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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-889f87317a184fe882398292d773dda7 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>>O=C(O)CCC(=O)c1cccc(Cl)c1 | C(CCC(=O)OC)(=O)OC.[Na].C(C)O.ClC=1C=C(C(=O)OC)C=CC1.C(CCC(=O)OC)(=O)OC>>ClC=1C=C(C(=O)CCC(=O)O)C=CC1 | COC(=O)[CH2:5][CH2:4][C:2](=[O:1])[O:3]C.CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | null | null | CCOCC | C-C Coupling | OtherReaction | 6d482de2a0c1fffe47581cf2d6dc0eefca79628574252eec326be9292f335afe | 1f69704fe402a3eb0e91a243a59f68f972592be61b4c787368515903d4c85726 | c1ccccc1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C.C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Carboxylic acid.Ketone | null | null | c1ccccc1 | HO- | CCOCC | null | null | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>CCOCC>O=C(O)CCC(=O)c1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4107cbb9265542ed86297db6dd6b41b9 | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | CC1=CC=C(C(=O)CCC(=O)O)C=C1.[Cl-].[Al+3].[Cl-].[Cl-].ClCl>>ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl | [CH3:1][c:2]1[cH:3][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1.[Cl:4][Cl:16]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][c:15]1[Cl:16] | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl | Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | d2a751fe92dcfde720edd5e4971c1aa6cc149bff4a6d230cc6b5cac59ec9498c | 861258def4b3bd7367f8a87cde43fe585d40dc3669ea29055dbcb9a2de101a4d | c1ccccc1 | [C;D1;H3:1]-[c:2]1:[cH;D2;+0:3]:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1.[Cl;H0;D1;+0:10]-[Cl;H0;D1;+0:11]>>[C;D1;H3:1]-[c:2]1:[c;H0;D3;+0:3](-[Cl;H0;D1;+0:10]):[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:11] | 44.2 | [{"value": 44.2, "product": "ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(Cl)Cl | null | null | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>C(Cl)Cl>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e3cc0d24c92424b96fce5ec22cba17e | C1=COCCC1.OCC#CCO>>OCC#CCOC1CCCCO1 | C(C#CCO)O.O1CCCC=C1>>O1C(CCCC1)OCC#CCO | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[OH:1][CH2:2][C:3]#[C:4][CH2:5][OH:6]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCC#CCO | OCC#CCOC1CCCCO1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 68.8 | [{"value": 68.8, "product": "O1C(CCCC1)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | CCOCC | null | null | C1=COCCC1.OCC#CCO>CCOCC>OCC#CCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ea2fb6c87de2423b8a84f6a9a4419031 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C1(CCCCC1)C#C.C=O.C=O>>C1(CCCCC1)C#CCO | [CH:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[O:1]=[CH2:2]>>[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C#CC1CCCCC1.C=O | OCC#CC1CCCCC1 | null | null | CCOCC | C-C Coupling | OtherReaction | b068d8bba9f864ba971dd324292d9b3526f0235b4ab7e3a9ce6aa76a39c4a1e7 | 22ebec2cc94dd24863aea8793d450cfe0691e1036be204d1a4c79c16effe90a4 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Primary alcohol.Alkyne | null | null | C1CCCCC1 | null | CCOCC | null | null | C#CC1CCCCC1.C=O>CCOCC>OCC#CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9050fa6258a9415bb85240ff78c07174 | O=C1CCC(c2ccc(Cl)cc2)=NN1>>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1CCC(NN1)=O.C(C)(=O)O.BrBr>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73c80fbcc9dd7a9125aaf1059d9d4eab31b342d21fc860abf5e65fd78456864b | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1ccc(-c2ccccc2)n[nH]1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[N;H0;D2;+0:11]-[NH;D2;+0:12]-1>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | 93.1 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | C1=NNCCC1 | c1cccnn1 | c1cccnn1.c1ccccc1 | null | O | null | null | O=C1CCC(c2ccc(Cl)cc2)=NN1>O>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a068a289c1114a798edc84425ca9f594 | FC1(F)CC(Cl)(Cl)C1(F)Cl>>FC1(F)C=C(Cl)C1(F)Cl | ClC1(C(C(C1)(F)F)(F)Cl)Cl.O.Cl>>ClC1(C(C=C1Cl)(F)F)F | Cl[C:5]1([Cl:6])[CH2:4][C:2]([F:1])([F:3])[C:7]1([F:8])[Cl:9]>>[F:1][C:2]1([F:3])[CH:4]=[C:5]([Cl:6])[C:7]1([F:8])[Cl:9] | FC1(F)CC(Cl)(Cl)C1(F)Cl | FC1(F)C=C(Cl)C1(F)Cl | null | null | CCOCC.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 0ca523bc88d44f4371960ac2ff9ed0bbb8882337b7061f7fba5b4787f1e02481 | 986b135105e7920109b424799136a4a8281fb4a0f49253ce1bf5d4426ed78637 | C1=CCC1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9] | 79 | [{"value": 79.0, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ethe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Alkenyl halide | C1CCC1 | C1=CCC1 | C1=CCC1 | HCl | CCOCC.C(C)N(CC)CC | null | 8 | FC1(F)CC(Cl)(Cl)C1(F)Cl>CCOCC.C(C)N(CC)CC>FC1(F)C=C(Cl)C1(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51c7ba5d9752485ca16303527dfa9966 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>>O=C(O)C(F)C(F)(F)C(=O)O | ClC(C(C(=O)O)(F)F)(C(=O)O)F>>FC(C(=O)O)(C(C(=O)O)F)F | Cl[C:6]([C:4]([C:2](=[O:1])[OH:3])([F:5])[F:7])([F:8])[C:9](=[O:10])[OH:11]>>[O:1]=[C:2]([OH:3])[CH:4]([F:5])[C:6]([F:7])([F:8])[C:9](=[O:10])[OH:11] | O=C(O)C(F)(F)C(F)(Cl)C(=O)O | O=C(O)C(F)C(F)(F)C(=O)O | null | [Zn] | O1CCOCC1 | Functional Group Addition | Dehalogenation | 7f145230bfb0115349e969b2f2fa1359cfafe8c166e52b50a867192005e1f5bc | d6722b0df465660a9eeeaca5a8f5b3dbb2d1ebccb44917f2eca97a85bf850d06 | null | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:7]-[CH;D3;+0:6](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:8])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 40.7 | [{"value": 32.0, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide.Secondary halide | null | null | null | Other | [Zn].O1CCOCC1 | null | 10 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>[Zn].O1CCOCC1>O=C(O)C(F)C(F)(F)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cda8deef8464fdbb84bc3f44d4fe1f5 | O=C1CCC(=O)O1.c1ccc2ccccc2c1>>O=C(O)CCC(=O)c1cccc2ccccc12 | Cl.[Cl-].[Cl-].[Cl-].[Al+3].C1=CC=CC2=CC=CC=C12.C1(CCC(=O)O1)=O>>C1(=CC=CC2=CC=CC=C12)C(=O)CCC(=O)O | [O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1.[cH:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | O=C1CCC(=O)O1.c1ccc2ccccc2c1 | O=C(O)CCC(=O)c1cccc2ccccc12 | null | null | [N+](=O)([O-])C1=CC=CC=C1 | C-C Coupling | OtherReaction | d1b47ca78c3ceb45955ddf79d2b2d22c1a0978cf9fa8ded4c5ee0a8331deac4e | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccc2ccccc2c1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | C1CCOC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [N+](=O)([O-])C1=CC=CC=C1 | null | null | O=C1CCC(=O)O1.c1ccc2ccccc2c1>[N+](=O)([O-])C1=CC=CC=C1>O=C(O)CCC(=O)c1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eff35b6820384eb2a5f2f60a585c840d | NN.O=C(O)CCCC(=O)c1ccccc1>>O=c1cccc(-c2ccccc2)nn1 | C(C1=CC=CC=C1)(=O)CCCC(=O)O.NN.O>>C1(=CC=CC=C1)C1=CC=CC(N=N1)=O | [NH2:13][NH2:14].O=[C:6]([CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1 | NN.O=C(O)CCCC(=O)c1ccccc1 | O=c1cccc(-c2ccccc2)nn1 | null | null | C1(=CC=CC=C1)C.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a31553d36b14882561a6dcdd04ef456bc0e14ea189c472490f94f02ebbe3ca3f | eadf9e657b4bde18ed656e299092aac7dd81eee1face1030775c3edd6ccba31c | O=c1cccc(-c2ccccc2)nn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0... | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C1=CC=CC(N=N1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 10g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | null | null | c1cccc[nH]n1 | c1cccc[nH]n1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CCOCC | null | null | NN.O=C(O)CCCC(=O)c1ccccc1>C1(=CC=CC=C1)C.CCOCC>O=c1cccc(-c2ccccc2)nn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-85c5b1a3dd694c5d823ad82e2974b06f | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>>COC(=O)C1Cc2cc(Cl)ccc2C1=O | COC(OC)=O.[H-].[Na+].ClC=1C=C2CCC(C2=CC1)=O.[H][H]>>C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Cl)ccc21 | COC(=O)C1Cc2cc(Cl)ccc2C1=O | null | null | C(OC)COC | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(OC)COC | 60 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>C(OC)COC>COC(=O)C1Cc2cc(Cl)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d54af9d4762649be9b45711704142f42 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 | C([O-])([O-])=O.[K+].[K+].P(=O)(Cl)(Cl)Cl.CN(C)C=O.ClC1=CC=C(C=C1)CC(=O)O>>ClC1=CC=C(C=C1)C(C=O)=CN(C)C | O=[CH:4][N:2]([CH3:1])[CH3:3].O=[C:6]([CH2:5][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[OH:7]>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1 | CN(C)C=C(C=O)c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cbf378fe57a2b8d8304e623fb5ce9ee6fb9f6e90d9c6f965226d56b103180e6d | a9c635686380f13b6b5c45d80d4aef36b30fdab0aef140b81f04c277f7ba737d | c1ccccc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[CH;D2;+0:7]=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Enamine.Aldehyde | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 8 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>C1(=CC=CC=C1)C>CN(C)C=C(C=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a2c011f1b3e4de5a080b95b7446e37f | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C.ClC1=CC=C(C=C1)C(C=O)=CN(C)C.C[O-].[Na+].C(#N)CC(=O)N>>C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O | CN(C)[CH:13]=[C:5]([CH:4]=O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[N:1]#[C:2][CH2:3][C:15]([NH2:14])=[O:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14][c:15]1=[O:16] | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 4fb69599b2ad512416349de44ee025f314a8ccdb2c8ad729cdf94ea75cf3109a | 46cf335065eccd013987994a3f086665eb273ac87eb3153099a47e61dd329581 | O=c1ccc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:1]:[nH;D2;+0:13]:[c;H0;D3;+0... | null | [] | null | null | null | null | To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic add (50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1 | HO- | CO.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>CO.O>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-045750bf97304072902ebfbcb4032b67 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)C=1C=CC(NC1)=O | N#C[c:3]1[c:2](=[O:1])[nH:14][cH:13][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | null | null | OP(=O)(O)O | Miscellaneous | OtherReaction | 145adc421652def73603eb299eace1e2e3a197522b719b6949c0145a4308d11b | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | O=c1ccc(-c2ccccc2)c[nH]1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | 75.6 | [{"value": 75.6, "product": "ClC1=CC=C(C=C1)C=1C=CC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-cyano-5-(4-chlorophenyl)-2-pyridinone (4.6 g) and 85% H3PO4 (60 ml) was heated at reflux for 16 hours. The resulting mixture was cooled to room temperature, poured into ice/water and filtered yielding 3.1 g of 5-(4-chlorophenyl)-2-pyridinone as a yellow solid.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnccc1 | c1cccnc1 | c1cccnc1.c1ccccc1 | Other | OP(=O)(O)O | null | null | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>OP(=O)(O)O>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9509a42332a49fcbb34674de68bb37b | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | [Cl-].[NH4+].[H-].[Na+].N1C(C=CC=C1)=O.CCCCCC.C(C)(=O)OCC.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=CC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[CH2:9]([CH3:10])[CH2:15][CH2:14][CH2:12][CH3:11].[nH:6]1[cH:7][cH:8][cH:16][cH:17][c:18]1=[O:19].[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-] | CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | c16e53991381708a0d74f5092b5e25b0353184189763eaae006dd565c1174ab9 | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[Cl-;H0;D0:11].[O;D1;H0:12]=[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:6]2:[cH;D2;+0:5]:[cH;D2;+0:... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8099fc1e3494ad8923c576fec19c417 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | C(C)(=O)OCC.ClC1=CC=C(N)C=C1.N1=CC=CC=C1.C(C=CC1=CC=CC=C1)(=O)Cl>>ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.Cl[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.O | 0 | 0.25 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>C1(=CC=CC=C1)C.O>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-771487d5281b4f96990cdc8a7a9c2bb2 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>>O=c1ccc2c(Cl)cccc2[nH]1 | ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C2C=CC(NC2=CC=C1)=O | c1ccc([CH:4]=[CH:3][C:2](=[O:1])[NH:12][c:11]2[cH:5][cH:8][c:6]([Cl:7])[cH:9][cH:10]2)cc1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[nH:12]1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | O=c1ccc2c(Cl)cccc2[nH]1 | null | null | ClC1=CC=CC=C1 | Reduction | OtherReaction | ebe7e954f82f1e726cf9b7a8863216fec31733c3d8bfbb1cc71c49312cec65ac | 10d6d5b071f1d84b20b253ce9eadaed211c373c6ee607356078792f13319351a | O=c1ccc2ccccc2[nH]1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-c2:c:c:c:c:c:2):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:11]:[c:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+... | null | [] | 125 | CELSIUS | 3 | HOUR | To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | Other | ClC1=CC=CC=C1 | 125 | 3 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>ClC1=CC=CC=C1>O=c1ccc2c(Cl)cccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d045ba7bb254c15a155333d94ac21c7 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>>CCC#CCn1c(=O)ccc2c(Cl)cccc21 | [Cl-].