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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e87e8b45cb4e463291e44ca41c4cfad3 | Cc1ccc(F)cc1Cl>>Cc1cc([N+](=O)[O-])c(F)cc1Cl | ClC1=C(C=CC(=C1)F)C.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])C | [CH3:1][c:2]1[cH:3][cH:4][c:8]([F:9])[cH:10][c:11]1[Cl:12]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[c:8]([F:9])[cH:10][c:11]1[Cl:12] | Cc1ccc(F)cc1Cl | Cc1cc([N+](=O)[O-])c(F)cc1Cl | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 795.3 | [{"value": 80.0, "product": "ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 795.3, "product": "ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 2-chloro-4-fluorotoluene (2.000 g, 1.383 mmol, Aldrich, used as received) in conc. H2SO4 (15.0 mL) at 0° C., KNO3 (1.400 g, 1.385 mmol) was added in one lot. The resulting pale yellow solution was allowed to warm to 28° C. and stirred overnight at 28° C. It was then poured into ice (100 g) and ... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Cc1ccc(F)cc1Cl>OS(=O)(=O)O>Cc1cc([N+](=O)[O-])c(F)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ad3a05284c3544a09486d2295e29d42a | Cc1cc([N+](=O)[O-])c(F)cc1Cl.NCC(=O)[O-]>>Cc1cc([N+](=O)[O-])c(NCC(=O)[O-])cc1Cl | ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])C.NCC(=O)[O-].[Na+]>>[Na+].ClC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])C | F[c:8]1[c:4]([N+:5](=[O:6])[O-:7])[cH:3][c:2]([CH3:1])[c:15]([Cl:16])[cH:14]1.[NH2:9][CH2:10][C:11](=[O:12])[O-:13]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[c:8]([NH:9][CH2:10][C:11](=[O:12])[O-:13])[cH:14][c:15]1[Cl:16] | Cc1cc([N+](=O)[O-])c(F)cc1Cl.NCC(=O)[O-] | Cc1cc([N+](=O)[O-])c(NCC(=O)[O-])cc1Cl | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | null | [] | 70 | CELSIUS | 8 | HOUR | To a stirred solution of 2-chloro-4-fluoro-5-nitrotoluene (2.080 g, 10.97 mmol, as prepared above) in DMF (11.0 mL) at 70° C., was added dropwise, a solution of sodium glycinate (1.065 g, 10.97 mmol, Aldrich, used as received) in water (11.0 mL). The resulting suspension was stirred overnight at 70° C., cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CN(C)C=O | 70 | 8 | Cc1cc([N+](=O)[O-])c(F)cc1Cl.NCC(=O)[O-]>O.CN(C)C=O>Cc1cc([N+](=O)[O-])c(NCC(=O)[O-])cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-320d60f9a6d0463695a7580e7e302485 | Cc1cc([N+](=O)[O-])c(NCC(=O)O)cc1Cl>>Cc1cc2c(cc1Cl)NCC(=O)N2 | ClC=1C(=CC(=C(C1)NCC(=O)O)[N+](=O)[O-])C.O.O.[Sn](Cl)Cl>>ClC=1C=C2NCC(NC2=CC1C)=O | O=[N+:13]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:7]([Cl:8])[cH:6][c:5]1[NH:9][CH2:10][C:11](O)=[O:12]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Cl:8])[NH:9][CH2:10][C:11](=[O:12])[NH:13]2 | Cc1cc([N+](=O)[O-])c(NCC(=O)O)cc1Cl | Cc1cc2c(cc1Cl)NCC(=O)N2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 248a0ced66d35d5637fd333df7859a163df67de7a5eafc38f3d14fb913b635e3 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1CNc2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[c:5]:[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[#7:4]-[c:5]:[c:6](:[c:8])-[NH;D2;+0:7]-1 | 31.2 | [{"value": 31.0, "product": "ClC=1C=C2NCC(NC2=CC1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.2, "product": "ClC=1C=C2NCC(NC2=CC1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(5'-chloro-4'-methyl-2'-nitrophenyl)glycine (1.000 g, 4.088 mmol, as prepared above) and tin (II) chloride dihydrate (2.767 g, 12.26 mmol, Aldrich, used as received) in ethanol (20.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the precipitated solid was filtered, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | Cc1cc([N+](=O)[O-])c(NCC(=O)O)cc1Cl>C(C)O>Cc1cc2c(cc1Cl)NCC(=O)N2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-542fdfd736c04d64ac3410cac1f60bbe | Cc1cc(F)ccc1Cl>>Cc1cc(F)c([N+](=O)[O-])cc1Cl | ClC1=C(C=C(C=C1)F)C.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:10][c:11]1[Cl:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12] | Cc1cc(F)ccc1Cl | Cc1cc(F)c([N+](=O)[O-])cc1Cl | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 94 | [{"value": 94.0, "product": "ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 2-chloro-5-fluorotoluene (0.500 g, 3.46 mmol, Lancaster, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.350 g, 3.46 mmol) was added in one lot. The resulting pale yellow solution was allowed to warm to 28° C. and stirred overnight at 28° C. It was then poured into ice (50 g) and ex... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Cc1cc(F)ccc1Cl>OS(=O)(=O)O>Cc1cc(F)c([N+](=O)[O-])cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6f15bb650df74b71ae3950aa217798c8 | Cc1cc(F)c([N+](=O)[O-])cc1Cl.NCC(=O)[O-]>>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl | ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C.NCC(=O)[O-].[Na+]>>[Na+].ClC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-] | F[c:4]1[cH:3][c:2]([CH3:1])[c:15]([Cl:16])[cH:14][c:10]1[N+:11](=[O:12])[O-:13].[NH2:5][CH2:6][C:7](=[O:8])[O-:9]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][C:7](=[O:8])[O-:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[Cl:16] | Cc1cc(F)c([N+](=O)[O-])cc1Cl.NCC(=O)[O-] | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | null | [] | 70 | CELSIUS | 8 | HOUR | To a stirred solution of 2-chloro-5-fluoro-4-nitrotoluene (0.605 g, 3.19 mmol, as prepared above) in DMF (3.0 mL) at 70° C., was added dropwise, a solution of sodium glycinate (0.310 g, 3.19 mmol, Aldrich, used as received) in water (3.0 mL). The resulting suspension was stirred overnight at 70° C. The suspension was c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CN(C)C=O | 70 | 8 | Cc1cc(F)c([N+](=O)[O-])cc1Cl.NCC(=O)[O-]>O.CN(C)C=O>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cddbda38d6b149dc93731d7fe0f4c254 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>>Cc1cc2c(cc1Cl)NC(=O)CN2 | [Na+].ClC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-].O.O.[Sn](Cl)Cl>>ClC1=C(C=C2NCC(NC2=C1)=O)C | O=[N+:9]([O-])[c:5]1[c:4]([NH:13][CH2:12][C:10]([O-])=[O:11])[cH:3][c:2]([CH3:1])[c:7]([Cl:8])[cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Cl:8])[NH:9][C:10](=[O:11])[CH2:12][NH:13]2 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl | Cc1cc2c(cc1Cl)NC(=O)CN2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 66.2 | [{"value": 66.0, "product": "ClC1=C(C=C2NCC(NC2=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "ClC1=C(C=C2NCC(NC2=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(4'-chloro-5'-methyl-2'-nitrophenyl)glycine sodium salt (0.300 g, 1.23 mmol, as prepared above) and tin (II) chloride dihydrate (0.830 g, 3.68 mmol, Aldrich, used as received) in ethanol (4.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the precipitated solid was filtered, was... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>C(C)O>Cc1cc2c(cc1Cl)NC(=O)CN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-20edf21ec70840f0a6212c3319d100fd | Clc1ccc(Cl)c(Br)c1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl | BrC1=C(C=CC(=C1)Cl)Cl.[N+](=O)(O)[O-]>>ClC1=C(C=C(C(=C1)[N+](=O)[O-])Cl)Br | [cH:4]1[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]1[Cl:12].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]1[Cl:12] | Clc1ccc(Cl)c(Br)c1.O=[N+]([O-])O | O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | null | null | A solution of 2-bromo-1,4-dichlorobenzene (1.000 g, 4.443 mmol, Aldrich, used as received) in fuming HNO3 (7.0 mL) was stirred at 50° C. for 1.5 h and poured into ice (80 g). Yellowish white solid was filtered, washed with water (10 mL), and dried under vacuum to obtain 1.14 g (95%) of pure (1H NMR) title compound as a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | Clc1ccc(Cl)c(Br)c1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0b069435ba774dba9ff2497ddd53fbd5 | NCC(=O)O.O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl>>O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-] | ClC1=C(C=C(C(=C1)[N+](=O)[O-])Cl)Br.C(=O)(O)[O-].[Na+].NCC(=O)O>>[Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])Cl | [O:1]=[C:2]([OH:3])[CH2:4][NH2:5].Cl[c:6]1[cH:7][c:8]([Br:9])[c:10]([Cl:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[O:1]=[C:2]([O-:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([Cl:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | NCC(=O)O.O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl | O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-] | null | null | O.CN(C)C=O | Functional Group Interconversion | OtherReaction | a2430459d1d806b76ea5929617ab6a3b4b60e59fbb7c728918866c9a46a4773e | ebd1e2e92d10853bf82065836c155b592d0f6786d464f94a738662626a68c1ab | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10]):[c:2]:[c:3] | null | [] | 65 | CELSIUS | 65 | HOUR | To a stirred solution of 2,5-dichloro-4-nitrobromobenzene (1.000 g, 3.691 mmol, as prepared above) in DMF (10.0 mL) at 65° C., was added, dropwise, a solution of NaHCO3 (0.316 g, 3.76 mmol) and glycine (0.280 g, 3.73 mmol, Aldrich, used as received) in water (3.8 mL). The resulting suspension was stirred at 65° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.CN(C)C=O | 65 | 65 | NCC(=O)O.O=[N+]([O-])c1cc(Cl)c(Br)cc1Cl>O.CN(C)C=O>O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ca172412065f4dc89cc0ba64cadecc2a | O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-]>>O=C1CNc2cc(Br)c(Cl)cc2N1 | [Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])Cl.O.O.[Sn](Cl)Cl>>BrC=1C=C2NCC(NC2=CC1Cl)=O | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2]([O-])=[O:1])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11][c:12]2[NH:13]1 | O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-] | O=C1CNc2cc(Br)c(Cl)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 86 | [{"value": 86.0, "product": "BrC=1C=C2NCC(NC2=CC1Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of N-(5'-bromo-4'-chloro-2'-nitrophenyl)glycine sodium salt (0.255 g, 0.824 mmol, as prepared above) and tin (II) chloride dihydrate (0.560 g, 2.48 mmol, Aldrich, used as received) in ethanol (6 mL) was refluxed for 3 h. It was then cooled to room temperature and allowed to stand overnight at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | 8 | O=C([O-])CNc1cc(Br)c(Cl)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(Br)c(Cl)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-334f56af14ba41f48cdc5075bfda0fb6 | O=C1CNc2cc(Br)c(Cl)cc2N1.O=[N+]([O-])O>>O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1 | BrC=1C=C2NCC(NC2=CC1Cl)=O.[N+](=O)(O)[O-]>>BrC=1C(=C2N=CC(NC2=CC1Cl)=O)[N+](=O)[O-] | [O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:10]([Br:11])[c:12]([Cl:13])[cH:14][c:15]2[NH:16]1.O[N+:7](=[O:8])[O-:9]>>[O:1]=[c:2]1[cH:3][n:4][c:5]2[c:6]([N+:7](=[O:8])[O-:9])[c:10]([Br:11])[c:12]([Cl:13])[cH:14][c:15]2[nH:16]1 | O=C1CNc2cc(Br)c(Cl)cc2N1.O=[N+]([O-])O | O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1 | null | null | C(=O)(C(F)(F)F)O | Functional Group Addition | OtherReaction | e6922c8d1ed2e684d16228320675145012a12d1c7c6f08012225825ad76b19cd | 92db0dea6f4127973fddae387509b31c8597671f173224c34b8f168e75366373 | O=c1cnc2ccccc2[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[c:8]2:[c:9](:[cH;D2;+0:10]:1)-[NH;D2;+0:11]-[CH2;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:15]-2>>[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[c:8]2:[nH;D2;+0:15]:[c;H0;D3;+0:13](=[O;D1;H0:14]):[cH;D2;+0:12]:[n;H0;D2;+0:11]:[c:9]:2:[c;H0;D3;+0:10]... | 70 | [{"value": 70.0, "product": "BrC=1C(=C2N=CC(NC2=CC1Cl)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "BrC=1C(=C2N=CC(NC2=CC1Cl)=O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred suspension of 6-bromo-7-chloro-3,4-dihydroquinoxaline-2(1H)-one (0.06 g, 0.23 mmol, as obtained above) in CF3COOH (0.5 mL) was added fuming HNO3 (0.02 mL, 0.46 mmol) and the resulting reddish yellow suspension was stirred at room temperature overnight. The cream colored suspension so obtained was poured in... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Secondary amide.Secondary amine | Nitro group | c1ccc2c(c1)NCCN2 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HO- | C(=O)(C(F)(F)F)O | null | 8 | O=C1CNc2cc(Br)c(Cl)cc2N1.O=[N+]([O-])O>C(=O)(C(F)(F)F)O>O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-94d496ef03ff467399e1d332ac63af12 | O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1>>O=c1[nH]c2cc(Cl)c(Br)c([N+](=O)[O-])c2[nH]c1=O | BrC=1C(=C2N=CC(NC2=CC1Cl)=O)[N+](=O)[O-].[N+](=O)([O-])[O-].[K+]>>BrC=1C(=C2NC(C(NC2=CC1Cl)=O)=O)[N+](=O)[O-] | [O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]2[n:15][cH:16]1>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]2[nH:15][c:16]1=[O:17] | O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1 | O=c1[nH]c2cc(Cl)c(Br)c([N+](=O)[O-])c2[nH]c1=O | null | null | OS(=O)(=O)O | Oxidation | OtherReaction | 96c202f6e3cb7e50a66333c2dba6347f7ff3c54edf2c49e23e682f9d93af3dd2 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=c1[nH]c2ccccc2[nH]c1=O | [O;D1;H0:1]=[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n;H0;D2;+0:8]:[cH;D2;+0:9]:1>>[O;D1;H0:10]=[c;H0;D3;+0:9]1:[nH;D2;+0:8]:[c:6](:[c:7]):[c:4](:[c:5]):[#7;a:3]:[c:2]:1=[O;D1;H0:1] | null | [] | null | null | 65 | HOUR | To a stirred solution of 6-bromo-7-chloro-5-nitroquinoxaline-2(1H)-one (0.025 g, 0.082 mmol, as prepared above) in conc. H2SO4 (0.5 mL) was added KNO3 (0.011 g, 0.11 mmol) and the resulting dark red solution was stirred at room temperature for 65 h. The solution was then cooled in an ice-bath and diluted with ice to a ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2nccnc2c1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | OS(=O)(=O)O | null | 65 | O=c1cnc2c([N+](=O)[O-])c(Br)c(Cl)cc2[nH]1>OS(=O)(=O)O>O=c1[nH]c2cc(Cl)c(Br)c([N+](=O)[O-])c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b5dd336517fb420bb79c1a6528361ef7 | Fc1ccc(F)c(Br)c1>>O=[N+]([O-])c1cc(F)c(Br)cc1F | BrC1=C(C=CC(=C1)F)F.[N+](=O)([O-])[O-].[K+]>>BrC1=C(C=C(C(=C1)F)[N+](=O)[O-])F | [cH:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12] | Fc1ccc(F)c(Br)c1 | O=[N+]([O-])c1cc(F)c(Br)cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 89.4 | [{"value": 89.0, "product": "BrC1=C(C=C(C(=C1)F)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "BrC1=C(C=C(C(=C1)F)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 1-bromo-2,5-difluorobenzene (1.000 g, 5.181 mmol, Aldrich, used as received) in conc. H2SO4 (8.0 mL) at 0° C., KNO3 (0.525 g, 5.19 mmol) was added in one lot. The resulting yellow solution was allowed to warm to 28° C. and stirred at 28° C. overnight. It was then poured into ice (80 g) and extr... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Fc1ccc(F)c(Br)c1>OS(=O)(=O)O>O=[N+]([O-])c1cc(F)c(Br)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1bdba27d99f44e589e147105b04a762a | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Br)cc1F>>O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-] | BrC1=C(C=C(C(=C1)F)[N+](=O)[O-])F.NCC(=O)[O-].[Na+]>>[Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F | [O:1]=[C:2]([O-:3])[CH2:4][NH2:5].F[c:6]1[cH:7][c:8]([Br:9])[c:10]([F:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[O:1]=[C:2]([O-:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([F:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Br)cc1F | O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-] | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | 35 | [{"value": 35.0, "product": "[Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "[Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | To a stirred solution of 1-bromo-2,5-difluoro-4-nitrobenzene (1.100 g, 4.622 mmol, as prepared above) in DMF (11.0 mL) at 70° C., was added, dropwise, a solution of sodium glycinate (0.451 g, 4.65 mmol, Aldrich, used as received) in water (5.0 mL). The resulting solution was stirred overnight at 70° C. The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CN(C)C=O | 70 | 8 | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Br)cc1F>O.CN(C)C=O>O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-15e37d10d88148d9bb4bb35e4f153e2c | O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-]>>O=C1CNc2cc(Br)c(F)cc2N1 | [Na+].BrC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F.O.O.