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-58de8242ae774164a8154c623f6db4b7 | Nc1nc(Cl)cc(CCl)n1>>Cl.Nc1nc(Cl)cc(CCl)n1 | NC1=NC(=CC(=N1)Cl)CCl>>Cl.NC1=NC(=CC(=N1)Cl)CCl | [Cl:1][c:5]1[n:4][c:3]([NH2:2])[n:11][c:8]([CH2:9][Cl:10])[cH:7]1>>[ClH:1].[NH2:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][c:8]([CH2:9][Cl:10])[n:11]1 | Nc1nc(Cl)cc(CCl)n1 | Cl.Nc1nc(Cl)cc(CCl)n1 | null | null | Cl.C(C)OCC | Functional Group Addition | OtherReaction | d1940a01ac09b52e3df5605eae2f2b54e1dcf3b3f31d49daef712f84cd8407da | 17a9a6e76f23306269dfc9ff7cfb24ac0056e82d505bd97a13af06a0d24be036 | c1cncnc1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[c:8]:1>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6](-[Cl;D1;H0:9]):[c:8]:1.[ClH;D0;+0:7] | null | [] | null | null | null | null | 3.56 Parts of 2-amino-4-chloro-6-chloromethylpyrimidine was dissolved in 53 parts of dry diethyl ether and dry hydrogen chloride was bubbled through the solution, with stirring, until no further solid precipitated the solid was filtered, washed with ether and dried in vacuo. Recrystallisation from acetone gave 2-amino-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | Cl.C(C)OCC | null | null | Nc1nc(Cl)cc(CCl)n1>Cl.C(C)OCC>Cl.Nc1nc(Cl)cc(CCl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf45258a6b514b10a95b14738e45793c | Nc1nc(Cl)cc(CCl)n1.OCC(F)(F)F>>Nc1nc(CCl)cc(OCC(F)(F)F)n1 | [Na].NC1=NC(=CC(=N1)Cl)CCl.FC(CO)(F)F.[Na].FC(CO)(F)F.[Na].FC(CO)(F)F>>NC1=NC(=CC(=N1)CCl)OCC(F)(F)F | Cl[c:8]1[cH:7][c:4]([CH2:5][Cl:6])[n:3][c:2]([NH2:1])[n:15]1.[OH:9][CH2:10][C:11]([F:12])([F:13])[F:14]>>[NH2:1][c:2]1[n:3][c:4]([CH2:5][Cl:6])[cH:7][c:8]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])[n:15]1 | Nc1nc(Cl)cc(CCl)n1.OCC(F)(F)F | Nc1nc(CCl)cc(OCC(F)(F)F)n1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C:13]-[OH;D1;+0:14]>>[C:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:14]-[C:13]-[C:10](-[F;D1;H0:9])(-[F;D1;H0:11])-[F;D1;H0:12]):[c:8]:1 | null | [] | null | null | 24 | HOUR | 0.23 Parts of sodium metal was added to 10 parts of 2,2,2-trifluoroethanol with stirring and ice-bath cooling. The mixture was then stirred for several hours at room temperature until the sodium dissolved. This solution was added dropwise, over 30 minutes, to a stirred suspension of 1.78 parts of 2-amino-4-chloro-6-chl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | 24 | Nc1nc(Cl)cc(CCl)n1.OCC(F)(F)F>>Nc1nc(CCl)cc(OCC(F)(F)F)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f197a439b25842d9882c6684168e87b0 | CC(=O)O.Nc1nc(F)cc(CF)n1>>Nc1nc(CF)cc(=O)[nH]1 | NC1=NC(=CC(=N1)F)CF.C(C)(=O)O>>NC1=NC(=CC(N1)=O)CF | CC(O)=[O:9].F[c:8]1[cH:7][c:4]([CH2:5][F:6])[n:3][c:2]([NH2:1])[n:10]1>>[NH2:1][c:2]1[n:3][c:4]([CH2:5][F:6])[cH:7][c:8](=[O:9])[nH:10]1 | CC(=O)O.Nc1nc(F)cc(CF)n1 | Nc1nc(CF)cc(=O)[nH]1 | null | null | null | Miscellaneous | OtherReaction | 3b7c95cff8de3cd2e8ffb0a3fe87e5fae048784c0c2b684cb461784c32c32a67 | 3fbb180061815c1a91daf750f59d95354663c01e4c6076719644d5369bdccd52 | O=c1ccnc[nH]1 | C-C(-O)=[O;H0;D1;+0:1].F-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5]):[#7;a:6]:[c:7](-[N;D1;H2:8]):[n;H0;D2;+0:9]:1>>[C:5]-[c:4]1:[#7;a:6]:[c:7](-[N;D1;H2:8]):[nH;D2;+0:9]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[c:3]:1 | null | [] | null | null | null | null | 12.1 Parts of 2-amino-4-fluoro-6-fluoromethylpyrimidine was dissolved in 200 parts of 20% aqueous acetic acid at reflux, with stirring. The mixture was heated under reflux for 1 hour then cooled. The precipitated solid was filtered, washed with 50% aqueous acetic acid and then with acetone. The solid was dried in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | null | c1cncnc1 | c1ccncn1 | c1ccncn1 | HF | null | null | null | CC(=O)O.Nc1nc(F)cc(CF)n1>>Nc1nc(CF)cc(=O)[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5d15bfc6ae942d6b4900629eb592e0d | C=C(C=O)CC.CCOC(=O)C(=O)C(Cl)C(=O)OCC>>CCOC(=O)c1cc(CC)cnc1C(=O)OCC | CCC(=C)C=O.ClC(C(C(=O)OCC)=O)C(=O)OCC.S(N)([O-])(=O)=O.[NH4+]>>C(C)C=1C=C(C(=NC1)C(=O)OCC)C(=O)OCC | O=[CH:11][C:8](=[CH2:7])[CH2:9][CH3:10].O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:13](Cl)[C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][CH3:10])[cH:11][n:12][c:13]1[C:14](=[O:15])[O:16][CH2:17][CH3:18] | C=C(C=O)CC.CCOC(=O)C(=O)C(Cl)C(=O)OCC | CCOC(=O)c1cc(CC)cnc1C(=O)OCC | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 2edc089f0cf3d74f926b313035f603af8b9dbbd4bbfd77c6cb95812815e3bdbc | 031be6cc4a6b7d786406b9d5538993031d67614bb0af3fd8596c6810f77e773b | c1ccncc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C;H0;D3;+0:6](=O)-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].O=[CH;D2;+0:11]-[C;H0;D3;+0:12](=[CH2;D1;+0:13])-[C:14]-[C;D1;H3:15]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[#7;a:16]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[C:14]-[C;D1;H3:15]):[cH;D2;+0:13]:[c;H0;D3;+0:6]:1-[C:7... | 86 | [{"value": 75.0, "product": "C(C)C=1C=C(C(=NC1)C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "C(C)C=1C=C(C(=NC1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of ethacrolein, (4.2 g, 0.05 mol), diethyl 3-chloro-2-oxo-butanedioate, (11.2 g, 0.05 mol) and ammonium sulfamate, (15.4 g, 0.135 mol) in ethanol (37 mL) is heated at reflux. After 15 hours the mixture is cooled to room temperature and the solvent removed by distillation under reduced pressure. The re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ketone.Ester.Ester.Vinyl | Ester.Ester | null | c1ccncc1 | c1ccncc1 | HCl | C(C)O | null | null | C=C(C=O)CC.CCOC(=O)C(=O)C(Cl)C(=O)OCC>C(C)O>CCOC(=O)c1cc(CC)cnc1C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-24c7674dbf2448ab81e3a4fd1d43e7e8 | C=C(C=O)CC.CCOC(=O)C(Cl)C(C)=O.[NH4+]>>CCOC(=O)c1cc(CC)cnc1C | ClC(C(=O)OCC)C(=O)C.CCC(=C)C=O.C(C)(=O)[O-].[NH4+]>>C(C)C=1C=NC(=C(C(=O)OCC)C1)C | O=[CH:11][C:8](=[CH2:7])[CH2:9][CH3:10].O=[C:13]([CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:14].[NH4+:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][CH3:10])[cH:11][n:12][c:13]1[CH3:14] | C=C(C=O)CC.CCOC(=O)C(Cl)C(C)=O.[NH4+] | CCOC(=O)c1cc(CC)cnc1C | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | f9585c7c68d542c10f95249baa99b49f3eb5eb2f7f39cc3cffeb1fea794f841a | 4d3898f38879d7ebd900b51d85b456d661d4903a7d4362d5e83549b9252e0e9c | c1ccncc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C;H0;D3;+0:6](=O)-[C;D1;H3:7].O=[CH;D2;+0:8]-[C;H0;D3;+0:9](=[CH2;D1;+0:10])-[C:11]-[C;D1;H3:12].[NH4+;D0:13]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[cH;D2;+0:10]:[c;H0;D3;+0:9](-[C:11]-[C;D1;H3:12]):[cH;D2;+0:8]:[n;H0;D2;+0:13]:[c;H0;D3;+0:6]:1-[C;D1;H3:7] | 43.2 | [{"value": 43.2, "product": "C(C)C=1C=NC(=C(C(=O)OCC)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of ethacrolein (12.8 g 0.152 mole) and ammonium acetate (24.4 g 0.304 mole) in 50 cc acetonitrile is stirred at room temperature and a solution of ethyl 2-chloroacetoacetate (25 g 0.152 mole) in 30 cc acetonitrile is added dropwise over 15 minutes. The reaction mixture is heated at reflux for 16 hours, cooled... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ketone.Ester.Vinyl | Ester | null | c1ccncc1 | c1ccncc1 | HCl | C(C)#N | null | null | C=C(C=O)CC.CCOC(=O)C(Cl)C(C)=O.[NH4+]>C(C)#N>CCOC(=O)c1cc(CC)cnc1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3f1521d404b14cd4bf43a059b7950a8c | CCOC(C)(OCC)OCC.O=C1CCC(=O)N1Cl>>CCOC(CCl)(OCC)OCC | C(C)OC(C)(OCC)OCC.ClN1C(CCC1=O)=O>>ClCC(OCC)(OCC)OCC | [CH3:1][CH2:2][O:3][C:4]([CH3:5])([O:7][CH2:8][CH3:9])[O:10][CH2:11][CH3:12].O=C1CCC(=O)N1[Cl:6]>>[CH3:1][CH2:2][O:3][C:4]([CH2:5][Cl:6])([O:7][CH2:8][CH3:9])[O:10][CH2:11][CH3:12] | CCOC(C)(OCC)OCC.O=C1CCC(=O)N1Cl | CCOC(CCl)(OCC)OCC | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | null | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#8:2]-[C:3](-[#8:4])(-[#8:5])-[CH3;D1;+0:6]>>[#8:2]-[C:3](-[#8:4])(-[#8:5])-[CH2;D2;+0:6]-[Cl;H0;D1;+0:1] | 77.1 | [{"value": 77.1, "product": "ClCC(OCC)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | A mixture of 1,1,1-triethoxyethane (97.3 g) and N-chlorosuccinimide (88.1 g) in carbon tetrachloride (600 ml) was warmed to 40° C. and then irradiated with an ultraviolet lamp. The reaction became exothermic and then subsided upon completion of the reaction. The precipitated succinimide byproduct was filtered off and t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | null | HO- | C(Cl)(Cl)(Cl)Cl | 40 | null | CCOC(C)(OCC)OCC.O=C1CCC(=O)N1Cl>C(Cl)(Cl)(Cl)Cl>CCOC(CCl)(OCC)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7628ca281c8a4d939d7e63b118d19a45 | CCOC(CCl)(OCC)OCC.Nc1ccccc1S>>ClCc1nc2ccccc2s1 | ClCC(OCC)(OCC)OCC.NC1=C(C=CC=C1)S>>ClCC=1SC2=C(N1)C=CC=C2 | CCO[C:3](OCC)(OCC)[CH2:2][Cl:1].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[SH:11]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[s:11]1 | CCOC(CCl)(OCC)OCC.Nc1ccccc1S | ClCc1nc2ccccc2s1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | e5de7d300d69c2376e3c88b0ae7fe3f3606b9c04481bceab4001fddf2019dd6b | 44a67a3a6c22a911b9c94dbc9f3bdf155445bc6d1029e88ffe99c89ac7b0fcbd | c1ccc2scnc2c1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[SH;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[s;H0;D2;+0:8]:1 | 91.3 | [{"value": 90.0, "product": "ClCC=1SC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "ClCC=1SC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-chloro-1,1,1-triethoxyethane (5.9 g) and 2-aminothiophenol (2.5 g) was heated at 80° C. for 15 minutes. After cooling to room temperature, it was dissovled in methylene chloride (30 ml) and the resulting solution was washed with 3N HCl (10 ml) and then with water (20 ml). The organic portion was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Aromatic thiol | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HO- | C(Cl)Cl | null | null | CCOC(CCl)(OCC)OCC.Nc1ccccc1S>C(Cl)Cl>ClCc1nc2ccccc2s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-17f6266b5d2e48cc810a4fc82883f5f9 | CCOC(CCl)(OCC)OCC.Nc1cc(C(F)(F)F)ccc1S>>FC(F)(F)c1ccc2sc(CCl)nc2c1 | Cl.NC1=C(C=CC(=C1)C(F)(F)F)S.ClCC(OCC)(OCC)OCC>>ClCC=1SC2=C(N1)C=C(C=C2)C(F)(F)F | CCO[C:10](OCC)(OCC)[CH2:11][Cl:12].[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([SH:9])[c:14]([NH2:13])[cH:15]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[s:9][c:10]([CH2:11][Cl:12])[n:13][c:14]2[cH:15]1 | CCOC(CCl)(OCC)OCC.Nc1cc(C(F)(F)F)ccc1S | FC(F)(F)c1ccc2sc(CCl)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e5de7d300d69c2376e3c88b0ae7fe3f3606b9c04481bceab4001fddf2019dd6b | 44a67a3a6c22a911b9c94dbc9f3bdf155445bc6d1029e88ffe99c89ac7b0fcbd | c1ccc2scnc2c1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[SH;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[s;H0;D2;+0:8]:1 | null | [] | 60 | CELSIUS | null | null | To a solution of 2-amino-4-trifluoromethylthiophenol hydrochloride (30.0 g) in ethanol (125 ml) was added 2-chloro-1,1,1-triethoxyethane (31.0 g). The mixture was heated for 1 hour at 60° C. The solution was concentrated to remove excess ethanol and the resulting material was extracted with ether (500 ml). The organic ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Aromatic thiol | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HO- | C(C)O | 60 | null | CCOC(CCl)(OCC)OCC.Nc1cc(C(F)(F)F)ccc1S>C(C)O>FC(F)(F)c1ccc2sc(CCl)nc2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3b3a232422e4466d95c7b4b7201b4772 | CCOC(CCl)(OCC)OCC.Nc1ncccc1O>>ClCc1nc2ncccc2o1 | NC1=NC=CC=C1O.ClCC(OCC)(OCC)OCC>>ClCC=1OC=2C(=NC=CC2)N1 | CCO[C:3](OCC)(OCC)[CH2:2][Cl:1].[NH2:4][c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[o:11]1 | CCOC(CCl)(OCC)OCC.Nc1ncccc1O | ClCc1nc2ncccc2o1 | null | null | COCCOCCOC | Aromatic Heterocycle Formation | OtherReaction | a0990bb4e7f817e6bf9be55f3921a93abc6ed2173d18d4ab75597c6e27d9ecb7 | c16599c740ea3f3fc3d426822f92336b603c74c8c928d30d81021f33dd59c81e | c1cnc2ncoc2c1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[#7;a:6]:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[#7;a:6]:[c:7]):[c:8](:[c:10]):[o;H0;D2;+0:9]:1 | null | [] | null | null | 1 | HOUR | The commercially available 2-amino-3-hydroxypyridine (5.0 g) and diglyme (30 ml) were heated at 125° C. to obtain a solution. To this solution was added 2-chloro-1,1,1-triethoxyethane (9.9 g) and the mixture was held at 125° for 1 hour. The solution was cooled to room temperature and then decanted to remove a black byp... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Aromatic alcohol.Primary amine | null | c1ccncc1 | c1cnc2ncoc2c1 | c1cnc2ncoc2c1 | HO- | COCCOCCOC | null | 1 | CCOC(CCl)(OCC)OCC.Nc1ncccc1O>COCCOCCOC>ClCc1nc2ncccc2o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a0090fb00f2643b09c4adc1174b6350e | CCOC(CCl)(OCC)OCC.Nc1cccnc1S>>ClCc1nc2cccnc2s1 | NC=1C(=NC=CC1)S.ClCC(OCC)(OCC)OCC>>ClCC=1SC2=NC=CC=C2N1 | CCO[C:3](OCC)(OCC)[CH2:2][Cl:1].[NH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[SH:11]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[s:11]1 | CCOC(CCl)(OCC)OCC.Nc1cccnc1S | ClCc1nc2cccnc2s1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | b14c287969b5debc7a31532cc558397dd33d720112885e27237cc2dd5d862e8d | 44a67a3a6c22a911b9c94dbc9f3bdf155445bc6d1029e88ffe99c89ac7b0fcbd | c1cnc2scnc2c1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[SH;D1;+0:8]):[#7;a:9]:[c:10]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[#7;a:9]:[c:10]):[s;H0;D2;+0:8]:1 | null | [] | null | null | null | null | A mixture of 3-amino-2-mercaptopyridine (3.6 g) prepared by the method of J. Org. Chem., 29, 2652 (1963), 2-chloro-1,1,1-triethoxyethane (6.5 g) and ethanol (60 ml) was heated at 60° C. for 4 hours. The crude solid resulting from evaporation of ethanol was chromatographed over silica gel to obtain the product (2.94 g; ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Aromatic thiol | null | c1ccncc1 | c1cnc2scnc2c1 | c1cnc2scnc2c1 | HO- | C(C)O | null | null | CCOC(CCl)(OCC)OCC.Nc1cccnc1S>C(C)O>ClCc1nc2cccnc2s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8ec63ae82f0647afb2a58c8cce47600d | CCOC(CCl)(OCC)OCC.Nc1cc(Br)ccc1O>>ClCc1nc2cc(Br)ccc2o1 | NC1=C(C=CC(=C1)Br)O.ClCC(OCC)(OCC)OCC.O>>ClCC=1OC2=C(N1)C=C(C=C2)Br | CCO[C:3](OCC)(OCC)[CH2:2][Cl:1].[NH2:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[o:12]1 | CCOC(CCl)(OCC)OCC.Nc1cc(Br)ccc1O | ClCc1nc2cc(Br)ccc2o1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 22263c679cc4586638d130d5749e20740a2d5276fbcb003941512c86e7729e99 | c16599c740ea3f3fc3d426822f92336b603c74c8c928d30d81021f33dd59c81e | c1ccc2ocnc2c1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[Cl;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:1 | null | [] | null | null | null | null | 2-Amino-4-bromophenol (1.6 g) prepared according to U.S. Pat. No. 4,157,444 was dissolved in ethanol (5 ml) and 2-chloro-1,1,1-triethoxyethane (1.9 g) was added. The resulting solution was warmed on a steambath for 1.5 hour. After cooling the reaction mixture to room temperature, cold water (5 ml) was added. The precip... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | C(C)O | null | null | CCOC(CCl)(OCC)OCC.Nc1cc(Br)ccc1O>C(C)O>ClCc1nc2cc(Br)ccc2o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d3c2e62310254be1a1f64db4e6e7ec04 | CN(C)C=O.Sc1ccncc1>>O=C(O)c1cccnc1 | SC1=CC=NC=C1.[H-].[Na+].C1CCOC1.CN(C)C=O.SC1=CC=NC=C1.[Na]>>N1=CC(=CC=C1)C(=O)O | CN(C)[CH:2]=[O:1].S[c:4]1[cH:5][cH:6]nc[cH:9]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | CN(C)C=O.Sc1ccncc1 | O=C(O)c1cccnc1 | null | null | C1CCOC1.O | Acylation | OtherReaction | c39d3efd7e4acdb5c69e49c55f7c72e51c817aa0502d4f2236b6fdab5c6a070f | f54852146dfbc6b8aa408820ffdbd7a8df82680872aac9a04c20cc6ecd3fbb4a | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].S-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:n:c:[cH;D2;+0:6]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;D1;H1:7])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[c:8]:[#7;a:9]:[cH;D2;+0:6]:1 | null | [] | null | null | 1 | HOUR | 5.2 g of 90% pyridinium bromide perbromide was added in one portion to a solution of 5 g of 3-pyridinecarboxylic acid, 5-cyano-1,4-dihydro-2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-, ethyl ester and 1.2 ml pyridine in 150 ml of dry ethanol-free CHCl3 at -10° C. The mixture was stirred for 45 minutes at 0° C. and the b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aromatic thiol | Carboxylic acid | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C1CCOC1.O | null | 1 | CN(C)C=O.Sc1ccncc1>C1CCOC1.O>O=C(O)c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b143fd1c6e2c4163886e3bd89953e57f | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O>>CCOC(=O)CC(=O)c1ccc(C)nc1 | C(C)(=O)OCC.Cl.C(C)OC(C1=CN=C(C=C1)C)=O.C(C)OC(C1=CN=C(C=C1)C)=O.C[O-].