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-02ee2261663048188cf6d85d2cc96e3f | ord-0ff8025e8c5444e9b4b310a7c0c96dda | Nc1nc(N)nc(N)n1>>Nc1nc(N)nc(N)n1 | C=O.[OH-].[Na+].N1=C(N)N=C(N)N=C1N.[Na]>>C=O.N1=C(N)N=C(N)N=C1N | [NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | Nc1nc(N)nc(N)n1 | Nc1nc(N)nc(N)n1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | null | null | [] | 60 | CELSIUS | 30 | MINUTE | 50 parts of 20% liquor A (dispersion of aromatic isocyanate compound) and 100 parts of 30% liquor B (co-dispersion of imino compound-sensitizer) obtained in the above (1) were mixed with each other until a homogeneous mixture was obtained. 150 parts of the mixture of liquor A and liquor B was gradually added with 120 p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | null | O | 60 | 0.5 | Nc1nc(N)nc(N)n1>O>Nc1nc(N)nc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-988a2c53241846448be5b0c88940992d | Nc1nc(N)nc(N)n1>>Nc1nc(N)nc(N)n1 | [Na].C(=CC1=CC=CC=C1)/C/1=C/C(=O)OC1=O.N1=C(N)N=C(N)N=C1N.C=O.[OH-].[Na+]>>C=O.N1=C(N)N=C(N)N=C1N | [NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | Nc1nc(N)nc(N)n1 | Nc1nc(N)nc(N)n1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | null | null | [] | 60 | CELSIUS | 30 | MINUTE | Previously, 50 parts of 20% liquor A (dispersion of aromatic isocyanate compound) and 50 parts of 40% liquor B (co-dispersion of imino compound-sensitizer) obtained by grinding and dispersing in the above (1) were mixed with each other until a homogeneous mixture was obtained. The resulting homogeneous mixture of liquo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | null | O | 60 | 0.5 | Nc1nc(N)nc(N)n1>O>Nc1nc(N)nc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-532890acfa0c4878a648f53eab17e89c | Nc1nc(N)nc(N)n1>>Nc1nc(N)nc(N)n1 | [Na].N1=C(N)N=C(N)N=C1N.C=O.N.[OH-].[Na+].N>>C=O.N1=C(N)N=C(N)N=C1N | [NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | Nc1nc(N)nc(N)n1 | Nc1nc(N)nc(N)n1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | null | null | [] | 60 | CELSIUS | 30 | MINUTE | Previously, 50 parts of 20% liquor A (dispersion of aromatic isocyanate compound) and 100 parts of 30% liquor B (co-dispersion of imino compound-sensitizer) obtained by grinding and dispersing in the above (1) were mixed with each other until a homogeneous mixture was obtained. The resulting homogeneous mixture of liqu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | null | O | 60 | 0.5 | Nc1nc(N)nc(N)n1>O>Nc1nc(N)nc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ea88f85ac3924f1abb143061996c57cd | CC(C)(C)[C@@H](N)C(N)=O>>CC(C)(C)[C@H](N)C(N)=O | NC(C(C)(C)C)C(=O)N.N[C@@H](C(C)(C)C)C(=O)O.N[C@H](C(C)(C)C)C(=O)N>>N[C@@H](C(C)(C)C)C(=O)N | [CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([NH2:6])[C:7]([NH2:8])=[O:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]([NH2:6])[C:7]([NH2:8])=[O:9] | CC(C)(C)[C@@H](N)C(N)=O | CC(C)(C)[C@H](N)C(N)=O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | In the same way as in example VIII, an incubation was carried out with DL-tertiary leucine amide. Analysis of the remaining reaction mixture after 8 hours showed that both L-tertiary leucine and D-tertiary leucine amide with an e.e. of ≥99% were present in the reaction mixture.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | CC(C)(C)[C@@H](N)C(N)=O>>CC(C)(C)[C@H](N)C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-844e9b86e04349d6a419372f67937301 | CO.O=C(O)C(O)c1ccc(Br)cc1>>COC(=O)C(O)c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(C(=O)O)O.CO.S(O)(O)(=O)=O>>BrC1=CC=C(C=C1)C(C(=O)OC)O | [CH3:1][OH:2].O[C:3](=[O:4])[CH:5]([OH:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([OH:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1 | CO.O=C(O)C(O)c1ccc(Br)cc1 | COC(=O)C(O)c1ccc(Br)cc1 | null | null | O | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[O;D1;H1:4])-[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](-[O;D1;H1:4])-[c:5] | 92 | [{"value": 92.0, "product": "BrC1=CC=C(C=C1)C(C(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 20 g (87 mmol) of (±)-4-bromo-α-hydroxyphenylacetic acid, 200 ml of methanol and 2 ml of concentrated sulfuric acid was stirred for 3 hours at room temperature. To the mixture 50 ml of water was added. After the solution was extracted with ethyl acetate, the organic extract was washed with a saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | O | null | 3 | CO.O=C(O)C(O)c1ccc(Br)cc1>O>COC(=O)C(O)c1ccc(Br)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-82e83c02b9134508a72b2b79ba90c519 | CCCCCCCCOc1ccc(O)c(F)c1F.CCCCCCOc1ccc(C(=O)O)cc1>>CCCCCCCCOc1ccc(OC(=O)c2ccc(OCCCCCC)cc2)c(F)c1F | C(C)(C)(C)OO.C(CCC)[Li].C1(CCCCC1)N=C=NC1CCCCC1.C(CCCCC)OC1=CC=C(C(=O)O)C=C1.CN(C)C1=NC=CC=C1.FC1=C(C=CC(=C1F)OCCCCCCCC)O.FC(COC1=CC=CC=C1)C(CCCCC)F.C(C)(C)(C)OOC(C)(C)C.[Li]>>C(CCCCC)OC1=CC=C(C(=O)OC2=C(C(=C(C=C2)OCCCCCCCC)F)F)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[c:30]([F:31])[c:32]1[F:33].O[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:... | CCCCCCCCOc1ccc(O)c(F)c1F.CCCCCCOc1ccc(C(=O)O)cc1 | CCCCCCCCOc1ccc(OC(=O)c2ccc(OCCCCCC)cc2)c(F)c1F | null | null | ClCCl.CCOCC | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Oc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | HOUR | 0.1 mol of 4-hexyloxybenzoic acid, 0.01 mol of dimethylaminopyridine and 0.1 mol of 2,3-difluoro-4octyloxyphenol (preparable from 2,3-difluorooctyloxybenzene by lithiation at -70° to -80° and dropwise addition of a solution of lithium t-butylperoxide in ether prepared from 0.12 mol of t-butyl hydroperoxide and 0.12 mol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | ClCCl.CCOCC | null | 15 | CCCCCCCCOc1ccc(O)c(F)c1F.CCCCCCOc1ccc(C(=O)O)cc1>ClCCl.CCOCC>CCCCCCCCOc1ccc(OC(=O)c2ccc(OCCCCCC)cc2)c(F)c1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-709fc48404a84ef09737b5887db2472e | CCCCBr.CCCCC[C@@H]1CC[C@@H](COc2ccc(O)c(F)c2F)CC1>>CCCCC[C@@H]1CC[C@@H](COc2ccc(OCCCC)c(F)c2F)CC1 | FC1=C(C=CC(=C1F)OC[C@@H]1CC[C@H](CC1)CCCCC)O.C(CCC)Br.C([O-])([O-])=O.[K+].[K+]>>C(CCC)OC1=C(C(=C(C=C1)OC[C@@H]1CC[C@H](CC1)CCCCC)F)F | Br[CH2:17][CH2:18][CH2:19][CH3:20].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([OH:16])[c:21]([F:22])[c:23]2[F:24])[CH2:25][CH2:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][C... | CCCCBr.CCCCC[C@@H]1CC[C@@H](COc2ccc(O)c(F)c2F)CC1 | CCCCC[C@@H]1CC[C@@H](COc2ccc(OCCCC)c(F)c2F)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 0.1 mol of 2,3-difluoro-4-(trans-4-pentylcyclohexyl)methoxyphenol, 0.11 mol of butyl bromide and 0.11 mol of potassium carbonate are heated for 16 hours at 100° in 100 ml of dimethylformamide (DMF). After cooling, the inorganic salts are filtered off with suction, the filtrate is concentrated, and water is added. 1-but... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1CCCCC1.c1ccccc1 | HBr | CN(C=O)C | null | null | CCCCBr.CCCCC[C@@H]1CC[C@@H](COc2ccc(O)c(F)c2F)CC1>CN(C=O)C>CCCCC[C@@H]1CC[C@@H](COc2ccc(OCCCC)c(F)c2F)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-32048f4b38654a34b265cba539771b47 | Oc1cccc(F)c1F>>Oc1ccc(O)c(F)c1F | Cl.Cl.S(=O)([O-])[O-].[Na+].[Na+].[K].FC1=C(C=CC=C1F)O>>FC1=C(O)C=CC(=C1F)O | [OH:1][c:2]1[cH:3][cH:4][cH:5][c:7]([F:8])[c:9]1[F:10]>>[OH:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([F:8])[c:9]1[F:10] | Oc1cccc(F)c1F | Oc1ccc(O)c(F)c1F | null | null | [OH-].[Na+].C1(=CC=CC=C1)C | Oxidation | Aromatic hydroxylation | c7a66b348b8d881dd8ffccfacfb6192a695c6fe0c779e1e37631ad4085fe4603 | ac85d33a723c7a3c15eece7d0a6d9fb901e902291e4984dab36fdac38eba9375 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[O;D1;H1:7]):[c:5]:[c:6] | null | [] | null | null | 8 | HOUR | 1 mol of 2,3-difluorophenol is dissolved in 1 l of 10% sodium hydroxide solution, and a saturated aqueous solution of 1.1 mol of potassium peroxodisulphate is added dropwise over the course of 4 hours with ice cooling. During this addition, the temperature must not exceed 20o The mixture is stirred overnight at room te... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [OH-].[Na+].C1(=CC=CC=C1)C | null | 8 | Oc1cccc(F)c1F>[OH-].[Na+].C1(=CC=CC=C1)C>Oc1ccc(O)c(F)c1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ee06cc338d74b2ebea19761b8727ee9 | COC(=O)CCCCC(=O)ON1C(=O)CCC1=O>>O=C(O)CCCCC(=O)ON1C(=O)CCC1=O | C(CCCCC(=O)ON1C(CCC1=O)=O)(=O)OC.Cl[Si](C)(C)C.[I-].[Na+]>>C1(CCC(N1OC(CCCCC(=O)O)=O)=O)=O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[O:10][N:11]1[C:12](=[O:13])[CH2:14][CH2:15][C:16]1=[O:17]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[O:10][N:11]1[C:12](=[O:13])[CH2:14][CH2:15][C:16]1=[O:17] | COC(=O)CCCCC(=O)ON1C(=O)CCC1=O | O=C(O)CCCCC(=O)ON1C(=O)CCC1=O | null | null | C(C)#N.C(C)(=O)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCC(=O)N1 | 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] | 75.2 | [{"value": 71.0, "product": "C1(CCC(N1OC(CCCCC(=O)O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "C1(CCC(N1OC(CCCCC(=O)O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl succinimidyl adipate (4.5 g, 17.5 mmol), chlorotrimethylsilane (11.1 ml, 87.5 mmol) and sodium iodide (13.1 g, 87.5 mmol) in 10 ml of acetonitrile was heated at reflux for 12 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate. The reaction mixture was washed repea... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1 | Other | C(C)#N.C(C)(=O)OCC | null | null | COC(=O)CCCCC(=O)ON1C(=O)CCC1=O>C(C)#N.C(C)(=O)OCC>O=C(O)CCCCC(=O)ON1C(=O)CCC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1ed7b4f414b94a45a886575dff6a9247 | O=C1CCC(=O)N1O.O=C1CCCC(=O)O1>>O=C(O)CCCC(=O)O.O=C1CCC(=O)N1O | Cl.C1(CCCC(=O)O1)=O.ON1C(CCC1=O)=O.C(C)N(CC)CC>>C(CCCC(=O)O)(=O)O.ON1C(CCC1=O)=O | [O:3]=[C:14]1[CH2:13][CH2:12][C:11](=[O:10])[N:16]1[OH:17].[O:1]=[C:2]1[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[O:9]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[OH:9].[O:10]=[C:11]1[CH2:12][CH2:13][C:14](=[O:15])[N:16]1[OH:17] | O=C1CCC(=O)N1O.O=C1CCCC(=O)O1 | O=C(O)CCCC(=O)O.O=C1CCC(=O)N1O | null | null | ClCCl | Functional Group Addition | OtherReaction | 9788dff2a98060b369bf714f8584edc4415267d343a63106d8d813b535989e56 | 1376c454abf78648dfe038ea03fdaa7b24a002c84c34f33b09fae83b7b2b4302 | O=C1CCC(=O)N1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-1.[O;D1;H0:9]=[C:10]1-[C:11]-[C:12]-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[#7:15]-1-[O;D1;H1:16]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:14])-[C:3]-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8].[O;D1;H0:9]=[C:10]1-[C:11]-[C:12]-[C;H0;D3;+0:13](=... | null | [] | null | null | 40 | MINUTE | One mole of glutaric anhydride and one mole of N-hydroxysuccinimide were treated in dichloromethane with 1.2 equivalents of triethylamine. This reaction was stirred for 40 minutes, acidified by the addition of 0.5N hydrochloric acid (HCl) (aqueous), and then extracted with ethyl acetate to form mono N-hydroxysuccinimid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Tertiary amide | Carboxylic acid.Carboxylic acid.Tertiary amide | C1CC[NH]C1.C1CCOCC1 | C1CC[NH]C1 | C1CC[NH]C1 | Other | ClCCl | null | 0.666667 | O=C1CCC(=O)N1O.O=C1CCCC(=O)O1>ClCCl>O=C(O)CCCC(=O)O.O=C1CCC(=O)N1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e5f02821feab4e68bc5f37db01f810ce | O=P1(Oc2ccccc2)CCCC(CI)O1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC1CCCP(=O)(Oc2ccccc2)O1 | [N-]=[N+]=[N-].[Na+].O(C1=CC=CC=C1)P1(OC(CCC1)CI)=O>>O(C1=CC=CC=C1)P1(OC(CCC1)CN=[N+]=[N-])=O | I[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][P:9](=[O:10])([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[O:18]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][P:9](=[O:10])([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[O:18]1 | O=P1(Oc2ccccc2)CCCC(CI)O1.[N-]=[N+]=[N-] | [N-]=[N+]=NCC1CCCP(=O)(Oc2ccccc2)O1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1=CC=CC=C1.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | O=P1(Oc2ccccc2)CCCCO1 | I-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[#15:5].[N-;H0;D1:6]=[#7;+:7]=[N;-;D1;H0:8]>>[#15:5]-[#8:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8])-[C:3] | 96 | [{"value": 96.0, "product": "O(C1=CC=CC=C1)P1(OC(CCC1)CN=[N+]=[N-])=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension containing two equivalents of sodium azide, one equivalent of the above-prepared iodonated oxaphosphorinane and a catalytic amount of about 0.1 equivalent of tetrabutylammonium bromide in benzene/DMF (1:1) was heated to 60-80 degrees C. for 16 hours to produce 2-phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphospho... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | C1CC[P]OC1.c1ccccc1 | I- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1=CC=CC=C1.CN(C)C=O | null | null | O=P1(Oc2ccccc2)CCCC(CI)O1.[N-]=[N+]=[N-]>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1=CC=CC=C1.CN(C)C=O>[N-]=[N+]=NCC1CCCP(=O)(Oc2ccccc2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-722703b0bdef43369d32d6d5d22467c1 | CCOP(=O)(CCC(C)=O)OCC.Cn1cncn1>>CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC | CN1N=CN=C1.O=C(CCP(OCC)(OCC)=O)C>>OC(CCP(OCC)(OCC)=O)(C1=NC=NN1C)C | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][C:8]([CH3:9])=[O:10])[O:17][CH2:18][CH3:19].[cH:11]1[n:12][cH:13][n:14][n:15]1[CH3:16]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][C:8]([CH3:9])([OH:10])[c:11]1[n:12][cH:13][n:14][n:15]1[CH3:16])[O:17][CH2:18][CH3:19] | CCOP(=O)(CCC(C)=O)OCC.Cn1cncn1 | CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 03bf5a0330805602a21b72eff83b38685dda6b1b4723d3339e24164dfe8e144b | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1nc[nH]n1 | [C;D1;H3:1]-[#7;a:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[cH;D2;+0:6]:1.[C:7]-[C:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11]>>[C:7]-[C:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[OH;D1;+0:11])-[c;H0;D3;+0:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[#7;a:2]:1-[C;D1;H3:1] | 28.4 | [{"value": 28.0, "product": "OC(CCP(OCC)(OCC)=O)(C1=NC=NN1C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.4, "product": "OC(CCP(OCC)(OCC)=O)(C1=NC=NN1C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-methyl-1,2,4-triazole (3.0 g, 36.1 mmol) in tetrahydrofurane (60 ml) was added n-buthyllithium (43.3 mmol, 1.2 eq) at -78° C. under nitrogen. The mixture was stirred for 1 hour, then diethyl 3-oxo-butylphosphonate (8.3 g, 39.7 mmol, 1.1 eq) was added. The mixture was stirred for 2 hours and quenched ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1 | null | O1CCCC1 | null | 1 | CCOP(=O)(CCC(C)=O)OCC.Cn1cncn1>O1CCCC1>CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3ce26230d98c428aa71701a3a4059bb1 | CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC>>Cn1ncnc1C(C)(O)CCP(=O)(O)O | CO.OC(CCP(OCC)(OCC)=O)(C1=NC=NN1C)C.C[Si](C)(C)Br.C1C(C)O1>>OC(CCP(O)(O)=O)(C1=NC=NN1C)C | CC[O:14][P:12]([CH2:11][CH2:10][C:7]([c:6]1[n:2]([CH3:1])[n:3][cH:4][n:5]1)([CH3:8])[OH:9])(=[O:13])[O:15]CC>>[CH3:1][n:2]1[n:3][cH:4][n:5][c:6]1[C:7]([CH3:8])([OH:9])[CH2:10][CH2:11][P:12](=[O:13])([OH:14])[OH:15] | CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC | Cn1ncnc1C(C)(O)CCP(=O)(O)O | null | null | C(Cl)Cl.C(C)OCC | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1nc[nH]n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propylphosphonate (1.2 g, 4.12 mmol) in CH2Cl2 (24 ml) was added TMSBr (2.72 ml, 20.6 mmol, 5 eq) at room temperature under nitrogen. The reaction mixture was stirred for 16 hours. Then methanol (12 ml) was added to the mixture. After stirring f... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncn[nH]1 | Other | C(Cl)Cl.C(C)OCC | null | 16 | CCOP(=O)(CCC(C)(O)c1ncnn1C)OCC>C(Cl)Cl.C(C)OCC>Cn1ncnc1C(C)(O)CCP(=O)(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-52a1540eb16c4bf9bce3f0fea0589617 | COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C>>CC(C)(C)c1nc(C=Cc2cccnc2)nc(C(C)(C)C)c1O | CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)CC(O)C=1C=NC=CC1.C(C)(=O)[O-].