b934342464383a21037ee00b589 | ClCCl.Clc1ccc(CN2CCNCC2)cc1.O=C(Cl)CC(=O)Cl.[OH-]>>Cl.Cl.O.O=C(CC(=O)N1CCN(Cc2ccc(Cl)cc2)CC1)N1CCN(Cc2ccc(Cl)cc2)CC1 | [OH-].[Na+].ClC1=CC=C(CN2CCNCC2)C=C1.C(CC(=O)Cl)(=O)Cl.C(Cl)Cl>>O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)C(CC(=O)N2CCN(CC2)CC2=CC=C(C=C2)Cl)=O)C=C1 | Cl[CH2:35][Cl:32].[NH:9]1[CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1.[Cl:1][C:36]([CH2:6][C:5]([Cl:2])=[O:4])=[O:8].[OH-:3]>>[ClH:1].[ClH:2].[OH2:3].[O:4]=[C:5]([CH2:6][C:7](=[O:8])[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c... | ClCCl.Clc1ccc(CN2CCNCC2)cc1.O=C(Cl)CC(=O)Cl.[OH-] | Cl.Cl.O.O=C(CC(=O)N1CCN(Cc2ccc(Cl)cc2)CC1)N1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | ac379cbfa9f2e1769d6f1c27fb3ebb1edfecdf976ffc21a437ef9644b50637c7 | 41623b51c86655a69083ebffce0dd73032f5ac63ff2ccd2898fe0580e61913f7 | O=C(CC(=O)N1CCN(Cc2ccccc2)CC1)N1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[Cl;H0;D1;+0:2].[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[Cl;H0;D1;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[CH2;D2;+0:12]-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;D1;H0:15].[OH-;D0:16]>>[C:17]-[#7:18]1-[C:19]-[C:20]-[#7:21](-[C;H0;D3;+0:13](=[O;D1;H0:15])-[CH2;D2;+0:12]-[C:22](=[O;H0;D1;+0:11])-[N;H... | 45.1 | [{"value": 22.0, "product": "O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)C(CC(=O)N2CCN(CC2)CC2=CC=C(C=C2)Cl)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.1, "product": "O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)C(CC(=O)N2CCN(CC2)CC2=CC=C(C=C2)Cl)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | A mixture of 4.2 g of 1-(4-chlorobenzyl)piperazine, 1.4 g of malonyl dichloride, 10 g of methylene chloride and 2.0 g of triethylamine was stirred for 60 hours. The reaction mixture was made basic with 2N sodium hydroxide. The organic layer was separated, and the aqueous phase was extracted with three 50 ml portions of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary halide.Primary halide.Secondary amine | Aromatic halide.Tertiary amide.Tertiary amide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)N(CC)CC | null | 60 | ClCCl.Clc1ccc(CN2CCNCC2)cc1.O=C(Cl)CC(=O)Cl.[OH-]>C(C)N(CC)CC>Cl.Cl.O.O=C(CC(=O)N1CCN(Cc2ccc(Cl)cc2)CC1)N1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-17ee4450157049288fbf93d876e000e4 | CC(c1ccccc1)N1CCNCC1.ClCCCBr>>CC(c1ccccc1)N1CCN(CCCN2CCN(C(C)c3ccccc3)CC2)CC1.Cl.Cl.Cl.Cl | C1(=CC=CC=C1)C(C)N1CCNCC1.BrCCCCl>>Cl.Cl.Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCN1CCN(CC1)C(C)C1=CC=CC=C1 | [NH:9]1[CH2:17][CH2:18][N:19]([CH:20]([CH3:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1.Br[CH2:2][CH2:14][CH2:1][Cl:32]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH:20]([CH3:21])[c:22]3[cH:23][cH:24][cH:2... | CC(c1ccccc1)N1CCNCC1.ClCCCBr | CC(c1ccccc1)N1CCN(CCCN2CCN(C(C)c3ccccc3)CC2)CC1.Cl.Cl.Cl.Cl | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 6e158a54a631fccf88355586f2945a2595f247424e72404e0ad4bd3708ba00d6 | c7e09259e1b5abfe3121d0f0f4968272fe438d5dd27de348d3ddb2af70014c90 | c1ccc(CN2CCN(CCCN3CCN(Cc4ccccc4)CC3)CC2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[#7:6]1-[C:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-1>>[C:5]-[#7:6]1-[C:7]-[CH2;D2;+0:8]-[#7:12](-[C:13]-[CH2;D2;+0:2]-[C:14]-[#7:15]2-[C:16]-[C:17]-[N;H0;D3;+0:9](-[CH;D3;+0:1](-[CH3;D1;+0:3])-[c:18](:[c:19]):[c:20])-[C:21]-[C:22]-2)-[CH2;D2... | 211.9 | [{"value": 51.0, "product": "Cl.Cl.Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCN1CCN(CC1)C(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 211.9, "product": "Cl.Cl.Cl.Cl.C1(=CC=CC=C1)C(C)N1CCN(CC1)CCCN1CCN(CC1)C(C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7.6 g of 1-(1-phenylethyl)piperazine, 3.2 g of 1-bromo-3-chloropropane and 50 ml of reagent ethanol was refluxed for 5 hours. The solvent was then removed under vacuum, 75 ml of water were added, and the mixture was extracted with ether (3×150 ml). The ether extract was evaporated to an oil and chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Tertiary amine.Tertiary amine.Tertiary amine | C1CNCC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | Br- | C(C)O | null | null | CC(c1ccccc1)N1CCNCC1.ClCCCBr>C(C)O>CC(c1ccccc1)N1CCN(CCCN2CCN(C(C)c3ccccc3)CC2)CC1.Cl.Cl.