[Na+]>>C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O | CCO[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1 | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O | CCOC(=O)CC(=O)c1ccc(C)nc1 | null | null | C1(=CC=CC=C1)C.O | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[#8:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:12])-[CH2;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 33.6 | [{"value": 33.6, "product": "C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | 35.8 g (0.52 mol) of sodium methylate and 200 ml of toluene were put in a 750-ml sulfonation flask. The reaction mixture was heated to reflux temperature. A mixture of 55.7 g (0.33 mol) of 6-methyl nicotinic acid ethyl ester (produced according to Swiss Pat. No. 654 577) and 60.3 g (0.68 mol) of ethyl acetate was added... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccncc1 | HO- | C1(=CC=CC=C1)C.O | 20 | null | CCOC(=O)c1ccc(C)nc1.CCOC(C)=O>C1(=CC=CC=C1)C.O>CCOC(=O)CC(=O)c1ccc(C)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f2864fc6aa97413c9046a412cd850dc6 | CCOC(=O)CC(=O)c1ccc(C)nc1>>CCOC(=O)CC(O)c1ccc(C)nc1 | C(C)OC(CC(C1=CN=C(C=C1)C)=O)=O.[H][H]>>C(C)OC(CC(C=1C=CC(=NC1)C)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]1 | CCOC(=O)CC(=O)c1ccc(C)nc1 | CCOC(=O)CC(O)c1ccc(C)nc1 | null | [Pd] | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccncc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | 20 | CELSIUS | 6 | HOUR | 10.0 g (0.048 mol) of 6-methyl nicotinoyl acetic acid ethyl ester (distilled) was dissolved in 200 ml of 95 percent ethanol, mixed with 1 g of 5 percent palladium on activated carbon and poured into a 1-liter autoclave. The autoclave was put under 10 bars of hydrogen and stirred at 20° C. The hydrogenation ended after ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccncc1 | null | [Pd].C(C)O | 20 | 6 | CCOC(=O)CC(=O)c1ccc(C)nc1>[Pd].C(C)O>CCOC(=O)CC(O)c1ccc(C)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3cc606c8ff664f87bf65e6251ceebc09 | COC(=O)CC(O)c1ccc(C)nc1>>COC(=O)CCc1ccc(C)nc1 | CO.C(C)(=O)OC(C)=O.COC(CC(C=1C=CC(=NC1)C)O)=O.[H][H]>>COC(CCC=1C=CC(=NC1)C)=O | O[CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]1 | COC(=O)CC(O)c1ccc(C)nc1 | COC(=O)CCc1ccc(C)nc1 | null | [Pd] | C(C)(=O)O.C1(=CC=CC=C1)C | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccncc1 | O-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | 114 | [{"value": 114.0, "product": "COC(CCC=1C=CC(=NC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | 80.0 g (0.35 mol) of recrystallized 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid methyl ester was dissolved in 100 ml of toluene. 60.0 g (0.588 mol) of acetic anhydride and 0.1 g (0.0009 mol) of 4-dimethyl-aminopyridine were added, and the solution was stirred for 1 hour at 60° C. Then 20 ml of methanol was added. A... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccncc1 | Other | [Pd].C(C)(=O)O.C1(=CC=CC=C1)C | 60 | 1 | COC(=O)CC(O)c1ccc(C)nc1>[Pd].C(C)(=O)O.C1(=CC=CC=C1)C>COC(=O)CCc1ccc(C)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-51ef9f6ae2d14a58b7d97c8023ad50fd | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1>>CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 | [OH-].[Na+].C(C)OC(CC(C=1C=CC(=NC1)C)O)=O.C(C)(=O)OC(C)=O.N1=CC=CC=C1>>C(C)OC(CC(C=1C=CC(=NC1)C)OC(C)=O)=O | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[n:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([O:8][C:9]([CH3:10])=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[n:17][cH:18]1 | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1 | CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 | null | CN(C1=CC=NC=C1)C | null | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccncc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[c:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]>>[#7;a:4]:[c:5]:[c:6]-[C:7](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12])-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 90.4 | [{"value": 90.4, "product": "C(C)OC(CC(C=1C=CC(=NC1)C)OC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.3 g (0.021 mol) of 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester, 3.0 g (0.03 mol) of acetic anhydride, 2.7 g (0.034 mol) of pyridine and 0.17 g (0.0017 mol) of 4-dimethylaminopyridine were stirred at 0° C. for 24 hours. The solution was mixed with 25 ml of 5 percent sodium hydroxide solution and extrac... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C | null | null | CC(=O)OC(C)=O.CCOC(=O)CC(O)c1ccc(C)nc1>CN(C1=CC=NC=C1)C>CCOC(=O)CC(OC(C)=O)c1ccc(C)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-af619c8be0ee4e34923575da7dc53150 | CCCCCCCCc1ccc(-c2ccc(OC)cc2)nc1>>CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1 | COC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC.Br.O>>OC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC | C[O:17][c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:21][n:20]2)[cH:19][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]2)[n:20][cH:21]1 | CCCCCCCCc1ccc(-c2ccc(OC)cc2)nc1 | CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1 | null | null | C(C)(=O)O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The 2-(p-methoxyphenyl)-5-octylpyridine was dissolved in 100 ml of acetic acid. 8 ml of 48% hydrobromic acid was added to the reaction solution and the solution was heated for 15 hours under reflux. 100 ml of water was added to the reaction solution and the organic layer was extracted with chloroform. After washing the... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccncc1.c1ccccc1 | Other | C(C)(=O)O | null | null | CCCCCCCCc1ccc(-c2ccc(OC)cc2)nc1>C(C)(=O)O>CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-db779db8732644f49d9a577c43124856 | CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1.CCCCCC[C@@H](C)CCCBr>>CCCCCCCCc1ccc(-c2ccc(OCCC[C@H](C)CCCCCC)cc2)nc1 | [OH-].[Na+].OC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC.BrCCC[C@@H](CCCCCC)C>>C[C@@H](CCCOC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC)CCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:29][cH:30]2)[n:31][cH:32]1.Br[CH2:18][CH2:19][CH2:20][C@H:21]([CH3:22])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11... | CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1.CCCCCC[C@@H](C)CCCBr | CCCCCCCCc1ccc(-c2ccc(OCCC[C@H](C)CCCCCC)cc2)nc1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 47.1 | [{"value": 47.1, "product": "C[C@@H](CCCOC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC)CCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 20 ml of a 30% aqueous solution of sodium hydroxide was added dropwise to a mixture of 2 g (0.007 mol) of 2-(p-hydroxyphenyl)-5-octylpyridine and 1.65 g (0.007 mol) of (R)-1-bromo-(4-methyl)decane with stirring. The resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours. 150 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccccc1 | HBr | O | null | null | CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1.CCCCCC[C@@H](C)CCCBr>O>CCCCCCCCc1ccc(-c2ccc(OCCC[C@H](C)CCCCCC)cc2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3e38851339f345daa2b27e8a83160009 | CCCCCCCCc1ccc(-c2ccc(Br)cc2)nc1>>CCCCCCCCc1ccc(-c2ccc(C#N)cc2)nc1 | Cl.CN1C(CCC1)=O.BrC1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC.[Cu]C#N>>C(#N)C1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC | Br[c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:22][n:21]2)[cH:20][cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]2)[n:21][cH:22]1 | CCCCCCCCc1ccc(-c2ccc(Br)cc2)nc1 | CCCCCCCCc1ccc(-c2ccc(C#N)cc2)nc1 | null | [Fe](Cl)Cl | O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 94 ml of N-methylpyrrolidone was added to the 47.6 g (0.138 mol) of the 2-(p-bromophenyl)-5-octylpyridine. Then 19.3 g (0.216 mol) of copper (I) cyanide was added and the solution was refluxed for 2 hours. A mixture of 69 g of iron (II) chloride, 13.8 ml of concentrated hydrochloric acid and 69 ml of water was added to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | Br- | [Fe](Cl)Cl.O | null | null | CCCCCCCCc1ccc(-c2ccc(Br)cc2)nc1>[Fe](Cl)Cl.O>CCCCCCCCc1ccc(-c2ccc(C#N)cc2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c2ce3ae82b19475192f1d27047229762 | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)nc1.O=S(Cl)Cl>>CCCCCCCCc1ccc(-c2ccc(C(=O)Cl)cc2)nc1.Cl | C(CCCCCCC)C=1C=CC(=NC1)C1=CC=C(C(=O)O)C=C1.S(=O)(Cl)Cl>>Cl.C(CCCCCCC)C=1C=CC(=NC1)C1=CC=C(C(=O)Cl)C=C1 | O[C:17]([c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:23][n:22]2)[cH:21][cH:20]1)=[O:18].O=S([Cl:19])[Cl:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17](=[O:18])[Cl:19])[cH:... | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)nc1.O=S(Cl)Cl | CCCCCCCCc1ccc(-c2ccc(C(=O)Cl)cc2)nc1.Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=S(-[Cl;H0;D1;+0:6])-[Cl;H0;D1;+0:7]>>[Cl;H0;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[ClH;D0;+0:7] | 96.7 | [{"value": 96.7, "product": "Cl.C(CCCCCCC)C=1C=CC(=NC1)C1=CC=C(C(=O)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 30 g (0.102 mol) of the resulting p-(5-octylpyridyl)benzoic acid was added to 24.3 g (0.204 mol) of thionyl chloride and reflux was maintained for 5 hours. The surplus thionyl chloride was removed by distillation and the product was recrystallized from hexane to obtain 34.5 g (0.0986 mol) of p-(5-octylpyridyl)benzoylch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1ccccc1 | Other | null | null | null | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)nc1.O=S(Cl)Cl>>CCCCCCCCc1ccc(-c2ccc(C(=O)Cl)cc2)nc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fdcb81caf14240578e9ddd54ada0a201 | COC(=O)C(F)(F)C(F)(F)C(F)(F)F>>O=C([O-])C(F)(F)C(F)(F)C(F)(F)F | FC(C(=O)OC)(C(C(F)(F)F)(F)F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(=O)[O-])(C(C(F)(F)F)(F)F)F.[Na+] | C[O:3][C:2](=[O:1])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13] | COC(=O)C(F)(F)C(F)(F)C(F)(F)F | O=C([O-])C(F)(F)C(F)(F)C(F)(F)F | null | null | CCOCC | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4] | 84 | [{"value": 84.0, "product": "FC(C(=O)[O-])(C(C(F)(F)F)(F)F)F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "FC(C(=O)[O-])(C(C(F)(F)F)(F)F)F.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Methyl perfluorobutyrate (12.81 g, 56 mmol) was added dropwise to a stirred solution of sodium trimethylsilanolate (6.3 g, 56 mmol) in dry ether (300 mL) at room temperature under nitrogen. The reaction mixture was stirred overnight. The solid was filtered under nitrogen, washed with dry ether, and dried under a stream... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | Other | CCOCC | null | 8 | COC(=O)C(F)(F)C(F)(F)C(F)(F)F>CCOCC>O=C([O-])C(F)(F)C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5f630d1d3b4c4d7485ff576d2f43ae27 | CCOC(=O)C(F)(F)C(F)(F)F>>O=C([O-])C(F)(F)C(F)(F)F | FC(C(=O)OCC)(C(F)(F)F)F.C[Si]([O-])(C)C.[K+]>>FC(C(=O)[O-])(C(F)(F)F)F.[K+] | CC[O:3][C:2](=[O:1])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10] | CCOC(=O)C(F)(F)C(F)(F)F | O=C([O-])C(F)(F)C(F)(F)F | null | null | CCOCC | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4] | 93 | [{"value": 93.0, "product": "FC(C(=O)[O-])(C(F)(F)F)F.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "FC(C(=O)[O-])(C(F)(F)F)F.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using ethyl perfluoropropionate (4.8 g, 25 mmol), potassium trimethylsilanolate (3.2 g, 25 mmol), and dry ether (150 mL). Potassium perfluoropropionate (4.7 g, 93% yield) was isolated as a white solid: 19F NMR (D2O) δ -79.5 (m, CF3, 3F), -117.5 (m, CF2, 2F). Anal. Calcd. for C3F5... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | Other | CCOCC | null | null | CCOC(=O)C(F)(F)C(F)(F)F>CCOCC>O=C([O-])C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a68a06a0effb494f98d875d04106fb3e | O=C(OCc1ccccc1)c1ccccc1>>O=C([O-])c1ccccc1 | C(C1=CC=CC=C1)(=O)OCC1=CC=CC=C1.C[Si]([O-])(C)C.[Na+]>>C(C1=CC=CC=C1)(=O)[O-].[Na+] | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)cc1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=C(OCc1ccccc1)c1ccccc1 | O=C([O-])c1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | Ester to carboxylate | 813f249af327de8fabe746148d8e5b6f3b80a70975d016ae80055b5d6ea0624a | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O-;H0;D1:4]-[C:2](=[O;D1;H0:1])-[c:3] | 322 | [{"value": 64.0, "product": "C(C1=CC=CC=C1)(=O)[O-].[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 322.0, "product": "C(C1=CC=CC=C1)(=O)[O-].[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using benzyl benzoate (4.8 mL, 5 mmol), sodium trimethylsilanolate (2.82 g, 25 mmol), dry tetrahydrofuran (100 mL), and 6.25 h of heating at reflux. The reaction mixture was cooled to room temperature and sodium benzoate (2.32 g, 64% yield) was isolated as a white solid: 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccccc1 | null | c1ccccc1 | Other | O1CCCC1 | null | null | O=C(OCc1ccccc1)c1ccccc1>O1CCCC1>O=C([O-])c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a3fe8da2ee984deab1f5616cd4413322 | O=C(OCc1ccccc1)c1ccccc1>>O=C([O-])c1ccccc1 | C(C1=CC=CC=C1)(=O)OCC1=CC=CC=C1.C[Si]([O-])(C)C.[K+]>>C(C1=CC=CC=C1)(=O)[O-].[K+] | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)cc1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=C(OCc1ccccc1)c1ccccc1 | O=C([O-])c1ccccc1 | null | null | CCOCC | Functional Group Interconversion | Ester to carboxylate | 813f249af327de8fabe746148d8e5b6f3b80a70975d016ae80055b5d6ea0624a | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O-;H0;D1:4]-[C:2](=[O;D1;H0:1])-[c:3] | 73.7 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.7, "product": "C(C1=CC=CC=C1)(=O)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using benzyl benzoate (9.6 mL, 50 mmol), potassium trimethylsilanolate (6.42 g, 50 mmol), dry ether (150 mL), and a 2 h reaction mixture. Potassium benzoate (5.9 g, 73% yield) was isolated as a white solid: 1H NMR (D2O) δ 7.1-8.0 ppm (m, Ar--H's, 5H). Anal. Calcd. for C7H5KO2 : C... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccccc1 | null | c1ccccc1 | Other | CCOCC | null | null | O=C(OCc1ccccc1)c1ccccc1>CCOCC>O=C([O-])c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3800576022a3461eb93d34d2f8d0dcb9 | CCCCCCC(=O)OC>>CCCCCCC(=O)[O-] | C(CCCCCC)(=O)OC.C[Si]([O-])(C)C.[Li+]>>C(CCCCCC)(=O)[O-].[Li+] | C[O:9][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[O-:9] | CCCCCCC(=O)OC | CCCCCCC(=O)[O-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4] | 51.1 | [{"value": 51.0, "product": "C(CCCCCC)(=O)[O-].[Li+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.1, "product": "C(CCCCCC)(=O)[O-].[Li+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl heptanoate (5 mL, 30.2 mmol), lithium trimethylsilanolate (2.90 g, 30.2 mmol), dry toluene (50 mL) and 2.5 h of heating at reflux. Lithium heptanoate (2.1 g, 51% yield) was isolated as a white solid: 1H NMR (D2O) δ 0.7 (t, J=5.3 Hz, CH3, 3H), 0.9-1.7 (m, CH2, 8H), 2.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | Other | C1(=CC=CC=C1)C | null | null | CCCCCCC(=O)OC>C1(=CC=CC=C1)C>CCCCCCC(=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ee16a2a12b5a4c94a18c4647c3615c25 | COC(=O)c1ccc(Cl)cc1>>O=C([O-])c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)OC)C=C1.C[Si]([O-])(C)C.[K+]>>ClC1=CC=C(C(=O)[O-])C=C1.