[NH4+].N1C(C=CC2=CC=CC=C12)=O.[H-].[Na+].BrCC#CCC>>ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[nH:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[cH:12][cH:14][cH:15][cH:16][c:17]12.[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-] | CCC#CCn1c(=O)ccc2c(Cl)cccc21 | null | null | CN(C)C=O.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a61336fe7a89ec0981a525297b55629e44e830f13f91df56a44bf01390d8c69d | dbda6588fa29cbbc0e3c3f601e69924b300990bdcc56b8cec0535d1258039346 | O=c1ccc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[Cl-;H0;D0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:[nH;D2;+0:16]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]2:[c:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:5]):[c:10]:2:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CN(C)C=O.CCCCCC | 0 | null | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>CN(C)C=O.CCCCCC>CCC#CCn1c(=O)ccc2c(Cl)cccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-682083a1fe1b4917a49c1da58af0cb59 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | [Cl-].[NH4+].ClC1=CC=C(C=C1)C(C=O)=CN(C)C.NC(=O)N.Cl>>ClC1=CC=C(C=C1)C=1C=NC(NC1)=O | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]=O.[O:1]=[C:2]([NH2:3])[NH2:14]>>[O:1]=[c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O | O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 0e1bb7c6fc2fa2fbd0239b648ae136ef123b13ddeb9947c50b8f38d453d7d183 | 55a949c5abf218b0e7fd0015b81e86fb975fa441e5ac6bd395c3346bb38599f7 | O=c1ncc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:3]:[nH;D2;+0:9]:1 | 29.7 | [{"value": 29.7, "product": "ClC1=CC=C(C=C1)C=1C=NC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Urea | null | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>C(C)O.O>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b6e9c38f760d411e813e29218db44408 | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | [Cl-].[NH4+].CCCCCC.[H-].[Na+].N1C(C=CC=C1)=O.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].C[CH2:15][CH2:14][CH2:12][CH2:11][CH3:10].[nH:6]1[cH:7][cH:8][cH:16][cH:9][c:18]1=[O:19].[Cl-:13].[NH4+:17]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][n:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+] | CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | b4467fdd65493649554b053844b88f7aedac75ecb5e83a2819a9163270cc6b1f | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ncc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].C-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[Cl-;H0;D0:10].[NH4+;D0:11].[O;D1;H0:12]=[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:14]2... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3601c190422e4f1099ec81cc9afbdad4 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1C=CC(NN1)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=S | O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:1])(S2)S3>>[S:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e0da8be0c0e31372bc487fca4d998b8539b7ff5b84df07e1a6200efd3593e0bb | 13be3f637e1e22872d741944f46b7fcc1954fe982a3a8a0f7825545d455ab147 | S=c1ccc(-c2ccccc2)n[nH]1 | O=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 187.1 | [{"value": 187.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thiocarbonyl | c1cccnn1.S1P2SP3SP1SP(S2)S3 | c1cccnn1 | c1cccnn1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9444014702f243e4a6c2da6f4e2518a1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)NN)C=C1.ClCC(=O)Cl>>ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O | [NH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl | O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as whi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>O1CCOCC1>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a3d67c3bad7c44c29b9bc8727026575d | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>>O=C1NN=C(c2ccc(Cl)cc2)CS1 | BrCC(=O)C1=CC=C(C=C1)Cl.COC(=S)NN>>ClC1=CC=C(C=C1)C1=NNC(SC1)=O | C[O:1][C:2]([NH:3][NH2:4])=[S:14].O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13]Br>>[O:1]=[C:2]1[NH:3][N:4]=[C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][S:14]1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1 | O=C1NN=C(c2ccc(Cl)cc2)CS1 | null | null | C(C)#N | Acylation | OtherReaction | a0815ff887854434f061e02bb59e65917f2f792eefe3f407e6f67a241e834044 | b7ddc8c969600ae9a9b2d12841c66a24307741bcbfc0810c56e58eb7d0e4892d | O=C1NN=C(c2ccccc2)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].C-[O;H0;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[NH2;D1;+0:10]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-1 | 48.4 | [{"value": 48.4, "product": "ClC1=CC=C(C=C1)C1=NNC(SC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Ether.Thioamide | Hydrazone amide.Monosulfide | null | C1=NNCSC1 | C1=NNCSC1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>C(C)#N>O=C1NN=C(c2ccc(Cl)cc2)CS1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f7ecc08ca4a459c8bd54d42b7e2aa72 | O=C(O)CCC(=O)c1cccc(Cl)c1>>O=C(O)CCCc1cccc(Cl)c1 | ClC=1C=C(C(=O)CCC(=O)O)C=CC1.[OH-].[K+].NN>>ClC=1C=C(C=CC1)CCCC(=O)O | O=[C:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | O=C(O)CCCc1cccc(Cl)c1 | null | null | C(COCCO)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | 90.8 | [{"value": 90.8, "product": "ClC=1C=C(C=CC1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, With stirring, 23 g of 3-(3-chlorobenzoyl)propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | C(COCCO)O | null | null | O=C(O)CCC(=O)c1cccc(Cl)c1>C(COCCO)O>O=C(O)CCCc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce1f4e690dcc46599c10634baebf9087 | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>CN1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.CNN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O | [CH3:1][NH:2][NH2:3].O=[C:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH2:12][CH2:13][C:14](O)=[O:15]>>[CH3:1][N:2]1[N:3]=[C:4]([c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[CH2:12][CH2:13][C:14]1=[O:15] | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | CN1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(C)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10]1-[N;H0;D2;+0:11]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[C:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexan... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(C)O | null | null | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>CN1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-41e667fc94ef4b21b0e687948a96209d | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=O)C=C1.C(CCC(=O)C)(=O)O.N1CCCCC1.C1(=CC=CC=C1)C>>ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH3:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1 | O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>O>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f03ae878f504b23bfedb43e4307c94e | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>>COc1ccc(C(=O)O)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C.[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC | C[c:10]1[c:6]([C:7](=[O:8])[O-:9])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-] | COc1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ec2bcf645eed3485ae21dd491bac7887e7ecc8e6727067de36c08c87eaa3e98c | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]):[c:9]>>[#7;+:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7]):[c:9] | 76.6 | [{"value": 76.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 12 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>O1CCCC1>COc1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-07e514fe010d477b830fbb79e7963a40 | Cc1ccccc1.Cc1cccnc1C#N.O=S(=O)(O)O>>Cc1cccnc1C(=O)NC(C)(C)C | C1(=CC=CC=C1)C.C(#N)C1=NC=CC=C1C.N.OS(=O)(=O)O>>CC(C)(C)NC(=O)C1=NC=CC=C1C | c1c[cH:12][c:11]([CH3:14])[cH:13]c1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C:8]#[N:10].O=S(=O)(O)[OH:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C:8](=[O:9])[NH:10][C:11]([CH3:12])([CH3:13])[CH3:14] | Cc1ccccc1.Cc1cccnc1C#N.O=S(=O)(O)O | Cc1cccnc1C(=O)NC(C)(C)C | null | null | O.C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 780c5bd372645be2428cf4f314e6765c167cb2cb84e2e593d576e2f8633a9926 | aaa659fb1f3b655f5022532af787efa2716aa193a615252f400a1fe3a0f40998 | c1ccncc1 | O-S(=O)(=O)-[OH;D1;+0:1].[C;D1;H3:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:c:c:c:[cH;D2;+0:5]:1.[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:2]-[C;H0;D4;+0:3](-[CH3;D1;+0:4])(-[CH3;D1;+0:5])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:1])-[c:8](:[c:9]):[#7;a:10]:[c:11] | 97 | [{"value": 97.0, "product": "CC(C)(C)NC(=O)C1=NC=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | Suspend 2-cyano-3-methyl pyridine (400 g) in t-butanol (800 mL) and heat to 70° C. Add concentrated H2SO4 (400 mL) dropwise over 45 minutes. Maintain the temperature at 75° C., until the reaction is complete, and for an additional 30 minutes. Dilute the mixture with water (400 mL), charge with toluene (600 mL) and brin... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Secondary amide | c1ccccc1 | null | c1ccncc1 | Other | O.C(C)(C)(C)O | 70 | 0.5 | Cc1ccccc1.Cc1cccnc1C#N.O=S(=O)(O)O>O.C(C)(C)(C)O>Cc1cccnc1C(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b713158f99fb4e31b927599348f3f54c | N#Cc1ccc(CBr)cc1.O=C1NCCN1>>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | O.BrCC1=CC=C(C#N)C=C1.[H-].[Na+].N1C(NCC1)=O>>O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]1.[NH:8]1[CH2:9][CH2:15][NH:11][C:21]1=[O:22]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C:21]2=[O:22])[cH:23][cH:24]1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1 | N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 39571f641692bae0ab2e4fb7e56baf0a046bbe68e5d15065d8f936b61702d85c | 04064b000c1f037cb6379c4a9b891971302bcd094d2302ea56061b3b37327222 | O=C1N(Cc2ccccc2)CCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C:11]-[c:12](:[c:13]):[cH;D2;+0:8]:[c:14]:[c:15]-[C:16]-[N;H0;D3;+0:7]1-[C:17]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Nitrile | C1CNCN1 | C1C[NH]C[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Br- | CN(C=O)C | null | 1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>CN(C=O)C>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e289c3d74b254a4196a9c35ea0894330 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | NC(=O)N.CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C>>CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C | O=[C:13]([CH:8](O)[c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:21][cH:20]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[NH2:9][C:10](=[O:11])[NH2:12]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[nH:9][c:10](=[O:11])[nH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O | CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7a04490902783a9d1d6099ad78b95538301d0ef7b8b6cc364284d393dbdf37cd | 19da97726e6dc44d537eff971a50046c3e80ca62fdecca0b64533a3c10927d47 | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | O-[CH;D3;+0:1](-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[O;D1;H0:16]>>[O;D1;H0:16]=[c;H0;D3;+0:14]1:[nH;D2;+0:13]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:... | null | [] | 120 | CELSIUS | 2 | HOUR | To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Urea.Secondary alcohol | null | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1ccccc1 | HO- | C(C)(=O)O | 120 | 2 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>C(C)(=O)O>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aad224480b7f4172a95830c33af130b0 | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C#N)C=CC1.[H-].[Na+]>>C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27]1.[nH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:25]1=[O:26]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:1... | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chroma... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C=O)C>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-06bbfeb3be78487fb44540ecbac09d5f | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C(=O)OC)C=CC1.Cl>>COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29]1.[nH:11]1[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:... | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of Nail (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL D... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | 50 | 0.5 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C)C=O>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd90658687c84716b19eb33da57e2759 | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O.BrCC1=CC=C2C=CC(=CC2=C1)C#N>>C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O | Br[CH2:25][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]2[cH:37]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[nH:24][c:38]2=[O:39])[cH:40]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6... | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1n(Cc2ccccc2)c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl) methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1c[nH]cn1 | HBr | null | null | null | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f942832a149344ee8ae24b50f8c14966 | CO.O=C(O)C1Cc2ccccc2CN1>>COC(=O)C1Cc2ccccc2CN1 | C(C)(=O)Cl.CO.C1NC(CC2=CC=CC=C12)C(=O)O>>COC(=O)C1NCC2=CC=CC=C2C1 | O[CH3:1].