[Sn](Cl)Cl>>BrC=1C=C2NCC(NC2=CC1F)=O | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2]([O-])=[O:1])[cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11][c:12]2[NH:13]1 | O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-] | O=C1CNc2cc(Br)c(F)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 64 | [{"value": 64.0, "product": "BrC=1C=C2NCC(NC2=CC1F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.9, "product": "BrC=1C=C2NCC(NC2=CC1F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(5'-bromo-4'-fluoro-2'-nitrophenyl)glycine sodium salt (0.450 g, 1.54 mmol, as prepared above) and tin (II) chloride dihydrate (1.039 g, 4.605 mmol, Aldrich, used as received) in ethanol (7.0 mL) was refluxed for 30 min. It was then cooled to room temperature and solvent was removed under vacuum. The residue was dilu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | O=C([O-])CNc1cc(Br)c(F)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(Br)c(F)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8e5fea2bcbfc49a781474b90155555c6 | Fc1ccc(Br)c(F)c1>>O=[N+]([O-])c1cc(Br)c(F)cc1F | BrC1=C(C=C(C=C1)F)F.[N+](=O)([O-])[O-].[K+]>>BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)F | [cH:4]1[cH:5][c:6]([Br:7])[c:8]([F:9])[cH:10][c:11]1[F:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[c:8]([F:9])[cH:10][c:11]1[F:12] | Fc1ccc(Br)c(F)c1 | O=[N+]([O-])c1cc(Br)c(F)cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | null | [] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 1-bromo-2,4-difluorobenzene (0.512 g, 2.65 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.275 g, 2.72 mmol) was added in one lot. The resulting solution was allowed to warm to 28° C. and stirred at that temperature overnight. It was then poured into ice (50 g) and ex... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Fc1ccc(Br)c(F)c1>OS(=O)(=O)O>O=[N+]([O-])c1cc(Br)c(F)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3b2d4eb0ed2e4dee9788780360db7fee | O=C(O)CNc1cc(F)c(Br)cc1[N+](=O)[O-]>>O=C1CNc2cc(F)c(Br)cc2N1 | BrC1=CC(=C(C=C1F)NCC(=O)O)[N+](=O)[O-].BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)NCC(=O)O.O.O.[Sn](Cl)Cl>>BrC1=C(C=C2NCC(NC2=C1)=O)F | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2](O)=[O:1])[cH:6][c:7]([F:8])[c:9]([Br:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([F:8])[c:9]([Br:10])[cH:11][c:12]2[NH:13]1 | O=C(O)CNc1cc(F)c(Br)cc1[N+](=O)[O-] | O=C1CNc2cc(F)c(Br)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 248a0ced66d35d5637fd333df7859a163df67de7a5eafc38f3d14fb913b635e3 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1CNc2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[c:5]:[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[#7:4]-[c:5]:[c:6](:[c:8])-[NH;D2;+0:7]-1 | null | [] | null | null | null | null | A solution of a mixture of N-(4'-bromo-5'-fluoro-2'-nitrophenyl)glycine and N-(2'-bromo-5'-fluoro-4'-nitrophenyl)glycine (0.150 g, 0.512 mmol, as prepared above) and tin (II) chloride dihydrate (0.346 g, 1.53 mmol, Aldrich, used as received) in ethanol (3.0 mL) was refluxed for 30 min. It was then cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | O=C(O)CNc1cc(F)c(Br)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(F)c(Br)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-df080efb7627478b95dffad12a254006 | Cc1cc(F)ccc1Br>>Cc1cc(F)c([N+](=O)[O-])cc1Br | BrC1=C(C=C(C=C1)F)C.[N+](=O)([O-])[O-].[K+]>>BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:10][c:11]1[Br:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Br:12] | Cc1cc(F)ccc1Br | Cc1cc(F)c([N+](=O)[O-])cc1Br | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 99 | [{"value": 98.0, "product": "BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 2-bromo-5-fluorotoluene (1.495 g, 7.909 mmol, Aldrich, used as received) in conc. H2SO4 (10.0 mL) at 0° C., KNO3 (0.800 g, 7.91 mmol) was added in one lot. The resulting pale yellow solution was warmed to 28° C. and stirred overnight at 28° C. It was then poured into ice (50 g) and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Cc1cc(F)ccc1Br>OS(=O)(=O)O>Cc1cc(F)c([N+](=O)[O-])cc1Br |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1be67ca729984837a23c9cd02623e794 | Cc1cc(F)c([N+](=O)[O-])cc1Br.NCC(=O)[O-]>>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br | BrC1=C(C=C(C(=C1)[N+](=O)[O-])F)C.NCC(=O)[O-].[Na+]>>[Na+].BrC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-] | F[c:4]1[cH:3][c:2]([CH3:1])[c:15]([Br:16])[cH:14][c:10]1[N+:11](=[O:12])[O-:13].[NH2:5][CH2:6][C:7](=[O:8])[O-:9]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][C:7](=[O:8])[O-:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[Br:16] | Cc1cc(F)c([N+](=O)[O-])cc1Br.NCC(=O)[O-] | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | null | [] | 70 | CELSIUS | 8 | HOUR | To a stirred solution of 2-bromo-5-fluoro-4-nitrotoluene (1.662 g, 7.102 mmol, as prepared above) in DMF (7.0 mL) at 70° C., was added, dropwise, a solution of sodium glycinate (0.690 g, 7.11 mmol, Aldrich, used as received) in water (7.0 mL). The resulting suspension was stirred overnight at 70° C. The suspension was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CN(C)C=O | 70 | 8 | Cc1cc(F)c([N+](=O)[O-])cc1Br.NCC(=O)[O-]>O.CN(C)C=O>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-170bfe4b83bd411a95c389639b5e87c3 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br>>Cc1cc2c(cc1Br)NC(=O)CN2 | [Na+].BrC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-].O.O.[Sn](Cl)Cl>>BrC1=C(C=C2NCC(NC2=C1)=O)C | O=[N+:9]([O-])[c:5]1[c:4]([NH:13][CH2:12][C:10]([O-])=[O:11])[cH:3][c:2]([CH3:1])[c:7]([Br:8])[cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[NH:9][C:10](=[O:11])[CH2:12][NH:13]2 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br | Cc1cc2c(cc1Br)NC(=O)CN2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 38.4 | [{"value": 38.0, "product": "BrC1=C(C=C2NCC(NC2=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.4, "product": "BrC1=C(C=C2NCC(NC2=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(4'-bromo-5'-methyl-2'-nitrophenyl)glycine sodium salt (0.200 g, 0.692 mmol, as prepared above) and tin (II) chloride dihydrate (0.468 g, 2.07 mmol, Aldrich, used as received) in ethanol (2.0 mL) was refluxed for 30 min. It was then cooled to room temperature. The precipitated solid was filtered and dri... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Br>C(C)O>Cc1cc2c(cc1Br)NC(=O)CN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3d9b42a8b7534529b0009aa51e2fe56a | Fc1ccc(Cl)c(F)c1>>O=[N+]([O-])c1cc(Cl)c(F)cc1F | ClC1=C(C=C(C=C1)F)F.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)F | [cH:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][c:11]1[F:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][c:11]1[F:12] | Fc1ccc(Cl)c(F)c1 | O=[N+]([O-])c1cc(Cl)c(F)cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | null | [] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 1-chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol, Aldrich, used as received) in conc. H2SO4 (8.0 mL) at 0° C., KNO3 (0.565 g, 5.59 mmol) was added in one lot. The resulting solution was allowed to warm to 28° C. and stirred overnight at 28° C. It was then poured into ice (80 g) and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Fc1ccc(Cl)c(F)c1>OS(=O)(=O)O>O=[N+]([O-])c1cc(Cl)c(F)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b0b95af2a07c4e2ba77f3872c698d610 | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-]>>O=C1CNc2cc(F)c(Cl)cc2N1 | [Na+].ClC1=CC(=C(C=C1F)NCC(=O)[O-])[N+](=O)[O-].[Na+].ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)NCC(=O)[O-].O.O.[Sn](Cl)Cl>>ClC1=C(C=C2NCC(NC2=C1)=O)F | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2]([O-])=[O:1])[cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11][c:12]2[NH:13]1 | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-] | O=C1CNc2cc(F)c(Cl)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | A solution of a mixture of N-(4'-chloro-5'-fluoro-2'-nitrophenyl)glycine sodium salt and N-(2'-chloro-5'-fluoro-4'-nitrophenyl)glycine sodium salt (0.175 g, 0.704 mmol, as prepared above) and tin (II) chloride dihydrate (0.475 g, 2.11 mmol, Aldrich, used as received) in ethanol (3.5 mL) was refluxed for 30 min. It was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(F)c(Cl)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a5ae1c95958b469682aaea64e7a91558 | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[NH4+]>>Nc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | FC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-].[OH-].[NH4+].Cl>>NC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-] | F[c:2]1[c:3]([F:4])[cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]2[c:14]1[N+:15](=[O:16])[O-:17].[NH4+:1]>>[NH2:1][c:2]1[c:3]([F:4])[cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]2[c:14]1[N+:15](=[O:16])[O-:17] | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[NH4+] | Nc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | [OH-].[NH4+] | O | Functional Group Interconversion | OtherReaction | 8f4f69ff4fc6f6debd38e640de53e6bbf37fe0ffa13d22b66fd2d77e6c98fc57 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[F;D1;H0:12].[NH4+;D0:13]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:1]:1-[NH2;D1;+0:13] | 76 | [{"value": 76.0, "product": "NC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 20 mg (0.082 mmol) of 6,7-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione in 0.5 mL of DMSO-d6 was added 2 drops of 30% ammonium hydroxide and the solution was heated at 80° C. for 24 h. To the mixture was added one more drop of 30% ammonium hydroxide and it was heated at 80° C. for 10 h. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HF | [OH-].[NH4+].O | 80 | null | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[NH4+]>[OH-].[NH4+].O>Nc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4ac1b182a1b047c9bcfb08ee4bb87260 | C[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O>>COc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | FC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-].C[O-].[Na+].Cl>>FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OC | [CH3:1][O-:2].F[c:3]1[c:4]([F:5])[cH:6][c:7]2[nH:8][c:9](=[O:10])[c:11](=[O:12])[nH:13][c:14]2[c:15]1[N+:16](=[O:17])[O-:18]>>[CH3:1][O:2][c:3]1[c:4]([F:5])[cH:6][c:7]2[nH:8][c:9](=[O:10])[c:11](=[O:12])[nH:13][c:14]2[c:15]1[N+:16](=[O:17])[O-:18] | C[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O | COc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 8f5da7fe2bfdb6898cabd699e332b74d553c190b8b21b1599bb1f70cc864c524 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[F;D1;H0:12].[C;D1;H3:13]-[O-;H0;D1:14]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:14]-[C;D1;H3:13] | 77.5 | [{"value": 77.0, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | SECOND | To a solution of 21 mg (0.086 mmol) of 6,7-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione in 0.5 mL of DMSO-d6 was added 16 mg (0.29 mmol) of sodium methoxide. The solution was shaken in a vortex for 10 s and kept at room temperature for 3 h. It was then added to 3 mL of water and acidified with 2N HCl to pH=4. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | O | null | 0.002778 | C[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O>O>COc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e8c46cbae4c34f099d61289b32e13ed2 | CC[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O>>CCOc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | FC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-].[O-]CC.[Na+].Cl>>FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OCC | [CH3:1][CH2:2][O-:3].F[c:4]1[c:5]([F:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[c:12](=[O:13])[nH:14][c:15]2[c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([F:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[c:12](=[O:13])[nH:14][c:15]2[c:16]1[N+:17](=[O:18])[O-:19] | CC[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O | CCOc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 8f5da7fe2bfdb6898cabd699e332b74d553c190b8b21b1599bb1f70cc864c524 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[F;D1;H0:12].[C;D1;H3:13]-[C:14]-[O-;H0;D1:15]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:15]-[C:14]-[C;D1;H3:13] | 91 | [{"value": 91.0, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 24 mg (0.098 mmol) of 6,7-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione and 24 mg (0.33 mmol) of sodium ethoxide (96%) in 0.5 mL of DMSO-d6 was kept at room temperature for 5 h. The red solution was added to 3 mL of water and acidified with 2N HCl to pH=4. The precipitate was filtered, washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | O | null | null | CC[O-].O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O>O>CCOc1c(F)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d70cdbc2c5ed458ba2904ae61b20a51d | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[OH-]>>O=c1[nH]c2cc(F)c(O)c([N+](=O)[O-])c2[nH]c1=O | FC=1C(=C2NC(C(NC2=CC1F)=O)=O)[N+](=O)[O-].[OH-].[Na+].Cl>>FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])O | F[c:8]1[c:6]([F:7])[cH:5][c:4]2[nH:3][c:2](=[O:1])[c:16](=[O:17])[nH:15][c:14]2[c:10]1[N+:11](=[O:12])[O-:13].[OH-:9]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]2[nH:15][c:16]1=[O:17] | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[OH-] | O=c1[nH]c2cc(F)c(O)c([N+](=O)[O-])c2[nH]c1=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 8f69e382ad3e3b305956707d493f91d1500fa55eff550db7ecd715f8d3799832 | 05ba928edd770174a8e0738270a5c99182284743586e41e52e6183b77c44ac41 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[F;D1;H0:12].[OH-;D0:13]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:1]:1-[OH;D1;+0:13] | 80.4 | [{"value": 80.0, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "FC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | A mixture of 24 mg (0.098 mmol) of 6,7-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione and 19 mg (0.47 mmol) of sodium hydroxide in 0.6 mL of D2O was heated at 105° C. for 24 h. The mixture was added to 2 mL of water and acidified with 2N HCl to pH=1. The precipitate was filtered, washed with water, and dried to leav... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic alcohol | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | O | 105 | null | O=c1[nH]c2cc(F)c(F)c([N+](=O)[O-])c2[nH]c1=O.[OH-]>O>O=c1[nH]c2cc(F)c(O)c([N+](=O)[O-])c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-624cebb798804d829738a81171efb650 | Cc1cc(N)c(N)cc1C.O=C(O)C(=O)O>>Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C | CC1=CC(=C(C=C1C)N)N.C(C(=O)O)(=O)O>>CC=1C=C2NC(C(NC2=CC1C)=O)=O | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:11]([NH2:10])[cH:12][c:13]1[CH3:14].O[C:6](=[O:7])[C:8](O)=[O:9]>>[CH3:1][c:2]1[cH:3][c:4]2[nH:5][c:6](=[O:7])[c:8](=[O:9])[nH:10][c:11]2[cH:12][c:13]1[CH3:14] | Cc1cc(N)c(N)cc1C.O=C(O)C(=O)O | Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C | null | null | Cl.O | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c: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:6](:[c:7]):[nH;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 938.5 | [{"value": 94.0, "product": "CC=1C=C2NC(C(NC2=CC1C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 938.5, "product": "CC=1C=C2NC(C(NC2=CC1C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.72 g (2.0 mmol) of 4,5-dimethyl-1,2-phenylenediamine and 1.92 g (21.3 mmol) of oxalic acid in 30 mL of 2N HCl was refluxed for 2.5 h and cooled to room temperature. The mixture was diluted with 20 mL of H2O, filtered, washed with water, and dried to leave a pale-brown solid 3.57 g (94%); mp>250° C.; 1H N... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl.O | null | null | Cc1cc(N)c(N)cc1C.O=C(O)C(=O)O>Cl.O>Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b9209e1cd3964563a3a61efb57e33278 | Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C.O=[N+]([O-])O>>Cc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1C | CC=1C=C2NC(C(NC2=CC1C)=O)=O.