[K+] | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | COC(=O)c1ccc(Cl)cc1 | O=C([O-])c1ccc(Cl)cc1 | null | null | CCOCC | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4] | 84.1 | [{"value": 84.0, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl 4-chlorobenzoate (13.65 g, 80 mmol), potassium trimethylsilanolate (10.26 g, 80 mmol), dry ether (500 mL) and a 4 h reaction time. Potassium 4-chlorobenzoate (13.1 g, 84% yield) was isolated as a white solid: 1H NMR (D2O, DSS, 80 MHz) δ 7.68 ppm (ABq, Δν1-3 =29 Hz, J... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccccc1 | Other | CCOCC | null | null | COC(=O)c1ccc(Cl)cc1>CCOCC>O=C([O-])c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4e5e8dfb24b64e2785502aae5a36ffcf | COC(=O)c1ccc(Cl)cc1>>O=C([O-])c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)OC)C=C1.C[Si]([O-])(C)C.[Na+]>>ClC1=CC=C(C(=O)[O-])C=C1.[Na+] | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | COC(=O)c1ccc(Cl)cc1 | O=C([O-])c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4] | 94.7 | [{"value": 86.0, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.7, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl 4-chlorobenzoate (4.55 g, 26.6 mmol), sodium trimethylsilanolate (2.99 g, 26.6 mmol), dry toluene (150 mL), and 4 h of heating at 80°. Sodium 4-chlorobenzoate (4.50 g, 86% yield) was isolated as a white solid: 1H NMR (D2O, DSS, 80 MHz) δ 7.65 ppm (ABq, Δν1-3 =29 Hz, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COC(=O)c1ccc(Cl)cc1>C1(=CC=CC=C1)C>O=C([O-])c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6e6d66be1f8a416f914ae00c5029e6a2 | COC(=O)c1ccc(Cl)cc1>>O=C([O-])c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)OC)C=C1.C[Si]([O-])(C)C.[Li+]>>ClC1=CC=C(C(=O)[O-])C=C1.[Li+] | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | COC(=O)c1ccc(Cl)cc1 | O=C([O-])c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4] | 46.4 | [{"value": 46.0, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[Li+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "ClC1=CC=C(C(=O)[O-])C=C1.[Li+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl 4-chlorobenzoate (4.3 g, 25.2 mmol), lithium trimethylsilanolate (2.42 g, 25.2 mmol), and dry toluene (100 mL) and overnight heating at reflux. Lithium 4-chlorobenzoate (1.9 g, 46% yield) was isolated as a white solid: 1H NMR (D2O) δ 7.4 (ABq, Δν1-3 =31 Hz, J=9 Hz, A... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COC(=O)c1ccc(Cl)cc1>C1(=CC=CC=C1)C>O=C([O-])c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-246351cf446448bb94fc9b6d5752a45c | O=C(Oc1ccccc1)c1ccccc1>>O=C([O-])c1ccccc1 | C(C1=CC=CC=C1)(=O)OC1=CC=CC=C1.C[Si]([O-])(C)C.[K+]>>C(C1=CC=CC=C1)(=O)[O-].[K+] | c1ccc([O:3][C:2](=[O:1])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)cc1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=C(Oc1ccccc1)c1ccccc1 | O=C([O-])c1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 813f249af327de8fabe746148d8e5b6f3b80a70975d016ae80055b5d6ea0624a | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-c1:c:c:c:c:c:1>>[O-;H0;D1:4]-[C:2](=[O;D1;H0:1])-[c:3] | 74 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "C(C1=CC=CC=C1)(=O)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using phenyl benzoate (3.96 g, 20 mmol), potassium trimethylsilanolate (2.56 g, 20 mmol), dry tetrahydrofuran (50 mL), and a 5 h reaction time. Potassium benzoate (2.37 g, 74% yield) was isolated as a white solid: 1H NMR (D2O, DSS, 80 MHz) δ 7.4-8.0 (m, Ar--H's, 5H). Anal. Calcd.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccccc1 | null | c1ccccc1 | Other | O1CCCC1 | null | null | O=C(Oc1ccccc1)c1ccccc1>O1CCCC1>O=C([O-])c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a2a03d9eacb9456cbafbe3371aa2289a | COC(=O)c1ccco1>>O=C([O-])c1ccco1 | O1C(=CC=C1)C(=O)OC.C[Si]([O-])(C)C.[K+]>>O1C(=CC=C1)C(=O)[O-].[K+] | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][o:8]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][o:8]1 | COC(=O)c1ccco1 | O=C([O-])c1ccco1 | null | null | O1CCCC1 | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccoc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | 90.6 | [{"value": 90.0, "product": "O1C(=CC=C1)C(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "O1C(=CC=C1)C(=O)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl 2-furoate (2.52 g, 20 mmol), potassium trimethylsilanolate (2.56 g, 20 mmol), dry tetrahydrofuran (50 mL), and a 5 h reaction time. Potassium 2-furoate (2.72 g, 90% yield) was isolated as a light brown solid: 1H NMR (D2O, DSS) δ 6.55 (m, Ar--H, 1H), 7.0 (m, Ar--H, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccoc1 | Other | O1CCCC1 | null | null | COC(=O)c1ccco1>O1CCCC1>O=C([O-])c1ccco1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-67cb34ff7b604725838c1cc12c95539b | COC(=O)c1cccnc1>>O=C([O-])c1cccnc1 | C(C1=CN=CC=C1)(=O)OC.C[Si]([O-])(C)C.[K+]>>C(C1=CN=CC=C1)(=O)[O-].[K+] | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | COC(=O)c1cccnc1 | O=C([O-])c1cccnc1 | null | null | O1CCCC1 | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | c1ccncc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | 90.9 | [{"value": 90.0, "product": "C(C1=CN=CC=C1)(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "C(C1=CN=CC=C1)(=O)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl nicotinate (2.74 g, 20 mmol), potassium trimethylsilanolate (2.56 g, 20 mmol), dry tetrahydrofuran (50 mL), and a 5 h reaction time. Potassium nicotinate (2.93 g, 90% yield) was isolated as a white solid: 1H NMR (D2O, DSS) δ 7.55 (ddd, J=1.0, 5.3, 8.3 Hz, Ar--H, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccncc1 | Other | O1CCCC1 | null | null | COC(=O)c1cccnc1>O1CCCC1>O=C([O-])c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-09bf57ad4f744b61bd86e8e655bf212e | O=C(F)C(F)(C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(C(F)(F)F)C(F)(F)F | FC(C(=O)F)(C(F)(F)F)C(F)(F)F.C[Si]([O-])(C)C.[K+]>>FC(C(=O)[O-])(C(F)(F)F)C(F)(F)F.[K+] | F[C:2](=[O:1])[C:4]([F:5])([C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13] | O=C(F)C(F)(C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(C(F)(F)F)C(F)(F)F | null | null | CCOCC | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:3](-[F;D1;H0:4])(-[C;H0;D3;+0:1](-[O;-;D1;H0:13])=[O;D1;H0:2])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | 61 | [{"value": 61.0, "product": "FC(C(=O)[O-])(C(F)(F)F)C(F)(F)F.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "FC(C(=O)[O-])(C(F)(F)F)C(F)(F)F.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Perfluoroisobutyryl fluoride (17.76 g, 82 mmol) was distilled into a 3-neck flask (equipped with a cold finger condenser, mechanical stirrer and a nitrogen inlet) containing a slurry of potassium trimethylsilanolate (10.26 g, 80 mmol) in dry ether (500 mL). The mixture was stirred 3 h at room temperature with the conde... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | CCOCC | null | 3 | O=C(F)C(F)(C(F)(F)F)C(F)(F)F>CCOCC>O=C([O-])C(F)(C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e19db06fc1b6482fb435307594c07f67 | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | FC(C(=O)F)(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.C[Si]([O-])(C)C.[K+]>>FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[K+] | F[C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20] | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | null | null | CCOCC | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])(-[F;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[#8:4]-[C:3](-[F;D1;H0:5])(-[C;H0;D3;+0:1](-[O;-;D1;H0:10])=[O;D1;H0:2])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 72 | [{"value": 72.0, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[K+]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluoro-2-methyl-3-oxahexanoyl fluoride (16.6 g, 50 mmol), potassium trimethylsilanolate (6.41 g, 50 mmol), and dry ether (300 mL). Potassium perfluoro-2-methyl-3-oxahexanoate (12.3 g initially and 0.9 g by concentrating the filtrate under vacuum; total: 13.2 g, 72% yield... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | CCOCC | null | null | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>CCOCC>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-12ad0a1eb8d44e2fbf384c250faa7679 | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | FC(C(=O)F)(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+] | F[C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20] | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | null | null | ClC1=C(C=CC=C1)Cl | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])(-[F;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[#8:4]-[C:3](-[F;D1;H0:5])(-[C;H0;D3;+0:1](-[O;-;D1;H0:10])=[O;D1;H0:2])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 77.3 | [{"value": 77.0, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluoro-2-methyl-3-oxahexanoyl fluoride (16.6 g, 50 mmol), sodium trimethylsilanolate (5.6 g, 50 mmol), dry o-dichlorobenzene (200 mL), and 1 h at room temperature followed by rapid heating to 150°. Sodium perfluoro-2-methyl-3-oxahexanoate (13.6 g, 77% yield) was isolated... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | ClC1=C(C=CC=C1)Cl | null | null | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>ClC1=C(C=CC=C1)Cl>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a2d4c15aa91b4bc49e43d3bde49780ee | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | FC(C(=O)F)(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+] | F[C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20] | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])(-[F;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[#8:4]-[C:3](-[F;D1;H0:5])(-[C;H0;D3;+0:1](-[O;-;D1;H0:10])=[O;D1;H0:2])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 69.3 | [{"value": 69.0, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluoro-2-methyl-3-oxahexanoyl fluoride (16.6 g, 50 mmol), sodium trimethylsilanolate (5.6 g, 50 mmol), and dry tetrahydrofuran (100 mL), and a 2 h reaction time. Sodium perfluoro-2-methyl-3-oxahexanoate (12.2 g, 69% yield) was isolated as a white solid: The 19F NMR data ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | O1CCCC1 | null | null | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>O1CCCC1>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-13e5debefb0d4b96963cdfe09db40762 | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | FC(C(=O)F)(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+] | F[C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20] | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])(-[F;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[#8:4]-[C:3](-[F;D1;H0:5])(-[C;H0;D3;+0:1](-[O;-;D1;H0:10])=[O;D1;H0:2])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 66 | [{"value": 66.0, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "FC(C(=O)[O-])(OC(C(C(F)(F)F)(F)F)(F)F)C(F)(F)F.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluoro-2-methyl-3-oxahexanoyl fluoride (33.2 g, 0.1 mol), sodium trimethylsilanolate (11.2 g, 0.1 mol), dry toluene (200 mL), and 1.5 h of heating at reflux. Sodium perfluoro-2-methyl-3-oxahexanoate (23.1 g, 66% yield) was isolated as a white solid: The 19F NMR data were... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | C1(=CC=CC=C1)C | null | null | O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F>C1(=CC=CC=C1)C>O=C([O-])C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9f0abb4433aa4985acae6632fd7a6977 | CCCCCCCCC(C(=O)F)(C(F)(F)F)C(F)(F)F>>CCCCCCCCC(C(=O)[O-])(C(F)(F)F)C(F)(F)F | FC(C(C(=O)F)(CCCCCCCC)C(F)(F)F)(F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(C(=O)[O-])(CCCCCCCC)C(F)(F)F)(F)F.[Na+] | F[C:10]([C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:10](=[O:11])[O-:12])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20] | CCCCCCCCC(C(=O)F)(C(F)(F)F)C(F)(F)F | CCCCCCCCC(C(=O)[O-])(C(F)(F)F)C(F)(F)F | null | null | CCOCC | Functional Group Interconversion | OtherReaction | d095e23ed5f5958c7d6c3d149c44de77cdb6155f3f3b2fb5f6c7dda4e861af2a | b74349abf96e8fa01167569cbefe10dc6bea05a8ad70e6ae03fd3ac8f39a98e0 | null | F-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[O;-;D1;H0:13])=[O;D1;H0:2])(-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using 2,2-bis(trifluoromethyl)decanoyl fluoride (6.11 g, 19.7 mmol), sodium trimethylsilanolate (2.21 g, 19.7 mmol) and dry ether (20 mL). The product, sodium 2,2-bis(trifluoromethyl)decanoate, was isolated as a waxy solid (5.5 g, 85% yield) by concentrating the filtrate under va... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | null | CCOCC | null | null | CCCCCCCCC(C(=O)F)(C(F)(F)F)C(F)(F)F>CCOCC>CCCCCCCCC(C(=O)[O-])(C(F)(F)F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bced94d3b141486e89edeb33840b194b | O=S(=O)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F>>O=S(=O)([O-])C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F | FC(C(OC(C(F)(F)F)(F)F)(F)F)(S(=O)(=O)F)F.C[Si]([O-])(C)C.[K+].O1CCCC1>>FC(C(OC(C(F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+] | F[S:2](=[O:3])(=[O:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[O:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18]>>[O:1]=[S:2](=[O:3])([O-:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[O:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18] | O=S(=O)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F | O=S(=O)([O-])C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F | null | null | OCC(O)CO | Miscellaneous | OtherReaction | d7fb7b0f07cb8e4e2a97b1a3da4a2a38ed7ce03c4661dcd43c3228d42a77a1ba | 4b62ddffdc0614c171751abd5ea9e35064ed76a7a584ba64ae5e78c3e6e4cd42 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](-[O-;H0;D1:3])(=[O;D1;H0:8])=[O;D1;H0:2] | 65 | [{"value": 65.0, "product": "FC(C(OC(C(F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluoro-3-oxapentanesulfonyl fluoride (7.95 g, 25 mmol), potassium trimethylsilanolate (3.2 g, 25 mmol) and dry tetrahydrofuran (100 mL) while heating at reflux for 1.5 h. Potassium perfluoro-3-oxapentanesulfonate (3.79 g initially and 1.74 g by concentrating the filtrate... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | OCC(O)CO | null | null | O=S(=O)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F>OCC(O)CO>O=S(=O)([O-])C(F)(F)C(F)(F)OC(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-946e2dc288f24db892703f552d4c9402 | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)F)F.C[Si]([O-])(C)C.[K+]>>FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+] | F[S:2](=[O:3])(=[O:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23]>>[O:1]=[S:2](=[O:3])([O-:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23] | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | null | null | CCOCC | Miscellaneous | OtherReaction | d7fb7b0f07cb8e4e2a97b1a3da4a2a38ed7ce03c4661dcd43c3228d42a77a1ba | 4b62ddffdc0614c171751abd5ea9e35064ed76a7a584ba64ae5e78c3e6e4cd42 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](-[O-;H0;D1:3])(=[O;D1;H0:8])=[O;D1;H0:2] | 53.6 | [{"value": 53.0, "product": "FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.6, "product": "FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluorohexanesulfonyl fluoride (7.9 g, 19.6 mmol), potassium trimethylsilanolate (2.52 g, 19.6 mmol), dry ether (150 mL), and a reaction time of nine days. Potassium perfluorohexanesulfonate (4.6 g, 53% yield) was isolated as a white solid: 19F NMR (methanol) δ -81.1 (m, ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | CCOCC | null | null | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>CCOCC>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-882499053e0646b084d916bd6f5ca70b | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)F)F.C[Si]([O-])(C)C.