[OH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13][NH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13][NH:14]1 | CO.O=C(O)C1Cc2ccccc2CN1 | COC(=O)C1Cc2ccccc2CN1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccc2c(c1)CCNC2 | O-[CH3;D1;+0:1].[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | 46.6 | [{"value": 46.6, "product": "COC(=O)C1NCC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | Acetyl chloride (0.88 g) was added to methanol (100 ml) with stirring at 0° C. After 10 minutes, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (J. Am. Chem. Soc., 1962, 48, 4487-4494) (2.0 g) was added; the reaction was allowed to warm to room temperature and stirred overnight. DMF (1 ml) was then added and stirring... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2c(c1)CCNC2 | HO- | CN(C)C=O | 0 | 0.166667 | CO.O=C(O)C1Cc2ccccc2CN1>CN(C)C=O>COC(=O)C1Cc2ccccc2CN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c015ee7e7924c23b9f14267ea629a04 | CS(=O)(=O)OCOc1ccccc1.O=S(=O)(O)Cl>>COc1ccc(S(=O)(=O)Cl)cc1OS(C)(=O)=O | ClS(=O)(=O)O.CS(=O)(=O)OCOC1=CC=CC=C1.C(C(=O)Cl)(=O)Cl.C1(=CC=CC=C1)C.C(C(=O)Cl)(=O)Cl>>CS(=O)(=O)OC=1C=C(C=CC1OC)S(=O)(=O)Cl | [CH2:1]([O:2][c:3]1[cH:4][cH:5][cH:6][cH:11][cH:12]1)[O:13][S:14]([CH3:15])(=[O:16])=[O:17].O=[S:7]([OH:8])(=[O:9])[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:10])[cH:11][c:12]1[O:13][S:14]([CH3:15])(=[O:16])=[O:17] | CS(=O)(=O)OCOc1ccccc1.O=S(=O)(O)Cl | COc1ccc(S(=O)(=O)Cl)cc1OS(C)(=O)=O | null | CN(C)C=O | ClCCl | Functional Group Interconversion | OtherReaction | 4f315fa4b3128c51c380de69526b2c215346c70fd2b64d262976c5395499ed83 | 0e61b0140d418f3a714817b5060773e18c160606500a286b714ae0a828923f0e | c1ccccc1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[C;D1;H3:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[#8:11]-[c:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[cH;D2;+0:17]:1>>[C;D1;H3:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[O;H0;D2;+0:9]-[c;H0;D3;+0:17]1:[c:16]:[c;H0;D3;+0:15](-[S;H0;D4;+0... | null | [] | -10 | CELSIUS | 4 | HOUR | A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ether | Mesylate.Ether.Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CN(C)C=O.ClCCl | -10 | 4 | CS(=O)(=O)OCOc1ccccc1.O=S(=O)(O)Cl>CN(C)C=O.ClCCl>COc1ccc(S(=O)(=O)Cl)cc1OS(C)(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ff57e297cfdc46e5b5870e456c42198a | COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OS(C)(=O)=O>>COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O | CS(=O)(=O)OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12.[OH-].[Na+]>>OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12 | CS(=O)(=O)[O:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][c:20]1[OH:21] | COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OS(C)(=O)=O | COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O | null | null | null | Functional Group Interconversion | OtherReaction | ee3aaebba994f49df1ba424e944fca44eeafa016a3e36bf167dd8b29195eaed8 | 01728c3d642b2daee982c52b87a87c062dbb984fb985d3f341f8d76fc5df3eb8 | O=S(=O)(c1ccccc1)N1CCc2ccccc21 | C-S(=O)(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.5 | [{"value": 100.5, "product": "OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(3-methanesulphonyloxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole (1 g) and saturated aqueous sodium hydroxide solution (2 ml) was heated at 85°-90° C. for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (5 ml) and water (10 ml). The aqueous phase was acidif... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | null | null | null | COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OS(C)(=O)=O>>COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80b4d3c6a338477cbce6e4a97e49acd8 | COc1ccc(S(=O)(=O)Cl)cc1OC.c1ccc2c(c1)CCCN2>>COc1ccc(S(=O)(=O)N2CCCc3ccccc32)cc1OC | N1CCCC2=CC=CC=C12.COC=1C=C(C=CC1OC)S(=O)(=O)Cl.C(C)N(CC)CC>>COC=1C=C(C=CC1OC)S(=O)(=O)N1CCCC2=CC=CC=C12 | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[cH:20]1)(=[O:8])=[O:9].[NH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]32)[cH:20][c:21]1[O:22]... | COc1ccc(S(=O)(=O)Cl)cc1OC.c1ccc2c(c1)CCCN2 | COc1ccc(S(=O)(=O)N2CCCc3ccccc32)cc1OC | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | bdce99988baba5b5a8e112b2aa8881a4125937433bf8ddee5495587b5e0d21b3 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCCc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 24 | HOUR | 1,2,3,4-Tetrahydroquinoline (0.29 ml) was added to a suspension of 3,4-dimethoxybenzene sulphonyl chloride (0.50 g) in dichloromethane (15 ml) at room temperature. Triethylamine (0.44 ml) was added and the resulting mixture stirred for 24 hours at room temperature. The reaction mixture was then diluted with dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl | null | 24 | COc1ccc(S(=O)(=O)Cl)cc1OC.c1ccc2c(c1)CCCN2>ClCCl>COc1ccc(S(=O)(=O)N2CCCc3ccccc32)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-44bcaad266d04c4ebb5e17cd00e7e878 | BrCCCOc1ccccc1.COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O>>COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OCCCOc1ccccc1 | OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12.O(C1=CC=CC=C1)CCCBr.C([O-])([O-])=O.[Cs+].[Cs+]>>O(C1=CC=CC=C1)CCCOC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12 | Br[CH2:22][CH2:23][CH2:24][O:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][c:20]1[OH:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH... | BrCCCOc1ccccc1.COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O | COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OCCCOc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=S(=O)(c1cccc(OCCCOc2ccccc2)c1)N1CCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 86.8 | [{"value": 86.8, "product": "O(C1=CC=CC=C1)CCCOC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | A solution of N-(3-hydroxy-4-methoxybenzenesulphonyl)- 1,2-dihydroindole (0.2 g) and 3-phenoxypropylbromide (0.15 g) in N,N-dimethylformamide (20 ml) was treated with cesium carbonate (0.3 g) and heated at 75° C. overnight. The solvent was removed in vacuo and the residue partitioned between dichloromethane (30 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HBr | CN(C=O)C | 75 | null | BrCCCOc1ccccc1.COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1O>CN(C=O)C>COc1ccc(S(=O)(=O)N2CCc3ccccc32)cc1OCCCOc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1251e1d4efb04be2a0db094b4b863a07 | COc1ccc(S(=O)(=O)Cl)cc1OC.O=c1[nH]c(-c2ccccc2)cc2ccccc12>>COc1ccc(S(=O)(=O)n2c(-c3ccccc3)cc3ccccc3c2=O)cc1OC | C1(=CC=CC=C1)C=1NC(=O)C2=CC=CC=C2C1.[H-].[Na+].COC=1C=C(C=CC1OC)S(=O)(=O)Cl>>COC=1C=C(C=CC1OC)S(=O)(=O)N1C(=O)C2=CC=CC=C2C=C1C1=CC=CC=C1 | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]1)(=[O:8])=[O:9].[nH:10]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[c:25]1=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:... | COc1ccc(S(=O)(=O)Cl)cc1OC.O=c1[nH]c(-c2ccccc2)cc2ccccc12 | COc1ccc(S(=O)(=O)n2c(-c3ccccc3)cc3ccccc3c2=O)cc1OC | null | null | CN(C=O)C | Acylation | OtherReaction | c3c33c450ee7d635baa794cb37e7b92a990cfc48b9c0e915d3035acd3b32cd77 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=c1c2ccccc2cc(-c2ccccc2)n1S(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[O;D1;H0:7]=[c:8](:[c:9]):[nH;D2;+0:10]:[c:11](-[c:12]):[c:13]>>[O;D1;H0:7]=[c:8](:[c:9]):[n;H0;D3;+0:10](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:11](-[c:12]):[c:13] | 46.7 | [{"value": 46.7, "product": "COC=1C=C(C=CC1OC)S(=O)(=O)N1C(=O)C2=CC=CC=C2C=C1C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A solution of 3-phenylisocarbostyril (0.1 g) in N,N-dimethylformamide (2 ml) was cooled to 0° C. under an inert atmosphere. Sodium hydride (0.019 g) was added and the resulting mixture stirred at 0° C. for 5 minutes. 3,4-Dimethoxybenzenesulphonylchloride (0.107 g) was added over a 3 minute period, with continued stirri... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc2ccccc2cn1 | c1ccc2cnccc2c1 | c1ccccc1.c1ccccc1.c1ccc2cnccc2c1 | HCl | CN(C=O)C | 0 | 0.083333 | COc1ccc(S(=O)(=O)Cl)cc1OC.O=c1[nH]c(-c2ccccc2)cc2ccccc12>CN(C=O)C>COc1ccc(S(=O)(=O)n2c(-c3ccccc3)cc3ccccc3c2=O)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48f858c335dc420faf30089f06b9929d | COC(=O)C1Cc2ccccc2CN1S(=O)(=O)c1ccc(OC)c(OC)c1>>COc1ccc(S(=O)(=O)N2Cc3ccccc3CC2C(=O)O)cc1OC | COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC=C2CC1C(=O)OC.[OH-].[Li+]>>COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC=C2CC1C(=O)O | C[O:22][C:20]([CH:19]1[N:10]([S:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]2)(=[O:8])=[O:9])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18]1)=[O:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH2:18][CH:19]2[C:... | COC(=O)C1Cc2ccccc2CN1S(=O)(=O)c1ccc(OC)c(OC)c1 | COc1ccc(S(=O)(=O)N2Cc3ccccc3CC2C(=O)O)cc1OC | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(c1ccccc1)N1CCc2ccccc2C1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | A solution of N-(3,4-dimethoxybenzenesulphonyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-isoquinoline(0.5 g) in THF (30 ml) was treated with a saturated aqueous solution of lithium hydroxide (3 ml) at room temperature. After stirring overnight, the solvent was removed in vacuo. The residue was diluted with water (10 ml), w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]C2 | Other | C1CCOC1 | null | 8 | COC(=O)C1Cc2ccccc2CN1S(=O)(=O)c1ccc(OC)c(OC)c1>C1CCOC1>COc1ccc(S(=O)(=O)N2Cc3ccccc3CC2C(=O)O)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1fbe8bec2d7a4b37b8e811f839c2b36c | C#Cc1ccccn1.COc1ccc(S(=O)(=O)N2Cc3cccc(Br)c3C2)cc1OC>>COc1ccc(S(=O)(=O)N2Cc3cccc(C#Cc4ccccn4)c3C2)cc1OC | COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC(=C2C1)Br.C(C)N(CC)CC.C(#C)C1=NC=CC=C1.C(#C)C1=NC=CC=C1>>COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC(=C2C1)C#CC1=NC=CC=C1 | [CH:17]#[C:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1.Br[c:16]1[cH:15][cH:14][cH:13][c:12]2[c:25]1[CH2:26][N:10]([S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]1)(=[O:8])=[O:9])[CH2:11]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][c:1... | C#Cc1ccccn1.COc1ccc(S(=O)(=O)N2Cc3cccc(Br)c3C2)cc1OC | COc1ccc(S(=O)(=O)N2Cc3cccc(C#Cc4ccccn4)c3C2)cc1OC | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Pd] | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | f06f27dcb2a41374466bd91bd48dd25e8c6394917ee727f9b0b274433d7f9627 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=S(=O)(c1ccccc1)N1Cc2cccc(C#Cc3ccccn3)c2C1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6]-[#7:7].[#7;a:8]:[c:9]-[C:10]#[CH;D1;+0:11]>>[#7:7]-[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[C;H0;D2;+0:11]#[C:10]-[c:9]:[#7;a:8]):[c:2]:[c:3] | 12.5 | [{"value": 12.5, "product": "COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC(=C2C1)C#CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | DAY | 2-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline (0.19 g), triethylamine (0.10 ml), 2-ethynylpyridine(0.06 g) and bis (triphenylphosphine)palladium(II)chloride (10%) in anhydrous N,N-dimethylformamide(2 ml) were stirred together under an inert atmosphere and heated to 90° C. After 20 hours further 2-ethynylpyridine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Pd].CN(C=O)C.C(C)(=O)OCC | 90 | 72 | C#Cc1ccccn1.COc1ccc(S(=O)(=O)N2Cc3cccc(Br)c3C2)cc1OC>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Pd].CN(C=O)C.C(C)(=O)OCC>COc1ccc(S(=O)(=O)N2Cc3cccc(C#Cc4ccccn4)c3C2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ff129fa8213d45ca8f4648e29b01c951 | CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C>>CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C\C=CC=C(C)C(=O)C[C@@H]3CC[C@... | C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC.O>>C[C@@H]1CC[C@H]2CC(=O)C(=CC=C/C=C\[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H... | C[O:38][C@@H:37]1/[C:35]([CH3:36])=[CH:34]/[CH:33]=[CH:32]/[CH:31]=[CH:30]/[C@@H:28]([CH3:29])[CH2:27][C@@H:25]([CH3:26])[C:23](=[O:24])[C@H:20]([O:21][CH3:22])[C@H:18]([OH:19])/[C:16]([CH3:17])=[CH:15]/[C@@H:13]([CH3:14])[C:11](=[O:12])[CH2:10][C@@H:9]([C@@H:7]([CH2:6][C@H:5]2[CH2:4][C@@H:3]([O:2][CH3:1])[C@H:63]([OH:... | CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C | CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C\C=CC=C(C)C(=O)C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N3CCCC[C@H]3C(=O)O2)CC[C@H]1O | null | null | ClCCl | Miscellaneous | OtherReaction | 4ad29d9a9f8fa62d26ac0b34d9c9d494139463612a562b91246c4663134b934c | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1C=CC=C/C=C\CCCC(=O)CCC=CCC(=O)C[C@@H](CCC2CCCCC2)OC(=O)[C@@H]2CCCCN2C(=O)C(=O)C2CCC[C@@H](C1)O2 | C-[O;H0;D2;+0:1]-[C@@H;D3;+0:2](-[C:3]-[C:4]-[#8:5])/[C:6](-[C;D1;H3:7])=[C:8]/[C:9]=[C:10]/[C:11]=[C:12]>>[#8:5]-[C:4]-[C:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:6](-[C;D1;H3:7])=[C:8]-[C:9]=[C:10]/[C:11]=[C:12] | null | [] | null | null | 45 | MINUTE | To a solution of rapamycin (5 mg, 0.055 mmol) in dichloromethane (0.1 mL) was added water (0.02 mL) followed by DDQ (2.4 mg, 0.011 mmol), and the resulting dark brown suspension was stirred at room temperature for 45 min. The mixture was filtered through celite and then partitioned between dichloromethane and brine; th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=C/C=C/CC[C@@H]2CCC[C@H](CCN3CCCC[C@H]3COCCCC/C=C/CCCCCC/C=C/1)O2 | C1=C/C=C\CCCCCCC=CCCCCOC[C@@H]2CCCCN2CC[C@H]2CCC[C@@H](CCC=C1)O2 | C1CCCCC1.C1=C/C=C\CCCCCCC=CCCCCOC[C@@H]2CCCCN2CC[C@H]2CCC[C@@H](CCC=C1)O2 | Other | ClCCl | null | 0.75 | CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C>ClCCl>CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C\C=CC=C(C)C(=O)C[C@@H]3... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-45b51dfa48a4401f8cc762580c573748 | CCOC(=O)/N=N/C(=O)OCC.Cn1c(C=Cc2ccccc2O)cc2ccccc21>>COC(=O)[C@H](C)Oc1ccccc1C=Cc1cc2ccccc2n1C | OC1=C(C=CC=C1)C=CC=1N(C2=CC=CC=C2C1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)/N=N/C(=O)OCC.C1CCOC1>>COC(=O)[C@H](C)OC1=C(C=CC=C1)C=CC=1N(C2=CC=CC=C2C1)C | C[CH2:1][O:2][C:3](/N=N/C(=O)O[CH2:5][CH3:6])=[O:4].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH:14]=[CH:15][c:16]1[cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1[CH3:25]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH:14]=[CH:15][c:16]1[cH:17][c:18]2[cH:19][cH:2... | CCOC(=O)/N=N/C(=O)OCC.Cn1c(C=Cc2ccccc2O)cc2ccccc21 | COC(=O)[C@H](C)Oc1ccccc1C=Cc1cc2ccccc2n1C | null | null | [Cl-].[Na+].O | C-C Coupling | OtherReaction | 0f7daa1e28b94fa56e93d642499403664434ff60aef02861826759334413479d | e12cd616c68daa01974b9e799eaff061e9c3515771499b426b7524dd69fcfada | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | C-[CH2;D2;+0:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])/N=N/C(=O)-O-[CH2;D2;+0:5]-[C;D1;H3:6].[C:7]=[C:8]-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[C:7]=[C:8]-[c:9]:[c:10](-[O;H0;D2;+0:11]-[C@@H;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1]):[c:12] | 90 | [{"value": 90.0, "product": "COC(=O)[C@H](C)OC1=C(C=CC=C1)C=CC=1N(C2=CC=CC=C2C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1.50 g (6.02 mmol) of 2-[2-(2-hydroxyphenyl)vinyl]-1-methylindole, 1.89 g (7.21 mmol) of triphenylphosphine and 0.69 ml (7.22 mmol) of R-(+)-methyl lactate in 15 ml of THF was added 1.14 ml (7.24 mmol) of diethylazodicarboxylate under an ice-cooled condition, followed by stirring at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1cc2ccccc2[nH]1 | HO- | [Cl-].[Na+].O | null | 2 | CCOC(=O)/N=N/C(=O)OCC.Cn1c(C=Cc2ccccc2O)cc2ccccc21>[Cl-].[Na+].O>COC(=O)[C@H](C)Oc1ccccc1C=Cc1cc2ccccc2n1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc610c599a6a47cbbab5dcc6ac8c553a | COC(=O)CBr.c1ccc2c(Nc3ccncc3)noc2c1>>Br.COC(=O)Cn1ccc(=Nc2noc3ccccc23)cc1 | N1=CC=C(C=C1)NC1=NOC2=C1C=CC=C2.BrCC(=O)OC>>Br.COC(CN1C=CC(C=C1)=NC1=NOC2=C1C=CC=C2)=O | [Br:1][CH2:6][C:4]([O:3][CH3:2])=[O:5].[n:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][o:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[cH:21][cH:22]1>>[BrH:1].[CH3:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10](=[N:11][c:12]2[n:13][o:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[cH:21][cH:22]1 | COC(=O)CBr.c1ccc2c(Nc3ccncc3)noc2c1 | Br.COC(=O)Cn1ccc(=Nc2noc3ccccc23)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | a05baa0d189a78d43c66bc7586e891af508d8c2523abdfecef022b9457bc51ad | 350896f2b21b02a4330179c771d63e7fba34621d26da5f19b2e6779a93051bdb | c1ccc2c(N=c3cc[nH]cc3)noc2c1 | [#7;a:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1-[NH;D2;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11]:[c:12]:1.[Br;H0;D1;+0:13]-[CH2;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18]>>[BrH;D0;+0:13].[C;D1;H3:18]-[#8:17]-[C:15](=[O;D1;H0:16])-[CH2;D2;+0:14]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c;H0;D3;+0:7](=[N;H0;D2;+0:6]... | 70 | [{"value": 70.0, "product": "Br.COC(CN1C=CC(C=C1)=NC1=NOC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4-pyridinylamino)-1,2-benzisoxazole (0.9 g, 4.3 mmol) and methyl bromoacetate (0.44 mL, 1.1 eq) in acetonitrile (25 mL) was heated at reflux for one hour. The mixture was then allowed to cool to room temperature and the precipitated product was collected by filtration. The white solid was washed with di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2oncc2c1 | null | C(C)#N | null | null | COC(=O)CBr.c1ccc2c(Nc3ccncc3)noc2c1>C(C)#N>Br.COC(=O)Cn1ccc(=Nc2noc3ccccc23)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f35791fc5d9c4277b1f7f4b9129278c8 | FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCCO>>OCCCNc1cc(-c2ccnc(Nc3cccc(C(F)(F)F)c3)n2)ccn1 | FC(C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl)(F)F.NCCCO>>FC(C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO)(F)F | Cl[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]3)[n:25]2)[cH:26][cH:27][n:28]1.[OH:1][CH2:2][CH2:3][CH2:4][NH2:5]>>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18]... | FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCCO | OCCCNc1cc(-c2ccnc(Nc3cccc(C(F)(F)F)c3)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 50 mg (0.143 mmol) of N-(3-trifluoromethyl-phenyl)-4-(2-chloro4-pyridyl)-2-pyrimidineamine are stirred for 44 h at 100° in 1 ml of 3-amino-1-propanol. Concentration by evaporation and chromatography (methylene chloride:methanol=9:1) give N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCCO>>OCCCNc1cc(-c2ccnc(Nc3cccc(C(F)(F)F)c3)n2)ccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-160c9a75cc8c48d189fa78e2f7af0bda | N#Cc1ccnc(Cl)c1>>CC(=O)c1ccnc(Cl)c1 | ClC1=NC=CC(=C1)C#N.C[Mg]Cl.Cl.C(C)OCC>>C(C)(=O)C1=CC(=NC=C1)Cl | N#[C:2][c:4]1[cH:5][cH:6][n:7][c:8]([Cl:9])[cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8]([Cl:9])[cH:10]1 | N#Cc1ccnc(Cl)c1 | CC(=O)c1ccnc(Cl)c1 | null | null | null | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1ccncc1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1>>[C;D1;H3:8]-[C;H0;D3;+0:1](=[O;D1;H0:9])-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | 40 | HOUR | 24.61 g (177.62 mmol) of 2-chloro-4-cyano-pyridine are placed in 1.25 litres of diethyl ether under nitrogen, and 120 ml (22% in tetrahydrofuran, 353 mmol) of methyl-magnesium chloride are added. The red suspension is stirred for 40 h at RT, poured onto 1.25 litres of ice/water and 250 ml of 6N HCl and stirred for 14 h... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1ccncc1 | null | null | null | 40 | N#Cc1ccnc(Cl)c1>>CC(=O)c1ccnc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6eee014e31484dc4a5b6680a1edc957c | CC(=O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl>>CC(=O)c1ccnc(Cl)c1 | C(C)(=O)C1=CC=[N+](C=C1)[O-].P(=O)(Cl)(Cl)Cl.[OH-].[Na+]>>C(C)(=O)C1=CC(=NC=C1)Cl | [O-][n+:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:10][cH:8]1.O=P(Cl)(Cl)[Cl:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8]([Cl:9])[cH:10]1 | CC(=O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl | CC(=O)c1ccnc(Cl)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | a7e4b874c7a18ec6b4305e16cc93c9103d77bfb4ce559ead41b2d45f56dcb90f | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[cH;D2;+0:7]:[n+;H0;D3:8](-[O-]):[c:9]:[c:10]:1>>[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:8]:[c:9]:[c:10]:1 | null | [] | null | null | null | null | 5.0 g (36.5 mmol) of 4-acetyl-pyridine N-oxide and 6.64 ml (73 mmol) of phosphorus oxychloride are stirred in 50 ml of toluene for 2 h at 100°. The reaction mixture is stirred at 50° into 500 ml of 10N sodium hydroxide solution, extracted with ethyl acetate and treated with Tonsil (Fluka; bentonite--colloidal aqueous a... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HCl | C1(=CC=CC=C1)C | null | null | CC(=O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl>C1(=CC=CC=C1)C>CC(=O)c1ccnc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c9d27f69137047ca85c77482a3084a76 | CC(=O)c1ccncc1>>CC(=O)c1cc[n+]([O-])cc1 | C(C)(=O)C1=CC=NC=C1.ClC1=CC(=CC=C1)C(=O)OO>>C(C)(=O)C1=CC=[N+](C=C1)[O-] | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n+:7]([O-:8])[cH:9][cH:10]1 | CC(=O)c1ccncc1 | CC(=O)c1cc[n+]([O-])cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc[nH+]cc1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:4]:[c:5]):[c:2]:[c:1] | null | [] | null | null | null | null | The 4-acetyl-pyridine N-oxide used is prepared in the following manner: 11.0 ml (100 mmol) of 4-acetyl-pyridine and 31.3 g (100 mmol) of 55% m-chloro-perbenzoic acid are boiled under RF for 16 h in 200 ml of methylene chloride. Precipitation with 200 ml of diethyl ether gives 4-acetyl-pyridine N-oxide; m.p. 132°-133°.
... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(Cl)Cl | null | null | CC(=O)c1ccncc1>C(Cl)Cl>CC(=O)c1cc[n+]([O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-17f4a6bed6804e1a87ae17bb1cfb5ad3 | CC(=O)c1ccnc(Cl)c1.CCOC(OCC)N(C)C>>CN(C)C=CC(=O)c1ccnc(Cl)c1 | C(C)(=O)C1=CC(=NC=C1)Cl.C(C)OC(N(C)C)OCC>>CN(C=CC(=O)C1=CC(=NC=C1)Cl)C | [CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][n:11][c:12]([Cl:13])[cH:14]1.CCO[CH:4](OCC)[N:2]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][n:11][c:12]([Cl:13])[cH:14]1 | CC(=O)c1ccnc(Cl)c1.CCOC(OCC)N(C)C | CN(C)C=CC(=O)c1ccnc(Cl)c1 | null | null | null | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | c1ccncc1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | null | [] | null | null | null | null | 16.2 g (104.2 mmol) of 4-acetyl-2-chloro-pyridine are stirred at 110° with 116 ml of dimethylformamide diethylacetal for 1 h. Cooling to 0°, filtering and drying at 60° under HV give 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one; 1H-NMR (dimethyl sulfoxide): 2.98 (3H,s), 3.2 (3H,s), 5.9 (1H,d), 7.8 (3H,m), 8.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccncc1 | HO- | null | null | null | CC(=O)c1ccnc(Cl)c1.CCOC(OCC)N(C)C>>CN(C)C=CC(=O)c1ccnc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd9f79aff70f4e008da6da583aa08a55 | N#CN.Nc1cccc(C(F)(F)F)c1>>N=C(N)Nc1cccc(C(F)(F)F)c1 | N#CN.FC(C=1C=C(N)C=CC1)(F)F.[N+](=O)(O)[O-]>>[N+](=O)(O)[O-].FC(C=1C=C(C=CC1)NC(=N)N)(F)F | [N:1]#[C:2][NH2:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | N#CN.Nc1cccc(C(F)(F)F)c1 | N=C(N)Nc1cccc(C(F)(F)F)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a0cbddf5d7d81fe92104447f1edef14329807abeadc66f8268b3c04bddc38ea2 | 9b168a0be416143e92b99e2902110a4569d3f9f31721e83b72aa42867628c64d | c1ccccc1 | [N;D1;H2:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H2:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 6.3 g (150 mmol) of cyanamide (50% in water) are added to a suspension of 16.1 g (100 mmol) of 3-trifluoromethyl-aniline in 35 ml of ethanol. 7.0 ml of nitric acid (65%, 0.1 mol) are then added to the brown solution and the reaction mixture is heated for 20 h under RF. It is then cooled to 0° and filtered, and the mate... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | C(C)O | null | null | N#CN.Nc1cccc(C(F)(F)F)c1>C(C)O>N=C(N)Nc1cccc(C(F)(F)F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80c466f42a2f4da1817b28cc4a125e1c | CN(C)C=CC(=O)c1ccnc(Cl)c1.N=C(N)Nc1cccc(C(F)(F)F)c1>>FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | CN(C=CC(=O)C1=CC(=NC=C1)Cl)C.[N+](=O)(O)[O-].FC(C=1C=C(C=CC1)NC(=N)N)(F)F.[OH-].[Na+]>>FC(C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl)(F)F | CN(C)[CH:13]=[CH:14][C:15](=O)[c:16]1[cH:17][cH:18][n:19][c:20]([Cl:21])[cH:22]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[NH:12])[NH2:23])[cH:24]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][n:19][c:20]([Cl:21])[cH:2... | CN(C)C=CC(=O)c1ccnc(Cl)c1.N=C(N)Nc1cccc(C(F)(F)F)c1 | FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | null | null | CC(C)O | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:10]:1.[NH2;D1;+0:11]-[C;H0;D3;+0:12](=[NH;D1;+0:13])-[#7:14]-[c:15]>>[Cl;D1;H0:9]-[c:8]1:[#7;a:7]:[c:6]:[c:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:3]2:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:13]:[c;H0;D3;+0:12](-[#7:1... | null | [] | null | null | 18 | HOUR | 150 mg (0.71 mmol) of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one are suspended in 1.5 ml of 2-propanol. 190 mg (0.712 mmol) of 3-trifluoromethylphenyl-guanidine nitrate and 31 mg (0.783 mmol) of sodium hydroxide are added and the reaction mixture is stirred for 18 h under RF. It is then cooled to RT and filt... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HO- | CC(C)O | null | 18 | CN(C)C=CC(=O)c1ccnc(Cl)c1.N=C(N)Nc1cccc(C(F)(F)F)c1>CC(C)O>FC(F)(F)c1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d187a558f2cb415e8f8f2e8cc58499db | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1>>Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=[N+](C=C1)[O-].P(=O)(Cl)(Cl)Cl.[OH-].[Na+]>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl | O=P(Cl)(Cl)[Cl:18].