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7341df2adb3541c79cb658048cb382de | CO.ClCCCBr.ClCCl.Clc1cccc(CN2CCNCC2)c1.[NH4+].[OH-]>>Cl.Clc1cccc(CN2CCN(CCCN3CCN(Cc4cccc(Cl)c4)CC3)CC2)c1.O | C(Cl)Cl.CO.[OH-].[NH4+].ClC=1C=C(CN2CCNCC2)C=CC1.BrCCCCl.Cl>>O.Cl.Cl.ClC=1C=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC(=CC=C2)Cl)C=CC1 | O[CH3:28].Br[CH2:30][CH2:15][CH2:14][Cl:27].Cl[CH2:21][Cl:1].[Cl:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][N:10]2[CH2:11][CH2:12][NH:13][CH2:31][CH2:32]2)[cH:33]1.[NH4+:17].[OH-:34]>>[ClH:1].[Cl:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][N:20]([CH2... | CO.ClCCCBr.ClCCl.Clc1cccc(CN2CCNCC2)c1.[NH4+].[OH-] | Cl.Clc1cccc(CN2CCN(CCCN3CCN(Cc4cccc(Cl)c4)CC3)CC2)c1.O | null | null | C(C)O.O.C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | aa370d01081fc4e3cf6d3649b69e93c12fb8744fad75b2065fbda06b71b922b3 | 53faa84b34b0ef284a224692dfeee7f31714383e2d662b7a0243dcf1398f2ce0 | c1ccc(CN2CCN(CCCN3CCN(Cc4ccccc4)CC3)CC2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].Cl-[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].O-[CH3;D1;+0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1.[NH4+;D0:14].[OH-;D0:15]>>[Cl;H0;D1;+0:4]-[c:16](:[c:17]):[cH;D2;+0:7]:[c:18](-[CH2;D2;+0:5]-[#7:19]1-[C:20]-[C:21]-[N;H0;D3;+0:14](-[C:22]-[CH2;D2;+0:2]-[CH2;... | 68 | [{"value": 68.0, "product": "O.Cl.Cl.ClC=1C=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC(=CC=C2)Cl)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6.3 g of 1-(3-chlorobenzyl)piperazine, 2.4 g of 1-bromo-3-chloropropane, 50 ml of reagent ethanol and 3.0 g of triethylamine was refluxed for 4 hours. Water (70 ml) was added, and the mixture was concentrated under vacuum to about 70 ml. The resulting aqueous mixture was extracted with ether (3×150 ml), an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary halide.Primary halide.Secondary amine.Methanol | Aromatic halide.Tertiary amine.Tertiary amine.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | Br- | C(C)O.O.C(C)N(CC)CC | null | null | CO.ClCCCBr.ClCCl.Clc1cccc(CN2CCNCC2)c1.[NH4+].[OH-]>C(C)O.O.C(C)N(CC)CC>Cl.Clc1cccc(CN2CCN(CCCN3CCN(Cc4cccc(Cl)c4)CC3)CC2)c1.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-35f81a39a06a45d1ab9c40a8e88e5022 | COc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(OC)cc4)CC3)CC2)cc1>>Oc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(O)cc4)CC3)CC2)cc1 | COC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)OC)C=C1.Br>>OC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)O)C=C1 | C[O:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([CH2:18][c:19]4[cH:20][cH:21][c:22]([O:23]C)[cH:24][cH:25]4)[CH2:26][CH2:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][... | COc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(OC)cc4)CC3)CC2)cc1 | Oc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(O)cc4)CC3)CC2)cc1 | null | null | O | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(CN2CCN(CCCN3CCN(Cc4ccccc4)CC3)CC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 31 | [{"value": 31.0, "product": "OC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.8, "product": "OC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.5 g of 1,3-bis[4-(4-methoxybenzyl)-1-piperazinyl]propane from Example 19 and 125 ml of 49% hydrobromic acid was refluxed for 2 hours and was then cooled and diluted with 125 ml of water. After filtration the aqueous solution was neutralized with 2N sodium hydroxide to adjust the pH to 8. The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1 | Other | O | null | null | COc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(OC)cc4)CC3)CC2)cc1>O>Oc1ccc(CN2CCN(CCCN3CCN(Cc4ccc(O)cc4)CC3)CC2)cc1 |
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