[Li+]>>FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[Li+] | F[S:2](=[O:3])(=[O:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[C:23]([F:24])([F:25])[C:26]([F:27])([F:28])[F:29]>>[O:1]=[S:2](=[O:3])([O-:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F... | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | null | null | O1CCCC1 | Miscellaneous | OtherReaction | d7fb7b0f07cb8e4e2a97b1a3da4a2a38ed7ce03c4661dcd43c3228d42a77a1ba | 4b62ddffdc0614c171751abd5ea9e35064ed76a7a584ba64ae5e78c3e6e4cd42 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](-[O-;H0;D1:3])(=[O;D1;H0:8])=[O;D1;H0:2] | 55.7 | [{"value": 55.0, "product": "FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[Li+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.7, "product": "FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[Li+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | The procedure of Example 1 was followed using perfluorooctanesulfonyl fluoride (11.8 g, 23.5 mmol), lithium trimethylsilanolate (2.25 g, 23.4 mmol), and dry tetrahydrofuran (150 mL). The product, lithium perfluorooctanesulfonate (6.6 g, 55% yield), was isolated as a white solid by concentrating the filtrate under vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | O1CCCC1 | null | null | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>O1CCCC1>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5b16629f20d4fcaa1e3b54855eab8d8 | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)F)F.C[Si]([O-])(C)C.[K+]>>FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+] | F[S:2](=[O:3])(=[O:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23]>>[O:1]=[S:2](=[O:3])([O-:4])[C:5]([F:6])([F:7])[C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23] | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | d7fb7b0f07cb8e4e2a97b1a3da4a2a38ed7ce03c4661dcd43c3228d42a77a1ba | 4b62ddffdc0614c171751abd5ea9e35064ed76a7a584ba64ae5e78c3e6e4cd42 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](-[O-;H0;D1:3])(=[O;D1;H0:8])=[O;D1;H0:2] | 65.4 | [{"value": 65.0, "product": "FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using perfluorohexanesulfonyl fluoride (7.90 g, 19.6 mmol), potassium trimethylsilanolate (2.20 g, 17.1 mmol), and dry toluene (50 mL), while heating at 40° for 3.5 h. Potassium perfluorohexanesulfonate (4.9 g, 65% yield) was isolated as a white solid: 19F NMR (methanol) data wer... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | C1(=CC=CC=C1)C | null | null | O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>C1(=CC=CC=C1)C>O=S(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-38f5d19da7814e449f56363466a7475c | O=S(=O)(F)Cc1ccccc1>>O=S(=O)([O-])Cc1ccccc1 | C1(=CC=CC=C1)CS(=O)(=O)F.C[Si]([O-])(C)C.[K+]>>C1(=CC=CC=C1)CS(=O)(=O)[O-].[K+] | F[S:2](=[O:1])(=[O:3])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[S:2](=[O:3])([O-:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | O=S(=O)(F)Cc1ccccc1 | O=S(=O)([O-])Cc1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 6c113db978119dd30ec9ac70e3a1ccab457b8adfa2d854ef650cc9d0d938808f | 5664dc87dc3eea7f40384c1c98932c2b6f77a01ae2083f96843fa9d662971745 | c1ccccc1 | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[c:5]>>[O;-;D1;H0:6]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[c:5] | 58.3 | [{"value": 58.0, "product": "C1(=CC=CC=C1)CS(=O)(=O)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "C1(=CC=CC=C1)CS(=O)(=O)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using α-toluenesulfonyl fluoride (2.0 g, 11.5 mmol) in dry tetrahydrofuran (15 mL), potassium trimethylsilanolate (1.48 g, 11.5 mmol) and dry tetrahydrofuran (45 mL), and 2 h of heating at reflux. Potassium α-toluenesulfonate (1.41 g, 58% yield) was isolated as a white solid: 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | c1ccccc1 | null | O1CCCC1 | null | null | O=S(=O)(F)Cc1ccccc1>O1CCCC1>O=S(=O)([O-])Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ffca062de04148748522f2a63095a836 | CCOP(=O)(F)OCC>>CCOP(=O)([O-])OCC | C(C)OP(=O)(OCC)F.C[Si]([O-])(C)C.[K+]>>C(C)OP(=O)(OCC)[O-].[K+] | F[P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:7][CH2:8][CH3:9]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O-:6])[O:7][CH2:8][CH3:9] | CCOP(=O)(F)OCC | CCOP(=O)([O-])OCC | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | F-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[#8:3]-[C:4])-[#8:5]-[C:6]>>[C:4]-[#8:3]-[P;H0;D4;+0:1](-[O;-;D1;H0:7])(=[O;D1;H0:2])-[#8:5]-[C:6] | 54.5 | [{"value": 54.0, "product": "C(C)OP(=O)(OCC)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "C(C)OP(=O)(OCC)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed except that diethylfluorophosphate (0.9 mL, 6.4 mmol) was added by syringe to a slurry of potassium trimethylsilanolate (0.82 g, 6.4 mmol) in dry ether (25 mL) and a 5 h reaction time was used. Potassium diethylphosphate (0.67 g, 54% yield) was isolated as a tan solid: 1H NMR (D2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | CCOP(=O)(F)OCC>CCOCC>CCOP(=O)([O-])OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5d875633c19c4986b9ada2ce0e9357f6 | CCCCOP(=O)(OCCCC)OP(=O)(OCCCC)OCCCC>>CCCCOP(=O)([O-])OCCCC | C(CCC)OP(OCCCC)(=O)OP(=O)(OCCCC)OCCCC.C[Si]([O-])(C)C.[K+]>>C(CCC)OP(=O)(OCCCC)[O-].[K+] | CCCCOP(=O)(OCCCC)[O:8][P:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:7])[O:9][CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([O-:8])[O:9][CH2:10][CH2:11][CH2:12][CH3:13] | CCCCOP(=O)(OCCCC)OP(=O)(OCCCC)OCCCC | CCCCOP(=O)([O-])OCCCC | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | C-C-C-C-O-P(=O)(-O-C-C-C-C)-[O;H0;D2;+0:1]-[#15:2](-[#8:3])(-[#8:4])=[O;D1;H0:5]>>[#8:3]-[#15:2](-[#8:4])(-[O-;H0;D1:1])=[O;D1;H0:5] | 171.1 | [{"value": 90.0, "product": "C(CCC)OP(=O)(OCCCC)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 171.1, "product": "C(CCC)OP(=O)(OCCCC)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using tetrabutylpyrophosphate (4 mL, 10.5 mmol) in dry tetrahydrofuran (10 mL), potassium trimethylsilanolate (2.68 g, 21 mmol) in dry tetrahydrofuran (50 mL), and a 24 h reaction time. The product, potassium dibutylphosphate (4.46 g, 90% yield), was isolated as a white solid by ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | HO- | O1CCCC1 | null | null | CCCCOP(=O)(OCCCC)OP(=O)(OCCCC)OCCCC>O1CCCC1>CCCCOP(=O)([O-])OCCCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9878cbd083d94425a4a8b441d42547ca | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1>>O=P([O-])(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(OC1=CC=CC=C1)(=O)C1=CC=CC=C1.C[Si]([O-])(C)C.[K+]>>C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[K+] | c1ccc([O:3][P:2](=[O:1])([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)cc1>>[O:1]=[P:2]([O-:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1 | O=P([O-])(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 6d394203d43558548a956b7ff69ca941419ca6e78a5610ba2511b804704589dd | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=[PH](c1ccccc1)c1ccccc1 | [O;D1;H0:1]=[#15:2](-[c:3])(-[c:4])-[O;H0;D2;+0:5]-c1:c:c:c:c:c:1>>[O-;H0;D1:5]-[#15:2](=[O;D1;H0:1])(-[c:3])-[c:4] | 87 | [{"value": 87.0, "product": "C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed adding neat solid phenyl diphenylphosphinate (5.88 g, 20 mmol) to a slurry of potassium trimethylsilanolate (2.56 g, 20 mmol) in dry tetrahydrofuran (50 mL); a 4 h reaction time was used. Potassium diphenylphosphinate (4.46 g, 87% yield) was isolated as a white solid: 1H NMR (D2O... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | null | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1>O1CCCC1>O=P([O-])(c1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ce46e031884641d0ad46ce0b09b270af | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1>>O=P([O-])(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(OC1=CC=CC=C1)(=O)C1=CC=CC=C1.C[Si]([O-])(C)C.[Na+]>>C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[Na+] | c1ccc([O:3][P:2](=[O:1])([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)cc1>>[O:1]=[P:2]([O-:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1 | O=P([O-])(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 6d394203d43558548a956b7ff69ca941419ca6e78a5610ba2511b804704589dd | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=[PH](c1ccccc1)c1ccccc1 | [O;D1;H0:1]=[#15:2](-[c:3])(-[c:4])-[O;H0;D2;+0:5]-c1:c:c:c:c:c:1>>[O-;H0;D1:5]-[#15:2](=[O;D1;H0:1])(-[c:3])-[c:4] | 68 | [{"value": 68.0, "product": "C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "C1(=CC=CC=C1)P([O-])(=O)C1=CC=CC=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The procedure of Example 1 was followed except that a mixture of phenyl diphenylphosphinate (13.76 g, 46.7 mmol), sodium trimethylsilanolate (5.6 g, 50 mmol), and dry tetrahydrofuran (175 mL) was left standing overnight (as it became impossible to stir). Sodium diphenylphosphinate (7.6 g, 68% yield) was isolated as a w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 8 | O=P(Oc1ccccc1)(c1ccccc1)c1ccccc1>O1CCCC1>O=P([O-])(c1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-71c80b666f9146bca8517cd2a6af9e46 | CCOP(=O)(OCC)OCC>>CCOP(=O)([O-])OCC | C(C)OP(=O)(OCC)OCC.C[Si]([O-])(C)C.[K+]>>C(C)OP(=O)(OCC)[O-].[K+] | CC[O:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:7][CH2:8][CH3:9]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O-:6])[O:7][CH2:8][CH3:9] | CCOP(=O)(OCC)OCC | CCOP(=O)([O-])OCC | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | C-C-[O;H0;D2;+0:1]-[#15:2](-[#8:3])(-[#8:4])=[O;D1;H0:5]>>[#8:3]-[#15:2](-[#8:4])(-[O-;H0;D1:1])=[O;D1;H0:5] | 92.4 | [{"value": 92.0, "product": "C(C)OP(=O)(OCC)[O-].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "C(C)OP(=O)(OCC)[O-].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | The procedure of Example 1 was followed except that triethylphosphate (3.4 mL, 20 mmol) was added by syringe to a slurry of potassium trimethylsilanolate (2.56 g, 20 mmol) in dry tetrahydrofuran (50 mL), and a 2 h reaction time at room temperature was used, followed by 40 h of heating at reflux. Potassium diethylphosph... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O1CCCC1 | null | 40 | CCOP(=O)(OCC)OCC>O1CCCC1>CCOP(=O)([O-])OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e0d0cd5654d8408eaa2d8ff993c43dc8 | COC(=O)C(F)(OC(F)(C(=O)F)C(F)(F)F)C(F)(F)F>>O=C([O-])C(F)(OC(F)(C(=O)[O-])C(F)(F)F)C(F)(F)F.[K+] | C(=O)(OC)C(OC(C(=O)F)(C(F)(F)F)F)(C(F)(F)F)F.C[Si]([O-])(C)C.[K+]>>FC(C(=O)[O-])(OC(C(=O)[O-])(C(F)(F)F)F)C(F)(F)F.[K+].[K+] | C[O:3][C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([C:9](F)=[O:10])[C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([O:6][C:7]([F:8])([C:9](=[O:10])[O-:11])[C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19].[K+:21] | COC(=O)C(F)(OC(F)(C(=O)F)C(F)(F)F)C(F)(F)F | O=C([O-])C(F)(OC(F)(C(=O)[O-])C(F)(F)F)C(F)(F)F.[K+] | null | null | CCOCC | Miscellaneous | OtherReaction | 5029a2eadeeac78cc18cf37dd43228009f52935e824b37b4dc6eefea4d4c2608 | c18d6588e1bdd0859e41a5be98ab5269c37b70476114e809feed09b7bf7f3b87 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#8:5]-[C:6](-[F;D1;H0:7])(-[C;H0;D3;+0:8](-F)=[O;D1;H0:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[C:6](-[F;D1;H0:7])(-[#8:5]-[C:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[C;H0;D3;+0:8](-[O;-;D1;H0:14])=[O;D1;H0:9] | 98 | [{"value": 98.0, "product": "FC(C(=O)[O-])(OC(C(=O)[O-])(C(F)(F)F)F)C(F)(F)F.[K+].[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "FC(C(=O)[O-])(OC(C(=O)[O-])(C(F)(F)F)F)C(F)(F)F.[K+].[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using ~95% pure 4-carbomethoxyperfluoro-2-methyl-3-oxapentanoyl fluoride (12.5 g, 39 mmol), potassium trimethylsilanolate (10 g, 78 mmol), and dry ether (300 mL). Dipotassium perfluoro-2,4-dimethyl-3-oxa-1,5-pentanedioate (14.6 g, 98% yield) was isolated as a white solid: 19F NMR... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | null | null | null | null | null | CCOCC | null | null | COC(=O)C(F)(OC(F)(C(=O)F)C(F)(F)F)C(F)(F)F>CCOCC>O=C([O-])C(F)(OC(F)(C(=O)[O-])C(F)(F)F)C(F)(F)F.[K+] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-47f7fab3590a4b288fe5c9f9e0c471c5 | CCOC(=O)C(=O)OCC>>CCOC(=O)C(=O)[O-] | C(C(=O)OCC)(=O)OCC.C[Si]([O-])(C)C.[K+]>>C(C(=O)[O-])(=O)OCC.[K+] | CC[O:8][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[O-:8] | CCOC(=O)C(=O)OCC | CCOC(=O)C(=O)[O-] | null | null | CCOCC | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | 79.2 | [{"value": 79.0, "product": "C(C(=O)[O-])(=O)OCC.[K+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "C(C(=O)[O-])(=O)OCC.[K+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using diethyl oxalate (3.0 mL, 22 mmol), potassium trimethylsilanolate (3.85 g, 22 mmol), dry ether (70 mL), an ice bath to maintain room temperature initially, and a 1.5 h reaction time. Potassium ethyl oxalate (2.72 g, 79% yield) was isolated as a white solid: 1H NMR (D2O) δ 1.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | Other | CCOCC | null | null | CCOC(=O)C(=O)OCC>CCOCC>CCOC(=O)C(=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f50e1f0a36124d9191e96386a1984340 | COC(=O)C(F)(F)C(F)(F)F>>O=C([O-])C(F)(F)C(F)(F)F | FC(C(=O)OC)(C(F)(F)F)F.C[Si]([O-])(C)C.[Na+]>>FC(C(=O)[O-])(C(F)(F)F)F.[Na+] | C[O:3][C:2](=[O:1])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10] | COC(=O)C(F)(F)C(F)(F)F | O=C([O-])C(F)(F)C(F)(F)F | null | null | C(Cl)Cl | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4] | 92 | [{"value": 92.0, "product": "FC(C(=O)[O-])(C(F)(F)F)F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "FC(C(=O)[O-])(C(F)(F)F)F.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was followed using methyl perfluoropropionate (3 mL, 23.4 mmol), sodium trimethylsilanolate (2.63 g, 23.4 mmol), dry methylene chloride (100 mL), and a 1 h reaction time. Sodium perfluoropropionate (4.0 g, 92% yield) was obtained as a white solid: 1H NMR (D2O) δ -82.4 (t, J=2 Hz, CF3, 3F), -1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | null | Other | C(Cl)Cl | null | null | COC(=O)C(F)(F)C(F)(F)F>C(Cl)Cl>O=C([O-])C(F)(F)C(F)(F)F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-94ac55d97890402ca18eed45ab6448b2 | C=CCCCOc1ccc(Cl)cc1>>C=CCCOc1ccc(Cl)cc1 | ClC1=CC=C(C=C1)OCCCC=C.FC1=CC=C(C=C1)OCCCC=C>>C(CC=C)OC1=CC=C(C=C1)Cl | C=[CH:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | C=CCCCOc1ccc(Cl)cc1 | C=CCCOc1ccc(Cl)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 26c65af671b5d569a33e7ef2cfd24cabe9e1dc2f285faa562a9f40a5859e2b54 | 886944caadf47e5075b7ca13d4b57ac74376584435df95a916493cedb9574678 | c1ccccc1 | C=[CH;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:2]=[CH2;D1;+0:1] | null | [] | null | null | null | null | The 1-(3-butenyloxy)-4-chlorobenzene (5, R2 =4--Cl) was prepared by the procedure of Rius-Alonso and Wain, Ann. Apl. Biol. 88, 299 (1978), as were 4-chloro-1-(4-pentenyloxy)-benzene and 4-fluoro-1-(4-pentenyloxy)benzene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Allyl | null | null | c1ccccc1 | Other | null | null | null | C=CCCCOc1ccc(Cl)cc1>>C=CCCOc1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b653410a1d44cdf9990edd4a831a13b | CC(=O)N1CCC(C(=O)Cl)CC1.Fc1ccc(F)cc1>>CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1 | C(C)(=O)N1CCC(CC1)C(=O)Cl.FC1=CC=C(C=C1)F.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(=O)N1CCC(CC1)C(C1=C(C=CC(=C1)F)F)=O | Cl[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:19][CH2:18]1)=[O:9].[cH:10]1[cH:11][c:12]([F:13])[cH:14][cH:15][c:16]1[F:17]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[c:10]2[cH:11][c:12]([F:13])[cH:14][cH:15][c:16]2[F:17])[CH2:18][CH2:19]1 | CC(=O)N1CCC(C(=O)Cl)CC1.Fc1ccc(F)cc1 | CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[F;D1;H0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[F;D1;H0:6]):[c:8])-[C:5] | 52.1 | [{"value": 52.1, "product": "C(C)(=O)N1CCC(CC1)C(C1=C(C=CC(=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 100 g of 1-acetyl-4-piperidine carboxylic acid chloride in 500 ml of 1,4-difluorobenzene was added in aliquots, 211 g of anhydrous aluminum chloride. The mixture was stirred at reflux under nitrogen for 3 hrs and allowed to cool to room temperature. The mixture was poured into ice and extract... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HCl | null | null | null | CC(=O)N1CCC(C(=O)Cl)CC1.Fc1ccc(F)cc1>>CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2caa6a90f66045989bb3fe05bb837dcc | BrBr.CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1>>CC(=O)N1CCC(Br)(C(=O)c2cc(F)ccc2F)CC1 | C(C)(=O)N1CCC(CC1)C(C1=C(C=CC(=C1)F)F)=O.BrBr.O>>C(C)(=O)N1CCC(CC1)(Br)C(C1=C(C=CC(=C1)F)F)=O | Br[Br:8].