[O-][n+:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:21]3)[n:20]2)[cH:19][cH:17]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][n:16][c:17]([Cl:18])[cH:19]3)[n:20]2)[cH:21]1 | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1 | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | null | null | null | Miscellaneous | OtherReaction | a7e4b874c7a18ec6b4305e16cc93c9103d77bfb4ce559ead41b2d45f56dcb90f | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[n;H0;D2;+0:2]:1 | null | [] | null | null | null | null | 10.0 g (32 mmol) of N-(3-chloro-phenyl)-4-(N-oxido-4-pyridyl)-2-pyrimidineamine are stirred for 24 h in 100 ml of phosphorus oxychloride at 110°. The reaction mixture is stirred at 50° into 2N sodium hydroxide solution and extracted with tetrahydrofuran. Concentration and crystallisation (tetrahydrofuran/ethanol) of th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1>>Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a39fc3b67bbd45ff88d29b84e47f577f | Clc1cccc(Nc2nccc(-c3ccncc3)n2)c1>>[O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=NC=C1.ClC1=CC(=CC=C1)C(=O)OO>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=[N+](C=C1)[O-] | [n:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[n:19]2)[cH:20][cH:21]1>>[O-:1][n+:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[n:19]2)[cH:20][cH:21]1 | Clc1cccc(Nc2nccc(-c3ccncc3)n2)c1 | [O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(Nc2nccc(-c3cc[nH+]cc3)n2)cc1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4]:[c:5] | null | [] | null | null | null | null | 10 g (35.4 mmol) of N-(3-chloro-phenyl)-4-(4-pyridyl)-2-pyrimidineamine and 11.1 g (35.4 mmol) of m-chloroperbenzoic acid are stirred for 5 h at RT in 500 ml of methylene chloride. Concentration and crystallisation (acetic acid) of the residue give N-(3-chloro-phenyl)-4-(N-oxido4-pyridyl)-2-pyrimidineamine; m.p. 274°-2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1cncnc1.c1ccccc1 | null | C(Cl)Cl | null | null | Clc1cccc(Nc2nccc(-c3ccncc3)n2)c1>C(Cl)Cl>[O-][n+]1ccc(-c2ccnc(Nc3cccc(Cl)c3)n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69f537074c164129a11f9fadfb9978d6 | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCN>>NCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl.C(CN)N>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCN | Cl[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]3)[n:21]2)[cH:22][cH:23][n:24]1.[NH2:1][CH2:2][CH2:3][NH2:4]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]3)[n:21]2)[cH... | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCN | NCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 20 mg (0.063 mmol) of N-(3-chloro-phenyl)-4-(2-chloro-4-pyridyl)-2-pyrimidineamine are stirred for 26 h at 110° with 1 ml of ethylenediamine. Concentration and chromatography (methylene chloride:methanol:conc. ammonia solution=80:20: 1) give N-(3-chloro-phenyl)-4-[2-(2-amino-ethyl-amino)-4-pyridyl]-2-pyrimidineamine; R... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.NCCN>>NCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2c40033208b4111b3cb9a725ae2825c | NCCN.O=C(O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>>NCCNC(=O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)C(=O)O.Cl.C(C)N=C=NCCCN(C)C.ON1C(CCC1=O)=O.C(CN)N>>Cl.ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)C(=O)NCCN | [NH2:2][CH2:3][CH2:4][NH2:5].O[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[n:24]2)[cH:25][cH:26][n:27]1>>[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:2... | NCCN.O=C(O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | NCCNC(=O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | null | CN(C=O)C.CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 2.5 | HOUR | 80 mg (0.24 mmol) of N-[3-chloro-phenyl]-4-(2-carboxy-4-pyridyl)-2-pyrimidineamine, 70.8 mg (0.36 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride and 42 mg (0.36 mmol) of N-hydroxysuccinimide are dissolved in 3 ml of dimethylformamide and stirred for 2.5 h at RT. The reaction mixture is then adde... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1cncnc1.c1ccccc1 | HO- | CN(C=O)C.CN(C)C=O.C(C)(=O)OCC | null | 2.5 | NCCN.O=C(O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>CN(C=O)C.CN(C)C=O.C(C)(=O)OCC>NCCNC(=O)c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d75cb7565874f338140d42a8ca396c2 | CO.O=C(O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1>>COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 | C(=O)(O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO.S(O)(O)(=O)=O.CO>>COC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][n:19][c:20]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[cH:26]3)[n:27]2)[cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][n... | CO.O=C(O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 | COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 2.0 g (5.4 mmol) of N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine and 0.28 ml (5.4 mmol) of conc. sulfuric acid are boiled under RF in 150 ml of methanol for 24 h. After cooling to RT, the reaction mixture is concentrated to half the volume, diluted with 100 ml of ethyl acetate and ext... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1.c1cncnc1.c1ccncc1 | HO- | null | null | null | CO.O=C(O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1>>COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e95dea12efcf46abb4f2455c2c2c6569 | COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1.NCCCN>>NCCCNC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 | COC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO.NCCCN>>NCCCNC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO | CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][n:22][c:23]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])[cH:29]3)[n:30]2)[cH:31]1.[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5]>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([NH:13][c:14]2... | COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1.NCCCN | NCCCNC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 | null | null | C(C)(=O)OCC | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 100 mg (0.26 mmol) of N-[3-methoxycarbonyl-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine and 0.5 ml of 1,3-diamino-propane are stirred for 24 h at 90° and then diluted with 20 ml of ethyl acetate and extracted with 2×10 ml of sodium chloride solution. The organic phase is dried, concentrated and cr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1cncnc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | null | COC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1.NCCCN>C(C)(=O)OCC>NCCCNC(=O)c1cccc(Nc2nccc(-c3ccnc(NCCCO)c3)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b8f64beacb447798a17fed01f8b02fc | ClCCl.Clc1cccc(Nc2nccc(-c3ccnc(N4CCNCC4)c3)n2)c1>>C1CNCCN1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | C(Cl)Cl.ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1CCNCC1>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl.N1CCNCC1 | ClC[Cl:24].[CH2:1]1[CH2:2][NH:3][CH2:4][CH2:5][N:6]1[c:23]1[n:22][cH:21][cH:20][c:19](-[c:18]2[cH:17][cH:16][n:15][c:14]([NH:13][c:12]3[cH:11][cH:10][cH:9][c:8]([Cl:7])[cH:27]3)[n:26]2)[cH:25]1>>[CH2:1]1[CH2:2][NH:3][CH2:4][CH2:5][NH:6]1.[Cl:7][c:8]1[cH:9][cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][cH:17][c:18](-[... | ClCCl.Clc1cccc(Nc2nccc(-c3ccnc(N4CCNCC4)c3)n2)c1 | C1CNCCN1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | null | null | CO | Functional Group Interconversion | OtherReaction | accb083ee8fd7641a677dca692d5f564b73dc543c66b542e44a7304924f0d3b4 | b03e6f5e6e8d8a1bd25b5055e831596b4284cf0e900bac020435f2faffd27024 | C1CNCCN1.c1ccc(Nc2nccc(-c3ccncc3)n2)cc1 | Cl-C-[Cl;H0;D1;+0:1].[c:2]:[c:3]:[c;H0;D3;+0:4](-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1):[#7;a:11]:[c:12]>>[#7:8]1-[C:7]-[C:6]-[NH;D2;+0:5]-[C:10]-[C:9]-1.[Cl;H0;D1;+0:1]-[c;H0;D3;+0:4](:[#7;a:11]:[c:12]):[c:3]:[c:2] | null | [] | null | null | null | null | Analogously to Example 1, there is obtained from 100 mg (0.31 mmol) of N-[3-chloro-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine and 500 mg (5.63 mmol) of piperazine, from the melt after chromatography (methylene chloride:methanol=95:5), N-[3-chloro-phenyl]-4-[2-(1-piperazinyl)-4-pyridyl]-2-pyrimidineamine;
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Tertiary amine | Aromatic halide.Secondary amine | C1C[NH]CCN1.c1ccncc1 | C1CNCCN1.c1ccncc1 | C1CNCCN1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | CO | null | null | ClCCl.Clc1cccc(Nc2nccc(-c3ccnc(N4CCNCC4)c3)n2)c1>CO>C1CNCCN1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6188ee3573314f55babc64ae624ba785 | CC(=O)OC(C)=O.N[C@@H](CC(=O)OCc1ccccc1)C(=O)O>>CC(=O)NC(CC(=O)OCc1ccccc1)C(C)=O | C1=CC=C(C=C1)COC(=O)C[C@@H](C(=O)O)N.C(C)N(CC)CC.[OH-].[K+].C(C)(=O)OC(C)=O>>C(C)(=O)NC(CC(=O)OCC1=CC=CC=C1)C(C)=O | O=C(O[C:2]([CH3:1])=[O:3])[CH3:18].O[C:17]([C@@H:5]([NH2:4])[CH2:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:19]>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]([CH2:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17]([CH3:18])=[O:19] | CC(=O)OC(C)=O.N[C@@H](CC(=O)OCc1ccccc1)C(=O)O | CC(=O)NC(CC(=O)OCc1ccccc1)C(C)=O | null | CN(C1=CC=NC=C1)C | O | C-C Coupling | OtherReaction | b802459ff5eb68424777810c52e09960d8b0c0aeb6f75b59978e8d896c3dd42e | a9679e805e0145be1fc9e7c455e6b352598a150489d618752043f7ed3d22039c | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:3](-[NH2;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].O=C(-[CH3;D1;+0:10])-O-[C;H0;D3;+0:11](-[C;D1;H3:12])=[O;D1;H0:13]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]-[CH;D3;+0:3](-[NH;D2;+0:4]-[C;H0;D3;+0:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C;H0;D3;+0:1](-[CH3;D1;+0:10])=[O;D1;H0... | 82.8 | [{"value": 82.8, "product": "C(C)(=O)NC(CC(=O)OCC1=CC=CC=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | β-Benzyl L-aspartate (400 g, 1.79 mol) was suspended in triethylamine (748 ml, 5.37 mol) and acetic anhydride (676 ml, 7.16 mol) was dropwise added at 0° C. with stirring. After stirring for 30 minutes, 4-dimethylaminopyridine (20.0 g, 0.16 mol) was portionwise added under ice-cooling. The mixture was stirred overnight... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Primary amine | Ketone.Secondary amide | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.O | null | null | CC(=O)OC(C)=O.N[C@@H](CC(=O)OCc1ccccc1)C(=O)O>CN(C1=CC=NC=C1)C.O>CC(=O)NC(CC(=O)OCc1ccccc1)C(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b86b7517ec945ca8eeab9a8c1598395 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>O=C1CCC(c2ccc(Cl)cc2)=NN1 | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.O.NN>>ClC1=CC=C(C=C1)C=1CCC(NN1)=O | [NH2:13][NH2:14].O=[C:5]([CH2:4][CH2:3][C:2](O)=[O:1])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | null | null | C(C)O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1 | 81.5 | [{"value": 80.0, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | C1=NNCCC1.c1ccccc1 | HO- | C(C)O | null | null | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>O=C1CCC(c2ccc(Cl)cc2)=NN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-676eee09ab9444cfbed62b0de2f1342d | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>>O=C(O)CCC(=O)c1cccc(Cl)c1 | C(CCC(=O)OC)(=O)OC.[Na].C(C)O.ClC=1C=C(C(=O)OC)C=CC1.C(CCC(=O)OC)(=O)OC>>ClC=1C=C(C(=O)CCC(=O)O)C=CC1 | COC(=O)[CH2:5][CH2:4][C:2](=[O:1])[O:3]C.CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | null | null | CCOCC | C-C Coupling | OtherReaction | 6d482de2a0c1fffe47581cf2d6dc0eefca79628574252eec326be9292f335afe | 1f69704fe402a3eb0e91a243a59f68f972592be61b4c787368515903d4c85726 | c1ccccc1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C.C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Carboxylic acid.Ketone | null | null | c1ccccc1 | HO- | CCOCC | null | null | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>CCOCC>O=C(O)CCC(=O)c1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4c442c2d85c24feebbe8e0084018a86b | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O>>CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1.[N+](=O)(O)[O-]>>ClC1=C(C=C(C(=O)C(C(=O)O)C)C=C1)[N+](=O)[O-] | [CH3:1][CH:2]([C:3](=[O:4])[OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:17]1.O[N+:14](=[O:15])[O-:16]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O | CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | 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]-[C:10]=[O;D1;H0:11]>>[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]-[C:10]=[O;D1;H0:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | To fuming nitric acid (150 ml) was added p-chlorobenzoylpropionic acid (20.0 g), slowly portionwise at 0° C. After the addition was completed the resulting mixture was stirred at 0° C. for 30 minutes and the resulting white solid was suction filtered and washed with water until the pH of the washing liquids was neutral... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 0 | 0.5 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O>>CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64ad41c7f6d34083816470ce8e3c45fd | C1=COCCC1.OCC#CCO>>OCC#CCOC1CCCCO1 | C(C#CCO)O.O1CCCC=C1>>O1C(CCCC1)OCC#CCO | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[OH:1][CH2:2][C:3]#[C:4][CH2:5][OH:6]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCC#CCO | OCC#CCOC1CCCCO1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 68.8 | [{"value": 68.8, "product": "O1C(CCCC1)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC | null | null | C1=COCCC1.OCC#CCO>C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC>OCC#CCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b7fb0104fad94bc0b378012d50f6c0c8 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C1(CCCCC1)C#C.C=O.C=O>>C1(CCCCC1)C#CCO | [CH:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[O:1]=[CH2:2]>>[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C#CC1CCCCC1.C=O | OCC#CC1CCCCC1 | null | null | CCOCC | C-C Coupling | OtherReaction | b068d8bba9f864ba971dd324292d9b3526f0235b4ab7e3a9ce6aa76a39c4a1e7 | 22ebec2cc94dd24863aea8793d450cfe0691e1036be204d1a4c79c16effe90a4 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Primary alcohol.Alkyne | null | null | C1CCCCC1 | null | CCOCC | null | null | C#CC1CCCCC1.C=O>CCOCC>OCC#CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-836c8b6682c54c8ab49aa69cf992817b | O=C1CCC(c2ccc(Cl)cc2)=NN1>>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1CCC(NN1)=O.C(C)(=O)O.BrBr>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73c80fbcc9dd7a9125aaf1059d9d4eab31b342d21fc860abf5e65fd78456864b | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1ccc(-c2ccccc2)n[nH]1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[N;H0;D2;+0:11]-[NH;D2;+0:12]-1>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | 93.1 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | C1=NNCCC1 | c1cccnn1 | c1cccnn1.c1ccccc1 | null | O | null | null | O=C1CCC(c2ccc(Cl)cc2)=NN1>O>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6ba3063855543d494bab226d66b41f6 | FC1(F)CC(Cl)(Cl)C1(F)Cl>>FC1(F)C=C(Cl)C1(F)Cl | ClC1(C(C(C1)(F)F)(F)Cl)Cl.O.Cl>>ClC1(C(C=C1Cl)(F)F)F | Cl[C:5]1([Cl:6])[CH2:4][C:2]([F:1])([F:3])[C:7]1([F:8])[Cl:9]>>[F:1][C:2]1([F:3])[CH:4]=[C:5]([Cl:6])[C:7]1([F:8])[Cl:9] | FC1(F)CC(Cl)(Cl)C1(F)Cl | FC1(F)C=C(Cl)C1(F)Cl | null | null | CCOCC.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 0ca523bc88d44f4371960ac2ff9ed0bbb8882337b7061f7fba5b4787f1e02481 | 986b135105e7920109b424799136a4a8281fb4a0f49253ce1bf5d4426ed78637 | C1=CCC1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9] | 79 | [{"value": 79.0, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ethe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Alkenyl halide | C1CCC1 | C1=CCC1 | C1=CCC1 | HCl | CCOCC.C(C)N(CC)CC | null | 8 | FC1(F)CC(Cl)(Cl)C1(F)Cl>CCOCC.C(C)N(CC)CC>FC1(F)C=C(Cl)C1(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b94b41efbd25422b9fc00f014be629d5 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>>O=C(O)C(F)C(F)(F)C(=O)O | ClC(C(C(=O)O)(F)F)(C(=O)O)F>>FC(C(=O)O)(C(C(=O)O)F)F | Cl[C:6]([C:4]([C:2](=[O:1])[OH:3])([F:5])[F:7])([F:8])[C:9](=[O:10])[OH:11]>>[O:1]=[C:2]([OH:3])[CH:4]([F:5])[C:6]([F:7])([F:8])[C:9](=[O:10])[OH:11] | O=C(O)C(F)(F)C(F)(Cl)C(=O)O | O=C(O)C(F)C(F)(F)C(=O)O | null | [Zn] | O1CCOCC1 | Functional Group Addition | Dehalogenation | 7f145230bfb0115349e969b2f2fa1359cfafe8c166e52b50a867192005e1f5bc | d6722b0df465660a9eeeaca5a8f5b3dbb2d1ebccb44917f2eca97a85bf850d06 | null | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:7]-[CH;D3;+0:6](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:8])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 40.7 | [{"value": 32.0, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide.Secondary halide | null | null | null | Other | [Zn].O1CCOCC1 | null | 10 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>[Zn].O1CCOCC1>O=C(O)C(F)C(F)(F)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-09da337c3a844b5cb26234c0ea51edee | NN.O=C(O)CCCC(=O)c1ccccc1>>O=c1cccc(-c2ccccc2)nn1 | C(C1=CC=CC=C1)(=O)CCCC(=O)O.NN.O>>C1(=CC=CC=C1)C1=CC=CC(N=N1)=O | [NH2:13][NH2:14].O=[C:6]([CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1 | NN.O=C(O)CCCC(=O)c1ccccc1 | O=c1cccc(-c2ccccc2)nn1 | null | null | C1(=CC=CC=C1)C.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a31553d36b14882561a6dcdd04ef456bc0e14ea189c472490f94f02ebbe3ca3f | eadf9e657b4bde18ed656e299092aac7dd81eee1face1030775c3edd6ccba31c | O=c1cccc(-c2ccccc2)nn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0... | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C1=CC=CC(N=N1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | null | null | c1cccc[nH]n1 | c1cccc[nH]n1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CCOCC | null | null | NN.O=C(O)CCCC(=O)c1ccccc1>C1(=CC=CC=C1)C.CCOCC>O=c1cccc(-c2ccccc2)nn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3cf41a524c8b40e093b3d619340e8c02 | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>>COC(=O)C1Cc2cc(Cl)ccc2C1=O | COC(OC)=O.[H-].[Na+].ClC=1C=C2CCC(C2=CC1)=O.[H][H]>>C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Cl)ccc21 | COC(=O)C1Cc2cc(Cl)ccc2C1=O | null | null | C(OC)COC | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06. mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) w... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(OC)COC | 60 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>C(OC)COC>COC(=O)C1Cc2cc(Cl)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-351246f0dd44448ebbd806606156bbea | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 | C([O-])([O-])=O.[K+].[K+].P(=O)(Cl)(Cl)Cl.CN(C)C=O.ClC1=CC=C(C=C1)CC(=O)O>>ClC1=CC=C(C=C1)C(C=O)=CN(C)C | O=[CH:4][N:2]([CH3:1])[CH3:3].O=[C:6]([CH2:5][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[OH:7]>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1 | CN(C)C=C(C=O)c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cbf378fe57a2b8d8304e623fb5ce9ee6fb9f6e90d9c6f965226d56b103180e6d | a9c635686380f13b6b5c45d80d4aef36b30fdab0aef140b81f04c277f7ba737d | c1ccccc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[CH;D2;+0:7]=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Enamine.Aldehyde | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 8 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>C1(=CC=CC=C1)C>CN(C)C=C(C=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0e60e058e5c041cbbf3f3bd73811d422 | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | C(C)(=O)O.ClC1=CC=C(C=C1)C(C=O)=CN(C)C.C[O-].[Na+].C(#N)CC(=O)N>>C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O | CN(C)[CH:13]=[C:5]([CH:4]=O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[N:1]#[C:2][CH2:3][C:15]([NH2:14])=[O:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14][c:15]1=[O:16] | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 4fb69599b2ad512416349de44ee025f314a8ccdb2c8ad729cdf94ea75cf3109a | 46cf335065eccd013987994a3f086665eb273ac87eb3153099a47e61dd329581 | O=c1ccc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:1]:[nH;D2;+0:13]:[c;H0;D3;+0... | null | [] | null | null | null | null | To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1 | HO- | CO.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>CO.O>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-354b2e3cf6af4b84a2f7d3ebed5eb64d | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)C=1C=CC(NC1)=O | N#C[c:3]1[c:2](=[O:1])[nH:14][cH:13][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | null | null | OP(=O)(O)O | Miscellaneous | OtherReaction | 145adc421652def73603eb299eace1e2e3a197522b719b6949c0145a4308d11b | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | O=c1ccc(-c2ccccc2)c[nH]1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | 75.6 | [{"value": 75.6, "product": "ClC1=CC=C(C=C1)C=1C=CC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-cyano-5-(4-chlorophenyl)-2-pyridinone (4.6 g) and 85% H3PO4 (60 ml) was heated at reflux for 16 hours. The resulting mixture was cooled to room temperature, poured into ice/water and filtered yielding 3.1 g of 5-(4-chlorophenyl)-2-pyridinone as a yellow solid.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnccc1 | c1cccnc1 | c1cccnc1.c1ccccc1 | Other | OP(=O)(O)O | null | null | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>OP(=O)(O)O>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abf8a35446cd49678e6b7fb0a5cfdc74 | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | [Cl-].[NH4+].[H-].[Na+].N1C(C=CC=C1)=O.CCCCCC.C(C)(=O)OCC.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=CC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[CH2:9]([CH3:10])[CH2:15][CH2:14][CH2:12][CH3:11].[nH:6]1[cH:7][cH:8][cH:16][cH:17][c:18]1=[O:19].[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-] | CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | c16e53991381708a0d74f5092b5e25b0353184189763eaae006dd565c1174ab9 | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[Cl-;H0;D0:11].[O;D1;H0:12]=[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:6]2:[cH;D2;+0:5]:[cH;D2;+0:... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d0e6fc6e604f42b1aaa518cbc9b8ffed | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | C(C)(=O)OCC.ClC1=CC=C(N)C=C1.N1=CC=CC=C1.C(C=CC1=CC=CC=C1)(=O)Cl>>ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.Cl[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.O | 0 | 0.25 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>C1(=CC=CC=C1)C.O>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9b1470facdae4b2f84c618a3f6010aa4 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>>O=c1ccc2c(Cl)cccc2[nH]1 | ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C2C=CC(NC2=CC=C1)=O | c1ccc([CH:4]=[CH:3][C:2](=[O:1])[NH:12][c:11]2[cH:5][cH:8][c:6]([Cl:7])[cH:9][cH:10]2)cc1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[nH:12]1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | O=c1ccc2c(Cl)cccc2[nH]1 | null | null | ClC1=CC=CC=C1 | Reduction | OtherReaction | ebe7e954f82f1e726cf9b7a8863216fec31733c3d8bfbb1cc71c49312cec65ac | 10d6d5b071f1d84b20b253ce9eadaed211c373c6ee607356078792f13319351a | O=c1ccc2ccccc2[nH]1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-c2:c:c:c:c:c:2):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:11]:[c:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+... | null | [] | 125 | CELSIUS | 3 | HOUR | To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | Other | ClC1=CC=CC=C1 | 125 | 3 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>ClC1=CC=CC=C1>O=c1ccc2c(Cl)cccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-437fb7fada4948e496f111fd7c9c5c2e | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>>CCC#CCn1c(=O)ccc2c(Cl)cccc21 | [Cl-].[NH4+].N1C(C=CC2=CC=CC=C12)=O.[H-].[Na+].BrCC#CCC>>ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[nH:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[cH:12][cH:14][cH:15][cH:16][c:17]12.[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-] | CCC#CCn1c(=O)ccc2c(Cl)cccc21 | null | null | CN(C)C=O.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a61336fe7a89ec0981a525297b55629e44e830f13f91df56a44bf01390d8c69d | dbda6588fa29cbbc0e3c3f601e69924b300990bdcc56b8cec0535d1258039346 | O=c1ccc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[Cl-;H0;D0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:[nH;D2;+0:16]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]2:[c:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:5]):[c:10]:2:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CN(C)C=O.CCCCCC | 0 | null | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>CN(C)C=O.CCCCCC>CCC#CCn1c(=O)ccc2c(Cl)cccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8ade6c521814efe8e95d3631964bfae | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | [Cl-].[NH4+].ClC1=CC=C(C=C1)C(C=O)=CN(C)C.NC(=O)N.Cl>>ClC1=CC=C(C=C1)C=1C=NC(NC1)=O | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]=O.[O:1]=[C:2]([NH2:3])[NH2:14]>>[O:1]=[c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O | O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 0e1bb7c6fc2fa2fbd0239b648ae136ef123b13ddeb9947c50b8f38d453d7d183 | 55a949c5abf218b0e7fd0015b81e86fb975fa441e5ac6bd395c3346bb38599f7 | O=c1ncc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:3]:[nH;D2;+0:9]:1 | 29.7 | [{"value": 29.7, "product": "ClC1=CC=C(C=C1)C=1C=NC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Urea | null | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>C(C)O.O>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8693bdeb39847fdbe0763c20bb31a87 | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | [Cl-].[NH4+].CCCCCC.[H-].[Na+].N1C(C=CC=C1)=O.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].C[CH2:15][CH2:14][CH2:12][CH2:11][CH3:10].[nH:6]1[cH:7][cH:8][cH:16][cH:9][c:18]1=[O:19].[Cl-:13].[NH4+:17]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][n:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+] | CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | b4467fdd65493649554b053844b88f7aedac75ecb5e83a2819a9163270cc6b1f | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ncc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].C-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[Cl-;H0;D0:10].[NH4+;D0:11].[O;D1;H0:12]=[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:14]2... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6599866d48314986a02151e7cded27be | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1C=CC(NN1)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=S | O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:1])(S2)S3>>[S:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e0da8be0c0e31372bc487fca4d998b8539b7ff5b84df07e1a6200efd3593e0bb | 13be3f637e1e22872d741944f46b7fcc1954fe982a3a8a0f7825545d455ab147 | S=c1ccc(-c2ccccc2)n[nH]1 | O=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 187.1 | [{"value": 187.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thiocarbonyl | c1cccnn1.S1P2SP3SP1SP(S2)S3 | c1cccnn1 | c1cccnn1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d38b7b009446439cb95143c67e49b8ed | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)NN)C=C1.ClCC(=O)Cl>>ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O | [NH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl | O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as whi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>O1CCOCC1>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78ffab45f98b4d54bbf0b4abd3bad247 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>>O=C1NN=C(c2ccc(Cl)cc2)CS1 | BrCC(=O)C1=CC=C(C=C1)Cl.COC(=S)NN>>ClC1=CC=C(C=C1)C1=NNC(SC1)=O | C[O:1][C:2]([NH:3][NH2:4])=[S:14].O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13]Br>>[O:1]=[C:2]1[NH:3][N:4]=[C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][S:14]1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1 | O=C1NN=C(c2ccc(Cl)cc2)CS1 | null | null | C(C)#N | Acylation | OtherReaction | a0815ff887854434f061e02bb59e65917f2f792eefe3f407e6f67a241e834044 | b7ddc8c969600ae9a9b2d12841c66a24307741bcbfc0810c56e58eb7d0e4892d | O=C1NN=C(c2ccccc2)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].C-[O;H0;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[NH2;D1;+0:10]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-1 | 48.4 | [{"value": 48.4, "product": "ClC1=CC=C(C=C1)C1=NNC(SC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Ether.Thioamide | Hydrazone amide.Monosulfide | null | C1=NNCSC1 | C1=NNCSC1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>C(C)#N>O=C1NN=C(c2ccc(Cl)cc2)CS1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-071020b2a4f5457396b9e1aa29ee7de2 | O=C(O)CCC(=O)c1cccc(Cl)c1>>O=C(O)CCCc1cccc(Cl)c1 | ClC=1C=C(C(=O)CCC(=O)O)C=CC1.[OH-].[K+].NN>>ClC=1C=C(C=CC1)CCCC(=O)O | O=[C:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | O=C(O)CCCc1cccc(Cl)c1 | null | null | C(COCCO)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | 90.8 | [{"value": 90.8, "product": "ClC=1C=C(C=CC1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, with stirring, 23 g of 3-(3-chlorobenzoyl)propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | C(COCCO)O | null | null | O=C(O)CCC(=O)c1cccc(Cl)c1>C(COCCO)O>O=C(O)CCCc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ced7355b22f246b584e1e59141387906 | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>CN1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.CNN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O | [CH3:1][NH:2][NH2:3].O=[C:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH2:12][CH2:13][C:14](O)=[O:15]>>[CH3:1][N:2]1[N:3]=[C:4]([c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[CH2:12][CH2:13][C:14]1=[O:15] | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | CN1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(C)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10]1-[N;H0;D2;+0:11]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[C:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexan... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(C)O | null | null | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>CN1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-429297c02798479a94358463bcef7999 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=O)C=C1.C(CCC(=O)C)(=O)O.N1CCCCC1.C1(=CC=CC=C1)C>>ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH3:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1 | O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>O>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5fafd6034f39415a9b2fc5112a7c5611 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>>COc1ccc(C(=O)O)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C.[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC | C[c:10]1[c:6]([C:7](=[O:8])[O-:9])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-] | COc1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ec2bcf645eed3485ae21dd491bac7887e7ecc8e6727067de36c08c87eaa3e98c | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]):[c:9]>>[#7;+:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7]):[c:9] | 76.6 | [{"value": 76.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 12 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>O1CCCC1>COc1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1b8d0e577394df0ad9547d14447018b | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccc2ccccc12>>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1 | C1(=CC=CC2=CC=CC=C12)[Mg]Br.CN(C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC)C>>C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC | CN(C)[c:25]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][c:37]2[s:36]1.[Br][Mg][c:26]1[cH:27][cH:28][cH:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccc2ccccc12 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 1c8033480f43bfecb0046def01a62092035a5425c88b1aeef0ec98f9dc67e298 | 87044ac4bcbffcaa9a599921042d9edfcfa91aa179fb824aef73cbceb7ea02f9 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccc3ccccc23)sc2ccccc12 | C-N(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[c:8].[Br]-[Mg]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14]>>[O;D1;H0:7]=[C:6](-[c:8])-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14] | 58 | [{"value": 58.0, "product": "C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone (1.58 g, 3.6 mmol) (see U.S. Pat. No. 5,420,349) in tetrahydrofuran (THF, 12 mL) was cooled to 0° C. and treated with a 0.65M THF solution of 1-naphthylmagnesium bromide (20.0 mL, 13 mmol) (prepared from 1-bromonaphthale... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amine | null | c1ccc2sccc2c1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2sccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccc2sccc2c1 | HBr.Mg | O1CCCC1 | null | null | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccc2ccccc12>O1CCCC1>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-acaaec7f0b624f78bd5144946ae675b0 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1>>O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccc3ccccc23)sc2cc(O)ccc12 | C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC.C(C)S.[Cl-].[Al+3].[Cl-].[Cl-]>>C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O | C[O:34][c:33]1[cH:32][c:31]2[s:30][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]34)[c:18]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][N:10]4[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17]3)[c:37]2[cH:36][cH:35]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccc3ccccc23)sc2cc(O)ccc12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccc3ccccc23)sc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 53.4 | [{"value": 53.0, "product": "C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "C1(=CC=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Example 1 (1.00 g, 1.92 mmol), ethanethiol (0.45 mL, 6.18 mmol), and aluminum chloride (1.54 g, 11.55 mmol) in anhydrous methylene chloride (40 mL) was stirred for 3.5 hours. The mixture was quenched with saturated potassium sodium tartrate (also known as Rochelle's salt) and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccc2sccc2c1 | Other | C(Cl)Cl | null | null | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccc4ccccc34)sc2c1>C(Cl)Cl>O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccc3ccccc23)sc2cc(O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-091c17ec47894388ba59fc099d21a39b | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1ccc2ccccc2c1>>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1 | C1=C(C=CC2=CC=CC=C12)[Mg]Br.CN(C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC)C.CO>>C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC | CN(C)[c:25]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][c:37]2[s:36]1.[Br][Mg][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1ccc2ccccc2c1 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1 | null | null | C1CCOC1.C(Cl)Cl | C-C Coupling | OtherReaction | 1c8033480f43bfecb0046def01a62092035a5425c88b1aeef0ec98f9dc67e298 | 87044ac4bcbffcaa9a599921042d9edfcfa91aa179fb824aef73cbceb7ea02f9 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc3ccccc3c2)sc2ccccc12 | C-N(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[c:8].[Br]-[Mg]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[c:8])-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 75.1 | [{"value": 75.0, "product": "C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone (1.58 g, 3.6 mmol) in THF (12 mL) was reacted with a 0.65M THF solution of 2-naphthylmagnesium bromide (15 mL, 9.8 mmol) to provide, after chromatography (silica gel, 5% methanol in methylene chlo... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amine | null | c1ccc2sccc2c1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2sccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccc2sccc2c1 | HBr.Mg | C1CCOC1.C(Cl)Cl | null | null | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1ccc2ccccc2c1>C1CCOC1.C(Cl)Cl>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c366215603d74e8f80c204c070b5fd26 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1>>O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc3ccccc3c2)sc2cc(O)ccc12 | CO.C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC.C(C)S.[Cl-].[Al+3].[Cl-].[Cl-]>>C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O | C[O:34][c:33]1[cH:32][c:31]2[s:30][c:19](-[c:20]3[cH:21][cH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[cH:29]3)[c:18]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][N:10]4[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17]3)[c:37]2[cH:36][cH:35]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc3ccccc3c2)sc2cc(O)ccc12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc3ccccc3c2)sc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 98.1 | [{"value": 98.0, "product": "C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "C1=C(C=CC2=CC=CC=C12)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method described in Example 2, the product of Example 3 (1.35 g, 2.59 mmol), ethanethiol (0.56 mL, 7.69 mmol), and aluminum chloride (2.07 g, 15.52 mmol) were reacted in anhydrous methylene chloride (50 mL) to give, after chromatography (silica gel, 5% methanol in methylene chloride) 1.29 g (98%) of the title pr... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccc2sccc2c1 | Other | C(Cl)Cl | null | null | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc4ccccc4c3)sc2c1>C(Cl)Cl>O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc3ccccc3c2)sc2cc(O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dee584427df84216a8609fe44f49a665 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccs1>>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccs3)sc2c1 | S1C(=CC=C1)[Mg]Br.CN(C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC)C>>S1C(=CC=C1)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC | CN(C)[c:25]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][c:32]2[s:31]1.[Br][Mg][c:26]1[cH:27][cH:28][cH:29][s:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([C:8](=[O:9])[c:10]3[cH:11][... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccs1 | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccs3)sc2c1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 326d35adb6a1c10eb3af749bc3d574a7fea24f35eecef701ce7ed69d3577388e | 87044ac4bcbffcaa9a599921042d9edfcfa91aa179fb824aef73cbceb7ea02f9 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2cccs2)sc2ccccc12 | C-N(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[c:8].[Br]-[Mg]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[O;D1;H0:7]=[C:6](-[c:8])-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1 | 72.1 | [{"value": 72.0, "product": "S1C(=CC=C1)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "S1C(=CC=C1)C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone (1.97 g, 4.5 mmol) in THF (15 mL) was reacted with a 0.60M THF solution of 2-thienylmagnesium bromide (31.8 mL, 13.5 mmol) (prepared from 2-bromothiophene, n-butyllithium, and magnesium bromide in... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amine | null | c1ccc2sccc2c1.c1ccsc1 | c1ccsc1.c1ccc2sccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccsc1.c1ccc2sccc2c1 | HBr.Mg | C1CCOC1 | null | null | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1.