[N+](=O)(O)[O-]>>CC=1C(=C2NC(C(NC2=CC1C)=O)=O)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][c:4]2[nH:5][c:6](=[O:7])[c:8](=[O:9])[nH:10][c:11]2[cH:12][c:16]1[CH3:17].O[N+:13](=[O:14])[O-:15]>>[CH3:1][c:2]1[cH:3][c:4]2[nH:5][c:6](=[O:7])[c:8](=[O:9])[nH:10][c:11]2[c:12]([N+:13](=[O:14])[O-:15])[c:16]1[CH3:17] | Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C.O=[N+]([O-])O | Cc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1C | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | f306af00a66ff7115c5c95beb4c7becbc44efd79c2b514bddcddde59dc0f2d08 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c2ccccc2[nH]c1=O | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[c:8]2:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:[cH;D2;+0:14]:1>>[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[c:8]2:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:[c;H0;D3;+0:14]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | 60 | [{"value": 60.0, "product": "CC=1C(=C2NC(C(NC2=CC1C)=O)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution of 1.90 g (10.0 mmol) of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione in 25 mL of H2SO4 (97%) kept in an ice bath was added dropwise 1.2 mL of HNO3 (69-70%) and the solution was stirred at room temperature for 48 h. It was poured into 300 mL of ice-water and stirred for 10 min. The mixture was filtered, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | OS(=O)(=O)O | null | 48 | Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1C.O=[N+]([O-])O>OS(=O)(=O)O>Cc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a7276f51d6f4504a3428b3e11e65497 | CCc1cc(Br)cc(N)c1N.O=C(O)C(=O)O>>CCc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12 | NC1=C(C=C(C=C1CC)Br)N.O.O.C(C(=O)O)(=O)O>>BrC1=CC(=C2NC(C(NC2=C1)=O)=O)CC | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([NH2:9])[c:15]1[NH2:14].O=[C:12]([C:10](O)=[O:11])[OH:13]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[c:12](=[O:13])[nH:14][c:15]12 | CCc1cc(Br)cc(N)c1N.O=C(O)C(=O)O | CCc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12 | null | null | Cl.[OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[OH;D1;+0:4].[NH2;D1;+0:5]-[c: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:6](:[c:7]):[nH;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;H0;D1;+0:4] | 31.9 | [{"value": 31.9, "product": "BrC1=CC(=C2NC(C(NC2=C1)=O)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4N HCl (1.5 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl.[OH-].[Na+] | null | null | CCc1cc(Br)cc(N)c1N.O=C(O)C(=O)O>Cl.[OH-].[Na+]>CCc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-101ba999a0e442b7a1ebad51b3339ed1 | Cc1cc(C)c(N)c([N+](=O)[O-])c1>>Cc1cc(N)c(N)cc1C | CC1=CC(=C(N)C(=C1)C)[N+](=O)[O-].C(C)O>>NC1=C(C=C(C(=C1)C)C)N | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[cH:8][c:9]([CH3:10])[c:6]1[NH2:7]>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:6]([NH2:7])[cH:8][c:9]1[CH3:10] | Cc1cc(C)c(N)c([N+](=O)[O-])c1 | Cc1cc(N)c(N)cc1C | null | [Pd] | null | Functional Group Interconversion | OtherReaction | 1613b5fba4e86adb9547d5bf6e370cff331bfa463637841d4b06138778df9f24 | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[c;H0;D3;+0:9]:1-[N;D1;H2:10]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[c;H0;D3;+0:9](-[N;D1;H2:10]):[c:2](-[NH2;D1;+0:1]):[c:3]:[c;H0;D3;+0:4]:1-[C;D1;H3:5] | 96 | [{"value": 96.0, "product": "NC1=C(C=C(C(=C1)C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 4,6-dimethyl-2-nitroaniline (1.66 g, 10.0 mmole) and 10% Pd/C (200 mg) in ethanol (35 mL) was hydrogenated for 2 h at room temperature under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 1.300 g (96%) of 1,2-diamino-4,5-dimethylbenzene... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Pd] | null | 2 | Cc1cc(C)c(N)c([N+](=O)[O-])c1>[Pd]>Cc1cc(N)c(N)cc1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-43fa774a4335414e86153f409864b47c | Cc1cc(C)c(N)c(N)c1.O=C(O)C(=O)O>>Cc1cc(C)c2[nH]c(=O)c(=O)[nH]c2c1 | NC1=C(C=C(C=C1C)C)N.O.O.C(C(=O)O)(=O)O>>CC1=C2NC(C(NC2=CC(=C1)C)=O)=O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH2:7])[c:13]([NH2:12])[cH:14]1.O=[C:10]([C:8](O)=[O:9])[OH:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]2[cH:14]1 | Cc1cc(C)c(N)c(N)c1.O=C(O)C(=O)O | Cc1cc(C)c2[nH]c(=O)c(=O)[nH]c2c1 | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[OH;D1;+0:4].[NH2;D1;+0:5]-[c: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:6](:[c:7]):[nH;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;H0;D1;+0:4] | 87.2 | [{"value": 87.0, "product": "CC1=C2NC(C(NC2=CC(=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "CC1=C2NC(C(NC2=CC(=C1)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-diamino-4,6-dimethylbenzene (424 mg, 3.11 mmole) and oxalic acid dihydrate (432 mg, 3.43 mmole, used as received) in 4N HCl (20 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the supernatant was removed. The yellow solid was washed with cold wat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl | null | null | Cc1cc(C)c(N)c(N)c1.O=C(O)C(=O)O>Cl>Cc1cc(C)c2[nH]c(=O)c(=O)[nH]c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-63aacc9beb9f47a3a479f15e7d73ef6a | Nc1cc2ccccc2cc1N.O=C(O)C(=O)O>>O=c1[nH]c2cc3ccccc3cc2[nH]c1=O | C1=C(C(=CC2=CC=CC=C12)N)N.C(C(=O)O)(=O)O>>N1C(C(NC=2C=C3C(=CC12)C=CC=C3)=O)=O | [NH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]1[NH2:14].O[C:2](=[O:1])[C:15](O)=[O:16]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12][c:13]2[nH:14][c:15]1=[O:16] | Nc1cc2ccccc2cc1N.O=C(O)C(=O)O | O=c1[nH]c2cc3ccccc3cc2[nH]c1=O | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | f1fe36c6b10ba58e3cd86b5b0cd5c869c8ba039404150d34422ea91f8af3fc56 | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2cc3ccccc3cc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 99.3 | [{"value": 99.0, "product": "N1C(C(NC=2C=C3C(=CC12)C=CC=C3)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "N1C(C(NC=2C=C3C(=CC12)C=CC=C3)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 603 mg (3.81 mmol) of 2,3-naphthalenediamine and 382 mg (4.24 mmol) of oxalic acid in 5 mL of 2N HCl was refluxed for 3 h and cooled to room temperature. The mixture was filtered, washed with water, and dried to leave a brown solid 803 mg (99%); mp>250° C.; 1H NMR (DMSO-d6), 7.382 (dd, 2, J=3.16, 6.17), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccc2ccccc2c1 | C1=CNc2cc3ccccc3cc2N1 | C1=CNc2cc3ccccc3cc2N1 | HO- | Cl | null | null | Nc1cc2ccccc2cc1N.O=C(O)C(=O)O>Cl>O=c1[nH]c2cc3ccccc3cc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b25ce42331c840ea8602ce53d0963993 | Cc1cccc(N)c1N.O=C(O)C(=O)O>>Cc1cccc2[nH]c(=O)c(=O)[nH]c12 | [OH-].[Na+].NC1=C(C=CC=C1N)C.Cl.O.O.C(C(=O)O)(=O)O.Cl>>CC1=C2NC(C(NC2=CC=C1)=O)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[c:13]1[NH2:12].O=[C:8]([OH:9])[C:10](O)=[O:11]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]12 | Cc1cccc(N)c1N.O=C(O)C(=O)O | Cc1cccc2[nH]c(=O)c(=O)[nH]c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[OH;D1;+0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;H0;D1;+0:4] | 768.5 | [{"value": 64.0, "product": "CC1=C2NC(C(NC2=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 768.5, "product": "CC1=C2NC(C(NC2=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | To a stirred solution of 2,3-diaminotoluene (0.498 g, 0.407 mmol, Aldrich) in 2N HCl (6 mL, 12 mmol), oxalic acid dihydrate (0.520 g, 0.412 mmol, Fisher) was added in one portion. The resulting deep purple solution was refluxed for 13 h, to give a purple suspension. This was cooled to 25° C., filtered, washed with wate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | 25 | null | Cc1cccc(N)c1N.O=C(O)C(=O)O>>Cc1cccc2[nH]c(=O)c(=O)[nH]c12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-12fa4b7545e24913ba70142a23da9b9f | Cc1ccc(N)c(N)c1.O=C(O)C(=O)O>>Cc1ccc2[nH]c(=O)c(=O)[nH]c2c1 | [OH-].[Na+].NC=1C=C(C=CC1N)C.Cl.O.O.C(C(=O)O)(=O)O.Cl>>CC=1C=C2NC(C(NC2=CC1)=O)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:12]([NH2:11])[cH:13]1.O[C:7](=[O:8])[C:9](O)=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[cH:13]1 | Cc1ccc(N)c(N)c1.O=C(O)C(=O)O | Cc1ccc2[nH]c(=O)c(=O)[nH]c2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:4]=[c;H0;D3;+0:3]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:1]:1=[O;D1;H0:2] | 518.2 | [{"value": 43.0, "product": "CC=1C=C2NC(C(NC2=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 518.2, "product": "CC=1C=C2NC(C(NC2=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | To a stirred solution of 3,4-diaminotoluene (0.302 g, 0.247 mmol, Aldrich) in 2N HCl (4 mL, 8 mmol), oxalic acid dihydrate (0.330 g, 0.261 mmol, Fisher) was added in one portion. The resulting deep purple solution was refluxed for 13 h, to give a purple suspension. This was cooled to 25° C., filtered, washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | 25 | null | Cc1ccc(N)c(N)c1.O=C(O)C(=O)O>>Cc1ccc2[nH]c(=O)c(=O)[nH]c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cb4d580f1a1646c0b4045ba962cee035 | Cc1cc([N+](=O)[O-])c(N)c([N+](=O)[O-])c1>>Cc1cc(N)c(N)c([N+](=O)[O-])c1 | CC1=CC(=C(N)C(=C1)[N+](=O)[O-])[N+](=O)[O-]>>CC=1C=C(C(=C(C1)N)N)[N+](=O)[O-] | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[cH:12][c:8]([N+:9](=[O:10])[O-:11])[c:6]1[NH2:7]>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1 | Cc1cc([N+](=O)[O-])c(N)c([N+](=O)[O-])c1 | Cc1cc(N)c(N)c([N+](=O)[O-])c1 | null | null | O.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] | 85 | [{"value": 85.0, "product": "CC=1C=C(C(=C(C1)N)N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "CC=1C=C(C(=C(C1)N)N)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | null | null | The procedure of Gillespie et al., J. Org. Chem. 25:942 (1960) was adopted as follows. A dark black solution of 4-methyl-2,6-dinitroaniline (0.100 g, 0.561 mmol, Aldrich, used as received) in 6.66% aq. (NH4)2S (3.3 mL, prepared from 20% aq.(NH4)2S solution supplied by Aldrich) and ethanol (3.5 mL) was refluxed for 45 m... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O.C(C)O | 28 | null | Cc1cc([N+](=O)[O-])c(N)c([N+](=O)[O-])c1>O.C(C)O>Cc1cc(N)c(N)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c070473595ab44adbb5b496789489738 | Cc1cc(F)ccc1F>>Cc1cc(F)c([N+](=O)[O-])cc1F | FC1=C(C=C(C=C1)F)C.[N+](=O)([O-])[O-].[K+]>>FC1=C(C=C(C(=C1)[N+](=O)[O-])F)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:10][c:11]1[F:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[F:12] | Cc1cc(F)ccc1F | Cc1cc(F)c([N+](=O)[O-])cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 91 | [{"value": 91.0, "product": "FC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "FC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and ext... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | 28 | 8 | Cc1cc(F)ccc1F>OS(=O)(=O)O>Cc1cc(F)c([N+](=O)[O-])cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b1c07f4bc15f4967bc2ba5f088db89a5 | Cc1cc(F)c([N+](=O)[O-])cc1F.NCC(=O)[O-]>>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F | FC1=C(C=C(C(=C1)[N+](=O)[O-])F)C.NCC(=O)[O-].[Na+]>>[Na+].FC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-] | F[c:4]1[cH:3][c:2]([CH3:1])[c:15]([F:16])[cH:14][c:10]1[N+:11](=[O:12])[O-:13].[NH2:5][CH2:6][C:7](=[O:8])[O-:9]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][C:7](=[O:8])[O-:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[F:16] | Cc1cc(F)c([N+](=O)[O-])cc1F.NCC(=O)[O-] | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | null | [] | 28 | CELSIUS | 8 | HOUR | To a stirred solution of 2,5-difluoro-4-nitrotoluene (0.550 g. 3.18 mmol) in DMF (5.0 mL) was added dropwise a solution of sodium glycinate (0.308 g, 3.18 mmol, Aldrich, used as received) in water (1.0 mL). The resulting suspension was stirred at 28° C. overnight. The solid was filtered and dried under vacuum to give 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.CN(C)C=O | 28 | 8 | Cc1cc(F)c([N+](=O)[O-])cc1F.NCC(=O)[O-]>O.CN(C)C=O>Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-12229507d5aa4380966ce63e12a8945b | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F>>Cc1cc2c(cc1F)NC(=O)CN2 | [Na+].FC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-].O.O.[Sn](Cl)Cl>>FC1=C(C=C2NCC(NC2=C1)=O)C | O=[N+:9]([O-])[c:5]1[c:4]([NH:13][CH2:12][C:10]([O-])=[O:11])[cH:3][c:2]([CH3:1])[c:7]([F:8])[cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[F:8])[NH:9][C:10](=[O:11])[CH2:12][NH:13]2 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F | Cc1cc2c(cc1F)NC(=O)CN2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 32.4 | [{"value": 32.4, "product": "FC1=C(C=C2NCC(NC2=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(4-fluoro-5-methyl-2-nitrophenyl)glycine sodium salt (0.125 g, 0.548 mmol) and tin (II) chloride dihydrate (0.370 g, 1.64 mmol, Aldrich, used as received) in ethanol (3.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the solvent was removed under vacuum. The residue was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1F>C(C)O>Cc1cc2c(cc1F)NC(=O)CN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b037678c36524cf9b3abf748abca8e64 | N#Cc1c(Cl)c([N+](=O)[O-])cc2[nH]c(=O)c(=O)[nH]c12>>N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12 | ClC=1C(=C2NC(C(NC2=CC1[N+](=O)[O-])=O)=O)C#N.O.O.[Sn](Cl)Cl>>NC1=C(C(=C2NC(C(NC2=C1)=O)=O)C#N)Cl | O=[N+:7]([O-])[c:6]1[c:4]([Cl:5])[c:3]([C:2]#[N:1])[c:16]2[c:9]([cH:8]1)[nH:10][c:11](=[O:12])[c:13](=[O:14])[nH:15]2>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6]([NH2:7])[cH:8][c:9]2[nH:10][c:11](=[O:12])[c:13](=[O:14])[nH:15][c:16]12 | N#Cc1c(Cl)c([N+](=O)[O-])cc2[nH]c(=O)c(=O)[nH]c12 | N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c2ccccc2[nH]c1=O | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 88 | [{"value": 88.0, "product": "NC1=C(C(=C2NC(C(NC2=C1)=O)=O)C#N)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "NC1=C(C(=C2NC(C(NC2=C1)=O)=O)C#N)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 6-chloro-5-cyano-7-nitroquinoxaline-2(1H),3(4H)-dione (0.100 g, 0.38 mmol, as prepared above) and tin (II) chloride dihydrate (0.508 g, 2.25 mmol, Aldrich) in ethanol (4.0 mL) was refluxed for 24 h. The resulting suspension was then cooled to room temperature and the yellow solid was filtered, washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1=CNc2ccccc2N1 | Other | C(C)O | null | null | N#Cc1c(Cl)c([N+](=O)[O-])cc2[nH]c(=O)c(=O)[nH]c12>C(C)O>N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1a433fa6d1f2405e8e1c8446180bc673 | Cl.N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12>>N#Cc1c(Cl)c(Cl)cc2[nH]c(=O)c(=O)[nH]c12 | NC1=C(C(=C2NC(C(NC2=C1)=O)=O)C#N)Cl.N(=O)[O-].[Na+].Cl.Cl.N#N>>C(#N)C1=C2NC(C(NC2=CC(=C1Cl)Cl)=O)=O | [ClH:7].N[c:6]1[c:4]([Cl:5])[c:3]([C:2]#[N:1])[c:16]2[c:9]([cH:8]1)[nH:10][c:11](=[O:12])[c:13](=[O:14])[nH:15]2>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]2[nH:10][c:11](=[O:12])[c:13](=[O:14])[nH:15][c:16]12 | Cl.N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12 | N#Cc1c(Cl)c(Cl)cc2[nH]c(=O)c(=O)[nH]c12 | null | Cl[Cu] | O | Miscellaneous | OtherReaction | 023dfe963532b1779b3f5c5b05a8c601e35822f2a486d4ab398d090042dccad7 | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | O=c1[nH]c2ccccc2[nH]c1=O | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[c:10]:1-[Cl;D1;H0:11].[ClH;D0;+0:12]>>[Cl;D1;H0:11]-[c:10]1:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[Cl;H0;D1;+0:12] | 77 | [{"value": 77.0, "product": "C(#N)C1=C2NC(C(NC2=CC(=C1Cl)Cl)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of 7-amino-6-chloro-5-cyanoquinoxaline-2(1H),3(4H)-dione (0.035 g, 0.15 mmol, as prepared above) in concentrated HCl (1.5 mL) at 0° C., an aqueous solution of NaNO2 (0.060 g, 0.87 mmol) in water (0.20 mL) was added and the resulting turbid solution was stirred in an ice bath for 2 h. A solution of... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | Cl[Cu].O | null | 2 | Cl.N#Cc1c(Cl)c(N)cc2[nH]c(=O)c(=O)[nH]c12>Cl[Cu].O>N#Cc1c(Cl)c(Cl)cc2[nH]c(=O)c(=O)[nH]c12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bdab480f98884bfcb8fb5bb903a163a5 | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>>COc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])F.C[O-].[Na+]>>ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])OC | [CH3:1][O-:2].F[c:3]1[c:4]([Cl:5])[cH:6][c:7]2[nH:8][c:9](=[O:10])[c:11](=[O:12])[nH:13][c:14]2[c:15]1[N+:16](=[O:17])[O-:18]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[nH:8][c:9](=[O:10])[c:11](=[O:12])[nH:13][c:14]2[c:15]1[N+:16](=[O:17])[O-:18] | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O | COc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | Cl | O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 8f5da7fe2bfdb6898cabd699e332b74d553c190b8b21b1599bb1f70cc864c524 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[O-;H0;D1:14]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:14]-[C;D1;H3:13] | null | [] | null | null | 8 | HOUR | To a stirred solution of 7-Chloro-6-fluoro-5-nitroquinoxaline-2(1H),3(4H)-dione (0.100 g, 0.385 mmol, as prepared above) in DMSO (1.0 mL) at room temperature, sodium methoxide (0.125 g, 2.31 mmol, Mallinckrodt) was added in one portion. The resulting dark red solution was stirred overnight at room temperature. It was t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | Other | Cl.O.CS(=O)C | null | 8 | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>Cl.O.CS(=O)C>COc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8d301c6f54d46f7a3a3c206fb56c3c7 | CCc1ccc([N+](=O)[O-])cc1CC.CCc1cccc([N+](=O)[O-])c1CC>>CCc1ccc(N)cc1CC.CCc1cccc(N)c1CC | C(C)C1=C(C=C(C=C1)[N+](=O)[O-])CC.C(C)C1=C(C(=CC=C1)[N+](=O)[O-])CC>>C(C)C=1C=C(N)C=CC1CC.C(C)C1=C(N)C=CC=C1CC | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[c:9]([CH2:10][CH3:11])[cH:8]1.O=[N+:19]([O-])[c:18]1[cH:17][cH:16][cH:15][c:14]([CH2:13][CH3:12])[c:20]1[CH2:21][CH3:22]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:8][c:9]1[CH2:10][CH3:11].