[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([C:9](=[O:10])[c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]2[F:18])[CH2:19][CH2:20]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][C:7]([Br:8])([C:9](=[O:10])[c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]2[F:18])[CH2:19][CH2:20]1 | BrBr.CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1 | CC(=O)N1CCC(Br)(C(=O)c2cc(F)ccc2F)CC1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Functional Group Interconversion | Bromination | dba1030896db7f8c5fe3d695d1d890283e54f9fdd18b9239002152ae1c09582e | 6ec3f71a7b16ecb8b3d7f09ea088f160aabf7862c97e062437fea5d4b4e8602e | O=C(c1ccccc1)C1CCNCC1 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3](-[c:4])-[CH;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1>>[Br;H0;D1;+0:1]-[C;H0;D4;+0:5]1(-[C:3](=[O;D1;H0:2])-[c:4])-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1 | null | [] | null | null | 12.5 | MINUTE | To a stirred solution of 11.2 g of 1-acetyl-4-(2,5-difluorobenzoyl)piperidine in 225 ml of glacial acetic acid was added dropwise over 0.5 hr a solution of 13.5 ml (42.1 g) of bromine in 115 ml of glacial acetic acid at a rate such that the temperature remained between 10°-12° C. The mixture was stirred for an addition... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary halide | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HBr | C(C)(=O)O.C(C)(=O)OCC | null | 0.208333 | BrBr.CC(=O)N1CCC(C(=O)c2cc(F)ccc2F)CC1>C(C)(=O)O.C(C)(=O)OCC>CC(=O)N1CCC(Br)(C(=O)c2cc(F)ccc2F)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-83db2d9a2e8647bebb243a700d6a3748 | CN(C=O)c1ccccc1.Fc1ccc(F)cc1>>O=Cc1cc(F)ccc1F | CN(C1=CC=CC=C1)C=O.FC1=CC=C(C=C1)F.C(CCC)[Li].S(O)(O)(=O)=O>>FC1=C(C=O)C=C(C=C1)F | CN(c1ccccc1)[CH:2]=[O:1].[cH:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[F:10]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[F:10] | CN(C=O)c1ccccc1.Fc1ccc(F)cc1 | O=Cc1cc(F)ccc1F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[F;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[F;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7]:[c:8] | 77.6 | [{"value": 77.5, "product": "FC1=C(C=O)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "FC1=C(C=O)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | 1.5 | HOUR | To a stirred solution of 194.5 g (1.70 mol) of 1,4-difluorobenzene in 2 of dry tetrahydrofuran at -60° C. was added dropwise over 45 mins 1.70 mol (2.2 M in hexane) of n-butyllithium at a rate such that the temperature remained below -55° C. The reaction mixture was stirred for 45 mins at below -50° C. and 1.5 hr at -5... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | -60 | 1.5 | CN(C=O)c1ccccc1.Fc1ccc(F)cc1>O1CCCC1>O=Cc1cc(F)ccc1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3edec0cce6494ba6b7e98cbbbf5acffc | CC(=O)N1CCC(O)(C(=O)c2cc(F)ccc2F)CC1>>O=C(c1cc(F)ccc1F)C1(O)CCNCC1 | C(C)(=O)N1CCC(CC1)(O)C(C1=C(C=CC(=C1)F)F)=O>>FC1=C(C(=O)C2(CCNCC2)O)C=C(C=C1)F | CC(=O)[N:15]1[CH2:14][CH2:13][C:11]([C:2](=[O:1])[c:3]2[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]2[F:10])([OH:12])[CH2:17][CH2:16]1>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[F:10])[C:11]1([OH:12])[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | CC(=O)N1CCC(O)(C(=O)c2cc(F)ccc2F)CC1 | O=C(c1cc(F)ccc1F)C1(O)CCNCC1 | null | null | Cl | Reduction | Hydrogenolysis of tertiary amines | 9cdd96df6e11300c95adac7cb3ca680aaf7eb40dde9e356986268d54aaad8b12 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(c1ccccc1)C1CCNCC1 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 91.3 | [{"value": 80.0, "product": "FC1=C(C(=O)C2(CCNCC2)O)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "FC1=C(C(=O)C2(CCNCC2)O)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A suspension of 5.66 g of 1-acetyl-4-(2,5-difluorobenzoyl)-4-hydroxypiperidine in 10 ml of 6N hydrochloric acid was stirred at reflux, under nitrogen for 3.5 hrs. The reaction mixture was allowed to cool to 0° C. whereupon a solid separated. The solid was collected, washed with ice-cold acetone and dried to give 4.4 g ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | Cl | 0 | null | CC(=O)N1CCC(O)(C(=O)c2cc(F)ccc2F)CC1>Cl>O=C(c1cc(F)ccc1F)C1(O)CCNCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f8752192ea4e4df79d4fa06a0098bd68 | CC(=O)N1CCC(O)(C(=O)c2ccccc2F)CC1>>O=C(c1ccccc1F)C1(O)CCNCC1 | [OH-].[Na+].C(C)(=O)N1CCC(CC1)(O)C(C1=C(C=CC=C1)F)=O.Cl>>FC1=C(C(=O)C2(CCNCC2)O)C=CC=C1 | CC(=O)[N:14]1[CH2:13][CH2:12][C:10]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[F:9])([OH:11])[CH2:16][CH2:15]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[F:9])[C:10]1([OH:11])[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1 | CC(=O)N1CCC(O)(C(=O)c2ccccc2F)CC1 | O=C(c1ccccc1F)C1(O)CCNCC1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of tertiary amines | 9cdd96df6e11300c95adac7cb3ca680aaf7eb40dde9e356986268d54aaad8b12 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(c1ccccc1)C1CCNCC1 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 85 | [{"value": 85.0, "product": "FC1=C(C(=O)C2(CCNCC2)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "FC1=C(C(=O)C2(CCNCC2)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 13.3 g of 1-acetyl-4-(2-fluorobenzoyl)-4-hydroxypiperidine and 20 ml of 6N hydrochloric acid was stirred at reflux under nitrogen for 4 hrs. The reaction mixture was allowed to cool and poured onto ca. 100 g of ice. Methylene chloride was added, and the separated aqueous layer was made strongly basic by me... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | C(Cl)Cl | null | null | CC(=O)N1CCC(O)(C(=O)c2ccccc2F)CC1>C(Cl)Cl>O=C(c1ccccc1F)C1(O)CCNCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53a3ebdf15d441468909b1e846bdef45 | O=[N+]([O-])c1ccc(Cl)cc1[N+](=O)[O-]>>Nc1cc(Cl)ccc1[N+](=O)[O-] | [N+](=O)([O-])C=1C=C(C=CC1[N+](=O)[O-])Cl.[NH4+]>>[N+](=O)([O-])C1=C(N)C=C(C=C1)Cl | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11]>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11] | O=[N+]([O-])c1ccc(Cl)cc1[N+](=O)[O-] | Nc1cc(Cl)ccc1[N+](=O)[O-] | null | null | C(C)O | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | 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 | Compounds of formula I can be prepared without using the intermediate of formula II. For example, 3,4-dinitrochlorobenzene may be treated with liquid ammonium in a solvent such as ethanol to obtain 2-nitro-5-chloroaniline, which may then be treated with acetic anhydride in a solvent such as pyridine at 0°-5° C. to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | O=[N+]([O-])c1ccc(Cl)cc1[N+](=O)[O-]>C(C)O>Nc1cc(Cl)ccc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c7d8e13ae3ae4861ac0b9cc8bcfa101e | OCCC[Si](CCCO)(c1ccccc1)c1ccccc1>>C=CC(=O)OCCC[Si](CCCOC(=O)C=C)(c1ccccc1)c1ccccc1 | OCCC[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCCO>>C(C=C)(=O)OCCC[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCCOC(C=C)=O | [cH:1]1[c:24]([Si:9]([CH2:8][CH2:7][CH2:6][OH:5])([CH2:10][CH2:11][CH2:3][OH:4])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:25][cH:26][cH:27][cH:28]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][Si:9]([CH2:10][CH2:11][CH2:12][O:13][C:14](=[O:15])[CH:16]=[CH2:17])([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]... | OCCC[Si](CCCO)(c1ccccc1)c1ccccc1 | C=CC(=O)OCCC[Si](CCCOC(=O)C=C)(c1ccccc1)c1ccccc1 | null | null | O | Miscellaneous | OtherReaction | 5b1069b11aa659832ae3da3d62b2c031de6a74ce7a95981d64a418df0395c652 | 394c057dbfc0b828e89f069300ff458a32baf92dd452869de3f315a84c8e3ce1 | c1ccc([SiH2]c2ccccc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C:4]-[#14:5](-[c:6])(-[C:7]-[C:8]-[C:9]-[OH;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[#8:17]-[C:18]-[CH2;D2;+0:3]-[C:4]-[#14:5](-[c:6])(-[C:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:19]=[CH2;D1;+0:16])-[c;H0;D3;+0:1... | null | [] | null | null | null | null | After completion of the reaction, the reaction mixture was diluted with water and extracted with ether. The extract was dried over magnesium sulfate. The solvent was distilled off to obtain 24.2 g (yield: 94.8%) of bis(3-hydroxypropyl)diphenylsilane (B) (m.p. 80°-81° C.).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ester.Ester.Vinyl.Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O | null | null | OCCC[Si](CCCO)(c1ccccc1)c1ccccc1>O>C=CC(=O)OCCC[Si](CCCOC(=O)C=C)(c1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5dcd18cf32f744b38e1a3a9e2e554156 | COC(=O)Cc1ccccc1.O=C1CCC(=O)N1Br>>COC(=O)C(Br)c1ccccc1 | BrN1C(CCC1=O)=O.C1(=CC=CC=C1)CC(=O)OC>>BrC(C(=O)OC)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.O=C1CCC(=O)N1[Br:6]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([Br:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | COC(=O)Cc1ccccc1.O=C1CCC(=O)N1Br | COC(=O)C(Br)c1ccccc1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl secondary | 3f38b5884dced4ec8dd37f9fecb8c81145add99f2a1017bd9519b1712776da1f | 9deb701e8012c4f1578ccc05651bfed620e4410cab5fedb649aa1ac30c26adec | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[Br;H0;D1;+0:1]-[CH;D3;+0:6](-[C:4](=[O;D1;H0:5])-[#8:3]-[C;D1;H3:2])-[c:7](:[c:8]):[c:9] | 93.1 | [{"value": 93.1, "product": "BrC(C(=O)OC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | In this example, a mixture containing 5.93 g of N-bromosuccinimide, 5.0 g of methyl phenylacetate; and a catalytic amount (about 0.1 g) of benzoyl peroxide in 50 ml of carbon tetrachloride was warmed to reflux and then refluxed for about 12 hours. The mixture was then cooled to about 0° C. and filtered. The filtrate wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide.Tertiary amide | Secondary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl | 0 | null | COC(=O)Cc1ccccc1.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl>COC(=O)C(Br)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c156814239954cc794d18661347d1e7d | COC(=O)C(Br)c1ccccc1.C[NH3+]>>CNC(C(=O)OC)c1ccccc1 | BrC(C(=O)OC)C1=CC=CC=C1.[Cl-].C[NH3+].C([O-])(O)=O.[Na+].O>>CNC(C(=O)OC)C1=CC=CC=C1 | Br[CH:3]([C:4](=[O:5])[O:6][CH3:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][NH3+:2]>>[CH3:1][NH:2][CH:3]([C:4](=[O:5])[O:6][CH3:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | COC(=O)C(Br)c1ccccc1.C[NH3+] | CNC(C(=O)OC)c1ccccc1 | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 0c4f2bf090be7d221e12249685f7bcc6c91e2b1863388e584438530df396d8b2 | a9b3924160d5ba045fd0aacf5b47491360df00607ea02d6020369365920e85ac | c1ccccc1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH3+;D1:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:6](:[c:7]):[c:8] | 71.2 | [{"value": 71.2, "product": "CNC(C(=O)OC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In this example a mixture containing 30.7 g of methyl bromo-phenylacetate, 36.2 g of methyl ammonium chloride (i.e. CH3NH3Cl); 3.0 g of benzyltriethylammonium chloride and 67.5 g of sodium bicarbonate in about 300 ml of methylene chloride (and about 25 ml of water) was warmed to refluxed and refluxed for about 18 hours... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester.Secondary amine | null | null | c1ccccc1 | HBr | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl | null | null | COC(=O)C(Br)c1ccccc1.C[NH3+]>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl>CNC(C(=O)OC)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f360e909fa154e73a99b18eae08d738d | COC=C(C(=O)OC)c1ccccc1C.O=C1CCC(=O)N1Br>>COC=C(C(=O)OC)c1ccccc1CBr | CC1=C(C=CC=C1)C(C(=O)OC)=COC.BrN1C(CCC1=O)=O.C1(CCC(N1)=O)=O>>BrCC1=C(C=CC=C1)C(C(=O)OC)=COC | [CH3:1][O:2][CH:3]=[C:4]([C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[CH3:15].O=C1CCC(=O)N1[Br:16]>>[CH3:1][O:2][CH:3]=[C:4]([C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[CH2:15][Br:16] | COC=C(C(=O)OC)c1ccccc1C.O=C1CCC(=O)N1Br | COC=C(C(=O)OC)c1ccccc1CBr | null | N(=NC(C#N)(C)C)C(C#N)(C)C | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]=[C:3]-[c:4]:[c:5](-[CH3;D1;+0:6]):[c:7]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:6]-[c:5](:[c:7]):[c:4]-[C:3]=[C:2] | 97.3 | [{"value": 97.3, "product": "BrCC1=C(C=CC=C1)C(C(=O)OC)=COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 20.6 g of the methyl α-(2-methylphenyl)-β-methoxyacrylate obtained as described in method A, 17.65 g of N-bromosuccinimide, 0.2 g of azobisisobutyronitrile and 150 ml of CCl4 are slowly heated to 90° C. and kept at this temperature until all of the succinimide floats on the solvent. The mixture is filtered, the filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | N(=NC(C#N)(C)C)C(C#N)(C)C.C(Cl)(Cl)(Cl)Cl | 90 | null | COC=C(C(=O)OC)c1ccccc1C.O=C1CCC(=O)N1Br>N(=NC(C#N)(C)C)C(C#N)(C)C.C(Cl)(Cl)(Cl)Cl>COC=C(C(=O)OC)c1ccccc1CBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0089af8057e946a18b16755f3f9439f0 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1Cl>>COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | ClC1=C2C=CC(=CC2=CC=C1OC)[C@@H](C(=O)O)C>>COC=1C=C2C=CC(=CC2=CC1)[C@@H](C(=O)O)C | Cl[c:17]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]2[cH:17]1 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1Cl | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | null | [Al].[Ni] | [OH-].[Na+] | Functional Group Interconversion | Aromatic dehalogenation | b59c5c205c966b4215325ef1ee4f08427e93cdf8277de7587f9668b39e907bde | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2ccccc2c1 | Cl-[c;H0;D3;+0:1](:[c:2](:[c:3]):[c:4]):[c:5](-[#8:6]):[c:7]>>[#8:6]-[c:5](:[c:7]):[cH;D2;+0:1]:[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A solution of 1 g of (S)-2-(5-chloro-6-methoxy-2-naphthyl)-propionic acid in 20 ml of 10% aqueous sodium hydroxide solution at 90° C. is treated with 3 g of a nickel-aluminum alloy in small portions. After stirring the mixture for two hours, it is filtered, diluted with excess dilute hydrochloric acid and extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | Other | [Al].[Ni].[OH-].[Na+] | null | 2 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1Cl>[Al].[Ni].[OH-].[Na+]>COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-969a0003bb064226bfa65a3513e9c62c | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1>>COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1 | COC=1C=C2C=CC(=CC2=CC1)[C@@H](C(=O)O)C.[OH-].[Na+]>>COC=1C=C2C=CC(=CC2=CC1)[C@@H](C(=O)[O-])C.[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]2[cH:17]1 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1 | null | null | CO | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | c1ccc2ccccc2c1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | To a solution of 300 mg of (S)-2-(6-methoxy-2-naphthyl)-propionic acid in 5 ml of methanol is added a 1 molar equivalent of sodium hydroxide, in the form of a 0.1N solution. The solvent is evaporated in vacuo and the residue is taken up in 2 ml of methanol, followed by precipitation with ether, to yield crude sodium (S... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccc2ccccc2c1 | null | CO | null | null | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1>CO>COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b2fe1a99b9b4f7d9bf65ad29d804e7a | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1>>COc1ccc2cc([C@H](C)C(=O)OCC(C)C)ccc2c1 | COC=1C=C2C=CC(=CC2=CC1)[C@@H](C(=O)O)C.Cl>>COC=1C=C2C=CC(=CC2=CC1)[C@@H](C(=O)OCC(C)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[OH:13])[cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C@H:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18][cH:19][c:20]2[cH:21]1 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1 | COc1ccc2cc([C@H](C)C(=O)OCC(C)C)ccc2c1 | null | null | C(C(C)C)O | Miscellaneous | OtherReaction | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2ccccc2c1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:5]-[C:6]-[O;H0;D2;+0:4]-[C:2](-[C:1])=[O;D1;H0:3] | null | [] | null | null | 24 | HOUR | A solution of 300 mg of (S)-2-(6-methoxy-2-naphthyl)propionic acid in 5 ml of isobutyl alcohol is saturated with hydrogen chloride. After 24 hours, the excess alcohol is distilled off in vacuo and the residue is purified by chromatography using an alumina substrate to yield isobutyl (S)-2-(6-methoxy-2-naphthyl)propiona... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2ccccc2c1 | Other | C(C(C)C)O | null | 24 | COc1ccc2cc([C@H](C)C(=O)O)ccc2c1>C(C(C)C)O>COc1ccc2cc([C@H](C)C(=O)OCC(C)C)ccc2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e48263ea1c184915ac82de02fc1d25d1 | CC(=O)C=C(C)C.CCOC(=O)CC(C)=O>>CCOC(=O)C1C(C)=CC(=O)CC1(C)C | C(CC(=O)C)(=O)OCC.O=C(C)C=C(C)C.CCCCCCC>>O=C1C=C(C(C(C1)(C)C)C(=O)OCC)C | [CH3:9][C:10](=[O:11])[CH:12]=[C:13]([CH3:14])[CH3:15].O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7]([CH3:8])=[CH:9][C:10](=[O:11])[CH2:12][C:13]1([CH3:14])[CH3:15] | CC(=O)C=C(C)C.CCOC(=O)CC(C)=O | CCOC(=O)C1C(C)=CC(=O)CC1(C)C | null | [Cl-].[Zn+2].[Cl-] | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 9caf2ea3b4588269023cac4d0bec2473daf773ff2dbc278fbff741f1a82c9568 | e5a4879ba39f65932249d5c55ca80c162066a287cca16886a7d4b536be057c1f | O=C1C=CCCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[CH;D2;+0:11]-[C:12](-[CH3;D1;+0:13])=[O;D1;H0:14]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:3]1-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:13]-[C:12](=[O;D1;H0:14])-[CH2;D2;+0:11]-[C;H0;D4;+0:9]-1(-[C;... | 27 | [{"value": 27.0, "product": "O=C1C=C(C(C(C1)(C)C)C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 1020 ml (1041 g, 8.00 mol) of ethyl acetoacetate, 960 ml (824 g, 8.40 mol) of mesityl oxide, 1000 ml of heptane, 600 ml of toluene, and 175 g of zinc chloride was heated at reflux in a 5000 ml round bottom flask while stirring. The flask was equipped with a Dean-Stark trap and drying tube. After 24 h, an a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester | Ketone.Ester | null | C1=CCCCC1 | C1=CCCCC1 | HO- | [Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C | null | 24 | CC(=O)C=C(C)C.CCOC(=O)CC(C)=O>[Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C>CCOC(=O)C1C(C)=CC(=O)CC1(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-012a6b5e67c444bc94d607afb69c77fd | O=Nc1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 | C1(=CC=CC=C1)NC1=CC=C(C=C1)N=O.C(CCCCC)O.[OH-].[Na+]>>C1(=CC=CC=C1)NC1=CC=C(C=C1)N | O=[N:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | O=Nc1ccc(Nc2ccccc2)cc1 | Nc1ccc(Nc2ccccc2)cc1 | null | null | null | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1ccc(Nc2ccccc2)cc1 | O=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 100 | CELSIUS | 15 | MINUTE | To a 1-liter three-necked round bottom flask fitted with a stirrer, a condenser and a thermometer were added 99.0 (0.5 mole) N-phenyl-4-nitrosoaniline, 254 g n-hexanol and 40 g (0.5 mole) aqueous NaOH (50% by weight). The dark reddish brown solution was stirred, heated to 100° C., at which point an exotherm developed, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | 100 | 0.25 | O=Nc1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c383faf3f6174cd6aefc2d5b32c406fe | CC(C)Nc1ccc(N=O)cc1>>CC(C)Nc1ccc(N)cc1 | C(C)(C)NC1=CC=C(C=C1)N=O.[OH-].[Na+].C(CCCCC)O>>C(C)(C)NC1=CC=C(C=C1)N | O=[N:9][c:8]1[cH:7][cH:6][c:5]([NH:4][CH:2]([CH3:1])[CH3:3])[cH:11][cH:10]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][cH:11]1 | CC(C)Nc1ccc(N=O)cc1 | CC(C)Nc1ccc(N)cc1 | null | null | null | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1ccccc1 | O=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1.5 | HOUR | Following essentially the procedure of Example 1, 66.0 g (0.25 mole) N-isopropyl-4-nitrosoaniline, 20 g (50%) sodium hydroxide and 264 g n-hexanol were kept at 100° C. for 1.5 hours. HPLC analysis of the reaction mixture indicated absence of the nitroso starting compound. By vacuum distillation (95°-101° C. at 13.3-26.... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1ccccc1 | Other | null | null | 1.5 | CC(C)Nc1ccc(N=O)cc1>>CC(C)Nc1ccc(N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-37aa6ea9a1e04e1a9edfeac185572691 | O=Nc1ccc(NC2CCCCC2)cc1>>Nc1ccc(NC2CCCCC2)cc1 | C1(CCCCC1)NC1=CC=C(C=C1)N=O.[OH-].[Na+].C(CCCCC)O>>C1(CCCCC1)NC1=CC=C(C=C1)N | O=[N:1][c:2]1[cH:3][cH:4][c:5]([NH:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][cH:14]1 | O=Nc1ccc(NC2CCCCC2)cc1 | Nc1ccc(NC2CCCCC2)cc1 | null | null | null | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1ccc(NC2CCCCC2)cc1 | O=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 95 | CELSIUS | null | null | 51.0 g (0.25 mole) N-cyclohexyl-4-nitrosoaniline, 20.0 g (50%) NaOH and 135 g n-hexanol were charged to a 0.5 liter three-necked round bottom flask equipped with stirrer, condenser and thermometer, and heated while stirring to 95° C. until the development of an exotherm was observed. Heating was discontinued, the react... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1ccccc1.C1CCCCC1 | Other | null | 95 | null | O=Nc1ccc(NC2CCCCC2)cc1>>Nc1ccc(NC2CCCCC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-22ac62cc70144edcaeb56a8177416fc5 | COC(OC)/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1>>O=C/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 | CO.Cl.ClC1=CC=C(C=C1)\C(=C/C1=C(C=C(C=C1)Cl)Cl)\C(OC)OC>>ClC1=CC=C(C=C1)/C(/C=O)=C\C1=C(C=C(C=C1)Cl)Cl | CO[CH:2]([O:1]C)/[C:3](=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[O:1]=[CH:2]/[C:3](=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | COC(OC)/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 | O=C/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 | null | null | O | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | C(=Cc1ccccc1)c1ccccc1 | C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C)/[C:3](=[C:4]/[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]>>[O;H0;D1;+0:2]=[CH;D2;+0:1]/[C:3](=[C:4]/[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 98 | [{"value": 98.0, "product": "ClC1=CC=C(C=C1)/C(/C=O)=C\\C1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "ClC1=CC=C(C=C1)/C(/C=O)=C\\C1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Thereafter, a mixture of 1,000 ml of distilled water, 500 ml of methanol, 50 ml (59.7 g; 0.62 mole) of concentrated hydrochloric acid and 350 g (0.98 mole) of (E)-2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3,3-dimethoxyprop-1-ene (I) is refluxed for 4 hours, while stirring. The mixture is cooled to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccccc1.c1ccccc1 | HO- | O | null | null | COC(OC)/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1>O>O=C/C(=C/c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0ef1704cd51e4103bf0c70a5c34931c8 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | [BH4-].[Na+].[Cl-].[Ca+2].[Cl-].CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O.C(C)(=O)OC(=C)C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@@H:13]3[CH:14]=[CH:15][C:16]4=[CH:17][C:18](=[O:19])[CH:20]=[CH:21][C@:22]4([CH3:23])[C@H:24]3[CH2:25][CH2:26][C@:27]12[CH3:28]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | null | null | C(C)(=O)O.C(C)O.CO | Miscellaneous | OtherReaction | ce199a9717577b19e17b558ab580cac84b7eb6d1ac794349c63acafd3742f994 | 1e83e74425aad4068141e0cbe7e7aa16ea22ce64c64852761026bc116529d724 | C1=CC2C(=CC=C3[C@@H]4CCCC4CC[C@@H]32)CC1 | [C:1]-[C:2](-[C:3])-[C@@H;D3;+0:4]1-[CH;D2;+0:5]=[CH;D2;+0:6]-[C;H0;D3;+0:7]2=[CH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]=[C:12]-[C:13]-2(-[C;D1;H3:14])-[C:15]-1-[C:16]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH;D2;+0:6]=[C;H0;D3;+0:7]2-[CH2;D2;+0:8]-[CH;D3;+0:9](-[OH;D1;+0:10])-[C:11]=[C:12]-[C:13]... | 63 | [{"value": 63.0, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.5, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 6 | HOUR | To a mixture of 38 g (0.1 mol) of cholesta-1,4,6-trien-3-one and 17 g (0.1 mol) of paratoluenesulfonic acid were added 400 g (4 mol) of isopropenyl acetate, and the mixture was heated under reflux for 3 hours. The reaction solution was thoroughly washed with water until it was neutral, and dried over sodium sulfate A s... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol.Conjugated diene | C1=C[C@H]2C(=CC1)C=C[C@H]1[C@@H]3CCC[C@H]3CC[C@@H]12 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | null | C(C)(=O)O.C(C)O.CO | 0 | 6 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>C(C)(=O)O.C(C)O.CO>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a1fa50bc5b0d4b9783d5897925735776 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | C(C)(=O)OC(=C)C.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@@H:13]3[CH:14]=[CH:15][C:16]4=[CH:17][C:18](=[O:19])[CH:20]=[CH:21][C@:22]4([CH3:23])[C@H:24]3[CH2:25][CH2:26][C@:27]12[CH3:28]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | null | null | C(C)(=O)OCCCC | Miscellaneous | OtherReaction | ce199a9717577b19e17b558ab580cac84b7eb6d1ac794349c63acafd3742f994 | 1e83e74425aad4068141e0cbe7e7aa16ea22ce64c64852761026bc116529d724 | C1=CC2C(=CC=C3[C@@H]4CCCC4CC[C@@H]32)CC1 | [C:1]-[C:2](-[C:3])-[C@@H;D3;+0:4]1-[CH;D2;+0:5]=[CH;D2;+0:6]-[C;H0;D3;+0:7]2=[CH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]=[C:12]-[C:13]-2(-[C;D1;H3:14])-[C:15]-1-[C:16]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH;D2;+0:6]=[C;H0;D3;+0:7]2-[CH2;D2;+0:8]-[CH;D3;+0:9](-[OH;D1;+0:10])-[C:11]=[C:12]-[C:13]... | 66 | [{"value": 66.0, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 38 g (0.1 mol) of cholesta-1,4,6-trien-3-one (I) and 34 g (0.2 mol) of paratoluenesulfonic acid were added 200 ml of butyl acetate and further 200 g (2 mol) of isopropenyl acetate, and the resulting mixture was heated under reflux for 5 hours. After completion of the reaction, the same treatment as in E... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol.Conjugated diene | C1=C[C@H]2C(=CC1)C=C[C@H]1[C@@H]3CCC[C@H]3CC[C@@H]12 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | null | C(C)(=O)OCCCC | null | null | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>C(C)(=O)OCCCC>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d91476894bba4ff4b3f1ab9b2aac825a | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O.CS(=O)(=O)O.C(C)(=O)OC(=C)C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@@H:13]3[CH:14]=[CH:15][C:16]4=[CH:17][C:18](=[O:19])[CH:20]=[CH:21][C@:22]4([CH3:23])[C@H:24]3[CH2:25][CH2:26][C@:27]12[CH3:28]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | ce199a9717577b19e17b558ab580cac84b7eb6d1ac794349c63acafd3742f994 | 1e83e74425aad4068141e0cbe7e7aa16ea22ce64c64852761026bc116529d724 | C1=CC2C(=CC=C3[C@@H]4CCCC4CC[C@@H]32)CC1 | [C:1]-[C:2](-[C:3])-[C@@H;D3;+0:4]1-[CH;D2;+0:5]=[CH;D2;+0:6]-[C;H0;D3;+0:7]2=[CH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]=[C:12]-[C:13]-2(-[C;D1;H3:14])-[C:15]-1-[C:16]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH;D2;+0:6]=[C;H0;D3;+0:7]2-[CH2;D2;+0:8]-[CH;D3;+0:9](-[OH;D1;+0:10])-[C:11]=[C:12]-[C:13]... | 61.2 | [{"value": 61.0, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 19 g (0.05 mol) of cholesta-1,4,6-trien-3-one (I), 4.8 g (0.05 mol) of methanesulfonic acid and 200 g (2 mol) of isopropenyl acetate were added 200 ml of toluene, and the resulting mixture was then heated under reflux for 6 hours. After completion of the reaction, the same treatment as in Example 1 was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol.Conjugated diene | C1=C[C@H]2C(=CC1)C=C[C@H]1[C@@H]3CCC[C@H]3CC[C@@H]12 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | null | C1(=CC=CC=C1)C | null | null | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>C1(=CC=CC=C1)C>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8fa7272f95be4725909831043f7554af | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O.[K].C(C)(=O)OC(=C)C>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@@H:13]3[CH:14]=[CH:15][C:16]4=[CH:17][C:18](=[O:19])[CH:20]=[CH:21][C@:22]4([CH3:23])[C@H:24]3[CH2:25][CH2:26][C@:27]12[CH3:28]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C | null | null | C(C)(=O)OCCCC | Miscellaneous | OtherReaction | ce199a9717577b19e17b558ab580cac84b7eb6d1ac794349c63acafd3742f994 | 1e83e74425aad4068141e0cbe7e7aa16ea22ce64c64852761026bc116529d724 | C1=CC2C(=CC=C3[C@@H]4CCCC4CC[C@@H]32)CC1 | [C:1]-[C:2](-[C:3])-[C@@H;D3;+0:4]1-[CH;D2;+0:5]=[CH;D2;+0:6]-[C;H0;D3;+0:7]2=[CH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]=[C:12]-[C:13]-2(-[C;D1;H3:14])-[C:15]-1-[C:16]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH;D2;+0:6]=[C;H0;D3;+0:7]2-[CH2;D2;+0:8]-[CH;D3;+0:9](-[OH;D1;+0:10])-[C:11]=[C:12]-[C:13]... | 58 | [{"value": 58.0, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(C=C[C@]4(C)[C@H]3CC[C@]12C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 19 g (0.05 mol) of cholesta-1,4,6-trien-3-one (I), 6.8 g (0.05 mol) of potassium acid sulphate and 200 g (2 mol) of isopropenyl acetate were added 200 ml of butyl acetate, and the resulting mixture was heated under reflux for 7 hours. After completion of the reaction, the same treatment as in Example 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol.Conjugated diene | C1=C[C@H]2C(=CC1)C=C[C@H]1[C@@H]3CCC[C@H]3CC[C@@H]12 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | C1=C[C@H]2C(=CC=C3[C@@H]4CCC[C@H]4CC[C@@H]32)CC1 | null | C(C)(=O)OCCCC | null | null | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C>C(C)(=O)OCCCC>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-07290cbe3a6d4b7aa78af205e4526201 | O=C1CCC(O)CC1.Oc1ccc(-c2ccc(O)cc2)cc1>>Oc1ccc(C2(c3ccc(O)cc3)CCC(O)CC2)cc1 | C1(=CC=CC=C1)O.C1(=CC=C(C=C1)C1=CC=C(C=C1)O)O.OC1CCC(CC1)=O>>OC1=CC=C(C=C1)C1(CCC(CC1)O)C1=CC=C(C=C1)O | O=[C:6]1[CH2:14][CH2:15][CH:16]([OH:17])[CH2:18][CH2:19]1.[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[cH:20][cH:21]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([C:6]2([c:7]3[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]3)[CH2:14][CH2:15][CH:16]([OH:17])[CH2:18][CH2:19]2)[cH:20][cH:21]1 | O=C1CCC(O)CC1.Oc1ccc(-c2ccc(O)cc2)cc1 | Oc1ccc(C2(c3ccc(O)cc3)CCC(O)CC2)cc1 | null | null | null | C-C Coupling | OtherReaction | dd99a9bd4b753288da1485f0c223918688d4244e287fb3c7b6bdb83444cc0384 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | c1ccc(C2(c3ccccc3)CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[c:6]:[c:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:14]:[c:15]>>[C:3]-[C:2]-[C;H0;D4;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])(-[c;H0;D3;+0:8](:[c:7]:[c:6]):[c:14]:[c:15])-[C:4]-[C:5] | null | [] | null | null | null | null | A process for the preparation of 4,4'-biphenol which comprises reacting 4-hydroxycyclohexanone with phenol in the presence of an acid catalyst to give 4,4-bis(4-hydroxyphenyl)cyclohexanol of the formula (I) ##STR5## and successively subjecting 4,4-bis(4-hydroxyphenyl)cyclohexanol to decomposition and dehydrogenation re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | Other | null | null | null | O=C1CCC(O)CC1.Oc1ccc(-c2ccc(O)cc2)cc1>>Oc1ccc(C2(c3ccc(O)cc3)CCC(O)CC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9e27edb996dc4b2e8698c669aeab451a | CC(C)C(C#N)(CCCN(C)CCc1ccccc1)c1ccccc1.O=C(O)C(O)C(O)C(=O)O>>CC(C)C1(CCCN(C)CCc2ccccc2)C=CC=CC1CC=O | S(O)(O)(=O)=O.[H-].C(C(C)C)[Al+]CC(C)C.C1(=CC=CC=C1)CCN(CCCC(C#N)(C1=CC=CC=C1)C(C)C)C.[OH-].[K+].C(C(O)C(O)C(=O)O)(=O)O>>C1(=CC=CC=C1)CCN(CCCC1(C(C=CC=C1)CC=O)C(C)C)C | N#[C:24][C:4]([CH:2]([CH3:1])[CH3:3])([CH2:5][CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:22]1[cH:21][cH:20][cH:19][cH:18][cH:23]1.O=C(O)C(O)C(O)C(=O)[OH:25]>>[CH3:1][CH:2]([CH3:3])[C:4]1([CH2:5][CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16]... | CC(C)C(C#N)(CCCN(C)CCc1ccccc1)c1ccccc1.O=C(O)C(O)C(O)C(=O)O | CC(C)C1(CCCN(C)CCc2ccccc2)C=CC=CC1CC=O | null | null | CCCCCC.C(C)OCC | C-C Coupling | OtherReaction | 853eb36b76e9281298947a12c9a7f12093ddf1ab38a7d55d1c2fd8ab4d79dbf8 | a66f64b383d8409fe4892b449d427c78d23912d2db58b7c5bbe5f3ce93abd3da | C1=CCC(CCCNCCc2ccccc2)C=C1 | N#[C;H0;D2;+0:1]-[C;H0;D4;+0:2](-[C:3]-[C:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.O-C(-C(-O)-C(=O)-[OH;D1;+0:14])-C(-O)=O>>[C:4]-[C:3]-[C;H0;D4;+0:2]1(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[CH;D2;+0:12]=[CH;D2;+0:11]-[CH;D2;+0:10]=[CH;D2;+... | null | [] | null | null | 1.5 | HOUR | 180 ml of a 1M solution of diisobutylaluminum hydride in hexane were added dropwise, at -5° C., to a solution of 33.4 g (0.1 mole) of 2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile in 400 ml of diethyl ether. The mixture was stirred for 1.5 hours, after which 500 ml of 10% strength sulfuric acid w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Nitrile.Secondary alcohol.Secondary alcohol | Aldehyde.Conjugated diene | c1ccccc1 | C1=CCCC=C1 | c1ccccc1.C1=CCCC=C1 | HO- | CCCCCC.C(C)OCC | null | 1.5 | CC(C)C(C#N)(CCCN(C)CCc1ccccc1)c1ccccc1.O=C(O)C(O)C(O)C(=O)O>CCCCCC.C(C)OCC>CC(C)C1(CCCN(C)CCc2ccccc2)C=CC=CC1CC=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-34a0944dc3144a9f9ca25f89152134d8 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>>NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 | FC1=C(C(=O)N)C=CC=C1.ClC=1C=C2CCNC2=CC1.