[Na+].C(C)(=O)OC(C)=O>>CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C=CC=1C=NC=CC1 | COCCOC[O:23][c:22]1[c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:6][c:7]([CH2:8][CH:9](O)[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[n:16][c:17]1[C:18]([CH3:19])([CH3:20])[CH3:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[n:6][c:7]([CH:8]=[CH:9][c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[n:16][c:17]([C:18]([CH3:19])([CH3:20])[CH... | COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C | CC(C)(C)c1nc(C=Cc2cccnc2)nc(C(C)(C)C)c1O | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3ccc784524ce127fa6d3f650df3c3c4b6f3f837eae77b44298f6abb14acc1f54 | c8923c733b00c09c1c92f840cc716f59d71fd45875244f4527080cb33a30e6d8 | C(=Cc1ncccn1)c1cccnc1 | C-O-C-C-O-C-[O;H0;D2;+0:1]-[c:2]1:[c:3](-[C:4]):[#7;a:5]:[c:6](-[CH2;D2;+0:7]-[CH;D3;+0:8](-O)-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]):[#7;a:14]:[c:15]:1-[C:16]>>[C:4]-[c:3]1:[#7;a:5]:[c:6](-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]):[#7;a:14]:[c:15](-[C:16]):[c:2]:1-[OH;D1;+0:1] | 49.8 | [{"value": 40.0, "product": "CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C=CC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": "CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C=CC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 190 | CELSIUS | null | null | A mixture of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3 -pyridinyl)-2-pyrimidineethanol (350 mg), sodium acetate (10 g) and acetic anhydride (7 mL) in toluene (100 mL) is heated at reflux for 8 hours. The reaction mixture is cooled and the solvent is evaporated. Dichlorobenzene (30 mL) is added and th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Aromatic alcohol | null | null | c1cncnc1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | 190 | null | COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C>C1(=CC=CC=C1)C>CC(C)(C)c1nc(C=Cc2cccnc2)nc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-edc7f325608347ef9c24c27f7f1bcf0b | CC(=O)OC(C(=O)C(C)(C)C)C(=O)C(C)(C)C.[NH4+]>>Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1 | C(C)(=O)OC(C(C(C)(C)C)=O)C(C(C)(C)C)=O.C(C)(=O)[O-].[NH4+]>>CC(C)(C)C=1N=C(OC1C(C(C)(C)C)=O)C | O=[C:2]([CH3:1])[O:16][CH:9]([C:4](=O)[C:5]([CH3:6])([CH3:7])[CH3:8])[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15].[NH4+:3]>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[c:9]([C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[o:16]1 | CC(=O)OC(C(=O)C(C)(C)C)C(=O)C(C)(C)C.[NH4+] | Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1 | null | null | C(C)(=O)O.[OH-].[Na+].O | Aromatic Heterocycle Formation | OtherReaction | 513d6dc05be315534012c4ee040873e6fa4aee581b54c11940793fd4174b356e | d0e9f772275cfdec8d5b1c1cabb0557f331ce07d5a2ae2cab05542daef89be5d | c1cocn1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:3]-[CH;D3;+0:4](-[C:5](-[C:6])=[O;D1;H0:7])-[C;H0;D3;+0:8](=O)-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[NH4+;D0:13]>>[C:6]-[C:5](=[O;D1;H0:7])-[c;H0;D3;+0:4]1:[o;H0;D2;+0:3]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:13]:[c;H0;D3;+0:8]:1-[C:9](-[C;D1;H3:10])(-[C;D1;H3:1... | 92.5 | [{"value": 91.0, "product": "CC(C)(C)C=1N=C(OC1C(C(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "CC(C)(C)C=1N=C(OC1C(C(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(acetyloxy)-2,2,6,6-tetramethyl 3,5 heptanedione (22 g, 0.09 mol) in acetic acid (100 mL) is treated with ammonium acetate (44 g). The reaction mixture is heated at reflux overnight. The reaction mixture is diluted with water and neutralized (to pH 5) by the addition of aqueous sodium hydroxide. The pro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester | Ketone | null | c1cocn1 | c1cocn1 | HO- | C(C)(=O)O.[OH-].[Na+].O | null | null | CC(=O)OC(C(=O)C(C)(C)C)C(=O)C(C)(C)C.[NH4+]>C(C)(=O)O.[OH-].[Na+].O>Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c60e5ad8c697434fa67dd662437ae58d | Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1.[NH4+]>>Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1 | CC(C)(C)C=1N=C(OC1C(C(C)(C)C)=O)C.[OH-].[NH4+]>>CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C | O=[C:11]([c:9]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[n:16][c:2]([CH3:1])[o:10]1)[C:12]([CH3:13])([CH3:14])[CH3:15].[NH4+:3]>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[c:9]([OH:10])[c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[n:16]1 | Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1.[NH4+] | Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 2de4a4cfe89cbfa88f952fe89cdb000b1990949ca6496c79a95865617e4875da | f0f6c0aea42e131fa87fd5383e2df959f9ded0709f604973ae337694df8652bd | c1cncnc1 | O=[C;H0;D3;+0:1](-[c:2]1:[o;H0;D2;+0:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[n;H0;D2;+0:6]:[c;H0;D3;+0:7]:1-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15].[NH4+;D0:16]>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])(-[C;D1;H3:15])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:4](-[C;D1;H3:... | 75 | [{"value": 75.0, "product": "CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-[4-(1,1-dimethylethyl)-2 methyl-5-oxazolyl]-2,2-dimethyl-1 propanone (8.5 g, 38 mmol) and concentrated ammonium hydroxide (100 mL) is heated at 180° C. for 36 hours in a steel bomb. The reaction mixture is cooled and the excess ammonia is evaporated on the rotovap. The pH of the resulting mixture is adju... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Aromatic alcohol | c1cocn1 | c1cncnc1 | c1cncnc1 | HO- | null | null | null | Cc1nc(C(C)(C)C)c(C(=O)C(C)(C)C)o1.[NH4+]>>Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9502ecdb7f4d41659d2e170dd6a9e06b | COCCOCCl.Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1>>COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C | CC(C)(C)C1=NC(=NC(=C1O)C(C)(C)C)C.[H-].[Na+].COCCOCCl>>CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)C | Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][c:8]1[c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[n:14][c:15]([CH3:16])[n:17][c:18]1[C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[n:14][c:15]([CH3:16])[n:17][c:18]1[C:19]([CH3:20])([CH3:21])[CH3... | COCCOCCl.Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1 | COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C | null | null | C1CCOC1.O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1cncnc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[C:10]):[c:11]:1-[OH;D1;+0:12]>>[C:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[C:10]):[c:11]:1-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[#8:2]-[C:3] | null | [] | null | null | 4 | HOUR | 4,6-Bis(1,1-dimethylethyl) 5 hydroxy-2-methyl pyrimidine (9.8 g, 44.1 mmoles) is dissolved in 100 mL of tetrahydrofuran and added dropwise to a suspension of sodium hydride (1.2 g, 48.5 mmoles) in THF (50 mL) at 0° C. The reaction mixture is warmed to room temperature over 15 minutes. 2-Methoxyethoxymethyl chloride (7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1cncnc1 | HCl | C1CCOC1.O1CCCC1 | null | 4 | COCCOCCl.Cc1nc(C(C)(C)C)c(O)c(C(C)(C)C)n1>C1CCOC1.O1CCCC1>COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f8b7c078c1f34c738ce919fd25bc8ca3 | COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C.O=Cc1cccnc1>>COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C | N1=CC(=CC=C1)C=O.C(CCC)[Li].CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)C>>CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)CC(O)C=1C=NC=CC1 | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[n:14][c:15]([CH3:16])[n:25][c:26]1[C:27]([CH3:28])([CH3:29])[CH3:30].[CH:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[n:14][c:1... | COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C.O=Cc1cccnc1 | COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 995c7a5cbf37230035b00de18cd91aae550f6b3916b2678b4c13427cfa9d9370 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1cnc(CCc2cccnc2)nc1 | [CH3;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[OH;D1;+0:7]-[CH;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6])-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13] | 50 | [{"value": 50.0, "product": "CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)CC(O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "CC(C)(C)C1=NC(=NC(=C1OCOCCOC)C(C)(C)C)CC(O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | n-Butyllithium (1.5 mL of 1.6M solution in hexane, 2.4 mmol) is added dropwise to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine (750 mg, 2.4 mmol) in dry THF (12 mL) at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature for 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1cncnc1.c1ccncc1 | null | C1CCOC1 | null | 0.5 | COCCOCOc1c(C(C)(C)C)nc(C)nc1C(C)(C)C.O=Cc1cccnc1>C1CCOC1>COCCOCOc1c(C(C)(C)C)nc(CC(O)c2cccnc2)nc1C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e13a4705a5441f1b9a49bbde17a9f3c | Br.Nc1nc2cc(Cl)c(Cl)cc2[nH]1>>Clc1cc2nc(Br)[nH]c2cc1Cl | NC=1NC2=C(N1)C=C(C(=C2)Cl)Cl.Br.N(=O)[O-].[Na+]>>BrC=1NC2=C(N1)C=C(C(=C2)Cl)Cl | [BrH:7].N[c:6]1[n:5][c:4]2[cH:3][c:2]([Cl:1])[c:11]([Cl:12])[cH:10][c:9]2[nH:8]1>>[Cl:1][c:2]1[cH:3][c:4]2[n:5][c:6]([Br:7])[nH:8][c:9]2[cH:10][c:11]1[Cl:12] | Br.Nc1nc2cc(Cl)c(Cl)cc2[nH]1 | Clc1cc2nc(Br)[nH]c2cc1Cl | null | null | O | Miscellaneous | OtherReaction | 857c8f1e64ccd27863105cbe22e92e556631542f0a4a501417bddd8e9b7bc616 | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2[nH]cnc2c1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[BrH;D0;+0:6]>>[Br;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 26 | [{"value": 26.0, "product": "BrC=1NC2=C(N1)C=C(C(=C2)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Amino-5,6-dichlorobenzimidazole (3 g, 16 mmole) was suspended in 150 ml of water and brought into solution with 2 ml of HBr. Sodium nitrite (3.3 g, 55 mmole) was then added and the mixture was stirred at room temperature for 1 hr. Excess CuBr2 was then added and the mixture was heated on a steam bath for 1 hr. The aq... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | O | null | 1 | Br.Nc1nc2cc(Cl)c(Cl)cc2[nH]1>O>Clc1cc2nc(Br)[nH]c2cc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2ecad7da38b24e3d9a065c9be68c87c0 | CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1.Clc1nc2cc(Cl)c(Cl)cc2[nH]1>>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O | FC(C(O[Si](C)(C)C)=N[Si](C)(C)C)(F)F.ClC=1NC2=C(N1)C=C(C(=C2)Cl)Cl.[Si](C)(C)(C)S(=O)(=O)C(F)(F)F.C(C)(=O)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)[C@H](O1)COC(C1=CC=CC=C1)=O>>ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=C(C(=C2)Cl)Cl | CC(=O)O[C@@H:5]1[O:4][C@H:3]([CH2:2][O:1]C(=O)c2ccccc2)[C@@H:20]([O:21]C(=O)c2ccccc2)[C@H:18]1[O:19]C(=O)c1ccccc1.[nH:6]1[c:7]([Cl:8])[n:9][c:10]2[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]12>>[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]23)[... | CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1.Clc1nc2cc(Cl)c(Cl)cc2[nH]1 | OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | c642901dd79f8e49f810fd25b8a46c1aaa649572bdb579ffd97b77f2c228f59e | 21d64cf2032d78ffc90699b40c7d706de3ba73747db98398625e977d93d000d4 | c1ccc2c(c1)ncn2[C@H]1CCCO1 | C-C(=O)-O-[C@@H;D3;+0:1]1-[#8:2]-[C:3](-[C:4]-[O;H0;D2;+0:5]-C(=O)-c2:c:c:c:c:c:2)-[C:6](-[O;H0;D2;+0:7]-C(=O)-c2:c:c:c:c:c:2)-[C:8]-1-[O;H0;D2;+0:9]-C(=O)-c1:c:c:c:c:c:1.[Cl;D1;H0:10]-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[nH;D2;+0:17]:1>>[Cl;D1;H0:10]-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[n;H... | null | [] | 75 | CELSIUS | 45 | MINUTE | 2,5,6-Trichlorobenzimidazole (700 mg, 0.0032 moles) was dissolved in acetonitrile and BSTFA (1 ml, 0.0038 moles) was added. The mixture was heated at 75° C. for 20 minutes. TMSTf (1 ml, 0.0051 moles) and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (1.9 g, 0.0038 moles) were added while heating was continued for 45 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester.Ether | Ether.Primary alcohol.Secondary alcohol.Secondary alcohol | C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | C1CCOC1.c1ccc2[nH]cnc2c1 | C1CCOC1.c1ccc2[nH]cnc2c1 | HO- | C(C)#N | 75 | 0.75 | CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1.Clc1nc2cc(Cl)c(Cl)cc2[nH]1>C(C)#N>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2985c0e734b84302990b58baa671a5d0 | ClC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OCc1ccccc1.O=[N+]([O-])c1cc2nc(Cl)[nH]c2cc1[N+](=O)[O-]>>O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-] | ClC=1NC2=C(N1)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-].C(C1=CC=CC=C1)O[C@H]1C(O[C@@H]([C@H]1OCC1=CC=CC=C1)COCC1=CC=CC=C1)Cl.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>ClC1=NC2=C(N1[C@H]1[C@H](OCC3=CC=CC=C3)[C@H](OCC3=CC=CC=C3)[C@H](O1)COCC1=CC=CC=C1)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-] | Cl[CH:11]1[O:12][C@H:13]([CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C@@H:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[C@H:32]1[O:33][CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[n:7][c:8]([Cl:9])[nH:10][c:41]2[cH:42][c:43]1[N+:44](=[... | ClC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OCc1ccccc1.O=[N+]([O-])c1cc2nc(Cl)[nH]c2cc1[N+](=O)[O-] | O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-] | null | null | CC#N.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6c291171bb6e4032d543e33eca92380ebcd07cbb2d3668ca761f05e7d5702513 | dfebb98912d1cf9ca9bea5f0eb687cda9773eb2f7ac7378282049e4233a1d769 | c1ccc(COC[C@H]2O[C@@H](n3cnc4ccccc43)[C@H](OCc3ccccc3)[C@@H]2OCc2ccccc2)cc1 | Cl-[CH;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6].[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:14]:1>>[#8:6]-[C:5]1-[C:4]-[C:3]-[#8:2]-[C@H;D3;+0:1]-1-[n;H0;D3;+0:14]1:[c:12](:[c:13]):[c:10](:[c:11]):[#7;a:9]:[c:8]:1-[Cl;D1;H0:7] | 35 | [{"value": 35.0, "product": "ClC1=NC2=C(N1[C@H]1[C@H](OCC3=CC=CC=C3)[C@H](OCC3=CC=CC=C3)[C@H](O1)COCC1=CC=CC=C1)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 15 | MINUTE | To a mixture of 0.541 g (2.23 mmol) of 2-chloro-5,6-dinitrobenzimidazole in 12 mL of MeCN, was added 0.558 mL (2.23 mmol) of BSA. The reaction mixture was stirred at 75° C. for 15 min to give a clear solution. This solution was treated with the above MeCN solution of 2,3,5-tri-O-benzyl-D-ribofuranosyl chloride and 0.56... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether | Ether | C1CCOC1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.C1CCOC1 | c1ccc2[nH]cnc2c1.C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CC#N.CCOC(=O)C | 75 | 0.25 | ClC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OCc1ccccc1.O=[N+]([O-])c1cc2nc(Cl)[nH]c2cc1[N+](=O)[O-]>CC#N.CCOC(=O)C>O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-888777079fb14ca3a86b3b24b2f9e593 | O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-]>>O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2cc1[N+](=O)[O-] | CO.ClC1=NC2=C(N1[C@H]1[C@H](OCC3=CC=CC=C3)[C@H](OCC3=CC=CC=C3)[C@H](O1)COCC1=CC=CC=C1)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-].B(Cl)(Cl)Cl>>ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-] | c1ccc(C[O:15][CH2:14][C@H:13]2[O:12][C@@H:11]([n:10]3[c:8]([Cl:9])[n:7][c:6]4[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:22]([N+:23](=[O:24])[O-:25])[cH:21][c:20]43)[C@H:18]([O:19]Cc3ccccc3)[C@@H:16]2[O:17]Cc2ccccc2)cc1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[n:7][c:8]([Cl:9])[n:10]([C@@H:11]3[O:12][C@H:13]([CH2:14][OH:15])[C@... | O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-] | O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2cc1[N+](=O)[O-] | null | null | C(Cl)Cl.CCOC(=O)C | Deprotection | OtherReaction | a2ffff3fbeceaaf24517526a2c17f5b86a650947c9a6af47e884fd6d27207539 | e242dbd29e2c64f486ea1ce31c428d361e20176899376328dc1f9a6880949e31 | c1ccc2c(c1)ncn2[C@H]1CCCO1 | C(-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2)-[C:8]-1-[O;H0;D2;+0:9]-C-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 77.6 | [{"value": 77.6, "product": "ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=C(C(=C2)[N+](=O)[O-])[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | To a solution of 0.464 g (0.719 mmol) of 60 in 12 mL of CH2Cl2, was added dropwise 8.4 mL of 1M BCl3 at -78° C. The reaction mixture was stirred at -78° C. for 2 h and then at -40° C. for 2 h. MeOH (5 mL) was added and stirring was continued at -40° C. for 10 min. The reaction mixture was diluted with EtOAc (75 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Primary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]cnc2c1.C1CCOC1 | Other | C(Cl)Cl.CCOC(=O)C | -78 | 2 | O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c2cc1[N+](=O)[O-]>C(Cl)Cl.CCOC(=O)C>O=[N+]([O-])c1cc2nc(Cl)n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2cc1[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9fe5815b9f6446a0bb918644fe3631c0 | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.Clc1cc(Cl)c2[nH]c(Cl)nc2c1>>CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Cl)cc(Cl)cc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O | ClC=1NC2=C(N1)C=C(C=C2Cl)Cl.C(C)(=O)O[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C(=NC2=C1C=C(C=C2Cl)Cl)Cl | CC(=O)O[C@@H:8]1[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@@H:26]([O:27][C:28]([CH3:29])=[O:30])[C@H:21]1[O:22][C:23]([CH3:24])=[O:25].[nH:9]1[c:10]([Cl:11])[n:12][c:13]2[cH:19][c:17]([Cl:18])[cH:16][c:14]([Cl:15])[c:20]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[c:10]([Cl:11])[n:12][c:13]3[c... | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.Clc1cc(Cl)c2[nH]c(Cl)nc2c1 | CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Cl)cc(Cl)cc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | CC#N.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 808be96b2b3729670d01959e9d8dd2b734689aada507d6de2ba46319ea398d03 | ae9dd19f446bf9c0f4758602be629bf1e647ce5bccda6016d39f2be87aad806d | c1ccc2c(c1)ncn2[C@H]1CCCO1 | C-C(=O)-O-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[Cl;D1;H0:10]-[c:11]1:[#7;a:12]:[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[c:15](-[Cl;D1;H0:16]):[c:17]:[c;H0;D3;+0:18](-[Cl;D1;H0:19]):[c;H0;D3;+0:20]:2:[nH;D2;+0:21]:1>>[C;D1;H3:8]-[C:7](=[O;D1;H0:9])-[#8:6]-[C:5]1-[C:4]-[C:3]-[#8:2]-[C@... | 71.3 | [{"value": 71.3, "product": "C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C(=NC2=C1C=C(C=C2Cl)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 15 | MINUTE | To a suspension of 1.362 g (6.15 mmol) of 2,4,6-trichlorobenzimidazole in 31 mL of MeCN, was added 1.52 mL (6.15 mmol) of BSA. The reaction mixture was stirred at 80° C. for 15 min to give a clear solution. This solution was treated with 2.153 g (6.675 mmol) of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose and 1.426 mL (7.38... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether | Aromatic halide.Ether | C1CCOC1.c1ccc2[nH]cnc2c1 | C1CCOC1.c1ccc2nc[nH]c2c1 | C1CCOC1.c1ccc2nc[nH]c2c1 | HO- | CC#N.CCOC(=O)C | 80 | 0.25 | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.Clc1cc(Cl)c2[nH]c(Cl)nc2c1>CC#N.CCOC(=O)C>CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Cl)cc(Cl)cc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6b415f062b484284bdb4a8dfbb581067 | CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O>>OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](O)[C@@H]1O | ClC1=NC2=C(N1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)C=CC(=C2Br)Br>>ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=CC(=C2Br)Br | CC(=O)[O:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[c:11]([Br:12])[c:13]([Br:14])[cH:15][cH:16][c:17]23)[C@H:18]([O:19]C(C)=O)[C@@H:20]1[O:21]C(C)=O>>[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[c:11]([Br:12])[c:13]([Br:14])[cH:15][cH:16][c:17]23)[C@H:18]([OH:19])[C@@H:20]1[OH:... | CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O | OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](O)[C@@H]1O | null | null | N.CO | Reduction | OtherReaction | b1205f31a625dd524c4abcf6ea407c1a38966308677d8535d59411f69b7afe49 | 53784a05a6c1858c11deb702d4a1392e7852c783da9a57d4771755f87682c932 | c1ccc2c(c1)ncn2[C@H]1CCCO1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#8:4]-[C:5](-[C:6]-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#8:4]-[C:5](-[C:6]-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | null | [] | null | null | null | null | A solution of 0.529 g (0.930 mmol) of 84 in 25 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 h. Volatile materials were removed by evaporation and coevaporation with MeOH (3 x, bath temperature<40° C.). The resulting solid was recrystallized from MeOH/H2O to give 0.316 g (2 crops, 77%) of 8... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol | null | null | C1CCOC1.c1cc2nc[nH]c2cc1 | HO- | N.CO | null | null | CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O>N.CO>OC[C@H]1O[C@@H](n2c(Cl)nc3c(Br)c(Br)ccc32)[C@H](O)[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-970b971bcff641f38c1bdbadc4189929 | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3ccc(Cl)cc32)[C@H](O)[C@@H]1O>>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Br)c(Cl)cc32)[C@H](O)[C@@H]1O | ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=C(C=C2)Cl.BrBr.O>>BrC1=CC2=C(N(C(=N2)Cl)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)C=C1Cl | Br[Br:13].[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[cH:11][cH:12][c:14]([Cl:15])[cH:16][c:17]23)[C@H:18]([OH:19])[C@@H:20]1[OH:21]>>[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[c:14]([Cl:15])[cH:16][c:17]23)[C@H:18]([OH:19])[C@@H:20]1[OH:21] | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3ccc(Cl)cc32)[C@H](O)[C@@H]1O | OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Br)c(Cl)cc32)[C@H](O)[C@@H]1O | null | null | O | Functional Group Interconversion | Bromination | 85478af56c963644b81844bf5b7a011f7757bd89cb89f72df54391190362ce77 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)ncn2[C@H]1CCCO1 | Br-[Br;H0;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[cH;D2;+0:11]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1-[Cl;D1;H0:2] | null | [] | null | null | 3 | HOUR | To a suspension of 0.319 g (1.0 mmol) of 2,6-dichloro-1-β-D-ribofuranosylbenzimidazole in 10 mL of H2O, was added dropwise a sat. solution of Br2 /H2O at room temperature. After the addition has been completed, stirring was continued for 3 h. The reaction mixture was filtered and the solid was washed with portions of H... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2nc[nH]c2c1 | c1ccc2[nH]cnc2c1 | C1CCOC1.c1ccc2[nH]cnc2c1 | HBr | O | null | 3 | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3ccc(Cl)cc32)[C@H](O)[C@@H]1O>O>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Br)c(Cl)cc32)[C@H](O)[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a691585e35b4638beb7daeb4f74ee31 | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)ccc32)[C@H](O)[C@@H]1O>>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Br)cc32)[C@H](O)[C@@H]1O | ClC1=NC2=C(N1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C=CC(=C2)Cl.BrBr.O>>BrC=1C(=CC2=C(N(C(=N2)Cl)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)C1)Cl | Br[Br:15].[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[cH:11][c:12]([Cl:13])[cH:14][cH:16][c:17]23)[C@H:18]([OH:19])[C@@H:20]1[OH:21]>>[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([n:6]2[c:7]([Cl:8])[n:9][c:10]3[cH:11][c:12]([Cl:13])[c:14]([Br:15])[cH:16][c:17]23)[C@H:18]([OH:19])[C@@H:20]1[OH:21] | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)ccc32)[C@H](O)[C@@H]1O | OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Br)cc32)[C@H](O)[C@@H]1O | null | null | O | Functional Group Interconversion | Bromination | e4bd10f799acb6c33603007dd6dc4250314cca1654097931bb81aab38c07d1cb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)ncn2[C@H]1CCCO1 | Br-[Br;H0;D1;+0:1].[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9](-[Cl;D1;H0:10]):[cH;D2;+0:11]:[c:12]:[c:13]:1:2>>[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9](-[Cl;D1;H0:10]):[c;H0;D3;+0:11](-[Br;H0;D1;+0:1]):[c:12]:[c:13]:1:2 | null | [] | null | null | 6 | HOUR | To a suspension of 0.110 g (0.313 mmol, as C12H12Cl2N2O4MeOH) of 2,5-dichloro-1-β-D-ribofuranosylbenzimidazole in 3 mL of H2O was added dropwise 10 mL of a sat. solution of Br2 /H2O at room temperature. After the addition has been completed, stirring was continued for 6 h. The reaction mixture was filtered and the soli... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | C1CCOC1.c1ccc2[nH]cnc2c1 | HBr | O | null | 6 | BrBr.OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)ccc32)[C@H](O)[C@@H]1O>O>OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Br)cc32)[C@H](O)[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-54ee79e104304afe86e6fd203bcf0aac | CC(=O)c1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl>>CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1 | Cl.ClC1=C(C=NC=C1)[N+](=O)[O-].NC1=CC=C(C=C1)C(C)=O>>Cl.C(C)(=O)C1=CC=C(C=C1)NC1=C(C=NC=C1)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:18][cH:19]1.Cl[c:9]1[cH:10][cH:11][n:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[N+:15](=[O:16])[O-:17])[cH:18][cH:19]1 | CC(=O)c1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl | CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[#7;+:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;+:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 8 | HOUR | A solution of 4-chloro-3-nitropyridine hydrochloride (9.75 g, 50 mmol) in ethanol (40 ml) was added to a slurry of p-aminoacetophenone (6.76 g, 50 ml) in ethanol (25 ml), and the mixture was stirred at room temperature overnight. The mixture was chilled in ice, and the yellow solid filtered off and dried in vacuo. Yiel... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HCl | C(C)O | null | 8 | CC(=O)c1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl>C(C)O>CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a022d8b3e334c6db46c27f865df462d | CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1>>CC(=O)c1ccc(Nc2ccncc2N)cc1 | Cl.C(C)(=O)C1=CC=C(C=C1)NC1=C(C=NC=C1)[N+](=O)[O-].[OH-].[Na+].ClCCl>>C(C)(=O)C1=CC=C(C=C1)NC1=C(C=NC=C1)N | O=[N+:15]([O-])[c:14]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:17][cH:16]2)[cH:10][cH:11][n:12][cH:13]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[NH2:15])[cH:16][cH:17]1 | CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1 | CC(=O)c1ccc(Nc2ccncc2N)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccncc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 3.5 | HOUR | 4-(4-Acetylphenyl)amino-3-nitropyridine hydrochloride (2.0 g, 71.8 mmol) was partitioned between aqueous sodium hydroxide and dichloromethane (3×20 ml). The combined organic phases were washed with water (20 ml) and concentrated under reduced pressure to give a solid. Ethanol (20 ml) was added, and the solution was hyd... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Pd].C(C)O | null | 3.5 | CC(=O)c1ccc(Nc2ccncc2[N+](=O)[O-])cc1>[Pd].C(C)O>CC(=O)c1ccc(Nc2ccncc2N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c0a37bba41f04afd9a67999b126b0e4c | CCO.Cc1nc2cnccc2n1-c1ccc(C#N)cc1.[OH-]>>Cc1nc2cnccc2n1-c1ccc(C(=O)O)cc1 | C(#N)C1=CC=C(C=C1)N1C(=NC=2C=NC=CC21)C.[OH-].[Na+].C(C)O>>CC=1N(C2=C(C=NC=C2)N1)C1=CC=C(C(=O)O)C=C1 | CC[OH:17].N#[C:15][c:14]1[cH:13][cH:12][c:11](-[n:10]2[c:2]([CH3:1])[n:3][c:4]3[cH:5][n:6][cH:7][cH:8][c:9]32)[cH:19][cH:18]1.[OH-:16]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][cH:7][cH:8][c:9]2[n:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1 | CCO.Cc1nc2cnccc2n1-c1ccc(C#N)cc1.[OH-] | Cc1nc2cnccc2n1-c1ccc(C(=O)O)cc1 | null | null | null | Acylation | OtherReaction | e41cdaf6ecb9257286a05c8e01433d124042c5939fb4d758964487a1f4637b56 | e38d1b350c527156572f58ef95bb65354ed43ce776b83f166b6fd042d5d9aca9 | c1ccc(-n2cnc3cnccc32)cc1 | C-C-[OH;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | null | null | A mixture of 1-(4-cyanophenyl)-2-methylimidazo[4,5-c]pyridine (12.0 g, 51.3 mmol) and 40% aqueous sodium hydroxide (55 ml) in absolute ethanol (55 ml) was heated at reflux for 11/2 hours. The solvent was removed under reduced pressure, and the brown residue was dissolved in water. The solution was chilled to 0° C. by t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Carboxylic acid | null | null | c1nc2ccncc2[nH]1.c1ccccc1 | Other | null | 0 | null | CCO.Cc1nc2cnccc2n1-c1ccc(C#N)cc1.[OH-]>>Cc1nc2cnccc2n1-c1ccc(C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2bc83680343e4dc3bafc2ceb0ba1db4f | N#Cc1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl>>N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1 | C(#N)C1=CC=C(N)C=C1.ClC1=C(C=NC=C1)[N+](=O)[O-].C(C)O>>C(#N)C1=CC=C(C=C1)N1CC(=C(C=C1)N)[N+](=O)[O-] | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:11])[cH:17][cH:18]1.Cl[c:10]1[cH:9][cH:8][n:7][cH:16][c:12]1[N+:13](=[O:14])[O-:15]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH:8]=[CH:9][C:10]([NH2:11])=[C:12]([N+:13](=[O:14])[O-:15])[CH2:16]2)[cH:17][cH:18]1 | N#Cc1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl | N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f4972f1f841e9ba0e8e5b05ae7c079f1d0ec4fa3257eef450b530a4701a53eef | 7f5cb3bfcd0ac63af84eb2f0127a859aff886d9e3621027b9cba876ef76e284f | C1=CCN(c2ccccc2)C=C1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6]:1-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[NH2;D1;+0:10]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:6](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9])-[CH2;D2;+0:5]-[N;H0;D3;+0:4](-[c;H0;D3;+0:11](... | null | [] | null | null | 18 | HOUR | According to the method of J. C. S. Perkin Trans. I, 1979, 135, p-cyanoaniline (6.894 g, 58.4 mmol) was added to a solution of 4-chloro-3-nitropyridine (9.26 g, 58.4 mmol) in ethanol (200 ml) and the mixture was stirred at room temperature for 18 hours. The resulting yellow suspension was poured into 500 ml of ice-cold... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Primary amine | Enamine.Enamine.Enamine | c1ccccc1.c1ccncc1 | c1ccccc1.C1=CC[NH]C=C1 | c1ccccc1.C1=CC[NH]C=C1 | Other | null | null | 18 | N#Cc1ccc(N)cc1.O=[N+]([O-])c1cnccc1Cl>>N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bfb37d5ede1743f48bb523d01f9a756e | N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1>>N#Cc1ccc(Nc2ccncc2N)cc1 | O.O.[Sn](Cl)Cl.C(#N)C1=CC=C(C=C1)N1CC(=C(C=C1)N)[N+](=O)[O-].C(C)O>>NC=1C=NC=CC1NC1=CC=C(C=C1)C#N | O=[N+:14]([O-])[C:13]1=[C:12]([NH2:11])[CH:9]=[CH:10][N:7]([c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16][cH:15]2)[CH2:8]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[NH2:14])[cH:15][cH:16]1 | N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1 | N#Cc1ccc(Nc2ccncc2N)cc1 | null | null | Cl.O | Aromatic Heterocycle Formation | OtherReaction | 85fffbdc141f9269fd47c5c8c23470804b907d6e82687e1e8a45dc48bdd8e240 | 337a1a814f17d27a4b29bfe4c3705248b8640b97c12cd64cb063871ed264acd9 | c1ccc(Nc2ccncc2)cc1 | O=[N+;H0;D3:1](-[O-])-[C;H0;D3;+0:2]1=[C;H0;D3;+0:3](-[NH2;D1;+0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[N;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:11]-1>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:6]:[cH;D2;+0:5]:[c;H0;D3;+0:11]:1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | According to a modification of the method of Pharm. Helv. Acta, 1975, 50, 188., tin dichloride dihydrate (56.4 g, 250 mmol) was added to a suspension of N-(4-cyanophenyl)-4-amino-3-nitropyridine (12.0 g, 50 mmol) in 2N aqueous hydrochloric acid (35 ml), water (150 ml) and ethanol (75 ml) and the resulting mixture was h... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Enamine | Primary amine.Secondary amine | C1=CC[NH]C=C1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Other | Cl.O | null | null | N#Cc1ccc(N2C=CC(N)=C([N+](=O)[O-])C2)cc1>Cl.O>N#Cc1ccc(Nc2ccncc2N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1881b69a76034b96a687673d2018cfa2 | CCC(CC)(CC)C([O-])([O-])[O-].N#Cc1ccc(Nc2ccncc2N)cc1>>Cc1nc2cnccc2n1-c1ccc(C#N)cc1 | NC=1C=NC=CC1NC1=CC=C(C=C1)C#N.C(C)C(C([O-])([O-])[O-])(CC)CC>>C(#N)C1=CC=C(C=C1)N1C(=NC=2C=NC=CC21)C | CC[C:1](CC)(CC)[C:2]([O-])([O-])[O-].[NH2:3][c:4]1[cH:5][n:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][cH:7][cH:8][c:9]2[n:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1 | CCC(CC)(CC)C([O-])([O-])[O-].N#Cc1ccc(Nc2ccncc2N)cc1 | Cc1nc2cnccc2n1-c1ccc(C#N)cc1 | null | null | C(C)(=O)OC(C)=O | Aromatic Heterocycle Formation | OtherReaction | 99d7c43dad96eb181154231219720884f174b11d7b53ea87c0579a92d92b6894 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc(-n2cnc3cnccc32)cc1 | C-C-[C;H0;D4;+0:1](-C-C)(-C-C)-[C;H0;D4;+0:2](-[O-])(-[O-])-[O-].[NH2;D1;+0:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[c:9]:1-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[c:8]:[c:9]:2:[n;H0;D3;+0:10]:1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[... | null | [] | null | null | null | null | A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (9.31 g, 44.3 mmol), triethyl-orthoacetate (40 ml) and acetic anhydride (30 ml) was heated at reflux for 2 hours under nitrogen, cooled, then concentrated under reduced pressure. The brown residue was dissolved in 1M hydrochloric acid and washed with ethyl acetate (2... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccncc1 | c1nc2ccncc2[nH]1 | c1nc2ccncc2[nH]1.c1ccccc1 | HO- | C(C)(=O)OC(C)=O | null | null | CCC(CC)(CC)C([O-])([O-])[O-].N#Cc1ccc(Nc2ccncc2N)cc1>C(C)(=O)OC(C)=O>Cc1nc2cnccc2n1-c1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0b7ac1002a9c48df9ec7bd4af81498e1 | CCCCOC(=O)c1cc(=O)n(CCCC)c2ccccc12>>CCCCn1c(=O)cc(C(=O)O)c2ccccc21 | C(CCC)N1C(C=C(C2=CC=CC=C12)C(=O)OCCCC)=O.[OH-].[Na+].O>>C(CCC)N1C(C=C(C2=CC=CC=C12)C(=O)O)=O | CCCC[O:12][C:10]([c:9]1[cH:8][c:6](=[O:7])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:18]2[c:13]1[cH:14][cH:15][cH:16][cH:17]2)=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CCCCOC(=O)c1cc(=O)n(CCCC)c2ccccc12 | CCCCn1c(=O)cc(C(=O)O)c2ccccc21 | null | null | O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc2ccccc2[nH]1 | C-C-C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 87 | [{"value": 87.0, "product": "C(CCC)N1C(C=C(C2=CC=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "C(CCC)N1C(C=C(C2=CC=CC=C12)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 2.04 g (6.77 mmols) of Compound b, 0.54 g of sodium hydroxide, 40 ml of water and 40 mt of dioxane was stirred at room temperature for 30 minutes. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=5/1) to give 1.44... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1 | Other | O1CCOCC1 | null | 0.5 | CCCCOC(=O)c1cc(=O)n(CCCC)c2ccccc12>O1CCOCC1>CCCCn1c(=O)cc(C(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b0cbbbccef144c919960c98519e95613 | CC(=O)OC(C)=O.Cc1ccc2c(c1)C(=O)C(=O)N2>>CC(=O)N1C(=O)C(=O)c2cc(C)ccc21 | C([O-])(O)=O.[Na+].CC=1C=C2C(C(NC2=CC1)=O)=O.[H-].[Na+].C(C)(=O)OC(C)=O>>C(C)(=O)N1C(=O)C(=O)C2=CC(=CC=C12)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[C:5](=[O:6])[C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]21>>[CH3:1][C:2](=[O:3])[N:4]1[C:5](=[O:6])[C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]21 | CC(=O)OC(C)=O.Cc1ccc2c(c1)C(=O)C(=O)N2 | CC(=O)N1C(=O)C(=O)c2cc(C)ccc21 | null | null | C1(=CC=CC=C1)C | Acylation | Aminolysis of esters | 4a0f25f96b85e6dba36941728b4336dc91b0f1a4d810a1dfde51aa5c4671f3af | 6ade37977f95c6b33058b518e7f2719ed63964406d89a7d8f0d2f46ad042f783 | O=C1Nc2ccccc2C1=O | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]-[C:10]-1=[O;D1;H0:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:6]1-[C:5](=[O;D1;H0:4])-[C:10](=[O;D1;H0:11])-[c:9]:[c:7]-1:[c:8] | 47.6 | [{"value": 47.0, "product": "C(C)(=O)N1C(=O)C(=O)C2=CC(=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.6, "product": "C(C)(=O)N1C(=O)C(=O)C2=CC(=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | With stirring at 0° C., 8.06 g (50.0 mmols) of 5-methylisatin was added by small portions to a solution of 2.00 g (50.0 mmols) of sodium hydride in toluene. While stirring under ice cooling, 4.7 ml (50.0 mmols) of acetic anhydride was dropwise added to the mixture followed by heating at 80° C. for further an hour with ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amide | Substituted dicarboximide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HO- | C1(=CC=CC=C1)C | 0 | null | CC(=O)OC(C)=O.Cc1ccc2c(c1)C(=O)C(=O)N2>C1(=CC=CC=C1)C>CC(=O)N1C(=O)C(=O)c2cc(C)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8e967b2fdeb8454a83c24e9d3bcde951 | CC1(C)CC(=O)CC(=O)C1.O=C(Cl)c1cccc2nnsc12>>CC1(C)CC(=O)C=C(OC(=O)c2cccc3nnsc23)C1 | CC1(CC(CC(C1)=O)=O)C.C(C)N(CC)CC.S1N=NC2=C1C(=CC=C2)C(=O)Cl>>S1N=NC2=C1C(=CC=C2)C(=O)OC2=CC(CC(C2)(C)C)=O | [CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[CH2:7][C:8](=[O:9])[CH2:21]1.Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16]2[n:17][n:18][s:19][c:20]12>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[CH:7]=[C:8]([O:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[n:17][n:18][s:19][c:20]23)[CH2:21]1 | CC1(C)CC(=O)CC(=O)C1.O=C(Cl)c1cccc2nnsc12 | CC1(C)CC(=O)C=C(OC(=O)c2cccc3nnsc23)C1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6735d7ed13afeda04dc34e9d73db8318d3ee19ff8f52c74cf58af2674d2467cd | 7a1f26add480aea147c3ac5da9749e601111e151dc22e68815c1439775d80e22 | O=C1C=C(OC(=O)c2cccc3nnsc23)CCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]1:[#16;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:1.[O;D1;H0:10]=[C:11]1-[C:12]-[C:13]-[C:14]-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[CH2;D2;+0:17]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:16]-[C;H0;D3;+0:15]1=[CH;D2;+0:17]-[C:11](=[O;D1;H0:10])-[C:12]-[C:13]-[C:14]-1)-[c:3](:[c:4]):[c... | 87.5 | [{"value": 87.5, "product": "S1N=NC2=C1C(=CC=C2)C(=O)OC2=CC(CC(C2)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "S1N=NC2=C1C(=CC=C2)C(=O)OC2=CC(CC(C2)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 5.6 g (0.04 mol) of 5,5-dimethyl-1,3-cyclohexanedione are dissolved in a mixture of 4.4 g (0.044 mol) of triethylamine and 120 ml of ethyl acetate. 8.7 g (0.044 mol) of benzothiadiazole-7-carboxylic acid chloride are added dropwise at 15° to 20° C., and the mixture is subsequently stirred overnight at room temperature.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Ketone | Ketone.Ester | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccc2snnc2c1 | HCl | C(C)(=O)OCC | null | 8 | CC1(C)CC(=O)CC(=O)C1.O=C(Cl)c1cccc2nnsc12>C(C)(=O)OCC>CC1(C)CC(=O)C=C(OC(=O)c2cccc3nnsc23)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-48b492e5913b4918978d9c22b2beb223 | CCN(CC)CC.O=C(Cl)c1cccc2nnsc12.O=C([O-])CC(=O)[O-]>>CC1(C)OC(=O)C(c2cccc3nnsc23)C(=O)O1 | S1N=NC2=C1C(=CC=C2)C(=O)Cl.O1CCCC1.C(CC(=O)[O-])(=O)[O-].C(C)N(CC)CC>>S1N=NC2=C1C(=CC=C2)C2C(OC(OC2=O)(C)C)=O | CCN(CC)C[CH3:3].O=C(Cl)[c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][n:14][s:15][c:16]12.[O-:4][C:5](=[O:6])[CH2:7][C:17](=[O:18])[O-:19]>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[n:13][n:14][s:15][c:16]23)[C:17](=[O:18])[O:19]1 | CCN(CC)CC.O=C(Cl)c1cccc2nnsc12.O=C([O-])CC(=O)[O-] | CC1(C)OC(=O)C(c2cccc3nnsc23)C(=O)O1 | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | ae8949bd5389917d799d143b0271a3658b49bede264839d5632bbefb7933ab20 | d720e928948097b7f6c113ab62778b4f27788a4832f75effd2f635294ccbe152 | O=C1OCOC(=O)C1c1cccc2nnsc12 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-C(=O)-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]2:[#7;a:7]:[#7;a:8]:[#16;a:9]:[c:10]:2:1.[O-;H0;D1:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[C:15](-[O-;H0;D1:16])=[O;D1;H0:17]>>[C;D1;H3:18]-[C:19]1(-[CH3;D1;+0:1])-[O;H0;D2;+0:11]-[C:12](=[O;D1;H0:13])-[CH;D3;+0:14](-[c;H0;D3;+0:2]2:[c:3]:[c:... | null | [] | 0 | CELSIUS | 2 | HOUR | 5.5 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 10 ml of tetrahydrofuran are added dropwise to a solution, stirred at 0° C., of 3.6 g of cycloisopropylidene malonate, 7.6 ml of triethylamine and 2.0 g of 4-dimethylaminopyridine in 25 ml of dichloromethane. The reaction mixture is stirred for 2 hours at 0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amine | Ester.Ester | c1ccc2snnc2c1 | C1COCOC1.c1ccc2snnc2c1 | C1COCOC1.c1ccc2snnc2c1 | HCl | CN(C1=CC=NC=C1)C.ClCCl | 0 | 2 | CCN(CC)CC.O=C(Cl)c1cccc2nnsc12.O=C([O-])CC(=O)[O-]>CN(C1=CC=NC=C1)C.ClCCl>CC1(C)OC(=O)C(c2cccc3nnsc23)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ac19de6fdddf43cb807f1b8ce12dad02 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cccc2nnsc12>>CCOC(=O)C(C(=O)OCC)c1cccc2nnsc12 | Cl.S1N=NC2=C1C(=CC=C2)C(=O)Cl.[Cl-].[Mg+2].[Cl-].C(CC(=O)OCC)(=O)OCC>>S1N=NC2=C1C(=CC=C2)C(C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].O=C(Cl)[c:12]1[cH:13][cH:14][cH:15][c:16]2[n:17][n:18][s:19][c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][cH:15][c:16]2[n:17][n:18][s:19][c:20]12 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cccc2nnsc12 | CCOC(=O)C(C(=O)OCC)c1cccc2nnsc12 | null | null | C(C)#N.C(C)N(CC)CC | C-C Coupling | OtherReaction | 1827c9723f069e808d178933fb2dc8d05c44677163aabec504aa40d27d6c1785 | e28ec79096f04aff39f08a42e1f41a13d940f698d541817c5a1398a9c16c1710 | c1ccc2snnc2c1 | Cl-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[#7;a:7]:[#16;a:8]:[c:9]:2:1.[C:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18]>>[C:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[#... | 83.2 | [{"value": 83.2, "product": "S1N=NC2=C1C(=CC=C2)C(C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 4.8 g of magnesium chloride in 50 ml of acetonitrile are treated with 7.6 ml of diethyl malonate and 14 ml of triethylamine, with ice-cooling and stirring. The mixture is stirred for 20 minutes and then treated at 0°-5° C. with portions of a suspension of 9.6 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 5... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ester.Ester | c1ccc2snnc2c1 | c1ccc2snnc2c1 | c1ccc2snnc2c1 | HCl | C(C)#N.C(C)N(CC)CC | 0 | null | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cccc2nnsc12>C(C)#N.C(C)N(CC)CC>CCOC(=O)C(C(=O)OCC)c1cccc2nnsc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8551d82337ad4e2ca282f87e462a018c | CON=C(C(N)=O)c1ccccc1Oc1ccccc1>>CON=C(C#N)c1ccccc1Oc1ccccc1 | O(C1=CC=CC=C1)C1=C(C=CC=C1)C(C(=O)N)=NOC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>O(C1=CC=CC=C1)C1=C(C=CC=C1)C(C#N)=NOC | O=[C:5]([C:4](=[N:3][O:2][CH3:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[NH2:6]>>[CH3:1][O:2][N:3]=[C:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CON=C(C(N)=O)c1ccccc1Oc1ccccc1 | CON=C(C#N)c1ccccc1Oc1ccccc1 | null | null | Cl.N1=CC=CC=C1 | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccc(Oc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3](-[c:4])=[#7:5]-[#8:6]>>[#8:6]-[#7:5]=[C:3](-[c:4])-[C;H0;D2;+0:1]#[N;H0;D1;+0:2] | 96.9 | [{"value": 96.9, "product": "O(C1=CC=CC=C1)C1=C(C=CC=C1)C(C#N)=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 2-(2-Phenoxyphenyl)-2-methoxyiminoacetamide (3.77 g) was dissolved in pyridine (5.53 g). The solution was cooled to 0° C. Trifluoroacetic anhydride (4.40 g) was added dropwise. The mixture was stirred for 2 hours at 0° C., and then diluted with dil. hydrochloric acid and extracted with ethyl acetate. The extract was dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1ccccc1 | HO- | Cl.N1=CC=CC=C1 | 0 | 2 | CON=C(C(N)=O)c1ccccc1Oc1ccccc1>Cl.N1=CC=CC=C1>CON=C(C#N)c1ccccc1Oc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e555e7dc8bc3456baab94c706ef1c2ed | O=C(Br)CBr.O=C(c1ccccc1)c1cccc2c1NCCO2>>O=C(c1ccccc1)c1cccc2c1N(C(=O)CBr)CCO2 | C(C1=CC=CC=C1)(=O)C1=CC=CC2=C1NCCO2.N1=CC=CC=C1.BrCC(=O)Br.O>>BrCC(=O)N1CCOC2=C1C(=CC=C2)C(C2=CC=CC=C2)=O | Br[C:16](=[O:17])[CH2:18][Br:19].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:20][CH2:21][O:22]2>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[N:15]([C:16](=[O:17])[CH2:18][Br:19])[CH2:20][CH2:21][O:22]2 | O=C(Br)CBr.O=C(c1ccccc1)c1cccc2c1NCCO2 | O=C(c1ccccc1)c1cccc2c1N(C(=O)CBr)CCO2 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 01ebb2cf1a1c967cd091832d838545262f7647265a4fa9f17181e6a0858005ad | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)c1cccc2c1NCCO2 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8]1:[c:9]-[#8:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[c:9]:[c:8]-1:[c:7]-[C:6]=[O;D1;H0:5] | 69.4 | [{"value": 69.4, "product": "BrCC(=O)N1CCOC2=C1C(=CC=C2)C(C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-benzoyl-3,4-dihydro-2H-1,4-benzoxazine (5.74 g), pyridine (1.9 g) and methylene chloride (100 ml) was dropwise added a solution of bromoacetyl bromide (5.82 g) in methylene chloride (5 ml) at room temperature. After the mixture was stirred for 1.0 hour at the same temperature, water (100 ml) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)[NH]CCO2 | c1ccccc1.c1ccc2c(c1)[NH]CCO2 | HBr | C(Cl)Cl | null | null | O=C(Br)CBr.O=C(c1ccccc1)c1cccc2c1NCCO2>C(Cl)Cl>O=C(c1ccccc1)c1cccc2c1N(C(=O)CBr)CCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8a77560b32d4c18a9b1ab844404ff19 | N#Cc1cccc2c1NCC2.O=S(=O)(O)O.[OH-]>>O=C(O)c1cccc2c1NCC2 | C(#N)C=1C=CC=C2CCNC12.S(O)(O)(=O)=O.[OH-].[Na+]>>N1CCC2=CC=CC(=C12)C(=O)O | N#[C:2][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][CH2:11][CH2:12]2.O=S(=O)(O)[OH:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][CH2:11][CH2:12]2 | N#Cc1cccc2c1NCC2.O=S(=O)(O)O.[OH-] | O=C(O)c1cccc2c1NCC2 | null | null | null | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc2c(c1)CCN2 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5].O-S(=O)(=O)-[OH;D1;+0:6].[OH-;D0:7]>>[#7:5]-[c:4]:[c:2](-[C;H0;D3;+0:1](=[O;H0;D1;+0:6])-[OH;D1;+0:7]):[c:3] | null | [] | 5 | CELSIUS | 5.5 | HOUR | A mixture of 7-cyanoindoline (4.32 g) and 50% aqueous sulfuric acid (40 ml) was stirred at 110°-120° C. for 5.5 hours, cooled to 5° C. and adjusted to pH 7-8 with 24% aqueous sodium hydroxide. The mixture was washed with ethyl acetate and the aqueous layer was adjusted to pH 2.5-3.0 with 6N hydrochloric acid. The preci... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccc2c(c1)CCN2 | HO- | null | 5 | 5.5 | N#Cc1cccc2c1NCC2.O=S(=O)(O)O.[OH-]>>O=C(O)c1cccc2c1NCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9cac606d071b4395a00aaae08346ef5c | COC(=O)/C=C/c1ccccc1NCc1c[nH]cn1>>Cl.O=C(O)/C=C/c1ccccc1NCc1c[nH]cn1 | Cl.N1C=NC(=C1)CNC1=C(C=CC=C1)/C=C/C(=O)OC.[OH-].[Na+]>>Cl.Cl.N1C=NC(=C1)CNC1=C(C=CC=C1)/C=C/C(=O)O | C[O:5][C:4](=[O:3])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[NH:14][CH2:15][c:16]1[cH:17][nH:18][cH:19][n:20]1>>[ClH:2].