[CH3:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([NH2:19])[c:20]1[C... | CCc1ccc([N+](=O)[O-])cc1CC.CCc1cccc([N+](=O)[O-])c1CC | CCc1ccc(N)cc1CC.CCc1cccc(N)c1CC | null | null | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | f469aaae1e88945b257afa41cebe21597b9a3f326d9f2ab1d5670c64dd831541 | 86e032c8ebc9cbcd13a880d0d66c541ff63611af16d12657aad958d17abf4587 | c1ccccc1.c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | 71 | [{"value": 71.0, "product": "C(C)C=1C=C(N)C=CC1CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.0, "product": "C(C)C1=C(N)C=CC=C1CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | A mixture of 1,2-diethyl-4-nitrobenzene (16) and 1,2-diethyl-3-nitrobenzene (17) (1.4 g, 7.82 mmol) was dissolved in ethyl acetate (20 mL). To this solution was added 10% Pd--C (350 mg, 20%; Aldrich). The mixture was agitated at room temperature under a pressure of 35 psi (H2) for 10 h. The catalyst was removed through... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | null | 10 | CCc1ccc([N+](=O)[O-])cc1CC.CCc1cccc([N+](=O)[O-])c1CC>C(C)(=O)OCC>CCc1ccc(N)cc1CC.CCc1cccc(N)c1CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-88a736fe9b214bc981472e81f31e1d7b | CCc1cc(N)c([N+](=O)[O-])cc1CC>>CCc1cc(N)c(N)cc1CC | C(C)C1=CC(=C(N)C=C1CC)[N+](=O)[O-]>>C(C)C1=CC(=C(C=C1CC)N)N | O=[N+:8]([O-])[c:7]1[c:5]([NH2:6])[cH:4][c:3]([CH2:2][CH3:1])[c:10]([CH2:11][CH3:12])[cH:9]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([NH2:8])[cH:9][c:10]1[CH2:11][CH3:12] | CCc1cc(N)c([N+](=O)[O-])cc1CC | CCc1cc(N)c(N)cc1CC | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 96 | [{"value": 96.0, "product": "C(C)C1=CC(=C(C=C1CC)N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C(C)C1=CC(=C(C=C1CC)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 4,5-Diethyl-2-nitroaniline (23) (567 mg, 2.92 mmol) was dissolved in ethyl acetate (20 mL). To this solution was added 10% Pd--C (142 mg, 20%; Aldrich). The mixture was agitated at room temperature under a pressure of 35 psi (H2) for 5 h. The catalyst was removed through a column of Celite (5 g) and washed with ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)(=O)OCC | null | 5 | CCc1cc(N)c([N+](=O)[O-])cc1CC>C(C)(=O)OCC>CCc1cc(N)c(N)cc1CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d5dec3f0abf64b4793c94bbca73a6396 | CCc1cc(N)c(N)cc1CC.O=C(O)C(=O)O>>CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC | C(C)C1=CC(=C(C=C1CC)N)N.O.O.C(C(=O)O)(=O)O>>C(C)C=1C=C2NC(C(NC2=CC1CC)=O)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[c:12]([NH2:11])[cH:13][c:14]1[CH2:15][CH3:16].O=[C:9]([C:7](O)=[O:8])[OH:10]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[cH:13][c:14]1[CH2:15][CH3:16] | CCc1cc(N)c(N)cc1CC.O=C(O)C(=O)O | CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[OH;D1;+0:4].[NH2;D1;+0:5]-[c: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:6](:[c:7]):[nH;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;H0;D1;+0:4] | 88 | [{"value": 88.0, "product": "C(C)C=1C=C2NC(C(NC2=CC1CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.0, "product": "C(C)C=1C=C2NC(C(NC2=CC1CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4,5-Diethyl-1,2-diaminobenzene 24 (459 mg, 2.80 mmol) was dissolved in 4N hydrochloric acid (12 mL) at 90° C. Oxalic acid dihydrate (983 mg, 6.47 mmoL) was added to this solution in one portion with stirring under N2. The mixture was refluxed at 130°-5° C. (oil bath) for 3 h. A yellow solid precipitated, which was coll... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl | null | null | CCc1cc(N)c(N)cc1CC.O=C(O)C(=O)O>Cl>CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa96ed4539a240bb91e84eed224faea7 | CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC.O=[N+]([O-])[O-]>>CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1CC | C(C)C=1C=C2NC(C(NC2=CC1CC)=O)=O.FC(C(=O)O)(F)F.[N+](=O)([O-])[O-].[K+]>>[N+](=O)([O-])C1=C2NC(C(NC2=CC(=C1CC)CC)=O)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[cH:13][c:17]1[CH2:18][CH3:19].[O-][N+:14](=[O:15])[O-:16]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[c:13]([N+:14](=[O:15])[O-:16])[c:17]1[CH2:18][CH3:19] | CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC.O=[N+]([O-])[O-] | CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1CC | null | null | O | Functional Group Addition | Aromatic nitration with NO3 salt | f306af00a66ff7115c5c95beb4c7becbc44efd79c2b514bddcddde59dc0f2d08 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c2ccccc2[nH]c1=O | [C:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:[cH;D2;+0:11]:1.[O-]-[N+;H0;D3:12](-[O;-;D1;H0:13])=[O;D1;H0:14]>>[C:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:[c;H0;D3;+0:11]:1-[N+;H0;D3:12](-[O;-;D1;H0:13])=[O;D1;H0:14] | 69.1 | [{"value": 69.0, "product": "[N+](=O)([O-])C1=C2NC(C(NC2=CC(=C1CC)CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.1, "product": "[N+](=O)([O-])C1=C2NC(C(NC2=CC(=C1CC)CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6,7-Diethyl-2,3-quinoxalinedione 25 (218 mg, 1.0 mmol) was added to trifluoroacetic acid (8 mL; Sigma). To this suspension was added potassium nitrate (121.2 mg, 1.2 mmol; Baker) in one portion with stirring under N2. The reaction was stirred at room temperature for 48 h. Trifluoroacetic acid was evaporated in vacuo to... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | O | null | null | CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1CC.O=[N+]([O-])[O-]>O>CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-45212a821f1e4ebfacc57678d2b28b19 | CC(=O)OC(C)=O.Nc1ccc2c(c1)CCC2>>CC(=O)Nc1ccc2c(c1)CCC2 | NC=1C=C2CCCC2=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C2CCCC2=CC1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][CH2:13]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][CH2:13]2 | CC(=O)OC(C)=O.Nc1ccc2c(c1)CCC2 | CC(=O)Nc1ccc2c(c1)CCC2 | null | null | O1CCOCC1.O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2c(c1)CCC2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 91 | [{"value": 91.0, "product": "C(C)(=O)NC=1C=C2CCCC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "C(C)(=O)NC=1C=C2CCCC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 5.2 g (39 mmol) of 5-aminoindan in 15 mL of dioxane kept in an ice-bath was added dropwise 8 mL (8.6 g, 84 mmol) of acetic anhydride. The solution was stirred at room temperature for 16 h. It was diluted with 70 mL of water. The mixture was filtered, washed with water, and dried to leave a gray solid 6... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCC2 | HO- | O1CCOCC1.O | null | 16 | CC(=O)OC(C)=O.Nc1ccc2c(c1)CCC2>O1CCOCC1.O>CC(=O)Nc1ccc2c(c1)CCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6422effaf4d74f519eb3d457fcdf3521 | CC(=O)Nc1ccc2c(c1)CCC2.O=[N+]([O-])[O-]>>CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2 | [N+](=O)([O-])[O-].[K+].C(C)(=O)NC=1C=C2CCCC2=CC1>>C(C)(=O)NC=1C=C2CCCC2=CC1[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[CH2:14][CH2:15][CH2:16]2.[O-][N+:11](=[O:12])[O-:13]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1[N+:11](=[O:12])[O-:13])[CH2:14][CH2:15][CH2:16]2 | CC(=O)Nc1ccc2c(c1)CCC2.O=[N+]([O-])[O-] | CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2 | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with NO3 salt | cfd75387f50e1142b60c8213f482ef40b605d13135e71d44588a632fab28010f | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)CCC2 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9].[O-]-[N+;H0;D3:10](-[O;-;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:10](-[O;-;D1;H0:11])=[O;D1;H0:12]):[c:8]:[c:9] | 15.1 | [{"value": 15.0, "product": "C(C)(=O)NC=1C=C2CCCC2=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.1, "product": "C(C)(=O)NC=1C=C2CCCC2=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5.59 g (31.9 mmol) of 5-acetamidoindan in 55 mL of H2SO4 kept in an ice-bath was added portionwise 3.62 g of KNO3 (35.8 mmol). The solution was stirred in the ice-bath for 2 h and at room temperature overnight. It was added to 500 mL of ice-water and stirred for 1 h. The precipitate was filtered, washe... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | OS(=O)(=O)O | null | 1 | CC(=O)Nc1ccc2c(c1)CCC2.O=[N+]([O-])[O-]>OS(=O)(=O)O>CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c56d610317f54b7aa67c4261f2a9a716 | CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2>>Nc1cc2c(cc1[N+](=O)[O-])CCC2 | C(C)(=O)NC=1C=C2CCCC2=CC1[N+](=O)[O-]>>NC=1C=C2CCCC2=CC1[N+](=O)[O-] | CC(=O)[NH:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[N+:8](=[O:9])[O-:10])[CH2:11][CH2:12][CH2:13]2>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[N+:8](=[O:9])[O-:10])[CH2:11][CH2:12][CH2:13]2 | CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2 | Nc1cc2c(cc1[N+](=O)[O-])CCC2 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc2c(c1)CCC2 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.2 | [{"value": 97.0, "product": "NC=1C=C2CCCC2=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "NC=1C=C2CCCC2=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of 259 mg (1.16 mmol) of 5-acetamido-6-nitroindan in 4 mL of 2N HCl was heated at 85° C. for 9 h and cooled to room temperature. The solid precipitate was filtered, washed with water, and dried to leave 201 mg (97%) of a crystalline yellow solid. 1H NMR (CDCl3), 2.068 (m, 2), 2.843 (m, 4), 6.00 (sb, 2), 6.650... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)CCC2 | HO- | Cl | 85 | null | CC(=O)Nc1cc2c(cc1[N+](=O)[O-])CCC2>Cl>Nc1cc2c(cc1[N+](=O)[O-])CCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a086c150e15a42718188fdd2ed774274 | Nc1cc2c(cc1[N+](=O)[O-])CCC2>>Nc1cc2c(cc1N)CCC2 | NC=1C=C2CCCC2=CC1[N+](=O)[O-].Cl[Sn]Cl>>NC=1C=C2CCCC2=CC1N | O=[N+:8]([O-])[c:7]1[c:2]([NH2:1])[cH:3][c:4]2[c:5]([cH:6]1)[CH2:9][CH2:10][CH2:11]2>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[NH2:8])[CH2:9][CH2:10][CH2:11]2 | Nc1cc2c(cc1[N+](=O)[O-])CCC2 | Nc1cc2c(cc1N)CCC2 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)CCC2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.6 | [{"value": 97.0, "product": "NC=1C=C2CCCC2=CC1N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "NC=1C=C2CCCC2=CC1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 200 mg (1.12 mmol) of 5-amino-6-nitroindan and 1.14 g (6.01 mmol) of SnCl2 in 8 mL of ethanol was heated at 70° C. for 2 h. It was evaporated to remove the ethanol. The residue was treated with 40% aqueous NaOH to pH=12. The mixture was diluted with 4 mL of water and extracted with CHCl3 (3×10 mL). The ex... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCC2 | Other | C(C)O | null | null | Nc1cc2c(cc1[N+](=O)[O-])CCC2>C(C)O>Nc1cc2c(cc1N)CCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1f41145c35d14389a62208c891c594b4 | CCc1ccc([N+](=O)[O-])cc1Cl>>CCc1ccc(N)cc1Cl | ClC=1C=C(C=CC1CC)[N+](=O)[O-].O.O.Cl[Sn]Cl>>ClC=1C=C(N)C=CC1CC | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[c:9]([Cl:10])[cH:8]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:8][c:9]1[Cl:10] | CCc1ccc([N+](=O)[O-])cc1Cl | CCc1ccc(N)cc1Cl | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "ClC=1C=C(N)C=CC1CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "ClC=1C=C(N)C=CC1CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.9 g (48 mmol) of 31 and 54.6 g (241 mmol) of SnCl2.2H2O in 100 mL of absolute alcohol was refluxed for 1 h. It was evaporated to remove most of the solvent and the residue was treated with 2N NaOH to pH=9. The mixture was filtered and the solid was washed with methanol (10 mL) and ethyl acetate (200 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | null | null | null | CCc1ccc([N+](=O)[O-])cc1Cl>>CCc1ccc(N)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7dce83d20adb454489999b231737edc2 | CCc1cc2c(cc1Cl)NCC(=O)N2.O=[N+]([O-])O.O=c1[nH]c2cc3c(cc2[nH]c1=O)OCO3>>CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1Cl | C1OC=2C=C3NC(C(NC3=CC2O1)=O)=O.C1OC=2C=C3NC(C(NC3=CC2O1)=O)=O.C(C)C1=C(N)C=CC=C1CC.[N+](=O)(O)[O-].ClC=1C=C2NCC(NC2=CC1CC)=O>>ClC=1C(=C2NC(C(NC2=CC1CC)=O)=O)[N+](=O)[O-] | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:12]([cH:13][c:17]1[Cl:18])[NH:11][CH2:9][C:7](=[O:8])[NH:6]2.O[N+:14](=[O:15])[O-:16].O=c1[nH]c2cc3c(cc2[nH]c1=[O:10])OCO3>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[c:13]([N+:14](=[O:15])[O-:16])[c:17]1[Cl:18] | CCc1cc2c(cc1Cl)NCC(=O)N2.O=[N+]([O-])O.O=c1[nH]c2cc3c(cc2[nH]c1=O)OCO3 | CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1Cl | null | null | C(F)(F)(F)C(=O)O | Protection | OtherReaction | 668f49ce01915eb3f34d13ad94594d109e41c1b3034302953862f472217f0d55 | a459b17178d2549680121fc0f4a13d6f42b44a6ec99534453738493ce17d41a2 | O=c1[nH]c2ccccc2[nH]c1=O | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].O=c1:[nH]:c2:c:c3:c(:c:c:2:[nH]:c:1=[O;H0;D1;+0:4])-O-C-O-3.[Cl;D1;H0:5]-[c:6]1:[c:7]:[c:8]:[c:9]2:[c:10](:[cH;D2;+0:11]:1)-[NH;D2;+0:12]-[CH2;D2;+0:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[NH;D2;+0:16]-2>>[Cl;D1;H0:5]-[c:6]1:[c:7]:[c:8]:[c:9]2:[nH;D2;+0:16]:[c;H0;D3;+0:14](=[O;D1;... | null | [] | null | null | 10 | MINUTE | To a solution of 137 mg (0.65 mmol) of 36 in 4 mL of CF3CO2H kept in an ice bath was added dropwise 0.4 mL of fuming HNO3. The solution was stirred in the ice bath for 1 h and at room temperature overnight. It was evaporated and the residue was treated with 6 mL of water and stirred for 10 min. The mixture was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrate.Secondary amide.Secondary amine | Nitro group | c1ccc2c(c1)NCCN2.C1=CNc2cc3c(cc2N1)OCO3 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | C(F)(F)(F)C(=O)O | null | 0.166667 | CCc1cc2c(cc1Cl)NCC(=O)N2.O=[N+]([O-])O.O=c1[nH]c2cc3c(cc2[nH]c1=O)OCO3>C(F)(F)(F)C(=O)O>CCc1cc2[nH]c(=O)c(=O)[nH]c2c([N+](=O)[O-])c1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7be7b329106841c5a1cdf0b795ef6837 | CCc1cc([N+](=O)[O-])c(N)cc1Cl>>CCc1cc(N)c(N)cc1Cl | ClC=1C=C(N)C(=CC1CC)[N+](=O)[O-].O.O.Cl[Sn]Cl>>NC1=C(C=C(C(=C1)CC)Cl)N | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:10]([Cl:11])[cH:9][c:7]1[NH2:8]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([NH2:8])[cH:9][c:10]1[Cl:11] | CCc1cc([N+](=O)[O-])c(N)cc1Cl | CCc1cc(N)c(N)cc1Cl | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.4 | [{"value": 99.0, "product": "NC1=C(C=C(C(=C1)CC)Cl)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.4, "product": "NC1=C(C=C(C(=C1)CC)Cl)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 271 mg (1.35 mmol) of 34 and 1.24 g (5.49 mmol) of SnCl2.2H2O, in 5 mL of absolute alcohol was refluxed for 2 h. It was evaporated and the residue was treated with 1N NaOH to pH=10. The mixture was extracted with CH2Cl2 (3×10 mL). The extract was dried (MgSO4) and evaporated to leave 229 mg (99%) of a yel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | null | null | null | CCc1cc([N+](=O)[O-])c(N)cc1Cl>>CCc1cc(N)c(N)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-65de9c754ef24117815da28fff8b8ea2 | CCc1cc(N)c(N)cc1Cl.O=C(O)C(=O)O>>CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1Cl | NC1=C(C=C(C(=C1)CC)Cl)N.C(C(=O)O)(=O)O.Cl>>ClC=1C=C2NC(C(NC2=CC1CC)=O)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[c:12]([NH2:11])[cH:13][c:14]1[Cl:15].O[C:7](=[O:8])[C:9](O)=[O:10]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[cH:13][c:14]1[Cl:15] | CCc1cc(N)c(N)cc1Cl.O=C(O)C(=O)O | CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:4]=[c;H0;D3;+0:3]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:1]:1=[O;D1;H0:2] | 92 | [{"value": 92.0, "product": "ClC=1C=C2NC(C(NC2=CC1CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "ClC=1C=C2NC(C(NC2=CC1CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 228 mg (1.33 mmol) of 38 and 124 mg (1.38 mmol) of oxalic acid in 4 mL of aqueous 2N HCl was refluxed for 4 h. It was cooled to room temperature, filtered, and dried to leave 275 mg (92%) of a brown solid; mp>400° C.; 1H NMR (DMSO-d6), 1.134 (t, 3, J=7.4), 2.635 (q, 2, J=7.4), 7.026 (s, 1), 7.107 (s, 1), 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | null | null | CCc1cc(N)c(N)cc1Cl.O=C(O)C(=O)O>>CCc1cc2[nH]c(=O)c(=O)[nH]c2cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-824e083e88e1451d809db0bda97f1706 | COc1cc2c(cc1OC)=NC(=O)C(=O)N=2>>O=C1N=c2cc(O)c(O)cc2=NC1=O | Cl.B(Br)(Br)Br.[OH-].