[H-].[Na+]>>ClC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]21 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F | NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8].[c:9]:[c:10]1:[c:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[c:11]:[c:10]-1:[c:9]):[c:2]:[c:3] | 43.3 | [{"value": 43.3, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A slurry was prepared comprising 5-chloroindoline (15.3 gm, 0.1 mole), dimethylsulfoxide (DMSO) [50 ml] and sodium hydride (5.28 gm, 50% in oil, washed with hexane). The slurry was permitted to stir at room temperature for 1 hour. To this a solution of o-fluorobenzamide (15.2 gm, 1.1 eq.) in DMSO (20 ml) was added drop... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | CS(=O)C | null | 1 | Clc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>CS(=O)C>NC(=O)c1ccccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b2d4d3520054c488b87d1bb7fa2f7da | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21>>NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | ClC=1C=C2CCN(C2=C(C1)[N+](=O)[O-])C1=C(C(=O)N)C=CC=C1>>ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1 | O=[N+:19]([O-])[c:18]1[cH:17][c:15]([Cl:16])[cH:14][c:13]2[c:20]1[N:10]([c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1)[CH2:11][CH2:12]2>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Cl:16])[cH:17][c:18]([NH2:19])[c:20]21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | null | null | CN(C=O)C.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]>>[#7:5]-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 119.3 | [{"value": 119.3, "product": "ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To the solution of 2-(5-chloro-7-nitroindolin-1-yl)benzamide of Example 1b (10 gm, 26.5 mmoles) in dimethylformamide (DMF) [100 ml] and ethanol (100 ml) was added 1% Pt/carbon (2.0 gm). The mixture was shaken under hydrogen (59 psi) for 41/2 hours. The mixture was then filtered under nitrogen and concentrated to remove... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | CN(C=O)C.C(C)O | null | 2 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc([N+](=O)[O-])c21>CN(C=O)C.C(C)O>NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4bbfa46f3e4e40cb90638913d3ea938d | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21>>O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 | ClC=1C=C2CCN(C2=C(C1)N)C1=C(C(=O)N)C=CC=C1>>ClC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1 | N[C:2](=[O:1])[c:19]1[c:14]([N:11]2[c:10]3[c:4]([NH2:3])[cH:5][c:6]([Cl:7])[cH:8][c:9]3[CH2:13][CH2:12]2)[cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]3[c:10]2[N:11]([CH2:12][CH2:13]3)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21 | O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 | null | null | CO.ClCCl | Miscellaneous | OtherReaction | 699e7bfbbd46d2067058ea48bc645fe6abf364bea853a0751c83a61ba7a46d64 | f24c9f1ec9fd5abfe6f68cf1415b34cc6e64faf9d608cbf5712660ea976e20b3 | O=C1Nc2cccc3c2N(CC3)c2ccccc21 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-[#7:6]-[c:5]:[c:3]-1:[c:4] | null | [] | null | null | 2 | HOUR | 2-(5-chloro-7-aminoindolin-1-yl)benzamide of Example 1c (28.7 g, 0.10 mole) was dissolved in methanol/dichloromethane (DCM) solution (1:9 v/v) at 35° C. Silica gel (510 gm) was added to absorb the starting material, then the solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Secondary amide | null | c1ccc2c(c1)CNc1cccc3c1N2CC3 | c1ccc2c(c1)CNc1cccc3c1N2CC3 | Other | CO.ClCCl | null | 2 | NC(=O)c1ccccc1N1CCc2cc(Cl)cc(N)c21>CO.ClCCl>O=C1Nc2cc(Cl)cc3c2N(CC3)c2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1f60ae74bfc041b0a03d92e9aa374cd6 | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F>>CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | C(\C=C/C(=O)O)(=O)O.NC=1C=C(C=CC1F)N1CCC2=CC=CC=C12.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl.C(C)N(CC)CC.C(=O)(Cl)Cl>>C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)=[O:7].[NH2:8][c:9]1[cH:10][c:15]([N:16]2[CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]32)[cH:14][cH:13][c:11]1[F:12]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19]3... | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | null | null | C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl | Acylation | OtherReaction | e2d29a6723220f7540ade03be1350afcc1e105044dd661555a27f5f3b0755993 | aad7770ec49cc1fbb0c48907b32832faee613a05b9b63a5a2c921d89bf7e8d07 | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[#7:7](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[F;D1;H0:12]):[c;H0;D3;+0:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:1)-[c:16]>>[C:6]-[#7:7](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[F;D1;H0:12]):[cH;D2;+0:15]:[c;H0;D3;+0:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](... | null | [] | null | null | 15 | MINUTE | To a stirred solution under nitrogen, of 50.2 g (0.22 mole) of 1-(3-amino-4-fluorophenyl)indoline of Example 2b, and 66.7 g (0.66 mole) of triethylamine in 900 ml of chloroform was added 65.7 g (0.33 mole) of 4-methyl-1-piperazine carbonyl chloride hydrochloride in portions over 5 minutes. The reaction was refluxed for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Tertiary amide.Primary amine | Aromatic halide.Urea | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1cc(N2CCc3ccccc32)ccc1F>C(C)O.C1(=CC=CC=C1)C.O.C(Cl)(Cl)Cl>CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d05aba48e42f473683f66f9ad22c62c6 | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 | N1(CCC2=CC=CC=C12)C1=C(C=C(C=C1)F)NC(=O)N1CCN(CC1)C>>FC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH... | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 20.8 | [{"value": 20.8, "product": "FC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 10.6 g (0.030 mole) of N-[2-(2,3-dihydro-1H-indol-1-yl)-5-fluorophenyl]-4-methyl-1-piperazine carboxamide of Example 2c in 250 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure w... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(F)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(F)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eea358c9ce0f4dc59f03aa6553cefabd | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21>>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | C(\C=C/C(=O)O)(=O)O.BrC1=CC(=C(C=C1)N1CCC2=CC=CC=C12)N.C([O-])([O-])=O.[K+].[K+].Cl.CN1CCN(CC1)C(=O)Cl.C([O-])([O-])=O.[K+].[K+].C(=O)(Cl)Cl>>C(\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12 | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:26][CH2:25]1)=[O:7].[NH2:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[N:16]1[CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][c:19... | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | null | null | C(C)O.C(Cl)(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 39.8 | [{"value": 16.0, "product": "C(\\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "C(\\C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen of 43.5 g (0.15 mole) of 1-(4-bromo-2-aminophenyl)indoline of Example 3b and 82.8 g (0.60 mole) of milled potassium carbonate in 1000 ml of chloroform was added 44.7 g (0.225 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over 10 minutes. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)O.C(Cl)(Cl)Cl.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1cc(Br)ccc1N1CCc2ccccc21>C(C)O.C(Cl)(Cl)Cl.O>CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d09dbf951ae649f09f2b17df1b6aceb5 | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | BrC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][... | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 29.7 | [{"value": 29.7, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 9.14 g (0.022 mole) of N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 3c in 250 ml of phosphorus oxychloride was refluxed for 7 hours under nitrogen then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure with... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(Br)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8580d0aef4048cc80058e48c5dcb458 | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2>>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 | ClC1=C(C=C(C=C1)Cl)[N+](=O)[O-].N1CCC2=CC=CC=C12>>ClC1=CC(=C(C=C1)N1CCC2=CC=CC=C12)[N+](=O)[O-] | Cl[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Cl:7])[cH:8][cH:9]1.[NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | null | [] | null | null | null | null | A stirred solution of 38.4 g (0.20 mole) of 1,4-dichloro-2-nitrobenzene and 59.6 g (0.50 mole) of indoline in 400 ml of dimethylformamide (DMF) was heated under nitrogen at 140°-145° C. overnight (23 hours). The DMF solvent was then removed in vacuo and the residue was dissolved in 500 ml of dichloromethane. This solut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C=O)C | null | null | O=[N+]([O-])c1cc(Cl)ccc1Cl.c1ccc2c(c1)CCN2>CN(C=O)C>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a08d3688562f4ce18a1f8153c3a588f8 | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 | ClC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]3[N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][... | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 37 | [{"value": 37.0, "product": "ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "ClC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 6.30 g (0.017 mole) of N-[5-chloro-2-(2,3-dihydro-1H-indol-1-yl)-phenyl]-4-methyl-1piperazinecarboxamide of Example 4b in 100 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure w... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2cc(Cl)ccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3cc(Cl)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81328b540f06421c8f965823a6923595 | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1>>Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | C(\C=C/C(=O)O)(=O)O.C([O-])([O-])=O.[K+].[K+].C(=O)(Cl)Cl.NC1=C(C=CC(=C1)C)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].Cl.CN1CCN(CC1)C(=O)Cl>>C(\C=C/C(=O)O)(=O)O.CC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12 | Cl[C:17](=[O:18])[N:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[c:15]([NH2:16])[cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[c:15]([NH:16][C:17](=[O:18])[N:... | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1 | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | null | null | ClCCl.C(Cl)(Cl)Cl.CO.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen of 43.0 g (0.190 mole) of 1-(2-amino-4-methylphenyl)indoline of Example 5b and 105 g (0.76 mole) of milled potassium carbonate in 1000 ml of chloroform was added 56.7 (0.285 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over 10 minutes. The reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2.C1C[NH]CC[NH]1 | HCl | ClCCl.C(Cl)(Cl)Cl.CO.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Cc1ccc(N2CCc3ccccc32)c(N)c1>ClCCl.C(Cl)(Cl)Cl.CO.O>Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a89f4cd98dc64691ab260a3422a7f092 | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1>>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 | CC=1C=CC(=C(C1)NC(=O)N1CCN(CC1)C)N1CCC2=CC=CC=C12>>CC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1 | O=[C:9]([NH:8][c:6]1[c:5]([N:23]2[c:22]3[cH:17][cH:18][cH:19][cH:20][c:21]3[CH2:25][CH2:24]2)[cH:4][cH:3][c:2]([CH3:1])[cH:7]1)[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19]... | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1 | Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:14]-[#7:13](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12])-[C:15] | 41 | [{"value": 41.0, "product": "CC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 35.1 (0.10 mole) of N-[5-methyl-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 5c in 500 ml of phosphorus oxychloride was refluxed for 6 hours under nitrogen, then cooled to room temperature. The excess phosphorus oxychloride was removed at aspirator pressure with ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | Cc1ccc(N2CCc3ccccc32)c(NC(=O)N2CCN(C)CC2)c1>P(=O)(Cl)(Cl)Cl>Cc1ccc2c(c1)N=C(N1CCN(C)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1d2813a33d28473591d96037dace2e49 | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21>>CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | NC1=C(C=CC=C1)N1CCC2=CC=CC=C12.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl.C(\C=C/C(=O)O)(=O)O.C(C)N(CC)CC.Cl.CN1CCN(CC1)C(=O)Cl>>C(\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C | Cl[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)=[O:7].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20]... | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21 | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | null | null | C(Cl)(Cl)Cl.C(C)O.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(Nc1ccccc1N1CCc2ccccc21)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 53 | [{"value": 53.0, "product": "C(\\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.9, "product": "C(\\C=C/C(=O)O)(=O)O.N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution, under nitrogen, of 21.0 g (0.10 mole) of 1-(2-aminophenyl)indoline and 30.4 g (0.30 mole) of triethylamine in 400 ml of chloroform was added 29.9 g (0.15 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over about 5 minutes. The reaction was refluxed for 6 hours when an a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)(Cl)Cl.C(C)O.O | null | 0.25 | CN1CCN(C(=O)Cl)CC1.Nc1ccccc1N1CCc2ccccc21>C(Cl)(Cl)Cl.C(C)O.O>CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-772447eccb984215915d35d9b6ce22ed | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 | N1(CCC2=CC=CC=C12)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C>>CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:24][CH2:23]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][c:21]2[c:... | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 10 | [{"value": 10.0, "product": "CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.0, "product": "CN1CCN(CC1)C1=NC2=C(N3C4=C1C=CC=C4CC3)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 21.1 g (0.0627 mole) of N-[2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide of Example 7a was added 500 ml of phosphorus oxychloride and this was refluxed under nitrogen overnight. The excess POCl3 was then removed at aspirator pressure with warming. The residue was boiled and triturated on the ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCc3ccccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5daefc833f2940079d65494584a8475e | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl>>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | ClC=1C=C2CCNC2=CC1.ClC1=C(C=C(C=C1)Cl)[N+](=O)[O-].N1=C(C=C(C=C1C)C)C>>ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-] | [NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]21.Cl[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Cl:7])[cH:8][cH:9]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]21 | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | 40 | [{"value": 40.0, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 123 g (0.80 mole) of 5-chloroindoline, 134 g (0.70 mole) of 1,4-dichloronitrobenzene and 97 g (0.80 mole) of collidine in 1000 ml of dimethylformamide was heated under nitrogen at 150° C. for 48 hours. The mixture was then cooled, filtered from some insolubles, and the solvent was removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C=O)C | null | null | Clc1ccc2c(c1)CCN2.O=[N+]([O-])c1cc(Cl)ccc1Cl>CN(C=O)C>O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0d50972b8c6f417dabdfd558c12a27e4 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21>>CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | ClC=1C=C2CCN(C2=CC1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-].C1=CC=CC=C1>>C(C)[O-].Cl.NC1=C(C=CC(=C1)Cl)N1CCC2=CC(=CC=C12)Cl | [O-][N+:5](=[O:3])[c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][c:18]([Cl:4])[cH:20][cH:21][c:22]21>>[CH3:1][CH2:2][O-:3].