[Br][Mg][c]1cccs1>C1CCOC1>COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(-c3cccs3)sc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd1d646105624c93a6051c2970a32067 | COc1ccc([CH2][Mg][Br])cc1.COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1>>COc1ccc(Cc2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1 | COC1=CC=C(C[Mg]Br)C=C1.CN(C=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC)C>>COC1=CC=C(C=C1)CC=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC | [Br][Mg][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]1.CN(C)[c:8]1[s:9][c:10]2[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]2[c:18]1[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([O:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:... | COc1ccc([CH2][Mg][Br])cc1.COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1 | COc1ccc(Cc2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 4161a3f4e8978f6ed4d0727517bcf2ac9c3fb21b97d2835a8002b5dd124b6103 | 87044ac4bcbffcaa9a599921042d9edfcfa91aa179fb824aef73cbceb7ea02f9 | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(Cc2ccccc2)sc2ccccc12 | C-N(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[c:8].[Br]-[Mg]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6](-[c:8])-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | 29.4 | [{"value": 29.0, "product": "COC1=CC=C(C=C1)CC=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.4, "product": "COC1=CC=C(C=C1)CC=1SC2=C(C1C(=O)C1=CC=C(C=C1)OCCN1CCCCC1)C=CC(=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]-methanone (6.0 g, 13.7 mmol) in THF (51 mL) was reacted with a 0.83M THF solution of 4-methoxybenzylmagnesium bromide (19.8 mL, 16.4 mmol) (prepared from 4-methoxybenzylchloride and magnesium turnings in T... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amine | null | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1.c1ccccc1.C1CC[NH]CC1 | HBr.Mg | C1CCOC1 | null | null | COc1ccc([CH2][Mg][Br])cc1.COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(N(C)C)sc2c1>C1CCOC1>COc1ccc(Cc2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-137bd4435e364643b101a1a71a0e2096 | CCOC(=S)CC.CCOc1ccc(N)cc1>>CCOc1ccc2c(c1)CC(=O)N2 | C(C)N(CC)CC.C(C)OC1=CC=C(N)C=C1.CCC(=S)OCC.ClCl>>C(C)OC=1C=C2CC(NC2=CC1)=O | CC[O:12][C:11](=S)[CH2:10]C.[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:13])[cH:8][cH:9]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][C:11](=[O:12])[NH:13]2 | CCOC(=S)CC.CCOc1ccc(N)cc1 | CCOc1ccc2c(c1)CC(=O)N2 | null | null | C(Cl)Cl.O | Acylation | OtherReaction | a2a74f97cf7b487de6b223d2dc53dd6aa5e8f47b1840b7ace2677d5fc1e0131e | 7ad4bf7309306986e6cc349c7bc628011e853b7eb203cf188a8de27e64e52865 | O=C1Cc2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=S)-[CH2;D2;+0:3]-C.[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6])-[NH;D2;+0:4]-1 | null | [] | null | null | 5 | MINUTE | 23.6 g of ethyl methylthioacetate in 60 ml of DCM are added to a solution, cooled to about -70° C., of 12.5 g of chlorine in 400 ml of DCM. After stirring for 5 minutes at the same temperature, a solution of 4-ethoxyaniline (48.3 g) in 120 ml of DCM is added. The mixture is stirred for one hour at about -70° C., 39.3 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Thiocarbonyl | Secondary amide | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C(Cl)Cl.O | null | 0.083333 | CCOC(=S)CC.CCOc1ccc(N)cc1>C(Cl)Cl.O>CCOc1ccc2c(c1)CC(=O)N2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ff5774731954061858d03160b92b6f9 | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1>>O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 | ClC=1C=C2C(C(NC2=CC1)=O)=O.[Cl-].[Al+3].[Cl-].[Cl-].C1=CC=CC=C1>>ClC=1C=C2C(C(NC2=CC1)=O)(C1=CC=CC=C1)C1=CC=CC=C1 | O=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]21.[cH:12]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11]1([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1 | O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | dba4da327e7262cdcc29a8207cdf08b13f4d7581c1f62dc179c070e46d100989 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C1Nc2ccccc2C1(c1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[c:6]-1:[c:7].[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[O;D1;H0:3]=[C:2]1-[#7:4]-[c:5]:[c:6](:[c:7])-[C;H0;D4;+0:1]-1(-[c:14]1:[cH;D2;+0:13]:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1)-[c;H0;D3;+0:12](:[c:15]:[c:16]):[c:17]:[c:18] | null | [] | null | null | null | null | This compound is prepared by the method described in Helv. Chim. Acta, 1946, 29, 415-431, by the reaction of benzene with 5-chloroisatin in the presence of aluminum chloride. M.p.=281° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound is prepared by the method | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1 | null | null | null | null | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1>>O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-43d95d9c07ef43d581eb72b8af369b67 | CCO.O=C(Cl)c1ccc(F)cc1>>CCOC(=O)c1ccc(F)cc1 | FC1=CC=C(C(=O)Cl)C=C1.C(C)O>>FC1=CC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | CCO.O=C(Cl)c1ccc(F)cc1 | CCOC(=O)c1ccc(F)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture containing 35 g of 4-fluorobenzoyl chloride in 50 ml of 100% ethanol is refluxed for 15 minutes. 35 g of the ethyl 4-fluorobenzoate obtained are mixed with 22 g of imidazole and 61 g of potassium carbonate in 35 ml of DMSO. The mixture is heated for 18 hours at 120°-130° C. and 500 ml of iced water are then a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | null | null | null | CCO.O=C(Cl)c1ccc(F)cc1>>CCOC(=O)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-60883984e0a345f69557d95970310d78 | COC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | BrCC(=O)C1=CC=C(OCC(=O)OC)C=C1.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC)C=C1 | Br[CH2:13][C:11]([c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:27][cH:26]1)=[O:12].[NH:14]1[CH2:15][CH2:16][N:17]([c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18]3[... | COC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 1.5 | HOUR | A solution of methyl 4-bromoacetylphenoxyacetate (4.3 g) in acetonitrile (50 ml) was added dropwise over 40 minutes to a stirred solution of 1-(4-pyridyl)piperazine (4.9 g) in acetonitrile (100 ml). Stirring was continued for a further 1.5 hours, then the solution was filtered and the filtrate evaporated in vacuo. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | 1.5 | COC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-369459ec0ce24604a44164b3a522b96e | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>>O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC)C=C1.[OH-].[Na+]>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)O)C=C1 | C[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][n:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][n:20... | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | 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] | null | [] | 4 | CELSIUS | 2 | HOUR | A stirred solution of the product of Example 1 (550 mg) in methanol (10 ml) was treated with a M sodium hydroxide solution (1.65 ml) and stirring continued for a further 2 hours. The mixture was diluted with water (10 ml) and the resulting solution concentrated in vacuo. Water (20 ml) was added and then a M hydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | CO.O | 4 | 2 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>CO.O>O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2900eeef6bee4f96854b610d5c6665dc | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1OC>>COc1cc(C(=O)CN2CCN(c3ccncc3)CC2)ccc1OCC(=O)O | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC(=C(OCC(=O)OC)C=C1)OC>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC(=C(OCC(=O)O)C=C1)OC | C[O:28][C:26]([CH2:25][O:24][c:23]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[CH2:8][N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][n:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22]1)=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][n:16][cH:17][cH:18... | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1OC | COc1cc(C(=O)CN2CCN(c3ccncc3)CC2)ccc1OCC(=O)O | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | 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] | 47 | [{"value": 47.0, "product": "N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC(=C(OCC(=O)O)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner to Example 2, but starting from the product of Example 5, the title compound was prepared in 47% yield: m.p. 218°-224° C.; NMR(d6DMSO) δ 8.16(2H,d), 7.65(1H,dd), 7.53(1H,d), 6.92(1H,d), 6.85(2H,d), 4.73(2H,s), 3.86(2H,s), 3.82(3H,s), 3.36(4H,t), 2.63(4H,t); m/e 386(M+H)+ ; calculated for C20H23N3O5.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | O | null | null | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1OC>O>COc1cc(C(=O)CN2CCN(c3ccncc3)CC2)ccc1OCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4789241e5b8e4d179a6429cc6ce17888 | COC(=O)COc1ccccc1.O=C(Cl)CCCl>>COC(=O)COc1ccc(C(=O)CCCl)cc1 | O(C1=CC=CC=C1)CC(=O)OC.ClCCC(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>ClCCC(=O)C1=CC=C(OCC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][cH:16][cH:17]1.Cl[C:11](=[O:12])[CH2:13][CH2:14][Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][CH2:14][Cl:15])[cH:16][cH:17]1 | COC(=O)COc1ccccc1.O=C(Cl)CCCl | COC(=O)COc1ccc(C(=O)CCCl)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | 1 | HOUR | Aluminium chloride (33.35 g) was added portionwise to a stirred cooled (<0° C.) solution of methyl phenoxyacetate (14.46 ml) and 3-chloropropionyl chloride (9.55 ml) in dichloromethane (500 ml). After the addition the ice-bath was removed and the mixture stirred for 1 hour when it was poured into ice-water (500 ml). Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | ClCCl | null | 1 | COC(=O)COc1ccccc1.O=C(Cl)CCCl>ClCCl>COC(=O)COc1ccc(C(=O)CCCl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dec26e4a500a423b998283ba15ea943b | COC(=O)Cc1ccc(C(=O)CCl)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)Cc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | ClCC(=O)C1=CC=C(C=C1)CC(=O)OC.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(C=C1)CC(=O)OC | Cl[CH2:12][C:10]([c:9]1[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:26][cH:25]1)=[O:11].[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19... | COC(=O)Cc1ccc(C(=O)CCl)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)Cc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 8 | HOUR | A solution of methyl 4-chloroacetylphenylacetate (260 mg) in acetonitrile (4 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (375 mg) in acetonitrile (10 ml) and the mixture stirred overnight. The supernatent was decanted from the solid formed, concentrated in vacuo and purified ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HCl | C(C)#N | null | 8 | COC(=O)Cc1ccc(C(=O)CCl)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)Cc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77e50f1da1444b07b851d442f07f91b1 | CCC(=O)c1ccc(OCC(=O)OC)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)COc1ccc(C(=O)C(C)N2CCN(c3ccncc3)CC2)cc1 | CCC(=O)C1=CC=C(OCC(=O)OC)C=C1.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)C(C(=O)C1=CC=C(OCC(=O)OC)C=C1)C | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][CH3:14])[cH:27][cH:28]1.[NH:15]1[CH2:16][CH2:17][N:18]([c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH:13]([CH3:14])[N:15]2[CH2:16][CH2:17]... | CCC(=O)c1ccc(OCC(=O)OC)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)COc1ccc(C(=O)C(C)N2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 3a3ed397381e44670ce2e8342acad8222d2432ca85ece7a4615c2b6be4971f24 | 35f76118ef70465dec1f1daab296204894422630ea976731c8b4f0c910a4773f | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[C;D1;H3:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C;D1;H3:7]-[CH;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | null | [] | null | null | 8 | HOUR | A solution of RS methyl 4-(2-methylacetyl)phenoxyacetate (1.2 g) in acetonitrile (10 ml) was added dropwise over 30 minutes to a stirred solution of 1-(4-pyridyl)piperazine (1.3 g) in acetonitrile (30 ml) and the mixture stirred overnight. The mixture was then filtered and the filtrate evaporated to give an oil. Purifi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | C(C)#N | null | 8 | CCC(=O)c1ccc(OCC(=O)OC)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)COc1ccc(C(=O)C(C)N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9af742574ebf4d4aa094524fbbb466cc | CCOC(=O)CCCBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>>CCOC(=O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.[H-].[Na+].BrCCCC(=O)OCC>>N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCCCC(=O)OCC)C=C1 | Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([c:18]3[cH:19][cH:20][n:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([c:18]... | CCOC(=O)CCCBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | CCOC(=O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 1 | HOUR | A stirred suspension of 4-(4-(4-pyridyl)piperazin-1-yl)-phenol (1.34 g) in dry DMF (20 ml) was treated with sodium hydride (60% dispersion in mineral oil, 0.21 g) and the mixture stirred for 1 hour. To the resulting solution was added ethyl 4-bromobutyrate and the mixture was stirred for 16 hours. Solvent was evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | CCOC(=O)CCCBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>CN(C)C=O>CCOC(=O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
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