[Na+].COC1=CC2=NC(C(N=C2C=C1OC)=O)=O>>OC1=CC2=NC(C(N=C2C=C1O)=O)=O | C[O:7][c:6]1[cH:5][c:4]2[c:11]([cH:10][c:8]1[O:9]C)=[N:12][C:13](=[O:14])[C:2](=[O:1])[N:3]=2>>[O:1]=[C:2]1[N:3]=[c:4]2[cH:5][c:6]([OH:7])[c:8]([OH:9])[cH:10][c:11]2=[N:12][C:13]1=[O:14] | COc1cc2c(cc1OC)=NC(=O)C(=O)N=2 | O=C1N=c2cc(O)c(O)cc2=NC1=O | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C1N=c2ccccc2=NC1=O | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | 88.5 | [{"value": 88.0, "product": "OC1=CC2=NC(C(N=C2C=C1O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "OC1=CC2=NC(C(N=C2C=C1O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a suspension of 6,7-dimethoxy-2,3-quinoxalinedione (45) (222 mg, 1.0 mmol) in 2 mL of methylene dichloride was added 5 mL of a solution of boron tribromide in methylene dichloride (1M, Aldrich). The resulting mixture was stirred at room temperature for 24 hr. The mixture was then poured into ice-water (10 g) to form... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccc2c(c1)=NCCN=2 | Other | C(Cl)Cl | null | 24 | COc1cc2c(cc1OC)=NC(=O)C(=O)N=2>C(Cl)Cl>O=C1N=c2cc(O)c(O)cc2=NC1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-965407359eb34b6c9c540882c628652f | CC(=O)O.COc1cc2c(cc1OC)=NC(=O)C(=O)N=2>>COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2 | COC1=CC2=NC(C(N=C2C=C1OC)=O)=O.C(C)(=O)O.[N+](=O)(O)[O-]>>C(C)(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O | [OH:8][C:9]([CH3:10])=[O:11].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:12]1[O:13][CH3:14])=[N:15][C:16](=[O:17])[C:18](=[O:19])[N:20]=2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][C:9]([CH3:10])=[O:11])[c:12]1[O:13][CH3:14])=[N:15][C:16](=[O:17])[C:18](=[O:19])[N:20]=2 | CC(=O)O.COc1cc2c(cc1OC)=NC(=O)C(=O)N=2 | COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d165d1f90abcf4cf4c04ce8b0f0f275eeebb9a3a990c7710c17dc6ce017987f3 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | O=C1N=c2ccccc2=NC1=O | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]1:[c:6]=[#7:7]-[C:8](=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[#7:12]=1.[C;D1;H3:13]-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[O;H0;D2;+0:16]-[C:14](-[C;D1;H3:13])=[O;D1;H0:15]):[c:5]1:[c:6]=[#7:7]-[C:8](=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[#7:12]=1 | 54 | [{"value": 54.0, "product": "C(C)(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 6,7-Dimethoxy-2,3-quinoxalinedione (45) (222 mg, 1.0 mmol) was dissolved in glacial acetic acid (10 mL) at 100° C. (oil bath). The oil bath was removed and fuming nitric acid (53 μL, 1.2 mmol; Baker) was added dropwise to the solution. The reaction mixture was then stirred at room temperature for 24 h. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | c1ccc2c(c1)=NCCN=2 | c1ccc2c(c1)=NCCN=2 | c1ccc2c(c1)=NCCN=2 | null | null | null | 24 | CC(=O)O.COc1cc2c(cc1OC)=NC(=O)C(=O)N=2>>COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d3fd1de3a9bf4946b30dced194907e14 | COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2>>COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2 | C(C)(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O.[OH-].[Na+].Cl>>OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O | CC(=O)[O:8][c:7]1[c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:9]1[O:10][CH3:11])=[N:17][C:15](=[O:16])[C:13](=[O:14])[N:12]=2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([OH:8])[c:9]1[O:10][CH3:11])=[N:12][C:13](=[O:14])[C:15](=[O:16])[N:17]=2 | COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2 | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2 | null | null | O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | O=C1N=c2ccccc2=NC1=O | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]=[#7:5]>>[#7:5]=[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 91 | [{"value": 86.0, "product": "OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Acetyloxy-6,7-dimethoxy-2,3-quinoxalinedione (47) (30 mg, 0.107 mmol) was added to a single-necked 15-mL flask. Sodium hydroxide aqueous solution (2N, 1 mL) was added to the flask under nitrogen with stirring. The solution was then stirred at room temperature for 24 h. The solution was diluted with water (3 mL) and t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2c(c1)=NCCN=2 | HO- | O | null | null | COc1cc2c(c(OC(C)=O)c1OC)=NC(=O)C(=O)N=2>O>COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-34c2a14bc7e5483fa0ea763baa2fd8c7 | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2>>O=C1N=c2cc(O)c(O)c(O)c2=NC1=O | Cl.[B].[OH-].[Na+].OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O>>OC=1C2=NC(C(N=C2C=C(C1O)O)=O)=O | C[O:7][c:6]1[cH:5][c:4]2[c:12]([c:10]([OH:11])[c:8]1[O:9]C)=[N:13][C:14](=[O:15])[C:2](=[O:1])[N:3]=2>>[O:1]=[C:2]1[N:3]=[c:4]2[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([OH:11])[c:12]2=[N:13][C:14]1=[O:15] | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2 | O=C1N=c2cc(O)c(O)c(O)c2=NC1=O | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C1N=c2ccccc2=NC1=O | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | 80.8 | [{"value": 80.0, "product": "OC=1C2=NC(C(N=C2C=C(C1O)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "OC=1C2=NC(C(N=C2C=C(C1O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of 5-hydroxy-6,7-dimethoxy-2,3-quinoxalinedione (48) (50 mg, 0.22 mmol) in 2 mL of methylene dichloride was added 2 mL of a solution of boron tribomide in methylene dichloride (1M, Aldrich). The resulting mixture was stirred at room temperature for 12 hr. The mixture was poured into ice-water (5 g) to f... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccc2c(c1)=NCCN=2 | Other | C(Cl)Cl | null | 12 | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2>C(Cl)Cl>O=C1N=c2cc(O)c(O)c(O)c2=NC1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f001a64fe8f24ef6a5090cd755cd65c4 | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2.O=C(Cl)Cc1ccccc1>>COc1cc2c(c(OC(=O)Cc3ccccc3)c1OC)=NC(=O)C(=O)N=2 | C(C)N(CC)CC.C1(=CC=CC=C1)CC(=O)Cl.OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O>>C1(=CC=CC=C1)CC(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([OH:8])[c:18]1[O:19][CH3:20])=[N:21][C:22](=[O:23])[C:24](=[O:25])[N:26]=2.Cl[C:9](=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][C:9](=[O:10])[CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]1[O:19][CH3:20]... | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2.O=C(Cl)Cc1ccccc1 | COc1cc2c(c(OC(=O)Cc3ccccc3)c1OC)=NC(=O)C(=O)N=2 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(Cc1ccccc1)Oc1cccc2c1=NC(=O)C(=O)N=2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7:5]=[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:5]=[c:6]:[c:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:9] | 77 | [{"value": 77.0, "product": "C1(=CC=CC=C1)CC(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "C1(=CC=CC=C1)CC(=O)OC=1C2=NC(C(N=C2C=C(C1OC)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of 5-hydroxy-6,7-dimethoxy-2,3-quinoxalinedione (48) (50 mg, 0.22 mmol) in 3 mL of methylene dichloride was added 0.14 mL of triethylamine and phenylacetyl chloride (77.5 mg, 0.5 mmol, Aldrich) at 0° C. The resulting mixture was stirred at room temperature for 12 hr. The reaction mixture was then poured... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)=NCCN=2 | HCl | C(Cl)Cl | null | 12 | COc1cc2c(c(O)c1OC)=NC(=O)C(=O)N=2.O=C(Cl)Cc1ccccc1>C(Cl)Cl>COc1cc2c(c(OC(=O)Cc3ccccc3)c1OC)=NC(=O)C(=O)N=2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e5efc9f8d1154f20a3bdc405582e0e1b | Fc1ccc(F)c(Cl)c1>>O=[N+]([O-])c1cc(F)c(Cl)cc1F | ClC1=C(C=CC(=C1)F)F.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])F | [cH:4]1[cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10][c:11]1[F:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10][c:11]1[F:12] | Fc1ccc(F)c(Cl)c1 | O=[N+]([O-])c1cc(F)c(Cl)cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 85 | [{"value": 85.0, "product": "ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.3, "product": "ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 1-chloro-2,5-difluorobenzene (0.770 g, 5.18 mmol) in concd H2SO4 (8.0 mL) at 0° C., KNO3 (0.525 g, 5.19 mmol) was added in one lot. The resulting yellow solution was allowed to warm to room temperature and stirred overnight at room temperature. It was then poured into ice (80 g) and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | null | 8 | Fc1ccc(F)c(Cl)c1>OS(=O)(=O)O>O=[N+]([O-])c1cc(F)c(Cl)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6af7050892d54175aa064b56c9f69106 | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Cl)cc1F>>O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-] | ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])F.NCC(=O)[O-].[Na+]>>[Na+].ClC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F | [O:1]=[C:2]([O-:3])[CH2:4][NH2:5].F[c:6]1[cH:7][c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[O:1]=[C:2]([O-:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Cl)cc1F | O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-] | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11]):[c:2]:[c:3] | 64 | [{"value": 64.0, "product": "[Na+].ClC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.4, "product": "[Na+].ClC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 1-chloro-2,5-difluoro-4-nitrobenzene (0.825 g, 4.26 mmol) in ethanol (8.0 mL), was added a solution of sodium glycinate (0.415 g, 4.27 mmol) in water (1.5 mL). The resulting suspension was refluxed for 60 h. The solution was cooled to room temperature and the precipitated bright orange solid wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O.C(C)O | null | null | NCC(=O)[O-].O=[N+]([O-])c1cc(F)c(Cl)cc1F>O.C(C)O>O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-453ac216b75e4661a8e649ffaaf4878f | O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-]>>O=C1CNc2cc(Cl)c(F)cc2N1 | [Na+].ClC=1C(=CC(=C(C1)NCC(=O)[O-])[N+](=O)[O-])F.O.O.[Sn](Cl)Cl>>ClC=1C=C2NCC(NC2=CC1F)=O | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2]([O-])=[O:1])[cH:6][c:7]([Cl:8])[c:9]([F:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([Cl:8])[c:9]([F:10])[cH:11][c:12]2[NH:13]1 | O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-] | O=C1CNc2cc(Cl)c(F)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 59.4 | [{"value": 59.0, "product": "ClC=1C=C2NCC(NC2=CC1F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "ClC=1C=C2NCC(NC2=CC1F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of N-(5'-chloro-4'-fluoro-2'-nitrophenyl)glycine sodium salt (0.650 g, 2.61 mmol) and tin (II) chloride dihydrate (1.770 g, 7.845 mmol) in ethanol (10.5 mL) was refluxed for 1 h. It was then cooled to room temperature and ~5 mL ethanol was removed under vacuum. The precipitated solid was collected by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | O=C([O-])CNc1cc(Cl)c(F)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(Cl)c(F)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-542ed5268d7d4c67afd4a6169b794c6b | CC(=O)c1cc(Cl)ccc1Cl>>CCc1cc(Cl)ccc1Cl | ClC1=C(C=C(C=C1)Cl)C(C)=O>>ClC1=C(C=C(C=C1)Cl)CC | O=[C:2]([CH3:1])[c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[Cl:10]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[Cl:10] | CC(=O)c1cc(Cl)ccc1Cl | CCc1cc(Cl)ccc1Cl | null | [Zn] | Cl.O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A suspension of mossy zinc (10 g) and mercuric chloride (0.5 g) in concd HCl (0.5 mL) and water (5 mL) was shaken for ~5 min. The aqueous layer was then decanted. To the residue was added concd HCl (7.5 mL) and water (7.5 mL) followed by 2',5'-dichloroacetophenone (3.106 g, 16.43 mmol) and the suspension was refluxed f... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | [Zn].Cl.O | null | null | CC(=O)c1cc(Cl)ccc1Cl>[Zn].Cl.O>CCc1cc(Cl)ccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba407004792444bbb4dd640a7211cba6 | CCc1cc(Cl)ccc1Cl.O=[N+]([O-])[O-]>>CCc1cc(Cl)c([N+](=O)[O-])cc1Cl | ClC1=C(C=C(C=C1)Cl)CC.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)CC)Cl)[N+](=O)[O-] | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:11][c:12]1[Cl:13].[O-][N+:8](=[O:9])[O-:10]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[Cl:13] | CCc1cc(Cl)ccc1Cl.O=[N+]([O-])[O-] | CCc1cc(Cl)c([N+](=O)[O-])cc1Cl | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with NO3 salt | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[O-]-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 92 | [{"value": 92.0, "product": "ClC1=C(C=C(C(=C1)CC)Cl)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "ClC1=C(C=C(C(=C1)CC)Cl)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 2,5-dichloro-1-ethylbenzene (0.795 g, 4.68 mmol) in concd H2SO4 (4.5 mL) at 0° C., KNO3 (0.473 g, 4.68 mmol) was added in one portion. The resulting pale yellow solution was allowed to warm to room temperature and was stirred overnight at room temperature. It was then poured into ice (80 g) and... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | OS(=O)(=O)O | null | 8 | CCc1cc(Cl)ccc1Cl.O=[N+]([O-])[O-]>OS(=O)(=O)O>CCc1cc(Cl)c([N+](=O)[O-])cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4c819dd84db14c9db991f43604900434 | CCc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>>CCc1cc2c(cc1Cl)NC(=O)CN2 | [Na+].ClC1=CC(=C(C=C1CC)NCC(=O)[O-])[N+](=O)[O-].O.O.[Sn](Cl)Cl>>ClC1=C(C=C2NCC(NC2=C1)=O)CC | O=[N+:10]([O-])[c:6]1[c:5]([NH:14][CH2:13][C:11]([O-])=[O:12])[cH:4][c:3]([CH2:2][CH3:1])[c:8]([Cl:9])[cH:7]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[NH:10][C:11](=[O:12])[CH2:13][NH:14]2 | CCc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl | CCc1cc2c(cc1Cl)NC(=O)CN2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | A suspension of N-(4'-Chloro-5'-ethyl-2'-nitrophenyl)glycine sodium salt (0.082 g, 0.31 mmol) and tin (II) chloride dihydrate (0.215 g, 0.953 mmol) in ethanol (1.0 mL) was refluxed for 45 min. It was then cooled to room temperature and the precipitated solid was filtered, washed with ethanol (1.0 mL), and dried under v... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | CCc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>C(C)O>CCc1cc2c(cc1Cl)NC(=O)CN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-745046916d634bcd956d4328d02e4632 | Cc1cc2c(cc1Cl)NC(=O)CN2.O=C(O)C(F)(F)F.O=[N+]([O-])O>>Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | ClC1=C(C=C2NCC(NC2=C1)=O)C.[N+](=O)(O)[O-].C(=O)(C(F)(F)F)O>>ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])C | [CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]2[c:13]([cH:14]1)[NH:12][CH2:10][C:8](=[O:9])[NH:7]2.OC(C(F)(F)F)=[O:11].O[N+:15](=[O:16])[O-:17]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]2[c:14]1[N+:15](=[O:16])[O-:17] | Cc1cc2c(cc1Cl)NC(=O)CN2.O=C(O)C(F)(F)F.O=[N+]([O-])O | Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | null | null | Protection | OtherReaction | 80c677eaf05c9e3260cc2c36d32955f1a198302f695a8f6f7fdc8245e989ad9f | c3f6f8522c120ea155981de10cc58aa2ca6e015b56fcea863d9ab5f778379b6c | O=c1[nH]c2ccccc2[nH]c1=O | F-C(-F)(-F)-C(-O)=[O;H0;D1;+0:1].O-[N+;H0;D3:2](-[O;-;D1;H0:3])=[O;D1;H0:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9]2:[c:10](:[cH;D2;+0:11]:1)-[NH;D2;+0:12]-[CH2;D2;+0:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[NH;D2;+0:16]-2>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9]2:[nH;D2;+0:16]:[c;H0;D3;+0:14](=[O;D1;H0:15]):[c;H0;D3;+0:13](=[O;H... | null | [] | null | null | 8 | HOUR | To a stirred suspension of 7-chloro-3,4-Dihydro-6-methyl-quinoxaline-2(1H)-one (0.100 g, 0.51 mmol) in TFA (3.0 mL) prepared as in Example 8, excess fuming HNO3 (0.30 mL) was added and the resulting red solution was stirred overnight at room temperature. The solvent was removed under vacuum and the residue diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Nitrate.Secondary amide.Secondary amine | Nitro group | c1ccc2c(c1)NCCN2 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HF | null | null | 8 | Cc1cc2c(cc1Cl)NC(=O)CN2.O=C(O)C(F)(F)F.O=[N+]([O-])O>>Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c5c0bc97f38849c2b37ca0ba4d8a916b | Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-]>>Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1N | ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])C.O.O.