[ClH:4].[NH2:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:22]21 | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 | null | [Pt] | C(C)O | Functional Group Interconversion | Reduction of nitro groups to amines | 7d8327c707810ad9bf9cab994013125d90d07022ab441f2f6714198d54f0463b | 33553c41c42ab392a899ed959afa486593c8da248b31b16bda6197a51e957d22 | c1ccc(N2CCc3ccccc32)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[O-]-[N+;H0;D3:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:12]-[C:13]-[O-;H0;D1:8].[Cl;D1;H0:14]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:9](:[c:10]):[c:11].[ClH;D0;+0:1] | null | [] | null | null | null | null | A Parr bottle, charged with 12.4 g (0.040 mole) of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline of Example 8a, 100 ml of benzene, 100 ml of absolute ethanol and 0.5 g of 1% Pt/C was shaken under an initial hydrogen pressure of 57 psig until uptake ceased. The catalyst was then removed by filtration and the filtrate was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Aromatic halide.Primary amine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | [Pt].C(C)O | null | null | O=[N+]([O-])c1cc(Cl)ccc1N1CCc2cc(Cl)ccc21>[Pt].C(C)O>CC[O-].Cl.Nc1cc(Cl)ccc1N1CCc2cc(Cl)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b238208936bf4bfbbf0538d99e7cea57 | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>>NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 | BrC=1C=C2CCNC2=CC1.[H-].[Na+].FC1=C(C(=O)N)C=CC=C1>>BrC=1C=C2CCN(C2=CC1)C1=C(C(=O)N)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21.F[c:9]1[c:4]([C:2]([NH2:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]21 | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F | NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8].[c:9]:[c:10]1:[c:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[c:11]:[c:10]-1:[c:9]):[c:2]:[c:3] | null | [] | 55 | CELSIUS | 30 | MINUTE | A slurry was prepared from 5-bromoindoline (9.85 g, 50 mmoles) dimethylsulfoxide (DMSO) (35 ml), sodium hydride (2.6 g, 50% in oil, washed with hexane, 1.1 eq). The slurry was stirred for 30 minutes. To this a solution of o-fluorobenzamide (7.9 g, 1.1 eq) in DMSO (15 ml) was added dropwise with temperature between 12°-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | CS(=O)C | 55 | 0.5 | Brc1ccc2c(c1)CCN2.NC(=O)c1ccccc1F>CS(=O)C>NC(=O)c1ccccc1N1CCc2cc(Br)ccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e21dae76eb054e48bb6f93275e400669 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 | BrC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C>>BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][c:19]([Br:20])[cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Br:20])[... | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 | null | null | P(=O)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 57 | [{"value": 57.0, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "BrC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (11.5 g, 27.5 mmoles) and 750 ml of phosphorus oxychloride was stirred until a solution was obtained and then heated under reflux for 40 minutes. The reaction mixture was cooled. Excess phosphorus oxychloride was removed by evaporation at 5... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Br)ccc32)CC1>P(=O)(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Br)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a8f3b31d3fb8425495c20ef17ead3ee5 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1>>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | ClC=1C=C2CCN(C2=CC1)C1=C(C=CC=C1)NC(=O)N1CCN(CC1)C.ClCCCl>>ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1 | O=[C:6]([N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:25][CH2:24]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]1[CH2:15][CH2:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Cl:20])[... | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1 | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 9342c56621144aa392956de6f2aadf901c12c89e3fdbd3c69adf953d1dc389f5 | f23d083eedbb9394ba50c0c14a0d36693f8f0fc41220d025c09abb7bd8febef3 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6](-[C:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[#7:13](-[C:14])-[C:15]>>[C:7]-[#7:6]1-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[#7:13](-[C:14])-[C:15])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9] | 29.5 | [{"value": 28.0, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.5, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 15 | MINUTE | To N-[2-(5-chloro-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide (13.5 g, 36.5 mmoles) was added a solution of polyphosphoric acid ethyl ester and 1,2-dichloroethane (250 ml). The solution was heated at 75° C. for 4 hours with exclusion of moisture. The solution was cooled and poured into a mixture of ice-sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ccc2c(c1)CC[NH]2 | C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | ClCCl | 75 | 0.25 | CN1CCN(C(=O)Nc2ccccc2N2CCc3cc(Cl)ccc32)CC1>ClCCl>CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-242c4d5ab06745cab99e5588071de23e | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1>>Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 | C1(=CC=CC=C1)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1 | O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:28]2[c:27]3[c:22]1[cH:23][cH:24][cH:25][c:26]3[CH2:30][CH2:29]2.[NH:10]1[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([c:14]3[cH:15]... | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1 | Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Protection | OtherReaction | 98711646775885568a342f905905ff5ba0e597f682ac14122a128c5434eecc65 | cc3066bc8728393c812617a52db29f0bb6fceaa1e59ff8a41efec6544d2cffe9 | c1ccc(N2CCN(C3=Nc4ccccc4N4CCc5cccc3c54)CC2)cc1 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | 68 | [{"value": 68.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C2=CC=CC=C2)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 40.6 g (0.250 mole) of N-phenylpiperazine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | c1cc2c3c(c1)CNc1ccccc1N3CC2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.c1ccccc1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(N2CCNCC2)cc1>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCN(c3ccccc3)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-480f4ab5898942408e785b504ff992e5 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1>>Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 | C(C1=CC=CC=C1)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CC2=CC=CC=C2)C=CC=C4CC3)C=C1 | O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([Br:1])[cH:7]2)[N:29]2[c:28]3[c:23]1[cH:24][cH:25][cH:26][c:27]3[CH2:31][CH2:30]2.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH2:1... | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1 | Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Protection | OtherReaction | 98711646775885568a342f905905ff5ba0e597f682ac14122a128c5434eecc65 | cc3066bc8728393c812617a52db29f0bb6fceaa1e59ff8a41efec6544d2cffe9 | c1ccc(CN2CCN(C3=Nc4ccccc4N4CCc5cccc3c54)CC2)cc1 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 44.1 g (0.250 mole) of N-benzylpiperazine, followed by 14.2 g (0.0750 mole) of titanium tetrachloride. The m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | c1cc2c3c(c1)CNc1ccccc1N3CC2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.c1ccccc1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32.c1ccc(CN2CCNCC2)cc1>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Brc1ccc2c(c1)N=C(N1CCN(Cc3ccccc3)CC1)c1cccc3c1N2CC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-44d0fd9b16504ba9b51cb4b2287eb071 | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | C(CC)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1 | [CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:26][CH2:27]1.O=[C:8]1[NH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[N:17]2[CH2:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][c:24]1[c:25]32>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:8]2=[N:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[N:17]3[CH2:18... | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 237f558d3d4dc4c7b9112e11c22321b33ed2e8f12d9e26cb655dd9b67be9c0e9 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:4]:[c:3]1:[c:5]-[#7:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2)=[N;H0;D2;+0:2]-1 | 30.1 | [{"value": 30.0, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.1, "product": "BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)CCC)C=CC=C4CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated until a solution resulted. Then there was added 32.1 g (0.25 mole) of N-propylpiperazine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | null | CCCN1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CCCN1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dddd11ec791c4ce089d60453cc62ff79 | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>>CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | CCOC(=O)N1CCNCC1.BrC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N3C4=C(C(=N2)N2CCN(CC2)C(=O)OCC)C=CC=C4CC3)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:28][CH2:29]1.O=[C:10]1[NH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]2[N:19]2[CH2:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][c:26]1[c:27]32>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10]2=[N:11][c:12]3[cH:13][c:14]([Br:15])[cH:16][c... | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32 | CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 237f558d3d4dc4c7b9112e11c22321b33ed2e8f12d9e26cb655dd9b67be9c0e9 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:4]:[c:3]1:[c:5]-[#7:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2)=[N;H0;D2;+0:2]-1 | null | [] | null | null | 15 | MINUTE | A stirred mixture of 7.88 g (0.025 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml toluene was heated under nitrogen until a solution resulted. Then there was added 39.6 g (0.250 mole) of ethyl N-piperazinocarboxylate followed by 14.2 g (0.075 mole) of titanium tetrachloride. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | CCOC(=O)N1CCNCC1.O=C1Nc2cc(Br)ccc2N2CCc3cccc1c32>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>CCOC(=O)N1CCN(C2=Nc3cc(Br)ccc3N3CCc4cccc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4cb02cb743724486a8de82132d38307c | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1>>CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 | ClC=1C=C2C3=C(C(=NC4=C(N3CC2)C=CC=C4)N4CCN(CC4)C)C1>>ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]3[CH2:15][CH2:16][c:17]4[cH:18][c:19]([Cl:20])[cH:21][c:22]2[c:23]43)[CH2:24][CH2:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[n:14]3[cH:15][cH:16][c:17]4[cH:18][c:19]([Cl:20])[cH:2... | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1 | CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | d405feb4bf2466368676b67d597d545bfbabb71592669c396d3e89f5edb9d8b0 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2c(c1)N=C(N1CCNCC1)c1cccc3ccn-2c13 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11])-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[N;H0;D3;+0:14]-2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[#7:6]=[C:7]-[c:8]:[c:9]2:[c:10](:[c:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[n;H0;D3;+0:14]:2-1 | 63.7 | [{"value": 63.0, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "ClC=1C=C2C3=C(C(=NC4=C(N3C=C2)C=CC=C4)N4CCN(CC4)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (6 g, 17 mmoles), in chloroform (150 ml) was added manganese dioxide (10.5 g). The mixture was heated under reflux for 24 hours. The mixture was cooled, filtered and the solid was washed with dichloromethane (20... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1=Nc2ccccc2N2CCc3cccc1c32 | C1=Nc2ccccc2n2ccc3cccc1c32 | C1C[NH]CC[NH]1.C1=Nc2ccccc2n2ccc3cccc1c32 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | CN1CCN(C2=Nc3ccccc3N3CCc4cc(Cl)cc2c43)CC1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CN1CCN(C2=Nc3ccccc3-n3ccc4cc(Cl)cc2c43)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bfd48e74459e4aaeaded22c8bcaf5182 | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2>>Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 | CC=1C=C2C=3N(C4=C(C(N2)=O)C=CC=C4)CCC3C1.CN1CCNCC1>>CC=1C=C2C=3N(C4=C(C(=N2)N2CCN(CC2)C)C=CC=C4)CCC3C1 | [NH:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1.O=[C:9]1[NH:8][c:6]2[c:5]3[c:4]([cH:3][c:2]([CH3:1])[cH:7]2)[CH2:25][CH2:24][N:23]3[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19... | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2 | Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ebdcff6ea69ef8e3f8b8452dbdc2ecd5ea17480cbfbc99d1fe4894ddf896c9e5 | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1cc2c3c(c1)N=C(N1CCNCC1)c1ccccc1N3CC2 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:9]:[c:8]1:[c:7]-[#7:6]-[c:5]:[c:3](:[c:4])-[N;H0;D2;+0:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | null | null | 30 | MINUTE | A solution of 4-methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one (3.6 g, 14.3 mmoles), N-methylpiperazine (16 ml) and toluene (350 ml) was heated to 110° C. Titanium tetrachloride (4.3 ml) was added in three portions in two minute intervals. The mixture was heated under reflux for two hours and coole... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccc2c(c1)CNc1cccc3c1N2CC3 | C1C[NH]CC[NH]1.C1=Nc2cccc3c2N(CC3)c2ccccc21 | C1C[NH]CC[NH]1.C1=Nc2cccc3c2N(CC3)c2ccccc21 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.5 | CN1CCNCC1.Cc1cc2c3c(c1)NC(=O)c1ccccc1N3CC2>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Cc1cc2c3c(c1)N=C(N1CCN(C)CC1)c1ccccc1N3CC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-79f898b6c1714467beaef2298d35c83d | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3>>Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 | CC1=CC2=C(N3C4=C(C(N2)=O)C=CC=C4CC3)C=C1.CC1CCNCC1>>CC1=CC2=C(N3C4=C(C(=N2)N2CCC(CC2)C)C=CC=C4CC3)C=C1 | [NH:10]1[CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][CH2:16]1.O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[cH:7]2)[N:23]2[c:22]3[c:17]1[cH:18][cH:19][cH:20][c:21]3[CH2:25][CH2:24]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([N:10]1[CH2:11][CH2:12][CH:13]([CH3:14])[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:... | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3 | Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 | null | [Ti](Cl)(Cl)(Cl)Cl | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 98d409ed27efd2986317a1caf6aa32bc5bb9b6fd20baa673c7140c501309393d | 9ffe716926bd170b42c362e649c2b9497cc3b3fe59fe92798f9fc2d496d10516 | c1ccc2c(c1)N=C(N1CCCCC1)c1cccc3c1N2CC3 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]-[c:7]:[c:8]-1:[c:9])-[C:13]-[C:14] | null | [] | null | null | 15 | MINUTE | A stirred mixture of 6.26 g (0.0250 mole) of 9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 24.8 g (0.250 mole) of 4-methylpiperidine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | Tertiary amine | C1CCNCC1.c1cc2c3c(c1)CNc1ccccc1N3CC2 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | C1CC[NH]CC1.C1=Nc2ccccc2N2CCc3cccc1c32 | HO- | [Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 0.25 | CC1CCNCC1.Cc1ccc2c(c1)NC(=O)c1cccc3c1N2CC3>[Ti](Cl)(Cl)(Cl)Cl.C1(=CC=CC=C1)C>Cc1ccc2c(c1)N=C(N1CCC(C)CC1)c1cccc3c1N2CC3 |
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