[Sn](Cl)Cl>>NC1=C2NC(C(NC2=CC(=C1C)Cl)=O)=O | O=[N+:15]([O-])[c:14]1[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]21>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]2[nH:7][c:8](=[O:9])[c:10](=[O:11])[nH:12][c:13]2[c:14]1[NH2:15] | Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1N | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c2ccccc2[nH]c1=O | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | null | null | A suspension of 7-chloro-1,4-dihydro-6-methyl-5-nitroquinoxaline-2,3-dione (0.050 g, 0.20 mmol) and tin (II) chloride dihydrate (0.133 g, 0.60 mmol) in ethanol (1.0 mL) was refluxed for 6 h. The suspension was then cooled to room temperature and the solid was collected by vacuum filtration, washed with ethanol (1 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1=CNc2ccccc2N1 | Other | C(C)O | null | null | Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-]>C(C)O>Cc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e7df90c36ae44d7eb540bd7f7071a5b1 | Fc1ccc(Cl)c(F)c1>>O=[N+]([O-])c1cc(Cl)c(F)cc1F | ClC1=C(C=C(C=C1)F)F.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)F | [cH:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][c:11]1[F:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][c:11]1[F:12] | Fc1ccc(Cl)c(F)c1 | O=[N+]([O-])c1cc(Cl)c(F)cc1F | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | null | [] | null | null | 8 | HOUR | To a stirred solution of 1-chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol) in concd H2SO4 (8.0 mL) at 0° C., KNO3 (0.565 g, 5.59 mmol) was added in one portion. The resulting solution was allowed to warm to room temperature and stirred overnight at room temperature. It was then poured into ice (80 g) and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | null | 8 | Fc1ccc(Cl)c(F)c1>OS(=O)(=O)O>O=[N+]([O-])c1cc(Cl)c(F)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ad05905abd7d40db96cb11b9e5771e2e | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-]>>O=C1CNc2cc(F)c(Cl)cc2N1 | [Na+].ClC1=CC(=C(C=C1F)NCC(=O)[O-])[N+](=O)[O-].[Na+].ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)NCC(=O)[O-].O.O.[Sn](Cl)Cl>>ClC1=C(C=C2NCC(NC2=C1)=O)F | O=[N+:13]([O-])[c:12]1[c:5]([NH:4][CH2:3][C:2]([O-])=[O:1])[cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][NH:4][c:5]2[cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11][c:12]2[NH:13]1 | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-] | O=C1CNc2cc(F)c(Cl)cc2N1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | A suspension of N-(4'-chloro-5'-fluoro-2'-nitrophenyl)glycine sodium salt and N-(2'-chloro-5'-fluoro-4'-nitrophenyl)glycine sodium salt (0.175 g, 0.704 mmol) and tin (II) chloride dihydrate (0.475 g, 2.11 mmol) in ethanol (3.5 mL) was refluxed for 30 min. It was then cooled to room temperature and the solvent was remov... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | C(C)O | null | null | O=C([O-])CNc1cc(F)c(Cl)cc1[N+](=O)[O-]>C(C)O>O=C1CNc2cc(F)c(Cl)cc2N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8b969f968a774a71a47db4d035adaf78 | CCS.O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>>CCSc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])F.C(C)S.[Na]>>ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])SCC | [CH3:1][CH2:2][SH:3].F[c:4]1[c:5]([Cl:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[c:12](=[O:13])[nH:14][c:15]2[c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][CH2:2][S:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[c:12](=[O:13])[nH:14][c:15]2[c:16]1[N+:17](=[O:18])[O-:19] | CCS.O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O | CCSc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] | null | Cl | O.CS(=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 37d6a583faeeb606077eb6008f8ae442049fb9481db2190565bab57b55926369 | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | O=c1[nH]c2ccccc2[nH]c1=O | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[C:14]-[SH;D1;+0:15]>>[#7;+:3]-[c:2]1:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[S;H0;D2;+0:15]-[C:14]-[C;D1;H3:13] | null | [] | null | null | null | null | A solution of 7-Chloro-1,4-dihydro-6-fluoro-5-nitroquinoxaline-2,3-dione (0.100 g, 0.385 mmol) and ethanethiol, sodium salt (0.130 g, 1.55 mmol) in DMSO (1.0 mL) was stirred at room temperature for 24 h. The resulting solution was diluted with water (5 mL) and acidified with concd HCl (4-5 drops) to pH ~5. The precipit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HF | Cl.O.CS(=O)C | null | null | CCS.O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>Cl.O.CS(=O)C>CCSc1c(Cl)cc2[nH]c(=O)c(=O)[nH]c2c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1a076efc56904834b8e30dd331d929ed | Cc1cc(F)ccc1Cl>>Cc1cc(F)c([N+](=O)[O-])cc1Cl | ClC1=C(C=C(C=C1)F)C.[N+](=O)([O-])[O-].[K+]>>ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:10][c:11]1[Cl:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12] | Cc1cc(F)ccc1Cl | Cc1cc(F)c([N+](=O)[O-])cc1Cl | null | null | OS(=O)(=O)O | Functional Group Addition | OtherReaction | 6862453966ade01f48ad6e78fdee5c31f5f3bef2a50d1592f73a35f3caf6154f | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 90.4 | [{"value": 90.0, "product": "ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "ClC1=C(C=C(C(=C1)[N+](=O)[O-])F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 2-chloro-5-fluorotoluene (10.356 g, 71.628 mmol, Lancaster, used as received) in conc. H2SO4 (70 mL) at 0° C., KNO3 (7.252 g, 71.72 mmol) was added in four equal portions. The resulting pale yellow solution was allowed to warm to room temperature and was stirred overnight at room temperature. I... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | OS(=O)(=O)O | null | 8 | Cc1cc(F)ccc1Cl>OS(=O)(=O)O>Cc1cc(F)c([N+](=O)[O-])cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6defbbfc6e5a4b3791bf13861c906a5e | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>>Cc1cc2c(cc1Cl)NC(=O)CN2 | [K+].ClC1=CC(=C(C=C1C)NCC(=O)[O-])[N+](=O)[O-].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>ClC1=C(C=C2NCC(NC2=C1)=O)C | O=[N+:9]([O-])[c:5]1[c:4]([NH:13][CH2:12][C:10]([O-])=[O:11])[cH:3][c:2]([CH3:1])[c:7]([Cl:8])[cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Cl:8])[NH:9][C:10](=[O:11])[CH2:12][NH:13]2 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl | Cc1cc2c(cc1Cl)NC(=O)CN2 | null | null | O | Functional Group Interconversion | OtherReaction | 183261da32373f3dc4dd237e8a75ee7d967e6598ba6a325e2c313518785e8076 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | O=C1CNc2ccccc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6]-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:6]-[#7:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 87.6 | [{"value": 86.0, "product": "ClC1=C(C=C2NCC(NC2=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "ClC1=C(C=C2NCC(NC2=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a stirred bright orange solution of N-(4'-chloro-5'-methyl-2'-nitrophenyl)glycine potassium salt (0.097 g, 0.36 mmol) in water (5.0 mL) at 80° C., sodium dithionite (0.500 g, 2.87 mmol) was added in two equal portions. It instantly formed a white suspension, which was stirred at 80° C. for 1 h. It was then cooled at... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | c1ccc2c(c1)NCCN2 | c1ccc2c(c1)NCCN2 | Other | O | 80 | 1 | Cc1cc(NCC(=O)[O-])c([N+](=O)[O-])cc1Cl>O>Cc1cc2c(cc1Cl)NC(=O)CN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8dc8ca74650e49239a9ba862a47071df | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F>>N#Cc1n[nH]c(N)c1SC(F)(F)F | C(#N)C1=NNC(=C1SC(F)(F)F)NC(C(F)(F)F)=O.[OH-].[NH4+].Cl>>C(#N)C1=NNC(=C1SC(F)(F)F)N | O=C(C(F)(F)F)[NH:7][c:6]1[nH:5][n:4][c:3]([C:2]#[N:1])[c:8]1[S:9][C:10]([F:11])([F:12])[F:13]>>[N:1]#[C:2][c:3]1[n:4][nH:5][c:6]([NH2:7])[c:8]1[S:9][C:10]([F:11])([F:12])[F:13] | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F | N#Cc1n[nH]c(N)c1SC(F)(F)F | null | null | CO.C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1cn[nH]c1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1 | 87.6 | [{"value": 87.6, "product": "C(#N)C1=NNC(=C1SC(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | The product of Step E (55 g, 181 mmoles) was dissolved in methanol. 100 ml of ammonium hydroxide were added, the solution was refluxed for 3 hours and then stirred at room temperature for 15 hours. The methanolic solution was brought to pH7 using concentrated aqueous hydrochloric acid and diluted with ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1cn[nH]c1 | Other | CO.C(C)(=O)OCC | null | 15 | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F>CO.C(C)(=O)OCC>N#Cc1n[nH]c(N)c1SC(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d35c5951d44f43e7878bff135ef2e886 | O=C(N[C@H](CO)Cc1ccccc1)OCc1ccccc1>>O=C[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CS(=O)C.C(C(=O)Cl)(=O)Cl.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)CO>>C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C=O | [OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[CH:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(N[C@H](CO)Cc1ccccc1)OCc1ccccc1 | O=C[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1 | null | null | ClCCl.CCOCC.C(C)N(CC)CC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C(NCCc1ccccc1)OCc1ccccc1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7] | 103.2 | [{"value": 103.2, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To a solution of 1.8 ml of dimethyl sulfoxide in 20 ml of dichloromethane cooled to -78° C. was added slowly 1.65 ml of oxalyl chloride. The solution was stirred for 10 min at -78° C. and a solution of 3.6 g (0.012 mol) of N-((benzyloxy)carbonyl)-L-phenylalaninol in 45 ml of dichloromethane was added slowly. The result... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | ClCCl.CCOCC.C(C)N(CC)CC | -78 | 0.166667 | O=C(N[C@H](CO)Cc1ccccc1)OCc1ccccc1>ClCCl.CCOCC.C(C)N(CC)CC>O=C[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-08c659d86451420eab107de0c01f7ba3 | COC(=O)[C@](N)(N=C=O)C(C)C.OCc1ccccn1>>COC(=O)[C@@H](NC(=O)OCc1ccccn1)C(C)C | COC([C@@](N)(C(C)C)N=C=O)=O.N1=C(C=CC=C1)CO>>COC([C@@H](NC(=O)OCC1=NC=CC=C1)C(C)C)=O | N[C@@:5]([C:3]([O:2][CH3:1])=[O:4])([N:6]=[C:7]=[O:8])[CH:17]([CH3:18])[CH3:19].[OH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1)[CH:17]([CH3:18])[CH3:19] | COC(=O)[C@](N)(N=C=O)C(C)C.OCc1ccccn1 | COC(=O)[C@@H](NC(=O)OCc1ccccn1)C(C)C | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | a23be472936c50c173c2dd2734289c9dfae50efca7ef50b8a0cb8898e49c8803 | 594e835804772a869b7a162be980a733776c00b82a87e4b097f0a7da7fddd8e1 | c1ccncc1 | N-[C@@;H0;D4;+0:1](-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11].[#7;a:12]:[c:13]-[C:14]-[OH;D1;+0:15]>>[#7;a:12]:[c:13]-[C:14]-[O;H0;D2;+0:15]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C@@H;D3;+0:1](-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](=[O;D1... | 54.1 | [{"value": 54.0, "product": "COC([C@@H](NC(=O)OCC1=NC=CC=C1)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "COC([C@@H](NC(=O)OCC1=NC=CC=C1)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.78 g (5.0 mmol) of α-isocyanato-valine methyl ester and 0.55 ml (5.7 mmol) of pyridine-2-methanol in 30 mL of toluene was heated at reflux under N2 atmosphere for 4 h. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography using 2% methanol in chloroform to give 0.72... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Primary alcohol.Primary amine | Carbamic ester.Ester | null | null | c1ccncc1 | Other | C1(=CC=CC=C1)C | null | null | COC(=O)[C@](N)(N=C=O)C(C)C.OCc1ccccn1>C1(=CC=CC=C1)C>COC(=O)[C@@H](NC(=O)OCc1ccccn1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-26eb608ac2fb46d293186deb92007f42 | CC(C)(C)OC(=O)NCc1ccccn1.CI>>CN(Cc1ccccn1)C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NCC1=NC=CC=C1.[H-].[Na+].CI>>C(C)(C)(C)OC(=O)N(C)CC1=NC=CC=C1 | [NH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][n:9]1)[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].I[CH3:1]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][n:9]1)[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)OC(=O)NCc1ccccn1.CI | CN(Cc1ccccn1)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | c1ccncc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4]-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[#7;a:2]:[c:3]-[C:4]-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | 70.6 | [{"value": 70.0, "product": "C(C)(C)(C)OC(=O)N(C)CC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "C(C)(C)(C)OC(=O)N(C)CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 19.8 g (95 mmol) of 2-(N-(t-butyloxycarbonyl)aminomethyl)pyridine in anhydrous tetrahydrofuran was cooled under N2 atmosphere to 0° C. and treated with 4.95 g (124 mmol) of sodium hydride (60% dispersion in oil). The solution was stirred for 15 min, treated dropwise with 7.1 ml (114 mmol) of methyl iodide... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1ccncc1 | HI | O1CCCC1 | null | 0.25 | CC(C)(C)OC(=O)NCc1ccccn1.CI>O1CCCC1>CN(Cc1ccccn1)C(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e93e26de6b054b1f97fa7352b742e53d | CN1CCOCC1.COC(=O)[C@](N)(N=C=O)C(C)C.c1ccncc1>>COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C | Cl.Cl.N1=CC=CC=C1.COC([C@@](N)(C(C)C)N=C=O)=O.CN1CCOCC1>>COC([C@@H](NC(=O)N(CC1=NC=CC=C1)C)C(C)C)=O | C1C[N:9]([CH3:10])[CH2:11]CO1.N[C@@:5]([C:3]([O:2][CH3:1])=[O:4])([N:6]=[C:7]=[O:8])[CH:18]([CH3:19])[CH3:20].[cH:12]1[cH:13][cH:15][cH:14][cH:16][n:17]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[N:9]([CH3:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1)[CH:18]([CH3:19])[CH3:20] | CN1CCOCC1.COC(=O)[C@](N)(N=C=O)C(C)C.c1ccncc1 | COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C | null | null | ClCCl | Acylation | OtherReaction | 5f78e7a9317bbf5d5ac00daeea29dec8bf69abe7d4911d6308ca83fdb03a70d6 | 2effd315014811dadf8dba713f272b199ed3e0d3d89636a6a85d466106a03f82 | c1ccncc1 | N-[C@@;H0;D4;+0:1](-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11].[#7;a:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1.[C;D1;H3:18]-[N;H0;D3;+0:19]1-C-C-O-C-[CH2;D2;+0:20]-1>>[C;D1;H3:18]-[N;H0;D3;+0:19](-[CH2;D2;+0:20... | null | [] | null | null | 2 | HOUR | A mixture of 1.61 g (7.2 mmol) of 2-(N-methylamino)methyl)pyridine dihydrochloride and 1.14 g (7.2 mmol) of α-isocyanato-valine methyl ester in 40 ml of dichloromethane was treated with 2 ml (18 mmol) of 4-methylmorpholine. After being stirred for 2 h, the solution was partitioned between dichloromethane and water, dri... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Isocyanate.Primary amine.Tertiary amine | Ester.Urea | C1COCC[NH]1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | ClCCl | null | 2 | CN1CCOCC1.COC(=O)[C@](N)(N=C=O)C(C)C.c1ccncc1>ClCCl>COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-724f26f9de804657823e0d6bd96a4e01 | COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C>>CC(C)[C@H](NC(=O)N(C)Cc1ccccn1)C(=O)O | COC([C@@H](NC(=O)N(CC1=NC=CC=C1)C)C(C)C)=O.[OH-].[Li+]>>CN(CC1=NC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)O | C[O:19][C:17]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1)=[O:18]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1)[C:17](=[O:18])[OH:19] | COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C | CC(C)[C@H](NC(=O)N(C)Cc1ccccn1)C(=O)O | null | null | O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 85 | [{"value": 85.0, "product": "CN(CC1=NC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "CN(CC1=NC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4.47 g (16 mmol) of N-((N-methyl-N-((2-pyridinyl)methyl)amino)carbonyl)valine methyl ester in 65 ml of dioxane was treated with 65 ml of 0.5M aqueous lithium hydroxide. After being stirred at ambient temperature for 1 h, the resulting solution was concentrated in vacuo to a small volume (ca. 5 ml), neutra... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | O1CCOCC1 | null | 1 | COC(=O)[C@@H](NC(=O)N(C)Cc1ccccn1)C(C)C>O1CCOCC1>CC(C)[C@H](NC(=O)N(C)Cc1ccccn1)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b33e4cc98aef4ab5917079a082a85979 | CC(C)C(N)=S.O=C(CCl)CCl>>CC(C)c1nc(CCl)cs1.Cl | CC(C(N)=S)C.ClCC(=O)CCl.[O-]S(=O)(=O)[O-].[Mg+2]>>Cl.ClCC=1N=C(SC1)C(C)C | [CH3:1][CH:2]([CH3:3])[C:4]([NH2:5])=[S:10].O=[C:6]([CH2:7][Cl:8])[CH2:9][Cl:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][Cl:8])[cH:9][s:10]1.[ClH:11] | CC(C)C(N)=S.O=C(CCl)CCl | CC(C)c1nc(CCl)cs1.Cl | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1cscn1 | O=[C;H0;D3;+0:1](-[C:2]-[Cl;D1;H0:3])-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1](-[C:2]-[Cl;D1;H0:3]):[cH;D2;+0:4]:[s;H0;D2;+0:11]:1.[ClH;D0;+0:5] | null | [] | null | null | null | null | A mixture of 94.0 g (0.91 mol) of 2-methylpropaneothioamide, 115.7 g (0.91 mol) of 1,3-dichloroacetone, and 109.7 g (0.91 mol) of MgSO4 in 1.6 liters of acetone was heated at reflux for 3.5 h. The resulting mixture was allowed to cool, filtered, and the solvent was removed in vacuo to provide the crude desired compound... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1 | HO- | CC(=O)C | null | null | CC(C)C(N)=S.O=C(CCl)CCl>CC(=O)C>CC(C)c1nc(CCl)cs1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ad3df19240ba47bfa890ccd0addad581 | CC(C)c1nc(CCl)cs1.CN>>CNCc1csc(C(C)C)n1 | Cl.ClCC=1N=C(SC1)C(C)C.CN>>C(C)(C)C=1SC=C(N1)CNC | Cl[CH2:3][c:4]1[cH:5][s:6][c:7]([CH:8]([CH3:9])[CH3:10])[n:11]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][s:6][c:7]([CH:8]([CH3:9])[CH3:10])[n:11]1 | CC(C)c1nc(CCl)cs1.CN | CNCc1csc(C(C)C)n1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cscn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1 | 55 | [{"value": 55.0, "product": "C(C)(C)C=1SC=C(N1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 40 g of 4-(chloromethyl)-2-isopropylthiazole hydrochloride in 100 ml of water was added dropwise with stirring to 400 ml of 40% aqueous methylamine. The resulting solution was stirred for 1 h, then concentrated in vacuo. The residue was taken up in chloroform, dried over Na2SO4, and concentrated in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cscn1 | HCl | O | null | 1 | CC(C)c1nc(CCl)cs1.CN>O>CNCc1csc(C(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d0e8b0d3ed0b4d9ea6bc70ffabf5049e | COC(=O)[C@@H](N)C(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C | ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-].Cl.COC([C@@H](N)C(C)C)=O.CN1CCOCC1>>COC([C@@H](NC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH:19]([CH3:20])[CH3:21].Cl[C:7](=[O:8])[O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1)[CH:19]([CH3:20])[CH3:21] | COC(=O)[C@@H](N)C(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | A solution of 66.1 g (0.328 mol) of 4-nitrophenyl chloroformate in 1.2 liters of CH2Cl2 was cooled to 0° C. and treated with L-valine methyl ester hydrochloride. The resulting mixture was treated slowly, with stirring, with 68.9 ml (0.626 mol) of 4-methylmorpholine. The resulting solution was allowed to slowly warm to ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 8 | COC(=O)[C@@H](N)C(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>C(Cl)Cl>COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6d7205b94b6f456d88a89c4c418a3c7b | CNCc1csc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C>>COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C | C(C)N(CC)CC.C(C)(C)C=1SC=C(N1)CNC.COC([C@@H](NC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(C)C)=O>>COC([C@@H](NC(=O)N(CC=1N=C(SC1)C(C)C)C)C(C)C)=O | [NH:9]([CH3:10])[CH2:11][c:12]1[cH:13][s:14][c:15]([CH:16]([CH3:17])[CH3:18])[n:19]1.O=[N+]([O-])c1ccc(O[C:7]([NH:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH:20]([CH3:21])[CH3:22])=[O:8])cc1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[N:9]([CH3:10])[CH2:11][c:12]1[cH:13][s:14][c:15]([CH:16]([CH3:17])[CH3:18])[n:... | CNCc1csc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C | COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C | null | CN(C1=CC=NC=C1)C | C1CCOC1 | Acylation | OtherReaction | e2d977a702ed644c57a3c6a03e066457d8dc73a51640ae48afb0cf24b6adf835 | fc4b793bbeca2541e0488e7b2269d1dcbab20357be7785ff606aacdf4ebd8736 | c1cscn1 | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):c:c:1.[#16;a:8]:[c:9]:[c:10](-[C:11]-[NH;D2;+0:12]-[C;D1;H3:13]):[#7;a:14]>>[#16;a:8]:[c:9]:[c:10](-[C:11]-[N;H0;D3;+0:12](-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:14] | 72.1 | [{"value": 54.0, "product": "COC([C@@H](NC(=O)N(CC=1N=C(SC1)C(C)C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "COC([C@@H](NC(=O)N(CC=1N=C(SC1)C(C)C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 15.7 g (92 mmol) of 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole in 200 ml of THF was combined with a solution of 20.5 g (69 mmol) of N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester. The resulting solution was treated with 1.6 g of 4-dimethylaminopyridine and 12.9 ml (92 mmol) of triethylamine, ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Secondary amine | Urea | c1ccccc1 | null | c1cscn1 | HO- | CN(C1=CC=NC=C1)C.C1CCOC1 | null | null | CNCc1csc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C>CN(C1=CC=NC=C1)C.C1CCOC1>COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5eae13859e80465a8960583cb560c9e2 | COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C>>CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)cs1 | Cl.COC([C@@H](NC(=O)N(CC=1N=C(SC1)C(C)C)C)C(C)C)=O.[Li+].[OH-]>>CN(CC=1N=C(SC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O | C[O:16][C:14]([C@@H:13]([NH:12][C:10]([N:8]([CH2:7][c:6]1[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[s:21][cH:20]1)[CH3:9])=[O:11])[CH:17]([CH3:18])[CH3:19])=[O:15]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][N:8]([CH3:9])[C:10](=[O:11])[NH:12][C@H:13]([C:14](=[O:15])[OH:16])[CH:17]([CH3:18])[CH3:19])[cH:20][s:21]1 | COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C | CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)cs1 | null | null | O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 81.6 | [{"value": 81.0, "product": "CN(CC=1N=C(SC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "CN(CC=1N=C(SC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 1.42 g (4.3 mmol) N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester in 17 ml of dioxane was treated with 17.3 ml of 0.50M aqueous LiOH. The resulting solution was stirred at ambient temperature for 30 min, treated with 8.7 ml of 1M HCl, and concentrated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | O1CCOCC1 | null | 0.5 | COC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C>O1CCOCC1>CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)cs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-09967249e5c54fa28770a501c9324417 | CCOC(=O)CCl.CCOC=O>>CCOC(=O)C(Cl)C=O | CC(C)([O-])C.[K+].ClCC(=O)OCC.C(=O)OCC.Cl>>ClC(C(=O)OCC)C=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][Cl:7].CCO[CH:8]=[O:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([Cl:7])[CH:8]=[O:9] | CCOC(=O)CCl.CCOC=O | CCOC(=O)C(Cl)C=O | null | null | C(C)OCC.C1CCOC1 | C-C Coupling | OtherReaction | 3fc0b57ea3d3da606fb4d103c3a7d45c1f7249c90fa5736c3093ee79b9f9e4ef | 5f6d2dec246ebbf9bd8ff555f8e6b948874f1d470f439cfed67b1d917f8c57cb | null | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[Cl;D1;H0:8]>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[Cl;D1;H0:8])-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | 0 | CELSIUS | 1 | HOUR | To a three neck 2 L round bottom flask charged with potassium t-butoxide (0.5 mol, 500 mL of a 1M solution in THF) and 500 mL of dry THF cooled to 0° C. was added dropwise from an addition funnel a solution of ethyl chloroacetate (0.5 mol, 53.5 mL) and ethyl formate (0.5 mol, 40.4 mL), in 200 mL of THF over 3 hours. Af... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether | Secondary halide.Aldehyde | null | null | null | HO- | C(C)OCC.C1CCOC1 | 0 | 1 | CCOC(=O)CCl.CCOC=O>C(C)OCC.C1CCOC1>CCOC(=O)C(Cl)C=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9ad27e36ea8a4245a799e896435ce5b9 | CCOC(=O)C(Cl)C=O.NC=S>>CCOC(=O)c1cncs1 | C(=S)N.ClC(C(=O)OCC)C=O>>S1C=NC=C1C(=O)OCC | O=[CH:7][CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][CH:9]=[S:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][cH:9][s:10]1 | CCOC(=O)C(Cl)C=O.NC=S | CCOC(=O)c1cncs1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | ca1a491634351402ba53e022aaddc0a4c7ec0639045153b7668e78d316c6754f | b332eb5ea501618d8dbac38c7e3242fcefa783e31f17b6ca5d4aaeb74530fc69 | c1cscn1 | Cl-[CH;D3;+0:1](-[CH;D2;+0:2]=O)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[CH;D2;+0:8]=[S;H0;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[s;H0;D2;+0:9]:1 | 60 | [{"value": 60.0, "product": "S1C=NC=C1C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "S1C=NC=C1C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of ethyl 2-chloro-2-formylacetate. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ester.Thioamide | Ester | null | c1cscn1 | c1cscn1 | HCl | CC(=O)C | null | null | CCOC(=O)C(Cl)C=O.NC=S>CC(=O)C>CCOC(=O)c1cncs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-62b01f02baa24502b500f023bdca3e5a | O=C(Cl)Oc1ccc([N+](=O)[O-])cc1.OCc1cncs1>>O=C(OCc1cncs1)Oc1ccc([N+](=O)[O-])cc1 | OCC1=CN=CS1.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]>>C1=CC(=CC=C1[N+](=O)[O-])OC(=O)OCC2=CN=CS2 | Cl[C:2](=[O:1])[O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1.[OH:3][CH2:4][c:5]1[cH:6][n:7][cH:8][s:9]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][n:7][cH:8][s:9]1)[O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1 | O=C(Cl)Oc1ccc([N+](=O)[O-])cc1.OCc1cncs1 | O=C(OCc1cncs1)Oc1ccc([N+](=O)[O-])cc1 | null | null | C(Cl)(Cl)Cl.C(Cl)Cl | Acylation | Schotten-Baumann to ester | c7a3e8873fc25f3519e40d98cf7a48f9e19cf51f2928c1b7217b087e636631b6 | 025f705bf83a5228860243b04919f20e0b9a7bfb249341effd2e1aa6465736d3 | O=C(OCc1cncs1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[#16;a:5]:[c:6](-[C:7]-[OH;D1;+0:8]):[c:9]:[#7;a:10]>>[#16;a:5]:[c:6](-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4]):[c:9]:[#7;a:10] | 78 | [{"value": 78.0, "product": "C1=CC(=CC=C1[N+](=O)[O-])OC(=O)OCC2=CN=CS2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "C1=CC(=CC=C1[N+](=O)[O-])OC(=O)OCC2=CN=CS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 3.11 g (27 mmol) of 5-(hydroxymethyl)thiazole and excess N-methyl morphcline in 100 ml of methylene chloride was cooled to 0° C. and treated with 8.2 g (41 mmol) of 4-nitrophenyl chloroformate. After being stirred for 1 h, the reaction mixture was diluted with CHCl3, washed successively with 1N HCl, satur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Ether.Ether | null | null | c1cscn1.c1ccccc1 | HCl | C(Cl)(Cl)Cl.C(Cl)Cl | null | 1 | O=C(Cl)Oc1ccc([N+](=O)[O-])cc1.OCc1cncs1>C(Cl)(Cl)Cl.C(Cl)Cl>O=C(OCc1cncs1)Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c32fd0fc0a484c6db081584442ac1344 | CC(C)C(N)=O.O=C(CCl)CCl>>CC(C)C1=NC(O)(CCl)CO1 | C(C(C)C)(=O)N.ClCC(=O)CCl.C(=O)(O)[O-].[Na+].[O-]S(=O)(=O)[O-].[Mg+2]>>ClCC1(N=C(OC1)C(C)C)O | [CH3:1][CH:2]([CH3:3])[C:4]([NH2:5])=[O:11].Cl[CH2:10][C:6](=[O:7])[CH2:8][Cl:9]>>[CH3:1][CH:2]([CH3:3])[C:4]1=[N:5][C:6]([OH:7])([CH2:8][Cl:9])[CH2:10][O:11]1 | CC(C)C(N)=O.O=C(CCl)CCl | CC(C)C1=NC(O)(CCl)CO1 | null | null | CC(=O)C | Acylation | OtherReaction | 96b0c9b531b7ecf0c959da8409be7baafbdac9aad9b452ba4d5e43082e96ac79 | 8599b7dd32c3600e36d583ed13bb88d0962a835190be95a3561b48ff733289d8 | C1=NCCO1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]-[Cl;D1;H0:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[O;H0;D1;+0:11]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[C;H0;D3;+0:9]1=[N;H0;D2;+0:10]-[C;H0;D4;+0:2](-[OH;D1;+0:3])(-[C:4]-[Cl;D1;H0:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-1 | 46 | [{"value": 46.0, "product": "ClCC1(N=C(OC1)C(C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "ClCC1(N=C(OC1)C(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of isobutyramide (9.876 g, 0.1122 mol)in acetone (130 mL) was added 1,3-dichloroacetone (10.0 g, 0.0748 mol), NaHCO3 (9.429 g, 0.1122 mol), and MgSO4 (18.01 g, 0.1496 mol). The mixture was heated at reflux under argon for 63 hrs, then cooled to room temperature, vacuum filtered, and concentrated in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amide | Ether.Tertiary alcohol | null | C1=NCCO1 | C1=NCCO1 | HCl | CC(=O)C | null | null | CC(C)C(N)=O.O=C(CCl)CCl>CC(=O)C>CC(C)C1=NC(O)(CCl)CO1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5001dcc3f1c448c29ea30547f19ae029 | CC(C)C1=NC(O)(CCl)CO1>>CC(C)c1nc(CCl)co1 | ClCC1(N=C(OC1)C(C)C)O.O=S(Cl)Cl>>ClCC=1N=C(OC1)C(C)C | O[C:6]1([CH2:7][Cl:8])[N:5]=[C:4]([CH:2]([CH3:1])[CH3:3])[O:10][CH2:9]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][Cl:8])[cH:9][o:10]1 | CC(C)C1=NC(O)(CCl)CO1 | CC(C)c1nc(CCl)co1 | null | null | ClCCCl | Aromatic Heterocycle Formation | OtherReaction | 64419d6c7f4b17ce247ad9efaef19b4bef1aa2589b0263151d7cc8c07ae834f9 | 0058add5abc280cb9af66d568cb9bdb323ac1e806a9b79b330bb4ffe7b3d08f3 | c1cocn1 | O-[C;H0;D4;+0:1]1(-[C:2]-[Cl;D1;H0:3])-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])=[N;H0;D2;+0:10]-1>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])-[c;H0;D3;+0:6]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1](-[C:2]-[Cl;D1;H0:3]):[cH;D2;+0:4]:[o;H0;D2;+0:5]:1 | 96 | [{"value": 96.0, "product": "ClCC=1N=C(OC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "ClCC=1N=C(OC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | MINUTE | A solution of 4-chloromethyl-4-hydroxy-2-isopropyloxazoline (4.88 g, 0.0275 mol) in 1,2-dichloroethane (20 mL) was added to a solution of SOCl2 (2.40 mL, 0.0329 mol) in 1,2-dichloroethane (80 mL) at 0° C. under argon, and the solution was heated to 70° C. After 15 min at 70° C., the reaction was cooled to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary alcohol | null | C1=NCCO1 | c1cocn1 | c1cocn1 | HO- | ClCCCl | 70 | 0.25 | CC(C)C1=NC(O)(CCl)CO1>ClCCCl>CC(C)c1nc(CCl)co1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c0a1ae4aeb9043d29ee930653e08aad8 | CC(C)c1nc(CCl)co1.CN>>CNCc1coc(C(C)C)n1 | CN.ClCC=1N=C(OC1)C(C)C>>C(C)(C)C=1OC=C(N1)CNC | Cl[CH2:3][c:4]1[cH:5][o:6][c:7]([CH:8]([CH3:9])[CH3:10])[n:11]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][o:6][c:7]([CH:8]([CH3:9])[CH3:10])[n:11]1 | CC(C)c1nc(CCl)co1.CN | CNCc1coc(C(C)C)n1 | null | null | O1CCOCC1.O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cocn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1.[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1 | 71 | [{"value": 71.0, "product": "C(C)(C)C=1OC=C(N1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To 40% aqueous methylamine (100 mL) was added dropwise a suspension of 4-chloromethyl-2-isopropyloxazole (4.20 g, 0.0263 mol) in p-dioxane/H2O (1:1 (v/v), 20 mL) over a 25 min period. After stirring for 45 min at ambient temperature, the volume was reduced to ca. 50 mL by rotary evaporation in vacuo, and NaCl was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cocn1 | HCl | O1CCOCC1.O | null | 0.75 | CC(C)c1nc(CCl)co1.CN>O1CCOCC1.O>CNCc1coc(C(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3e31ff1c1629400b83005281e5fe567b | CNCc1coc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C>>COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C | COC([C@@H](NC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])C(C)C)=O.C(C)(C)C=1OC=C(N1)CNC>>COC([C@@H](NC(=O)N(CC=1N=C(OC1)C(C)C)C)C(C)C)=O | [NH:9]([CH3:10])[CH2:11][c:12]1[cH:13][o:14][c:15]([CH:16]([CH3:17])[CH3:18])[n:19]1.O=[N+]([O-])c1ccc(O[C:7]([NH:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH:20]([CH3:21])[CH3:22])=[O:8])cc1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[N:9]([CH3:10])[CH2:11][c:12]1[cH:13][o:14][c:15]([CH:16]([CH3:17])[CH3:18])[n:... | CNCc1coc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C | COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C | null | null | CN(C)C=O | Acylation | OtherReaction | e2d977a702ed644c57a3c6a03e066457d8dc73a51640ae48afb0cf24b6adf835 | fc4b793bbeca2541e0488e7b2269d1dcbab20357be7785ff606aacdf4ebd8736 | c1cocn1 | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):c:c:1.[#7;a:8]:[c:9](-[C:10]-[NH;D2;+0:11]-[C;D1;H3:12]):[c:13]:[#8;a:14]>>[#7;a:8]:[c:9](-[C:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):[c:13]:[#8;a:14] | 54.1 | [{"value": 54.0, "product": "COC([C@@H](NC(=O)N(CC=1N=C(OC1)C(C)C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "COC([C@@H](NC(=O)N(CC=1N=C(OC1)C(C)C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester (0.903 g, 0.00305 mol) in anhydrous DMF (6 mL) was added to a solution of 2-isopropyl-4-(((N-methyl)amino)methyl)oxazole (9, 0.470 g, 0.00305 mol) in anhydrous DMF (6 mL) under argon, and the yellow solution was stirred at room temperature for 30 min.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Secondary amine | Urea | c1ccccc1 | null | c1cocn1 | HO- | CN(C)C=O | null | 0.5 | CNCc1coc(C(C)C)n1.COC(=O)[C@@H](NC(=O)Oc1ccc([N+](=O)[O-])cc1)C(C)C>CN(C)C=O>COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-176ef9d7d5934107b54d7ee963182235 | COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C>>CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)co1 | COC([C@@H](NC(=O)N(CC=1N=C(OC1)C(C)C)C)C(C)C)=O>>CN(CC=1N=C(OC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O | C[O:16][C:14]([C@@H:13]([NH:12][C:10]([N:8]([CH2:7][c:6]1[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:21][cH:20]1)[CH3:9])=[O:11])[CH:17]([CH3:18])[CH3:19])=[O:15]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][N:8]([CH3:9])[C:10](=[O:11])[NH:12][C@H:13]([C:14](=[O:15])[OH:16])[CH:17]([CH3:18])[CH3:19])[cH:20][o:21]1 | COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C | CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)co1 | null | null | O1CCOCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cocn1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 98.2 | [{"value": 98.0, "product": "CN(CC=1N=C(OC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "CN(CC=1N=C(OC1)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine methyl ester 10 (0.511 g, 0.00164 mol) in p-dioxane (10 mL) and H2O (5 mL) was added LiOH monohydrate (0.103 g, 0.00246 mol). After stirring at room temperature for 1 hr, the p-dioxane was removed by rotary evaporation in vacuo, an... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cocn1 | Other | O1CCOCC1.O | null | 1 | COC(=O)[C@@H](NC(=O)N(C)Cc1coc(C(C)C)n1)C(C)C>O1CCOCC1.O>CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)O)C(C)C)co1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-58ee2bd126c54f2e9bb64ba134fc048c | C=CCC(O)CC.CCOC(=O)/C(Cl)=N\O>>CCOC(=O)C1=NOC(CCC(C)O)C1 | C(C)N(CC)CC.C(C)OCC.OC(CC)CC=C.CCOC(=O)/C(=N\O)/Cl.C(C)OCC>>C(=O)(OCC)C1=NOC(C1)CCC(C)O | [CH2:9]=[CH:10][CH2:11][CH:12]([CH2:13][CH3:15])[OH:14].Cl/[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7]/[OH:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[N:7][O:8][CH:9]([CH2:10][CH2:11][CH:12]([CH3:13])[OH:14])[CH2:15]1 | C=CCC(O)CC.CCOC(=O)/C(Cl)=N\O | CCOC(=O)C1=NOC(CCC(C)O)C1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5b6dad6070799c6f29fb7bc03432e54a0604aa32650a519a56da49e571e1dd2e | 22f69b79f1e698a66982b9d19d867aa041819fe03d3879a2be18cee17c0b9833 | C1=NOCC1 | Cl/[C;H0;D3;+0:1](=[#7:2]/[OH;D1;+0:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[CH2;D1;+0:8]=[CH;D2;+0:9]-[C:10]-[C:11](-[O;D1;H1:12])-[CH2;D2;+0:13]-[CH3;D1;+0:14]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:1]1=[#7:2]-[O;H0;D2;+0:3]-[CH;D3;+0:8](-[CH2;D2;+0:9]-[C:10]-[C:11](-[CH3;D1;+0:13])-[O;D1;H1:12])-[CH2;D2;+0:14]-1 | null | [] | 0 | CELSIUS | null | null | To a solution of 6 g of 3-hydroxy-5-hexene in 150 ml of diethyl ether was added 18.1 g of ethyl chlorooximidoacetate. The solution was cooled to 0° C., and a solution of 21 ml of triethylamine in 210 ml of diethyl ether was added over 2.5 h. The amine hydrochloride salt was filtered and the residue was purified by sili... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ester.Allyl.Oxime | Ester | null | C1=NOCC1 | C1=NOCC1 | HCl | null | 0 | null | C=CCC(O)CC.CCOC(=O)/C(Cl)=N\O>>CCOC(=O)C1=NOC(CCC(C)O)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a8c916b78d1346f5a0cda6c31c21aa14 | C#CCOC1CCCCO1.CCOC(OCC)OCC>>CCOC(C#CCOC1CCCCO1)OCC | C(C)[Mg]Br.C1CCOC1.C(C#C)OC1OCCCC1.C(C)OC(OCC)OCC>>C(C)OC(C#CCOC1OCCCC1)OCC | [CH:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:14]1.CCO[CH:4]([O:3][CH2:2][CH3:1])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][CH:4]([C:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:14]1)[O:15][CH2:16][CH3:17] | C#CCOC1CCCCO1.CCOC(OCC)OCC | CCOC(C#CCOC1CCCCO1)OCC | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 5c785d27c44a43526fd7fdd77cfc98b0f959dd7c7f379a09a381a32824fc27db | 6edbaa6dd32bc7980574a42cae4193d6efda2e147efbdfba916ce27407251dd7 | C1CCOCC1 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:3]-[#8:2]-[CH;D3;+0:1](-[#8:4]-[C:5])-[C;H0;D2;+0:8]#[C:7]-[C:6] | 79 | [{"value": 79.0, "product": "C(C)OC(C#CCOC1OCCCC1)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A 1M solution of ethylmagnesium bromide in THF (200 ml, 0.2 mol) was treated with 29 ml (0.2 mol) of a solution of 3,4,5,6-tetrahydro-2-(2-propynyloxy)-2H-pyran in toluene, while maintaining ambient temperature through use of a cool water bath. The resulting solution was stirred for 4 h and treated with 47 ml (0.28 mol... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Alkyne | Ether.Ether.Alkyne | null | null | C1CCOCC1 | HO- | C1(=CC=CC=C1)C | null | 4 | C#CCOC1CCCCO1.CCOC(OCC)OCC>C1(=CC=CC=C1)C>CCOC(C#CCOC1CCCCO1)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-94131f34c83b4b5ea02e7dfd9ab76786 | CN(C)C(N)=S.O=C(CCl)CCl>>CN(C)c1nc(CCl)cs1 | ClCC(=O)CCl.CN(C(=S)N)C.[O-]S(=O)(=O)[O-].[Mg+2]>>ClCC=1N=C(SC1)N(C)C | [CH3:1][N:2]([CH3:3])[C:4]([NH2:5])=[S:10].O=[C:6]([CH2:7][Cl:8])[CH2:9]Cl>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][Cl:8])[cH:9][s:10]1 | CN(C)C(N)=S.O=C(CCl)CCl | CN(C)c1nc(CCl)cs1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1cscn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3]-[Cl;D1;H0:4].[C;D1;H3:5]-[#7:6](-[C;D1;H3:7])-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10]>>[C;D1;H3:5]-[#7:6](-[C;D1;H3:7])-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:2](-[C:3]-[Cl;D1;H0:4]):[cH;D2;+0:1]:[s;H0;D2;+0:10]:1 | 70 | [{"value": 70.0, "product": "ClCC=1N=C(SC1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.0, "product": "ClCC=1N=C(SC1)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 15 g (144 mmol) of N,N-dimethylthiourea and excess MgSO4 in 350 ml of acetone was heated to reflux and treated dropwise with a solution of 18.3 g (144 mmol) of 1,3-dichloroacetone in 35 ml of acetone. The resulting mixture was heated at reflux for 1.5 h, allowed to cool, filtered, and concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1cscn1 | HCl | CC(=O)C | null | null | CN(C)C(N)=S.O=C(CCl)CCl>CC(=O)C>CN(C)c1nc(CCl)cs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ebd74e6522cb40efa3214dae18c5b7b6 | CN(C)c1nc(CCl)cs1.O>>CN(C)c1nc(CO)cs1 | C1CCOC1.O.ClCC=1N=C(SC1)N(C)C.C1CCOC1.O>>CN(C)C=1SC=C(N1)CO | Cl[CH2:7][c:6]1[n:5][c:4]([N:2]([CH3:1])[CH3:3])[s:10][cH:9]1.[OH2:8]>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][OH:8])[cH:9][s:10]1 | CN(C)c1nc(CCl)cs1.O | CN(C)c1nc(CO)cs1 | null | F[B-](F)(F)F.[Ag+] | null | Heteroatom Alkylation and Arylation | OtherReaction | 231253c55c0f42174a17340b823c6702155eb165c3d2f7b555bb09f54b91b1a3 | e7141d94960d4874394ef66bcefdd72176a955fa44e71bb38bf7656b1bd4e11a | c1cscn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[OH2;D0;+0:7]>>[OH;D1;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1 | null | [] | null | null | 1 | HOUR | A solution of 5.186 g (29 mmol) of 4-(chloromethyl)-2-(dimethylamino)thiazole in 100 ml of 1:1 THF/H2O was cooled to 0° C. and treated dropwise with a solution of 5.73 g (29 mmol) of silver tetrafluoroborate in 50 ml of 1:1 THF/H2O. After being stirred for 1 h, the mixture was filtered, the solid mass was washed with e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary alcohol | null | null | c1cscn1 | HCl | F[B-](F)(F)F.[Ag+] | null | 1 | CN(C)c1nc(CCl)cs1.O>F[B-](F)(F)F.[Ag+]>CN(C)c1nc(CO)cs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-00a13d5c9a94459f9f294cd9c829351b | CN(C)c1nc(CO)cs1.COC(=O)[C@](N)(N=C=O)C(C)C>>COC(=O)[C@@H](NC(=O)OCc1csc(N(C)C)n1)C(C)C | CN(C)C=1SC=C(N1)CO.COC([C@@](N)(C(C)C)N=C=O)=O>>COC([C@@H](NC(=O)OCC=1N=C(SC1)N(C)C)C(C)C)=O | [OH:9][CH2:10][c:11]1[cH:12][s:13][c:14]([N:15]([CH3:16])[CH3:17])[n:18]1.N[C@@:5]([C:3]([O:2][CH3:1])=[O:4])([N:6]=[C:7]=[O:8])[CH:19]([CH3:20])[CH3:21]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][s:13][c:14]([N:15]([CH3:16])[CH3:17])[n:18]1)[CH:19]([CH3:20])[CH3:21] | CN(C)c1nc(CO)cs1.COC(=O)[C@](N)(N=C=O)C(C)C | COC(=O)[C@@H](NC(=O)OCc1csc(N(C)C)n1)C(C)C | null | CN(C1=CC=NC=C1)C | ClCCl | Functional Group Interconversion | OtherReaction | a23be472936c50c173c2dd2734289c9dfae50efca7ef50b8a0cb8898e49c8803 | 594e835804772a869b7a162be980a733776c00b82a87e4b097f0a7da7fddd8e1 | c1cscn1 | N-[C@@;H0;D4;+0:1](-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11].[#16;a:12]:[c:13]:[c:14](-[C:15]-[OH;D1;+0:16]):[#7;a:17]>>[#16;a:12]:[c:13]:[c:14](-[C:15]-[O;H0;D2;+0:16]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C@@H;D3;+0:1](-[C:5](-[C;D1;H3:... | 95 | [{"value": 95.0, "product": "COC([C@@H](NC(=O)OCC=1N=C(SC1)N(C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "COC([C@@H](NC(=O)OCC=1N=C(SC1)N(C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 505 mg (3.19 mmol) of 2-(N,N-dimethylamino)-4-(hydroxymethyl)thiazole, 3.19 mmol of α-isocyanato-L-valine methyl ester, and 100 mg of 4-dimethylaminopyridine in 30 ml of dichloromethane was heated at reflux for 3 h. The resulting solution was allowed to cool, diluted with dichloromethane, washed sequentia... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Primary alcohol.Primary amine | Carbamic ester.Ester | null | null | c1cscn1 | Other | CN(C1=CC=NC=C1)C.ClCCl | null | null | CN(C)c1nc(CO)cs1.COC(=O)[C@](N)(N=C=O)C(C)C>CN(C1=CC=NC=C1)C.ClCCl>COC(=O)[C@@H](NC(=O)OCc1csc(N(C)C)n1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bb97273c68bf445e929cb09da7acb2ff | CCOC(=O)C(=O)CBr.NC(=S)N1CCOCC1>>CCOC(=O)c1csc(N2CCOCC2)n1 | NC(=S)N1CCOCC1.BrCC(C(=O)OCC)=O.[O-]S(=O)(=O)[O-].[Mg+2]>>N1(CCOCC1)C=1SC=C(N1)C(=O)OCC | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[S:8]=[C:9]([N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[NH2:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]1 | CCOC(=O)C(=O)CBr.NC(=S)N1CCOCC1 | CCOC(=O)c1csc(N2CCOCC2)n1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 2acf8b62928feda0eec79ae390961e4e289c4aabc8d6caf6e6ddc0eda363b75d | 86bbdfdfc5fa521b3981982705c3355aa8731992aa62c549aa1ec0eef245e5b9 | c1csc(N2CCOCC2)n1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[#7:8](-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11])-[C:12]>>[C:7]-[#7:8](-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]):[cH;D2;+0:1]:[s;H0;D2;+0:11]:1)-[C:12] | 55.2 | [{"value": 55.0, "product": "N1(CCOCC1)C=1SC=C(N1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "N1(CCOCC1)C=1SC=C(N1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.85 g (12.7 mmol) of 4-((amino)thiocarbonyl)morpholine, 1.59 ml (12.7 mmol) of ethyl bromopyruvate, and excess MgSO4 in 50 ml of acetone was heated at reflux for 2 h. The resulting mixture was allowed to cool, filtered, and concentrated in vacuo. The residue was taken up in chloroform, washed with aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Thiourea | Ester | null | c1cscn1 | c1cscn1.C1COCC[NH]1 | HBr | CC(=O)C | null | null | CCOC(=O)C(=O)CBr.NC(=S)N1CCOCC1>CC(=O)C>CCOC(=O)c1csc(N2CCOCC2)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7d854e66a30d4598ba3f260d83acb5fa | CCOC(=O)c1csc(N2CCOCC2)n1>>OCc1csc(N2CCOCC2)n1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].N1(CCOCC1)C=1SC=C(N1)C(=O)OCC>>N1(CCOCC1)C=1SC=C(N1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][s:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[n:13]1>>[OH:1][CH2:2][c:3]1[cH:4][s:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[n:13]1 | CCOC(=O)c1csc(N2CCOCC2)n1 | OCc1csc(N2CCOCC2)n1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1csc(N2CCOCC2)n1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1 | 61.1 | [{"value": 61.0, "product": "N1(CCOCC1)C=1SC=C(N1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "N1(CCOCC1)C=1SC=C(N1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of 7.0 ml (7.0 mmol) of lithium aluminum hydride in toluene was diluted with 10 ml of THF, cooled to 0° C., and treated with a solution of 1.7 g (7.0 mmol) of ethyl 2-(4-morpholinyl)thiazole-4-carboxylate in 25 ml of THF. The resulting solution was stirred for 1 h, quenched cautiously with aqueous Rochelle's... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cscn1.C1COCC[NH]1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | 0 | 1 | CCOC(=O)c1csc(N2CCOCC2)n1>C1(=CC=CC=C1)C.C1CCOC1>OCc1csc(N2CCOCC2)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4fd6ba6668b04b55b557b83207267fa9 | CCOC(=O)c1csc(N2CCCC2)n1>>OCc1csc(N2CCCC2)n1 | N1(CCCC1)C=1SC=C(N1)C(=O)OCC.CO>>N1(CCCC1)C=1SC=C(N1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][s:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[n:12]1>>[OH:1][CH2:2][c:3]1[cH:4][s:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[n:12]1 | CCOC(=O)c1csc(N2CCCC2)n1 | OCc1csc(N2CCCC2)n1 | null | null | C(Cl)(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1csc(N2CCCC2)n1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1 | 4 | [{"value": 4.0, "product": "N1(CCCC1)C=1SC=C(N1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 23C but replacing ethyl 2-(4-morpholinyl)thiazole-4-carboxylate with ethyl 2-(1-pyrrolidinyl)thiazole-4-carboxylate provided, after silica gel chromatography using 2-4% methanol in chloroform, the desired compound (Rf 0.26, 4% methanol in chloroform) in 53% yield. 1H NMR (CDCl3) δ2.04 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cscn1.C1CC[NH]C1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)c1csc(N2CCCC2)n1>C(Cl)(Cl)Cl>OCc1csc(N2CCCC2)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b61ac108471143a1be239e5bce7d401e | CC(C)[C@@](N)(N=C=O)C(=O)O.CNCc1csc(N(C)C)n1>>COC(=O)[C@@H](NC(=O)N(C)Cc1csc(N(C)C)n1)C(C)C | N(=C=O)[C@](N)(C(C)C)C(=O)O.CN(C)C=1SC=C(N1)CNC.ClCCl.ClCCl>>COC([C@@H](NC(=O)N(CC=1N=C(SC1)N(C)C)C)C(C)C)=O | N[C@@:5]([C:3]([OH:2])=[O:4])([N:6]=[C:7]=[O:8])[CH:20]([CH3:21])[CH3:22].[NH:9]([CH3:10])[CH2:11][c:12]1[cH:13][s:14][c:15]([N:16]([CH3:17])[CH3:18])[n:19]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[N:9]([CH3:10])[CH2:11][c:12]1[cH:13][s:14][c:15]([N:16]([CH3:17])[CH3:18])[n:19]1)[CH:20]([CH3:21])[CH3:22] | CC(C)[C@@](N)(N=C=O)C(=O)O.CNCc1csc(N(C)C)n1 | COC(=O)[C@@H](NC(=O)N(C)Cc1csc(N(C)C)n1)C(C)C | null | null | null | Functional Group Interconversion | OtherReaction | c380c012b5fe53dd6cd702dc61e4967ea3c8f8e7c8428aa9fc563de56876cc9c | 91a4ee2356b16742374f8224db1dc3afc61c8fe99d0b1285b4d7465b0deb162f | c1cscn1 | N-[C@@;H0;D4;+0:1](-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10].[#16;a:11]:[c:12]:[c:13](-[C:14]-[NH;D2;+0:15]-[C;D1;H3:16]):[#7;a:17]>>[#16;a:11]:[c:12]:[c:13](-[C:14]-[N;H0;D3;+0:15](-[C;D1;H3:16])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C@@H;D3;+0... | 34 | [{"value": 34.0, "product": "COC([C@@H](NC(=O)N(CC=1N=C(SC1)N(C)C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 741 mg (4.42 mmol) of α-isocyanato-L-valine in in 5 ml of dichloromethane was added to a solution of 720 mg (4.21 mmol) of 2-(N,N-dimethylamino)-4-(((N-methyl)amino)methyl)thiazole in 25 ml of dichloromethane. The resulting solution was stirred at ambient temperature for 16 h, partitioned between chlorofo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Isocyanate.Primary amine.Secondary amine | Ester.Urea | null | null | c1cscn1 | null | null | null | 16 | CC(C)[C@@](N)(N=C=O)C(=O)O.CNCc1csc(N(C)C)n1>>COC(=O)[C@@H](NC(=O)N(C)Cc1csc(N(C)C)n1)C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f7583450d6ad4da3b8ea9914bcf7f117 | C#CCOC1CCCCO1.CC(C)C(=O)Cl>>CC(C)C(=O)C#CCOC1CCCCO1 | C(C(C)C)(=O)Cl.C(C#C)OC1OCCCC1>>CC(C(C#CCOC1OCCCC1)=O)C | [CH:6]#[C:7][CH2:8][O:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:15]1.Cl[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[C:6]#[C:7][CH2:8][O:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:15]1 | C#CCOC1CCCCO1.CC(C)C(=O)Cl | CC(C)C(=O)C#CCOC1CCCCO1 | null | null | null | C-C Coupling | OtherReaction | a6f0b2b4226aa44d92013aea18c387b08c35f5add226dac668d88084e9d68d79 | 8ba6b48924727c95ba5477874811455682753922dd7cd313d89aad2a979363dd | C1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | null | [] | null | null | null | null | The desired compound was prepared from isobutyryl chloride and 3,4,5,6-tetrahydro-2-(2-propynyloxy)-2H-pyran by analogy to the procedure of Tohda, et. al. (Synthesis, 777 (1977)).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Alkyne | Ketone | null | null | C1CCOCC1 | HCl | null | null | null | C#CCOC1CCCCO1.CC(C)C(=O)Cl>>CC(C)C(=O)C#CCOC1CCCCO1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-387912939de7416b9e56f5247a2569aa | CC(=O)OC(C)=O.CC1(C)C=CC=CC1CCO>>CC(=O)OCCC1C=CC=CC1(C)C | CC1(C(CCO)C=CC=C1)C.C(C)(=O)OC(C)=O>>C(C)(=O)OCCC1C(C=CC=C1)(C)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]1([CH3:13])[CH3:14]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]1([CH3:13])[CH3:14] | CC(=O)OC(C)=O.CC1(C)C=CC=CC1CCO | CC(=O)OCCC1C=CC=CC1(C)C | null | null | N1=CC=CC=C1 | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | C1=CCCC=C1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 8 | HOUR | Dissolve 2,2-dimethylphenethyl alcohol (118.0 g, 0.786 mol) in pyridine (700 mL). Add, by dropwise addition, acetic anhydride (222 mL, 240.7 g, 2.358 mol) and stir overnight at room temperature. Evaporate the solvent in vacuo and purify by distillation to give the title compound as a clear colorless oil; bp 75° C. @ 0.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | C1=CCCC=C1 | HO- | N1=CC=CC=C1 | null | 8 | CC(=O)OC(C)=O.CC1(C)C=CC=CC1CCO>N1=CC=CC=C1>CC(=O)OCCC1C=CC=CC1(C)C |
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