[O:3]=[C:4]([OH:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[NH:14][CH2:15][c:16]1[cH:17][nH:18][cH:19][n:20]1 | COC(=O)/C=C/c1ccccc1NCc1c[nH]cn1 | Cl.O=C(O)/C=C/c1ccccc1NCc1c[nH]cn1 | null | null | CO | Functional Group Interconversion | Ester saponification (methyl deprotection) | b78ecd40845eb2270e6550c75ea2630cb164c9b25eda3fae0a944391d7396a3c | 6621c5a39698b382c2c29eacd30adc11ac3552c724c517b0f319c6099a4467de | c1ccc(NCc2c[nH]cn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])/[C:4]=[C:5]/[c:6] | null | [] | null | null | 20 | HOUR | To a solution of methyl (E)-3-[2-(4-imidazolylmethylamino)phenyl]propenoate (0.7 g) in methanol (7 ml) was added 1N sodium hydroxide aqueous solution (3 ml) and the mixture was stirred for 20 hours. After removal of methanol from the reaction mixture, water was added to the residue. The mixture was adjusted to pH 6 wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1c[nH]cn1 | null | CO | null | 20 | COC(=O)/C=C/c1ccccc1NCc1c[nH]cn1>CO>Cl.O=C(O)/C=C/c1ccccc1NCc1c[nH]cn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d66b4eef54b0430690c4005529ed7d6e | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>>CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12 | C(=O)(OCC1=CC=CC=C1)NCCC[C@H](N)C(=O)O.S(=O)(=O)(C1=CC=CC=2C(N(C)C)=CC=CC12)Cl.Cl>>CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC(C(=O)O)CCCNC(=O)OCC1=CC=CC=C1)C | Cl[S:10]([c:9]1[c:8]2[cH:7][cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:35]2[cH:34][cH:33][cH:32]1)(=[O:11])=[O:12].[NH2:13][C@@H:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[C:29](=[O:30])[OH:31]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]([S:... | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12 | null | null | [OH-].[Na+].O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCCCNS(=O)(=O)c1cccc2ccccc12)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[C@H;D3;+0:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[C:7]-[C:8]-[CH;D3;+0:9](-[NH;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | null | [] | 0 | CELSIUS | 15 | MINUTE | Nδ -Carbobenzyloxy-L-ornithine (39.6 g, 0.149 mol) was dissolved in a solution of 2N NaOH (90 mL) and tetrahydrofuran (200 mL) under nitrogen. After about 15 minutes at ambient temperature, the mixture was cooled to about 0° C. and subsequently treated with additional 2N NaOH (85 mL) and dansyl chloride (45.0 g, 0.167 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | [OH-].[Na+].O1CCCC1 | 0 | 0.25 | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>[OH-].[Na+].O1CCCC1>CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2d1677a7d55446d6936250ae86c5bfcb | CCC1CCNCC1.CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12>>CCC1CCN(C(=O)C(CCCNC(=O)OCc2ccccc2)NS(=O)(=O)c2cccc3c(N(C)C)cccc23)CC1 | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC(C(=O)O)CCCNC(=O)OCC1=CC=CC=C1)C.C(C)N(CC)CC.C(C)C1CCNCC1>>CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC(CCCNC(OCC1=CC=CC=C1)=O)C(=O)N1CCC(CC1)CC)C | [CH3:1][CH2:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:41][CH2:42]1.O[C:7](=[O:8])[CH:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[NH:24][S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][c:32]2[c:33]([N:34]([CH3:35])[CH3:36])[cH:37][cH:38][cH:39][c:40]12>>[CH3:1]... | CCC1CCNCC1.CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12 | CCC1CCN(C(=O)C(CCCNC(=O)OCc2ccccc2)NS(=O)(=O)c2cccc3c(N(C)C)cccc23)CC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCCC(NS(=O)(=O)c1cccc2ccccc12)C(=O)N1CCCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | 91.1 | [{"value": 45.0, "product": "CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC(CCCNC(OCC1=CC=CC=C1)=O)C(=O)N1CCC(CC1)CC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC(CCCNC(OCC1=CC=CC=C1)=O)C(=O)N1CCC(CC1)CC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 0 | CELSIUS | 2 | HOUR | To a cold (0° C.), nitrogen-blanketed mixture of 2d (48.90 g, 0.098 mol), triethylamine (25.0 mL, 0.18 mol) and 4-ethylpiperidine (20.0 g, 0.18 mol) in anhydrous dimethylformamide (160 mL) was added dropwise diphenylphosphoryl azide (21.1 mL, 0.098 mol). The mixture was stirred at about 0° C. for about 1 hour and at am... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2ccccc2c1 | HO- | CN(C=O)C | 0 | 2 | CCC1CCNCC1.CN(C)c1cccc2c(S(=O)(=O)NC(CCCNC(=O)OCc3ccccc3)C(=O)O)cccc12>CN(C=O)C>CCC1CCN(C(=O)C(CCCNC(=O)OCc2ccccc2)NS(=O)(=O)c2cccc3c(N(C)C)cccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-379118b96b384749848f4c9aace367b8 | Cc1ccc(S(=O)(=O)Cl)cc1.N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O>>Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1 | C(=O)(OCC1=CC=CC=C1)NCCCC[C@H](N)C(=O)O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.Cl>>CC1=CC=C(C=C1)S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:30][cH:29]1)(=[O:7])=[O:8].[NH2:9][C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[C:26](=[O:27])[OH:28]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][CH:10]([CH2:11][CH2:12][CH2:13][CH2:1... | Cc1ccc(S(=O)(=O)Cl)cc1.N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O | Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1 | null | null | [OH-].[Na+].C(C)(=O)OCC.O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 84f0a2c480e4021adb28613388cdf35ca03a8bd65bbdad356e160a1b94684976 | 2988afdf4a13d931f021994343ac8648c6e63ca3a4c0ba598a4b99bbffc001c8 | O=C(NCCCCCNS(=O)(=O)c1ccccc1)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[C@H;D3;+0:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[C:7]-[C:8]-[CH;D3;+0:9](-[NH;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | 81,024.5 | [{"value": 81.0, "product": "CC1=CC=C(C=C1)S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81024.5, "product": "CC1=CC=C(C=C1)S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Nε -Carbobenzyloxy-L-lysine (30.0 g, 0.107 mmol) was dissolved in a solution of 2N NaOH (60 mL) and dioxane (150 mL) under nitrogen. After about 15 minutes at room temperature, the mixture was cooled to about 0° C. and subsequently treated with additional 2N NaOH (60 mL) and p-toluenesulfonyl chloride (20.4 g, 0.107 mm... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | [OH-].[Na+].C(C)(=O)OCC.O1CCOCC1 | 0 | 0.25 | Cc1ccc(S(=O)(=O)Cl)cc1.N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O>[OH-].[Na+].C(C)(=O)OCC.O1CCOCC1>Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e91d8d7e54a4b55a7abb98099f7788c | C1CCNCC1.Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1>>Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)N2CCCCC2)cc1 | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].CC1=CC=C(C=C1)S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1.C(C)N(CC)CC.N1CCCCC1>>N1(CCCCC1)C(C(CCCCNC(OCC1=CC=CC=C1)=O)NS(=O)(=O)C1=CC=C(C=C1)C)=O | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1.O[C:26]([CH:10]([NH:9][S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]1)(=[O:7])=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)=[O:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9]... | C1CCNCC1.Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1 | Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)N2CCCCC2)cc1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCCCC(NS(=O)(=O)c1ccccc1)C(=O)N1CCCCC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | 100.6 | [{"value": 100.0, "product": "N1(CCCCC1)C(C(CCCCNC(OCC1=CC=CC=C1)=O)NS(=O)(=O)C1=CC=C(C=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.6, "product": "N1(CCCCC1)C(C(CCCCNC(OCC1=CC=CC=C1)=O)NS(=O)(=O)C1=CC=C(C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a cold (0° C.), nitrogen-blanketed mixture of 2-[[(4-methylphenyl]sulfonyl]amino]-6-[[(phenylmethoxy)carbonyl]amino]hexanoic acid (18.00 g, 44.43 mmol), triethylamine (5.80 mL, 41.43 mmol) and piperidine (4.10 mL, 41.43 mmol) in anhydrous dimethylformamide (80 mL) was added dropwise diphenylphosphoryl azide (8.90 mL... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HO- | CN(C=O)C | 0 | 2 | C1CCNCC1.Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)O)cc1>CN(C=O)C>Cc1ccc(S(=O)(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)N2CCCCC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6b1f0e71dd3a42bb9faf589b927dc731 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>>CN1CCC[C@H]1c1cccnc1 | C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1.C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1>>N1=CC=CC(=C1)[C@H]1N(C)CCC1 | N[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10](O)c(O)[cH:12]1.O=S(=O)(O)CCN1CC[N:11](CCO)CC1.O=S(=O)(O)CCN1CC[N:2]([CH2:1]CO)[CH2:3][CH2:4]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1 | CN1CCC[C@H]1c1cccnc1 | null | null | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | Heteroatom Alkylation and Arylation | OtherReaction | 19fc9a872b549396d811b42e2ef2bc61edfc6ad753a9b784038fcb2d26d8bd1b | 22424af31acac19f7bdb5717c7b71b423c8772246143962540fd1af6bf911444 | c1cncc([C@@H]2CCCN2)c1 | N-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O):c(-O):[cH;D2;+0:7]:1.O-C-C-[N;H0;D3;+0:8]1-C-C-N(-C-C-S(-O)(=O)=O)-C-C-1.O-C-[CH2;D2;+0:9]-[N;H0;D3;+0:10]1-C-C-N(-C-C-S(-O)(=O)=O)-[CH2;D2;+0:11]-[C:12]-1>>[CH3;D1;+0:9]-[N;H0;D3;+0:10]1-[C:12]-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[C@H;D3;+0:2]-1-[c:3]1:[c:4]... | null | [] | null | null | 10 | MINUTE | Dopamine release was measured by preparing synaptosomes from the striatal area of rat brain obtained from Sprague-Dawley rats generally according to the procedures set forth by Nagy, et al., J. Neurochem., Vol. 43, pp. 1114-1123 (1984). Striata from 4 rats were homogenized in 2 ml of 0.32M sucrose buffered with 5 mM HE... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol.Aromatic alcohol.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Sulfonic acid.Sulfonic acid | Tertiary amine | c1ccccc1.C1CNCC[NH]1.C1CNCC[NH]1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HO- | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | null | 0.166667 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>CN1CCC[C@H]1c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8e62ba77ab194d9c9cc5595ca51f8d17 | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.Oc1cccnc1>>COc1ccc(OCc2ccccc2)cc1C(=O)COc1cccnc1 | C(C1=CC=CC=C1)OC=1C=CC(=C(C(CBr)=O)C1)OC.OC=1C=NC=CC1.O.[H-].[Na+]>>N1=CC(=CC=C1)OCC(=O)C1=C(C=CC(=C1)OCC1=CC=CC=C1)OC | Br[CH2:19][C:17]([c:16]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1)=[O:18].[OH:20][c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]1[C:17](=[O:18])[CH2:19][O:20][c... | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.Oc1cccnc1 | COc1ccc(OCc2ccccc2)cc1C(=O)COc1cccnc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1cccnc1)c1cccc(OCc2ccccc2)c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | 25.7 | [{"value": 25.7, "product": "N1=CC(=CC=C1)OCC(=O)C1=C(C=CC(=C1)OCC1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To 5-benzyloxy-2-methoxyphenacyl bromide (4.0 g, 0.0119 mol) in 80 ml of dry dimethylformamide was added 3-hydroxypyridine (1.24 g, 0.013 mol, 1.1 equiv) followed by NaH (50% in oil, 0.604 g, 1.1 equiv). After stirring for 18 hours under N2, the mixture was poured into 500 ml of ice and water, and extracted 2×500 ml et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HBr | CN(C=O)C | null | 18 | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.Oc1cccnc1>CN(C=O)C>COc1ccc(OCc2ccccc2)cc1C(=O)COc1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d914eb82cf014fdb8c3669a45bdd545d | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.COc1cccc(O)c1>>COc1cccc(OCC(=O)c2cc(OCc3ccccc3)ccc2OC)c1 | COC=1C=C(C=CC1)O.OC=1C=NC=CC1.C(C1=CC=CC=C1)OC=1C=CC(=C(C(CBr)=O)C1)OC>>COC=1C=C(C=CC1)OCC(=O)C1=C(C=CC(=C1)OCC1=CC=CC=C1)OC | Br[CH2:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24][c:25]1[O:26][CH3:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH2:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:... | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.COc1cccc(O)c1 | COc1cccc(OCC(=O)c2cc(OCc3ccccc3)ccc2OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1cccc(OCc2ccccc2)c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | By the method of Example 1, substituting a molar equivalent of 3-methoxyphenol for 3-hydroxypyridine, 5-benzyloxy-2-methoxyphenacyl bromide was converted to present title product; mp 76°-77° C.; IR (KBr) 1680 cm-1 ; MS 378 (M+); Anal. C 73.05, H 5.74, calcd. C 73.00, H 5.86.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | COc1ccc(OCc2ccccc2)cc1C(=O)CBr.COc1cccc(O)c1>>COc1cccc(OCC(=O)c2cc(OCc3ccccc3)ccc2OC)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b5deb4b9277448c289c6682e2181b440 | CC(=O)c1cccc(OCc2ccccc2)c1.O=Cc1cccnc1>>O=C(C=Cc1cccnc1)c1ccccc1OCc1ccccc1 | N1=CC(=CC=C1)C=O.CC(=O)C1=CC(=CC=C1)OCC2=CC=CC=C2.[OH-].[Na+].C(C)O>>C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(C=CC=1C=NC=CC1)=O | [O:1]=[C:2]([CH3:3])[c:11]1[cH:12][cH:13][cH:14][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:15]1.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:... | CC(=O)c1cccc(OCc2ccccc2)c1.O=Cc1cccnc1 | O=C(C=Cc1cccnc1)c1ccccc1OCc1ccccc1 | null | null | O | C-C Coupling | OtherReaction | 9fff1ed552b676da41a76495351538077f3ef1283fc0ddc29dc8ab32ab8f15a5 | 21d425db6b546152ab81006f738d4037a554ffa9ba484cf666f8f3284e58e404 | O=C(C=Cc1cccnc1)c1ccccc1OCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[c;H0;D3;+0:13](-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16]):[cH;D2;+0:17]:1>>[C:7]-[#8:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:17]:[cH;D2;+0:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:1-[C:14](=[O;D1;H0:16])-[CH;D2;+0:15]=[CH;D2;+0:1]-[c:... | null | [] | null | null | 18 | HOUR | To a solution of NaOH (0.488 g) in 10 ml of H2O was added 5 ml of 95% ethanol, followed by 3-benzyloxyacetophenone (2.5 g). The resulting solution was cooled to 0°-5° C. and pyridine-3-carbaldehyde (0.903 ml) added. After standing at 0°-5° C. for 18 hours, present title product was recovered by filtration and purified ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ether | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | O | null | 18 | CC(=O)c1cccc(OCc2ccccc2)c1.O=Cc1cccnc1>O>O=C(C=Cc1cccnc1)c1ccccc1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-02e63018c7f6403a9ad3b2d6de31b313 | CC(=O)c1cccc(OCc2ccccc2)c1.COC(=O)c1cccc(C=O)c1>>COC(=O)c1cccc(C=CC(=O)c2cccc(OCc3ccccc3)c2)c1 | C(C)(=O)O.CC(=O)C1=CC(=CC=C1)OCC2=CC=CC=C2.C(=O)C=1C=C(C(=O)OC)C=CC1.CO[Na]>>C(C1=CC=CC=C1)OC=1C=C(C=CC1)C(C=CC1=CC(=CC=C1)C(=O)OC)=O | [CH3:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27]1.O=[CH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH:10]=[CH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][c:18](... | CC(=O)c1cccc(OCc2ccccc2)c1.COC(=O)c1cccc(C=O)c1 | COC(=O)c1cccc(C=CC(=O)c2cccc(OCc3ccccc3)c2)c1 | null | null | CO.O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)c1cccc(OCc2ccccc2)c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | To CH3ONa (0.45 g, 0.0082 mol) stirring in 20 ml of dry CH3OH at 10° C. was added 3-benzyloxyacetophenone (5.0 g, 0.019 mol) and methyl 3-formylbenzoate (3.12 g, 0.019 mol). A heavy precipitate formed almost immediately, and the mixture was diluted with 20 ml CH3OH, warmed to room temperature and stirred for 18 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CO.O | null | 18 | CC(=O)c1cccc(OCc2ccccc2)c1.COC(=O)c1cccc(C=O)c1>CO.O>COC(=O)c1cccc(C=CC(=O)c2cccc(OCc3ccccc3)c2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cb967cd9eaa84622bff0d06681a8f931 | CCOC(=O)c1cc2cc(N)ccc2s1.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>>CCOC(=O)c1cc2cc(N)ccc2o1 | [N+](=O)([O-])C=1C=CC2=C(C=C(O2)C(=O)O)C1.NC=1C=CC2=C(C=C(S2)C(=O)OCC)C1>>NC=1C=CC2=C(C=C(O2)C(=O)OCC)C1 | Nc1ccc2sc([C:4]([O:3][CH2:2][CH3:1])=[O:5])cc2c1.O=C(O)[c:6]1[cH:7][c:8]2[cH:9][c:10]([N+:11](=O)[O-])[cH:12][cH:13][c:14]2[o:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[o:15]1 | CCOC(=O)c1cc2cc(N)ccc2s1.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1 | CCOC(=O)c1cc2cc(N)ccc2o1 | null | null | null | Functional Group Interconversion | OtherReaction | 6730e883247c168fcd3cda868e87253b047ed8e691a4c4fd4ce9586e7a554631 | 72229b1116248466325a77b051119920514293961507228730ef3aee179224a8 | c1ccc2occc2c1 | N-c1:c:c:c2:s:c(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]):c:c:2:c:1.O-C(=O)-[c;H0;D3;+0:5]1:[#8;a:6]:[c:7]:[c:8](:[c:9]:1):[c:10]:[c:11](-[N+;H0;D3:12](=O)-[O-]):[c:13]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:5]1:[#8;a:6]:[c:7]:[c:8](:[c:9]:1):[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13] | null | [] | null | null | null | null | The appropriate arylcarboxylic acid is synthesized by the coupling of indole-2-carboxylic acid, benzofuran-2-carboxylic acid or benzothiophene-2-carboxylic acid with ethyl 5-amino-aryl-2-carboxylate in DMF with EDCI, and saponification of the ester. Ethyl 5-aminoindole-2-carboxylate is formed by catalytic hydrogenation... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Nitro group.Primary amine | Ester.Primary amine | c1ccc2sccc2c1.c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1 | Other | null | null | null | CCOC(=O)c1cc2cc(N)ccc2s1.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>>CCOC(=O)c1cc2cc(N)ccc2o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3aa3f09df1fc4b0da83e26f362069cf6 | ClCCl>>Cl | [OH-].[Na+].C(Cl)Cl.O.CN[C@H]1CC[C@H](C2=C1C=CC=C2)C=3C=CC(=C(C3)Cl)Cl.C(C(O)C1=CC=CC=C1)(=O)[O-]>>CN[C@H]1CC[C@H](C2=C1C=CC=C2)C=3C=CC(=C(C3)Cl)Cl.Cl | ClC[Cl:21]>>[ClH:21] | ClCCl | Cl | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 64e2f1d14467658fcb89f1934b11f73bcbe5aab8b019240f858e5d4d92949b50 | 65e22ac5ac73e4dc94c17b99f93076354fa5a281d80003bd5a6c5af277cafff7 | null | Cl-C-[Cl;H0;D1;+0:1]>>[ClH;D0;+0:1] | null | [] | 50 | CELSIUS | 3 | HOUR | To a 12 liter, 3 neck round-bottom flask equipped with mechanical stirrer, 4287ml of methylene chloride, 2553ml water and 638.3gms sertraline mandelate were combined. A 10% sodium hydroxide solution, 383ml, was then added and the resulting two clear layers were separated. The aqueous layer was further extracted with 2×... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | null | null | HCl | C(C)(C)O | 50 | 3 | ClCCl>C(C)(C)O>Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f88643d947a34b82bf524f131968accd | C#CCCCOC.NS(=O)(=O)c1ccccc1I>>COCCCC#Cc1ccccc1S(N)(=O)=O | IC1=C(C=CC=C1)S(=O)(=O)N.C(CCC#C)OC.CN(C=O)C>>COCCCC#CC1=C(C=CC=C1)S(=O)(=O)N | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].I[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14]([NH2:15])(=[O:16])=[O:17]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14]([NH2:15])(=[O:16])=[O:17] | C#CCCCOC.NS(=O)(=O)c1ccccc1I | COCCCC#Cc1ccccc1S(N)(=O)=O | null | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[#16:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | 22 | HOUR | 135 ml of N,N-dimethylformamide and 22 ml of triethylamine are taken and 7.5 g of 2-iodobenzenesulfonamide, 2.6 g of pent-4-yn-1-yl-methyl ether as well as 0.067 g of copper(I) iodide and 0.144 g of bis(triphenylphosphine)palladium(II) dichloride are added. The reaction mixture is heated to 65° and stirred for 22 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)N(CC)CC | null | 22 | C#CCCCOC.NS(=O)(=O)c1ccccc1I>[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)N(CC)CC>COCCCC#Cc1ccccc1S(N)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c34b896f8df643aab6bb098bc5e91b2c | C#CCC.NS(=O)(=O)c1ccccc1I>>CCC#Cc1ccccc1S(N)(=O)=O | IC1=C(C=CC=C1)S(=O)(=O)N.C(C)N(CC)CC.IC1=C(C=CC=C1)S(=O)(=O)N.C#CCC>>C(#CCC)C1=C(C=CC=C1)S(=O)(=O)N | [CH3:1][CH2:2][C:3]#[CH:4].I[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11]([NH2:12])(=[O:13])=[O:14]>>[CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11]([NH2:12])(=[O:13])=[O:14] | C#CCC.NS(=O)(=O)c1ccccc1I | CCC#Cc1ccccc1S(N)(=O)=O | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | CN(C=O)C | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[#16:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | 18 | HOUR | 0.1 g of bis(triphenylphosphine)palladium(II) chloride, 0.05 g of copper iodide and 18.5 ml of triethylamine are added to a solution of 5 g of 2-iodobenzenesulfonamide in 70 ml of N,N-dimethylformamide. At room temperature, argon and 1-butyne are slowly introduced. After 18 hours the thin-layer chromatogram no longer s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.CN(C=O)C | null | 18 | C#CCC.NS(=O)(=O)c1ccccc1I>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.CN(C=O)C>CCC#Cc1ccccc1S(N)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e6a9ee111b684577b5ee1b441df9ca2a | CC(=O)Cl.NS(=O)(=O)c1ccccc1C#CCCCO>>CC(=O)OCCCC#Cc1ccccc1S(N)(=O)=O | OCCCC#CC1=C(C=CC=C1)S(=O)(=O)N.N1=CC=CC=C1.C(C)(=O)Cl.C(C)N(CC)CC>>C(C)(=O)OCCCC#CC1=C(C=CC=C1)S(=O)(=O)N | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16]([NH2:17])(=[O:18])=[O:19]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16]([NH2:17])(=[O:18])=[O:19] | CC(=O)Cl.NS(=O)(=O)c1ccccc1C#CCCCO | CC(=O)OCCCC#Cc1ccccc1S(N)(=O)=O | null | null | C1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | The starting material and analogous starting material may be prepared as follows: 3.0 g of 2-(5-hydroxypent-1-yn-1-yl)-benzenesulfonamide and 4.7 ml of pyridine are dissolved at 45° in 200 ml of benzene. The solution is cooled to room temperature and 1.23 ml of acetyl chloride and 3.2 ml of triethylamine are added. The... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | C1=CC=CC=C1 | null | 1 | CC(=O)Cl.NS(=O)(=O)c1ccccc1C#CCCCO>C1=CC=CC=C1>CC(=O)OCCCC#Cc1ccccc1S(N)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-855ec966bfce4a599c81dfe20ff188e7 | CC(=O)OC(C)=O.CC(O)CC#Cc1ccccc1S(N)(=O)=O>>CC(=O)OC(C)CC#Cc1ccccc1S(N)(=O)=O | OC(CC#CC1=C(C=CC=C1)S(=O)(=O)N)C.C(C)(=O)OC(C)=O>>C(C)(=O)OC(CC#CC1=C(C=CC=C1)S(=O)(=O)N)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH:5]([CH3:6])[CH2:7][C:8]#[C:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16]([NH2:17])(=[O:18])=[O:19]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH3:6])[CH2:7][C:8]#[C:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16]([NH2:17])(=[O:18])=[O:19] | CC(=O)OC(C)=O.CC(O)CC#Cc1ccccc1S(N)(=O)=O | CC(=O)OC(C)CC#Cc1ccccc1S(N)(=O)=O | null | null | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]#[C:5]-[C:6]-[C:7](-[C;D1;H3:8])-[OH;D1;+0:9]>>[C:4]#[C:5]-[C:6]-[C:7](-[C;D1;H3:8])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 14 | HOUR | 1 g of 2-(4-hydroxy-pent-1-yn-1-yl)-benzenesulfonamide is dissolved in 9 ml of pyridine and cooled to 5°, and 0.44 ml of acetic anhydride is added. The reaction mixture is stirred under argon at 5° for 14 hours and then at room temperature for a further 24 hours. The reaction mixture is then poured onto 100 ml of ice-c... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | c1ccccc1 | HO- | N1=CC=CC=C1 | null | 14 | CC(=O)OC(C)=O.CC(O)CC#Cc1ccccc1S(N)(=O)=O>N1=CC=CC=C1>CC(=O)OC(C)CC#Cc1ccccc1S(N)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a86cb8e6d2cf4b918a68d5f5c49a6347 | COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCOC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>>COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCO)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | O.[OH-].[Li+].O.C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CCCCOC(C)=O)C=C1)OC>>C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CCCCO)C=C1)OC | CC(=O)[O:23][CH2:22][CH2:21][CH2:20][C:19]#[C:18][c:17]1[c:12]([S:9]([NH:8][C:6]([c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([CH2:27][c:28]3[cH:29][n:30]([CH3:31])[c:32]4[cH:33][cH:34][c:35]([NH:36][C:37](=[O:38])[O:39][CH:40]5[CH2:41][CH2:42][CH2:43][CH2:44]5)[cH:45][c:46]34)[cH:25][cH:24]2)=[O:7])(=[O:10])=[O:11])[cH:13][c... | COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCOC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCO)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | null | null | CO.O1CCCC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(Nc1ccc2[nH]cc(Cc3ccc(C(=O)NS(=O)(=O)c4ccccc4)cc3)c2c1)OC1CCCC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 97.7 | [{"value": 97.7, "product": "C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CCCCO)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 0.37 g of lithium hydroxide monohydrate and 10 ml of water are added to a solution of 1.2 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(5-acetoxy-pent-1-yn-1-yl)-benzenesulfonamide in 40 ml of methanol/tetrahydrofuran=1/1. The mixture is stirred for 16 hours at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CCCC1 | HO- | CO.O1CCCC1 | null | 16 | COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCOC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>CO.O1CCCC1>COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CCCCO)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a0f180715a4a474e864218093f7ef149 | CC(=O)OC(C)=O.COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>>COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)OC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | C(C)(=O)OC(C)=O.C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CC(C)(C)O)C=C1)OC>>C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CC(C)(C)OC(C)=O)C=C1)OC | CC(=O)O[C:24]([CH3:25])=[O:26].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]#[C:19][C:20]([CH3:21])([CH3:22])[OH:23])[cH:27][cH:28][c:29]1[CH2:30][c:31]1[cH:32][n:33]([CH3:34])[c:35]2[cH:36][cH:37][c:38]([NH:39][C:40](=[O:41])[O:42][CH:43]3[CH2:... | CC(=O)OC(C)=O.COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)OC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1.C(C)(=O)OCC | Acylation | Transesterification | 7845e6caeb9ebcfc4e11ccde0ca862e171727c1b0b0f5c55f250826811ed7095 | aad6c0b0b2e56c19696d13bcd56b340e680e45229f4a56b765d97baaf778738e | O=C(Nc1ccc2[nH]cc(Cc3ccc(C(=O)NS(=O)(=O)c4ccccc4)cc3)c2c1)OC1CCCC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[C:8]#[C:9]-[c:10]>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C:8]#[C:9]-[c:10])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 20 | HOUR | 0.44 g of acetic anhydride and 0.1 g of 4-dimethylaminopyridine are added to a solution of 1.0 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide in 6 ml of pyridine. The reaction solution is stirred for 20 hours at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Tertiary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CCCC1 | HO- | CN(C1=CC=NC=C1)C.N1=CC=CC=C1.C(C)(=O)OCC | null | 20 | CC(=O)OC(C)=O.COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>CN(C1=CC=NC=C1)C.N1=CC=CC=C1.C(C)(=O)OCC>COc1cc(C(=O)NS(=O)(=O)c2ccccc2C#CC(C)(C)OC(C)=O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6fd576943ae3459bb74deb1e7f415740 | CCCC#Cc1ccccc1S(N)(=O)=O.COc1cc(C(=O)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>>CCCC#Cc1ccccc1S(=O)(=O)NC(=O)c1ccc(Cc2cn(C)c3ccc(NC(=O)OC4CCCC4)cc23)c(OC)c1 | C(#CCCC)C1=C(C=CC=C1)S(=O)(=O)N.C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)O)C=C1)OC>>C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CCCC)C=C1)OC | [CH3:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[S:12](=[O:13])(=[O:14])[NH2:15].O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH2:22][c:23]2[cH:24][n:25]([CH3:26])[c:27]3[cH:28][cH:29][c:30]([NH:31][C:32](=[O:33])[O:34][CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39]4)[cH:40][c:41]23)[c:42]([O:43][CH3:44]... | CCCC#Cc1ccccc1S(N)(=O)=O.COc1cc(C(=O)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12 | CCCC#Cc1ccccc1S(=O)(=O)NC(=O)c1ccc(Cc2cn(C)c3ccc(NC(=O)OC4CCCC4)cc23)c(OC)c1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(Nc1ccc2[nH]cc(Cc3ccc(C(=O)NS(=O)(=O)c4ccccc4)cc3)c2c1)OC1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[O;D1;H0:8]=[#16:7](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 74 | [{"value": 74.0, "product": "C1(CCCC1)OC(=O)NC=1C=C2C(=CN(C2=CC1)C)CC1=C(C=C(C(=O)NS(=O)(=O)C2=C(C=CC=C2)C#CCCC)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 1.07 g of 2-(pent-1-yn-1-yl)-benzenesulfonamide and 0.94 g of 3-[N-dimethylaminopropyl]-N-ethylcarbodiimide hydrochloride as well as 0.6 g of 4-dimethylaminopyridine are added to a solution of 2.0 g of 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid in 50 ml of methylene chloride. ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CCCC1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 20 | CCCC#Cc1ccccc1S(N)(=O)=O.COc1cc(C(=O)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12>CN(C1=CC=NC=C1)C.C(Cl)Cl>CCCC#Cc1ccccc1S(=O)(=O)NC(=O)c1ccc(Cc2cn(C)c3ccc(NC(=O)OC4CCCC4)cc23)c(OC)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-324cff6c10c54f0e868e67759e4a7ad4 | O=CCc1ccccc1.SCCCS>>c1ccc(CC2SCCCS2)cc1 | [OH-].[K+].C1(=CC=CC=C1)CC=O.C(CCS)S.B(F)(F)F.CCOCC>>C1(=CC=CC=C1)CC1SCCCS1 | O=[CH:6][CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:13][cH:12]1.[SH:7][CH2:8][CH2:9][CH2:10][SH:11]>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH:6]2[S:7][CH2:8][CH2:9][CH2:10][S:11]2)[cH:12][cH:13]1 | O=CCc1ccccc1.SCCCS | c1ccc(CC2SCCCS2)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b6aa94cc288ccc335d16ebca7b7871ddfb2ace95135c953bbcca74128ef9ab0d | b33952daa52c823aed54928e18035128d6174ef232f045e0b3aec8d00e876322 | c1ccc(CC2SCCCS2)cc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[SH;D1;+0:4]-[C:5]-[C:6]-[C:7]-[SH;D1;+0:8]>>[c:3]-[C:2]-[CH;D3;+0:1]1-[S;H0;D2;+0:4]-[C:5]-[C:6]-[C:7]-[S;H0;D2;+0:8]-1 | 91 | [{"value": 91.0, "product": "C1(=CC=CC=C1)CC1SCCCS1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "C1(=CC=CC=C1)CC1SCCCS1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 33.9 g (280 mmol) of phenylacetaldehyde and 35.6 g (330 mmol) of 1,3-propanedithiol in 300 mL of methylene chloride at 0° C., was added, dropwise over a period of 30 minutes, 10 mL of boron trifluoride etherate. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h at ambi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aliphatic thiol.Aliphatic thiol | Monosulfide.Monosulfide | null | C1CSCSC1 | c1ccccc1.C1CSCSC1 | HO- | C(Cl)Cl | null | 3 | O=CCc1ccccc1.SCCCS>C(Cl)Cl>c1ccc(CC2SCCCS2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-534cc09434c845448a5acfd9ab4503ac | COc1ccc2c(c1)CCCC2=O.[C-]#N>>COc1ccc2c(c1)CCC=C2C#N | C[Si](C)(C)C#N.COC1=CC2=C(C=C1)C(=O)CCC2.[C-]#N.[Li+]>>C(#N)C1=CCCC2=CC(=CC=C12)OC | O=[C:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][CH2:11]1.[C-:13]#[N:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]=[C:12]2[C:13]#[N:14] | COc1ccc2c(c1)CCCC2=O.[C-]#N | COc1ccc2c(c1)CCC=C2C#N | null | null | CN(C=O)C.O1CCCC1 | C-C Coupling | OtherReaction | e01b01043bfaeb01c3e2361338f006aba25607dec206a9f74552ce86fadfe00b | 38173ffb46d9f636178242326a427b3d459fe7c0171d4d0447e25702c6b09e58 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[C-;H0;D1:8]#[N;D1;H0:9]>>[N;D1;H0:9]#[C;H0;D2;+0:8]-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | 60.4 | [{"value": 60.0, "product": "C(#N)C1=CCCC2=CC(=CC=C12)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "C(#N)C1=CCCC2=CC(=CC=C12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Trimethylsilylcyanide (50.0 g, 510 mmol) was added to a suspension of 75.0 g (430 mmol) of 6-methoxy-α-tetralone (commercially available from Aldrich Chemical Company) in 75 mL of anhydrous tetrahydrofuran (THF) at ambient temperature. Lithium cyanide (100 mL of a 0.5M solution in N,N-dimethylformamide (DMF) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Nitrile | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | CN(C=O)C.O1CCCC1 | null | 1.5 | COc1ccc2c(c1)CCCC2=O.[C-]#N>CN(C=O)C.O1CCCC1>COc1ccc2c(c1)CCC=C2C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f0032e6d5bdc4d0cbe0c7fbec8b6a737 | COc1ccc2c(c1)CCC1C2CN(C)C1Cc1ccccc1.O=C(Cl)Cc1ccccc1>>COc1ccc2c(c1)CCC1C2CN(C(=O)Cc2ccccc2)C1Cc1ccccc1 | C1(=CC=CC=C1)CC(=O)Cl.O.COC1=CC2=C(C3CN(C(C3CC2)CC2=CC=CC=C2)C)C=C1.Cl.N1=CC=CC=C1>>COC1=CC2=C(C3CN(C(C3CC2)CC2=CC=CC=C2)C(=O)CC2=CC=CC=C2)C=C1 | C[N:14]1[CH2:13][CH:12]2[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]3[CH2:9][CH2:10][CH:11]2[CH:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.Cl[C:15](=[O:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][N:14... | COc1ccc2c(c1)CCC1C2CN(C)C1Cc1ccccc1.O=C(Cl)Cc1ccccc1 | COc1ccc2c(c1)CCC1C2CN(C(=O)Cc2ccccc2)C1Cc1ccccc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 8e71e5d3e73017a7aac5b3eac1bfbf3e65d703de2d576d29676f344087117844 | 7da20c2e2c34d1dd982a91b3333ed3c480165fa1ae9d2aa385b5b9d2065f54c9 | O=C(Cc1ccccc1)N1CC2c3ccccc3CCC2C1Cc1ccccc1 | C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6].Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[c:10]>>[C:6]-[C:5]1-[C:4]-[C:3]-[C:2]-[N;H0;D3;+0:1]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[c:10] | null | [] | 0 | CELSIUS | 3 | MINUTE | 2,3,3a,4,5,9b-Hexahydro-7-methoxy-2-methyl-3-phenylmethyl-1H-benz[e]isoindole (0.80 g, 2.73 mmol), the product of Example 1, was dissolved in 10 mL of methylene chloride and approximately 5 mL of pyridine was added to the resultant solution. The solution was cooled to 0° C. and approximately 2.5 mL of phenylacetyl chlo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amine | Tertiary amide | c1ccc2c(c1)CCC1C[NH]CC21 | c1ccc2c(c1)CCC1C[NH]CC21 | c1ccc2c(c1)CCC1C[NH]CC21.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.05 | COc1ccc2c(c1)CCC1C2CN(C)C1Cc1ccccc1.O=C(Cl)Cc1ccccc1>C(Cl)Cl>COc1ccc2c(c1)CCC1C2CN(C(=O)Cc2ccccc2)C1Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4393075ba1aa42428cf8d5fd71a2583e | Cc1cccc(CC(=O)C2CCc3ccccc3C2C#N)c1>>Cc1cccc(CC2NCC3c4ccccc4CCC23)c1 | C(#N)C1C(CCC2=CC=CC=C12)C(=O)CC1=CC(=CC=C1)C.C(#N)C1C(CCC2=CC(=CC=C12)OC)C(=O)CC1=CC=CC=C1.C(#N)C1C(CCC2=CC(=CC=C12)OC)C(=O)CC1=CC=CC=C1.C(#N)C1C(CCC2=CC=CC=C12)C(=O)CC1=CC(=CC=C1)C>>CC=1C=C(C=CC1)CC1NCC2C3=C(CCC12)C=CC=C3 | O=[C:8]([CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:21]1)[CH:20]1[CH:11]([C:10]#[N:9])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18][CH2:19]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH:8]2[NH:9][CH2:10][CH:11]3[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[CH2:18][CH2:19][CH:20]23)[cH:21]1 | Cc1cccc(CC(=O)C2CCc3ccccc3C2C#N)c1 | Cc1cccc(CC2NCC3c4ccccc4CCC23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2c3bf11ecf1545c8757368ea4475f8a4703f783649587bec86e10bafd8a0cc6b | cb00476b0efaa1487253fc572e1edb8b26b4ce9be61ac2320fd61511c421df80 | c1ccc(CC2NCC3c4ccccc4CCC23)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[C:4](-[C:5])-[C:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8])-[c:9]>>[C:5]-[C:4]1-[C:6](-[c:9])-[CH2;D2;+0:7]-[NH;D2;+0:8]-[CH;D3;+0:1]-1-[C:2]-[c:3] | null | [] | null | null | null | null | Following the procedures described in Step 2 of Example 6, replacing 1-cyano-6-methoxy-2-phenylmethylcarbonyl-1,2,3,4-tetrahydronaphthalene (the product of Step 1 of Example 6) with the product of Step 1 above, 1-cyano-2-(3-methylphenyl)methylcarbonyl-1,2,3,4-tetrahydronaphthalene, the title compound was prepared; MS D... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile | Secondary amine | null | c1ccc2c(c1)CCC1CNCC21 | c1ccccc1.c1ccc2c(c1)CCC1CNCC21 | Other | null | null | null | Cc1cccc(CC(=O)C2CCc3ccccc3C2C#N)c1>>Cc1cccc(CC2NCC3c4ccccc4CCC23)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d8b557851dd4629afee23bc916f9121 | C1CSCSC1.Fc1cccc(CBr)c1>>Fc1cccc(CC2SCCCS2)c1 | C(CCC)[Li].S1CSCCC1.FC=1C=C(CBr)C=CC1>>FC=1C=C(C=CC1)CC1SCCCS1 | [CH2:8]1[S:9][CH2:10][CH2:11][CH2:12][S:13]1.Br[CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:14]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH:8]2[S:9][CH2:10][CH2:11][CH2:12][S:13]2)[cH:14]1 | C1CSCSC1.Fc1cccc(CBr)c1 | Fc1cccc(CC2SCCCS2)c1 | null | null | CCCCCC.C1CCOC1.C(Cl)Cl | C-C Coupling | OtherReaction | ab0114b4a4cb6005c4898e16d6c0a2b288ca25c97a67a873f171ed1d3be6a47c | 4efa513f567c8dda6a947e269b70f7a500c3fa9b005a8552cb1e41aa23aad50b | c1ccc(CC2SCCCS2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#16:6]-[CH2;D2;+0:7]-[#16:8]-[C:9]>>[C:5]-[#16:6]-[CH;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8]-[C:9] | 66.7 | [{"value": 66.7, "product": "FC=1C=C(C=CC1)CC1SCCCS1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "FC=1C=C(C=CC1)CC1SCCCS1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -23 | CELSIUS | 0.5 | HOUR | 1,3-Dithiane (12 g, 0.1 mol) was dissolved in 150 mL of anhydrous THF under a nitrogen atmosphere. The resultant solution was cooled to -78° C. and n-butyllithium (44 mL of a 2.5M solution of in hexane, 0.11 mol) was added. The reaction mixture was warmed to -23° C. and then stirred at -23° C. for 0.5 h. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide.Monosulfide | Monosulfide.Monosulfide | C1CSCSC1 | C1CSCSC1 | c1ccccc1.C1CSCSC1 | HBr | CCCCCC.C1CCOC1.C(Cl)Cl | -23 | 0.5 | C1CSCSC1.Fc1cccc(CBr)c1>CCCCCC.C1CCOC1.C(Cl)Cl>Fc1cccc(CC2SCCCS2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e05e51d0b3d34018a312b37d4ef0a1b6 | C1CSCSC1.Fc1cccc(CBr)c1>>Fc1ccc(CC2SCCCS2)cc1 | C(CCC)[Li].S1CSCCC1.C1CCOC1.FC=1C=C(CBr)C=CC1>>FC1=CC=C(C=C1)CC1SCCCS1 | [CH2:7]1[S:8][CH2:9][CH2:10][CH2:11][S:12]1.Br[CH2:6][c:5]1[cH:13][cH:4][cH:3][c:2]([F:1])[cH:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]2[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[cH:13][cH:14]1 | C1CSCSC1.Fc1cccc(CBr)c1 | Fc1ccc(CC2SCCCS2)cc1 | null | null | CCCCCC | C-C Coupling | OtherReaction | 7eb7099aaef7a8e030bb6c6581c2bc2d7fb58e3cc95becfcad9c064e11ef082d | 4efa513f567c8dda6a947e269b70f7a500c3fa9b005a8552cb1e41aa23aad50b | c1ccc(CC2SCCCS2)cc1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5]:[c:6](-[F;D1;H0:7]):[cH;D2;+0:8]:1.[C:9]-[#16:10]-[CH2;D2;+0:11]-[#16:12]-[C:13]>>[C:9]-[#16:10]-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:8]:[c:6](-[F;D1;H0:7]):[c:5]:[cH;D2;+0:4]:1)-[#16:12]-[C:13] | 94 | [{"value": 94.0, "product": "FC1=CC=C(C=C1)CC1SCCCS1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | 1,3-Dithiane (20 g, 166 mmol) was dissolved in 250 mL of anhydrous THF under a nitrogen atmosphere. The resultant solution was cooled to -78° C. and n-butyllithium (128 mL of a 1.5M solution of in hexane, 199 m mol) was added. The reaction mixture was warmed to 0° C. and then stirred at 0° C. for 0.5 h. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide.Monosulfide | Monosulfide.Monosulfide | C1CSCSC1.c1ccccc1 | c1ccccc1.C1CSCSC1 | c1ccccc1.C1CSCSC1 | HBr | CCCCCC | 0 | 0.5 | C1CSCSC1.Fc1cccc(CBr)c1>CCCCCC>Fc1ccc(CC2SCCCS2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a42d9fa1cdc4bb59ca4fa196c120674 | COC(=O)C1=CCCc2ccccc21.O=[N+]([O-])CCc1cccc([N+](=O)[O-])c1>>COC(=O)C1c2ccccc2CCC1C(Cc1cccc([N+](=O)[O-])c1)[N+](=O)[O-] | C(=O)(OC)C1=CCCC2=CC=CC=C12.[N+](=O)([O-])C=1C=C(C=CC1)CC[N+](=O)[O-].N12CCCCCC2=NCCC1>>C(=O)(OC)C1C(CCC2=CC=CC=C12)C(CC1=CC(=CC=C1)[N+](=O)[O-])[N+](=O)[O-] | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[CH:14][CH2:13][CH2:12][c:11]2[c:6]1[cH:7][cH:8][cH:9][cH:10]2.[CH2:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1)[N+:26](=[O:27])[O-:28]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][CH2:13][CH:14]1[CH:15]([CH2:16][c:17... | COC(=O)C1=CCCc2ccccc21.O=[N+]([O-])CCc1cccc([N+](=O)[O-])c1 | COC(=O)C1c2ccccc2CCC1C(Cc1cccc([N+](=O)[O-])c1)[N+](=O)[O-] | null | null | C(C)#N.C(C)(=O)OCC | C-C Coupling | OtherReaction | aaeb29b9af1b9b99616f9dc60e090eeceff0100c4c89fb2f957c0ec91b7320ff | 6f872e1e6593abcdd0d9fb5775fd31c259676a11a338f4f9b2b3594108a0aabd | c1ccc(CCC2CCc3ccccc3C2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5]1=[CH;D2;+0:6]-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11].[O;-;D1;H0:12]-[#7;+:13](=[O;D1;H0:14])-[CH2;D2;+0:15]-[C:16]-[c:17]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH;D3;+0:6](-[CH;D3;+0:15](-[C:16]-[c:17])-[#7;+:13](-[O;-;D1;H0:12])=[O;D1;H0:14])-[C:7]-[C:8... | 97.2 | [{"value": 97.0, "product": "C(=O)(OC)C1C(CCC2=CC=CC=C12)C(CC1=CC(=CC=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "C(=O)(OC)C1C(CCC2=CC=CC=C12)C(CC1=CC(=CC=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a mixture of 2 g (10.6 mmol) of 1-carbomethoxy-3,4-dihydronaphthalene, from Step 1 of Example 46, and 2.08 g (10.6 mmol) of 2-(3-nitrophenyl)-1-nitroethane, from Step 2, in 1 mL of acetonitrile was added 0.2 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction mixture was stirred at ambient temperature for 0... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Ester.Nitro group | C1=Cc2ccccc2CC1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | null | C(C)#N.C(C)(=O)OCC | null | 0.5 | COC(=O)C1=CCCc2ccccc21.O=[N+]([O-])CCc1cccc([N+](=O)[O-])c1>C(C)#N.C(C)(=O)OCC>COC(=O)C1c2ccccc2CCC1C(Cc1cccc([N+](=O)[O-])c1)[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a9dfc9e6b4442e382afa28c9f122cb5 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1>>O=[N+]([O-])C=Cc1cccc(Cl)c1 | [OH-].[K+].ClC=1C=C(C=O)C=CC1.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])C>>ClC=1C=C(C=CC1)C=C[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH3:4].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1>>[O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1 | O=[N+]([O-])C=Cc1cccc(Cl)c1 | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 28.11 g (200 mmol) of 3-chlorobenzaldehyde, 15.4 g of ammonium acetate and 32.5 mL of nitromethane in 230 mL of glacial acetic acid was heated at reflux temperature for 3 h and then poured onto ice. The resultant aqueous mixture was made basic by the addition of 45% aqueous potassium hydroxide. The precipi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | C(C)(=O)O | null | null | C[N+](=O)[O-].O=Cc1cccc(Cl)c1>C(C)(=O)O>O=[N+]([O-])C=Cc1cccc(Cl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8ba885339f8d41249dc7afe4b839d218 | O=[N+]([O-])C=Cc1cccc(Cl)c1>>O=[N+]([O-])CCc1cccc(Cl)c1 | ClC=1C=C(C=CC1)C=C[N+](=O)[O-].[BH4-].[Na+]>>ClC=1C=C(C=CC1)CC[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1>>[O:1]=[N+:2]([O-:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | O=[N+]([O-])C=Cc1cccc(Cl)c1 | O=[N+]([O-])CCc1cccc(Cl)c1 | null | null | C(C)O.O1CCOCC1 | Reduction | Hydrogenation (double to single) | 1897ddb5557a7164dfa80083adb557accafa4233396f9576d5bfde28d2818919 | 92f8c31381fee05ef128b294b51ee13ebdada3b3789c3c4a7dc0a1d2ea4408c2 | c1ccccc1 | [O;-;D1;H0:1]-[#7;+:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;-;D1;H0:1]-[#7;+:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 48 | [{"value": 48.0, "product": "ClC=1C=C(C=CC1)CC[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "ClC=1C=C(C=CC1)CC[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 13.5 g (72 mmol) of 2-(3-Chlorophenyl)-1-nitroethene, from Step 2, in 200 mL of dioxane was added dropwise to a stirred suspension of 6 g (157 mmol) of sodium borohydride in a mixture of 140 mL of dioxane and 60 mL of ethanol. The reaction mixture was stirred at ambient temperature for 2 h and then the ex... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | C(C)O.O1CCOCC1 | null | 2 | O=[N+]([O-])C=Cc1cccc(Cl)c1>C(C)O.O1CCOCC1>O=[N+]([O-])CCc1cccc(Cl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0e9e6791f66b44a5853ffa9b8e1fcd15 | CO.N#CC1=CCCc2cc(Cl)ccc21.O>>COC(=O)C1=CCCc2cc(Cl)ccc21 | CO.ClC=1C=C2CCC=C(C2=CC1)C#N.O>>C(=O)(OC)C1=CCCC2=CC(=CC=C12)Cl | [CH3:1][OH:2].N#[C:3][C:5]1=[CH:6][CH2:7][CH2:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]21.[OH2:4]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[CH:6][CH2:7][CH2:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]21 | CO.N#CC1=CCCc2cc(Cl)ccc21.O | COC(=O)C1=CCCc2cc(Cl)ccc21 | null | null | S(O)(O)(=O)=O | Acylation | OtherReaction | 25b7d3e2396602529eceda3adc077f79d6fd790da73e87e4e1fbd1265f44d7b0 | 477d3ec3ec37df7b1359a7d22cd39dadb1daeb5d9957363442952ac99d03b083 | C1=Cc2ccccc2CC1 | N#[C;H0;D2;+0:1]-[C:2](=[C:3]-[C:4])-[c:5].[C;D1;H3:6]-[OH;D1;+0:7].[OH2;D0;+0:8]>>[C:4]-[C:3]=[C:2](-[C;H0;D3;+0:1](=[O;H0;D1;+0:8])-[O;H0;D2;+0:7]-[C;D1;H3:6])-[c:5] | 26 | [{"value": 26.0, "product": "C(=O)(OC)C1=CCCC2=CC(=CC=C12)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 6-Chloro-1-cyano-3,4-dihydronaphthalene (5 g, 263 mmol), lit ref, was dissolved in 77% sulfuric acid in methanol and the resulting solution was heated at 95°-100° C. for 2.5 h. The reaction mixture was allowed to cool to ambient temperature and 45 mL was added, followed by 5 mL of water. The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Methanol | Ester | null | null | C1=Cc2ccccc2CC1 | Other | S(O)(O)(=O)=O | null | 48 | CO.N#CC1=CCCc2cc(Cl)ccc21.O>S(O)(O)(=O)=O>COC(=O)C1=CCCc2cc(Cl)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5be24c88fc2e4cc8b1960a9fe0a69a5d | N#CC1=CCCc2ccccc21.N#CCCc1ccccc1>>N#CC(Cc1ccccc1)C1CCc2ccccc2C1C#N | C1(=CC=CC=C1)CCC#N.C(#N)C1=CCCC2=CC=CC=C12.C(#N)C1=CCCC2=CC=CC=C12.C(C)(C)NC(C)C.C(CCC)[Li]>>C(#N)C1C(CCC2=CC=CC=C12)C(CC1=CC=CC=C1)C#N | [CH:11]1=[C:20]([C:21]#[N:22])[c:19]2[c:14]([cH:15][cH:16][cH:17][cH:18]2)[CH2:13][CH2:12]1.[N:1]#[C:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[N:1]#[C:2][CH:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[CH:20]1[C:21]#[N:22] | N#CC1=CCCc2ccccc21.N#CCCc1ccccc1 | N#CC(Cc1ccccc1)C1CCc2ccccc2C1C#N | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 0129aeb1246532f294262ba021b68c7ed1f5c6b93ed3160aab4a60666db55baa | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc(CCC2CCc3ccccc3C2)cc1 | [N;D1;H0:1]#[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C:5]-[C:6]-[c:7]:[c:8]-1:[c:9].[N;D1;H0:10]#[C:11]-[CH2;D2;+0:12]-[C:13]-[c:14]>>[N;D1;H0:10]#[C:11]-[CH;D3;+0:12](-[C:13]-[c:14])-[CH;D3;+0:4]1-[C:5]-[C:6]-[c:7]:[c:8](:[c:9])-[CH;D3;+0:3]-1-[C:2]#[N;D1;H0:1] | 99.5 | [{"value": 99.5, "product": "C(#N)C1C(CCC2=CC=CC=C12)C(CC1=CC=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 3.5 mL (25 mmol) of diisopropylamine in 40 mL of THF at -78° C., under a nitrogen atmosphere, was added n-butyllithium (9.5 mL of a 2.5M solution in THF, 23.7 mmol) and the resultant solution was stirred at -78° C. for 0.5 h. To the stirred solution was slowly added a solution of 2.75 g (21 mmol) of 3-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2CC1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | null | C1CCOC1 | -78 | 0.5 | N#CC1=CCCc2ccccc21.N#CCCc1ccccc1>C1CCOC1>N#CC(Cc1ccccc1)C1CCc2ccccc2C1C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2381c22df2194b6c83a6f440b9b07972 | COc1ccc2c(c1)CCC=C2C#N.COc1ccc2c(c1)CCC=C2C#N>>COc1ccc2c(c1)CCC(CC#N)C2C#N | C(#N)C1=CCCC2=CC(=CC=C12)OC.C(#N)C1=CCCC2=CC(=CC=C12)OC.C(C)(C)NC(C)C.C(CCC)[Li].C(C)#N>>C(#N)C1C(CCC2=CC(=CC=C12)OC)CC#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]=[C:15]2[C:16]#[N:17].COc1ccc2c(c1)CCC=[C:12]2[C:13]#[N:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]([CH2:12][C:13]#[N:14])[CH:15]2[C:16]#[N:17] | COc1ccc2c(c1)CCC=C2C#N.COc1ccc2c(c1)CCC=C2C#N | COc1ccc2c(c1)CCC(CC#N)C2C#N | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 9c3387d0730f2e56be401d9834ef01667c6e3c89b1208a31c2c7da5d6214475b | a5693ad0ff37ba299a3384a72fcc8b66e16e2c53e1f48e2cc3e13008b4273e5a | c1ccc2c(c1)CCCC2 | C-O-c1:c:c:c2:c(:c:1)-C-C-C=[C;H0;D3;+0:1]-2-[C:2]#[N;D1;H0:3].[N;D1;H0:4]#[C:5]-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:7]1-[C:8]-[C:9]-[c:10]:[c:11](:[c:12])-[CH;D3;+0:6]-1-[C:5]#[N;D1;H0:4] | 74.2 | [{"value": 74.0, "product": "C(#N)C1C(CCC2=CC(=CC=C12)OC)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "C(#N)C1C(CCC2=CC(=CC=C12)OC)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 40 | MINUTE | To a solution of 1.05 mL (7.5 mmol) of diisopropylamine in 10 mL of THF at -78° C., under a nitrogen atmosphere, was added n-butyllithium (2.2 mL of a 2.5M solution in THF, 5.5 mmol) and the resultant solution was stirred at -78° C. for 40 min. To the stirred solution was added, dropwise over a 25 minute period, a solu... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1=Cc2ccccc2CC1.C1=Cc2ccccc2CC1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C1CCOC1 | -78 | 0.666667 | COc1ccc2c(c1)CCC=C2C#N.COc1ccc2c(c1)CCC=C2C#N>C1CCOC1>COc1ccc2c(c1)CCC(CC#N)C2C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4f061f4471424f05a5f309faf9ef5632 | COC(=O)CC(=O)Cc1ccccc1.COc1ccc2c(c1)CCC=C2C#N>>COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N | C1CCC2=NCCCN2CC1.O=C(CC(=O)OC)CC1=CC=CC=C1.C(#N)C1=CCCC2=CC(=CC=C12)OC.C(#N)C1=CCCC2=CC(=CC=C12)OC.C1CCC2=NCCCN2CC1>>O=C(C(C(=O)OC)C1C(C2=CC=C(C=C2CC1)OC)C#N)CC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH:15]1=[C:26]([C:27]#[N:28])[c:25]2[c:18]([cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]2)[CH2:17][CH2:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]1[CH2:16][CH2:1... | COC(=O)CC(=O)Cc1ccccc1.COc1ccc2c(c1)CCC=C2C#N | COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N | null | null | C(C)#N | C-C Coupling | OtherReaction | 06b659e430c38d7049f44cf9f81483d3fe02a4c18a09fabdaf216969690bdca0 | 94c7364692188ef8ef531518cf74a9fca9728a2aa5d4b3e96a01bb7b82219171 | O=C(Cc1ccccc1)CC1CCc2ccccc2C1 | [C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].[N;D1;H0:9]#[C:10]-[C;H0;D3;+0:11]1=[CH;D2;+0:12]-[C:13]-[C:14]-[c:15]:[c:16]-1:[c:17]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[CH;D3;+0:12]1-[C:13]-[C:14]-[c:15]:[c:16](:[c:17])-[CH;D3;+0:11]-1-[C:10... | 65 | [{"value": 65.0, "product": "O=C(C(C(=O)OC)C1C(C2=CC=C(C=C2CC1)OC)C#N)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "O=C(C(C(=O)OC)C1C(C2=CC=C(C=C2CC1)OC)C#N)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methyl 3-oxo-4-phenylbutyrate (29.33 g, 153 mmol) and 1-cyano-6-methoxy-3,4-dihydronaphthalene (25.7, 139 mmol), the product of Step 2 of Example 1, were dissolved in 25 mL of acetonitrile. DBU (1.5 mL) was added and the reaction mixture was stirred for 2 h at ambient temperature. A second aliquot of DBU (1.5 mL) was t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ester | C1=Cc2ccccc2CC1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | null | C(C)#N | null | 2 | COC(=O)CC(=O)Cc1ccccc1.COc1ccc2c(c1)CCC=C2C#N>C(C)#N>COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b7636b58c9434354a2f9df4dde371baa | COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N>>COc1ccc2c(c1)CCC(CC(=O)Cc1ccccc1)C2C#N | Cl.O=C(C(C(=O)OC)C1C(C2=CC=C(C=C2CC1)OC)C#N)CC1=CC=CC=C1.[OH-].[Li+]>>C(#N)C1C(CCC2=CC(=CC=C12)OC)CC(CC1=CC=CC=C1)=O | COC(=O)[CH:12]([CH:11]1[CH2:10][CH2:9][c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH:22]1[C:23]#[N:24])[C:13](=[O:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]([CH2:12][C:13](=[O:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c... | COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N | COc1ccc2c(c1)CCC(CC(=O)Cc1ccccc1)C2C#N | null | null | CO | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | O=C(Cc1ccccc1)CC1CCc2ccccc2C1 | C-O-C(=O)-[CH;D3;+0:1](-[C:2](-[C:3])-[C:4])-[C:5](-[C:6])=[O;D1;H0:7]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[C:5](-[C:6])=[O;D1;H0:7])-[C:4] | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate (4.63 g, 12 mmol), from Step 1, was dissolved in 100 mL of methanol and lithium hydroxide (77 mL of a 1.0M solution) was added. The reaction mixture was stirred overnight at ambient temperature and then acidified with 1N aqueous hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | CO | null | 8 | COC(=O)C(C(=O)Cc1ccccc1)C1CCc2cc(OC)ccc2C1C#N>CO>COc1ccc2c(c1)CCC(CC(=O)Cc1ccccc1)C2C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6af1fdb47b964a16a7ec980db7c96d8b | CCOC(=O)CCC1CCc2ccccc2C1=O.[C-]#N>>CCOC(=O)CCC1=C(C#N)c2ccccc2CC1 | [C-]#N.[Li+].C(C)OC(=O)CCC1C(C2=CC=CC=C2CC1)=O.C(#N)P(OCC)(OCC)=O.O>>C(#N)C1=C(CCC2=CC=CC=C12)CCC(=O)OCC | O=[C:9]1[CH:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:19][CH2:18][c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2.[C-:10]#[N:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8]1=[C:9]([C:10]#[N:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18][CH2:19]1 | CCOC(=O)CCC1CCc2ccccc2C1=O.[C-]#N | CCOC(=O)CCC1=C(C#N)c2ccccc2CC1 | null | null | CN(C)C=O.C1CCOC1 | C-C Coupling | OtherReaction | e01b01043bfaeb01c3e2361338f006aba25607dec206a9f74552ce86fadfe00b | 38173ffb46d9f636178242326a427b3d459fe7c0171d4d0447e25702c6b09e58 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH;D3;+0:2](-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12].[C-;H0;D1:13]#[N;D1;H0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:2]1=[C;H0;D3;+0:1](-[C;H0;D2;+0:13]#[N;D1;H0:14])-[c:11](:[c:12]):[c:10]-[C:9]-[C:8]-1 | 64.2 | [{"value": 64.2, "product": "C(#N)C1=C(CCC2=CC=CC=C12)CCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "C(#N)C1=C(CCC2=CC=CC=C12)CCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-(2-Ethoxycarbonylethyl)-3,4-dihydro-1(2H)-naphthalenone (19.7 g, 80 mmol), from Step 1, was dissolved in 200 mL of dry THF and diethyl cyanophosphonate (23.6 mL, 160 mmol), commercially available from Aldrich Chemical Company, was added, followed by 160 mL of a 0.5M solution of lithium cyanide in DMF. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Nitrile | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | CN(C)C=O.C1CCOC1 | null | 8 | CCOC(=O)CCC1CCc2ccccc2C1=O.[C-]#N>CN(C)C=O.C1CCOC1>CCOC(=O)CCC1=C(C#N)c2ccccc2CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6e03421e3f554cada4678867b24aa606 | CCOC(=O)CCC1CCc2c(OC)cccc2C1=O.[C-]#N>>CCOC(=O)CCC1=C(C#N)c2cccc(OC)c2CC1 | [C-]#N.[Li+].C(C)OC(=O)CCC1C(C2=CC=CC(=C2CC1)OC)=O.C(#N)P(OCC)(OCC)=O.O>>C(#N)C1=C(CCC2=C(C=CC=C12)OC)CCC(=O)OCC | O=[C:9]1[CH:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:21][CH2:20][c:19]2[c:12]1[cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18].[C-:10]#[N:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8]1=[C:9]([C:10]#[N:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]2[CH2:20][CH2:21]1 | CCOC(=O)CCC1CCc2c(OC)cccc2C1=O.[C-]#N | CCOC(=O)CCC1=C(C#N)c2cccc(OC)c2CC1 | null | null | CN(C)C=O.C1CCOC1 | C-C Coupling | OtherReaction | e01b01043bfaeb01c3e2361338f006aba25607dec206a9f74552ce86fadfe00b | 38173ffb46d9f636178242326a427b3d459fe7c0171d4d0447e25702c6b09e58 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH;D3;+0:2](-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12].[C-;H0;D1:13]#[N;D1;H0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:2]1=[C;H0;D3;+0:1](-[C;H0;D2;+0:13]#[N;D1;H0:14])-[c:11](:[c:12]):[c:10]-[C:9]-[C:8]-1 | 70.1 | [{"value": 70.0, "product": "C(#N)C1=C(CCC2=C(C=CC=C12)OC)CCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "C(#N)C1=C(CCC2=C(C=CC=C12)OC)CCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 2-(2-Ethoxycarbonylethyl)-3,4-dihydro-5-methoxy-1(2H)-naphthalenone (1.1 g, 4 mmol), from Step 1, was dissolved in 15 mL of dry THF and cooled to 0° C. Diethyl cyanophosphonate (1.18 mL, 8 mmol), commercially available from Aldrich Chemical Company, was added, followed by 8 mL of a 0.5M solution of lithium cyanide (4 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Nitrile | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | CN(C)C=O.C1CCOC1 | 0 | 8 | CCOC(=O)CCC1CCc2c(OC)cccc2C1=O.[C-]#N>CN(C)C=O.C1CCOC1>CCOC(=O)CCC1=C(C#N)c2cccc(OC)c2CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-43574d7d6f5f4aa8866fdde3b5c2f0dc | BrCc1ccccc1.O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1>>O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1Cc1ccccc1 | O.CC(C)([O-])C.[K+].O=C1CC[C@H]2[C@@H](CN1)C1=CC=CC=C1CC2.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C[C@@H]2[C@H](CCC1=O)CCC1=CC=CC=C12 | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[O:1]=[C:2]1[CH2:3][CH2:4][C@@H:5]2[CH2:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[C@@H:14]2[CH2:15][NH:16]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C@@H:5]2[CH2:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[C@@H:14]2[CH2:15][N:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21... | BrCc1ccccc1.O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1 | O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1Cc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8d8dca04155cc1bc79249673a734d568d6a2f78b16832b1110970efacca8a1e5 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[C:10]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8](=[O;D1;H0:9])-[C:10] | 79 | [{"value": 79.0, "product": "C(C1=CC=CC=C1)N1C[C@@H]2[C@H](CCC1=O)CCC1=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "C(C1=CC=CC=C1)N1C[C@@H]2[C@H](CCC1=O)CCC1=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a suspension of cis-1,3,4,5,5a,6,7,11b-octahydro-3-oxo-2H-naphth[1,2-c]azepine (1.0 g, 4.65 mmol), from Step 3 of Example 75, in 20 mL of dry THF, was added potassium t-butoxide (0.78 g, 6.9 mmol). The reaction mixture was stirred at ambient temperature for 0.5 h and then cooled to 0° C. and benzyl bromide (0.8 mL, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CC[C@H]1CCCNC[C@@H]21 | c1ccc2c(c1)CC[C@H]1CCC[NH]C[C@@H]21 | c1ccc2c(c1)CC[C@H]1CCC[NH]C[C@@H]21.c1ccccc1 | HBr | C1CCOC1 | null | 0.5 | BrCc1ccccc1.O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1>C1CCOC1>O=C1CC[C@@H]2CCc3ccccc3[C@@H]2CN1Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f3ba761238a143e1b68d0ab2aac52f4d | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>>C=C(C)C(=O)OCCOC(=O)C(=O)OCC | C(C(=C)C)(=O)OCCO.C(C(=O)OCC)(=O)OCC.C(C)O>>C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][OH:9].CCO[C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16] | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC | C=C(C)C(=O)OCCOC(=O)C(=O)OCC | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(O)=CC=C(O)C=C1 | null | Acylation | Transesterification | 78fca4eb4a1c9bfa8e423f92a9d12c264c52db88a588463b687f679a6641c521 | b13152bdbecf5f32acc9bbb4c1c2e172eebaff97800b4381979bc284516946c9 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | 76.5 | [{"value": 76.5, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A 500 ml flask equipped with a decanter, a thermometer, a stirrer and an inlet for nitrogen gas was charged with 65.1 g (0.5 mol) of 2-hydroxyethyl methacrylate and 365.4 g (2.5 mol) of diethyl oxalate, to which 2 g (10 mmol) of p-toluenesulfonic acid (catalyst) and 4 g of hydroquinone (polymerization inhibitor) were a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary alcohol | Ester.Ester | null | null | null | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(O)=CC=C(O)C=C1 | null | 4 | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(O)=CC=C(O)C=C1>C=C(C)C(=O)OCCOC(=O)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5bb43bb802e74697b19c498517a29caa | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>>C=C(C)C(=O)OCCOC(=O)C(=O)OCC | C(C(=C)C)(=O)OCCO.C(C(=O)OCC)(=O)OCC.C(C)O>>C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][OH:9].CCO[C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16] | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC | C=C(C)C(=O)OCCOC(=O)C(=O)OCC | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=CC(=C1)O | null | Acylation | Transesterification | 78fca4eb4a1c9bfa8e423f92a9d12c264c52db88a588463b687f679a6641c521 | b13152bdbecf5f32acc9bbb4c1c2e172eebaff97800b4381979bc284516946c9 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | 76.5 | [{"value": 76.5, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 500 ml flask equipped with a decanter, a thermometer, a stirrer and an inlet for nitrogen gas was charged with 65.1 g (0.5 mol) of 2-hydroxyethyl methacrylate and 365.4 g (2.5 mol) of diethyl oxalate, to which 2 g (10 mmol) of p-toluenesulfonic acid (catalyst) and 4 g of 2-t-butylhydroquinone (polymerization inhibito... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary alcohol | Ester.Ester | null | null | null | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=CC(=C1)O | null | 3 | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=CC(=C1)O>C=C(C)C(=O)OCCOC(=O)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55437dbf90b64b46927be1c1700be2ac | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>>C=C(C)C(=O)OCCOC(=O)C(=O)OCC | C(C(=C)C)(=O)OCCO.C(C(=O)OCC)(=O)OCC.C(C)O>>C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][OH:9].CCO[C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16] | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC | C=C(C)C(=O)OCCOC(=O)C(=O)OCC | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C | null | Acylation | Transesterification | 78fca4eb4a1c9bfa8e423f92a9d12c264c52db88a588463b687f679a6641c521 | b13152bdbecf5f32acc9bbb4c1c2e172eebaff97800b4381979bc284516946c9 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | 56.3 | [{"value": 52.4, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 500 ml flask equipped with a decanter, a thermometer, a stirrer and an inlet for nitrogen gas was charged with 65.1 g (0.5 mol) of 2-hydroxyethyl methacrylate and 365.4 g (2.5 mol) of diethyl oxalate, to which 2 g (10 mmol) of p-toluenesulfonic acid (catalyst) and 4 g of 2,5-di-t-butylhydroquinone (polymerization inh... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary alcohol | Ester.Ester | null | null | null | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C | null | 3 | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C>C=C(C)C(=O)OCCOC(=O)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e1b570bc8ce444bb33a68c096a4880b | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>>C=C(C)C(=O)OCCOC(=O)C(=O)OCC | C(C(=C)C)(=O)OCCO.C(C(=O)OCC)(=O)OCC.C(C)O>>C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][OH:9].CCO[C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16] | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC | C=C(C)C(=O)OCCOC(=O)C(=O)OCC | null | C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C | null | Acylation | Transesterification | 78fca4eb4a1c9bfa8e423f92a9d12c264c52db88a588463b687f679a6641c521 | b13152bdbecf5f32acc9bbb4c1c2e172eebaff97800b4381979bc284516946c9 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | 73.2 | [{"value": 73.2, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "C(C(=C)C)(=O)OCCOC(=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500 ml flask equipped with a decanter, a thermometer, a stirrer and an inlet for nitrogen gas was charged with 65.1 g (0.5 mol) of 2-hydroxyethyl methacrylate and 365.4 g (2.5 mol) of diethyl oxalate, to which 2 g (10 mmol) of dibutyltin dilaurate (catalyst) and 4 g of 2,5-di-t-butylhydroquinone (polymerization inhib... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary alcohol | Ester.Ester | null | null | null | HO- | C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C | null | null | C=C(C)C(=O)OCCO.CCOC(=O)C(=O)OCC>C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC.C(C)(C)(C)C1=C(O)C=C(C(=C1)O)C(C)(C)C>C=C(C)C(=O)OCCOC(=O)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eb42087260a94c678501a68bb3d83b03 | C=Cc1ccc(CCO)cc1.CCOC(=O)C(=O)Cl>>C=Cc1ccc(CCOC(=O)C(=O)OCC)cc1 | C(=O)(C(=O)OCC)Cl.OCCC1=CC=C(C=C)C=C1.C(C)N(CC)CC>>C(=O)(C(=O)OCC)OCCC1=CC=C(C=C)C=C1 | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:17][cH:18]1.Cl[C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][C:10](=[O:11])[C:12](=[O:13])[O:14][CH2:15][CH3:16])[cH:17][cH:18]1 | C=Cc1ccc(CCO)cc1.CCOC(=O)C(=O)Cl | C=Cc1ccc(CCOC(=O)C(=O)OCC)cc1 | null | null | C1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | c6e09616b6bb08f487e50f4272dd934070dd97cfdd94b0ca77f05cb1b1832016 | 674ca7f6a5419c8179935ec7795e4632b99c82de6c610aa384dddefb222306c5 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | null | [] | 10 | CELSIUS | 2 | HOUR | A 200 ml flask equipped with a stirrer, a thermometer and a dropping funnel was charged with 14.8 g (0.1 mol) of p-hydroxyethylstyrene, 150 ml of benzene and 10.1 g (0.1 mol) of triethylamine and cooled to 10° C. To the mixture was added dropwise with stirring 13.7 g (0.1 mol) of ethoxalyl chloride for one hour at 10° ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary alcohol | Ester.Ester | null | null | c1ccccc1 | HCl | C1=CC=CC=C1 | 10 | 2 | C=Cc1ccc(CCO)cc1.CCOC(=O)C(=O)Cl>C1=CC=CC=C1>C=Cc1ccc(CCOC(=O)C(=O)OCC)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-52ecedb5e4fd4c16b5bdf50423b6140d | CCCCCCCCCCCCN.[N-]=C=O>>CCCCCCCCCCCCNC(N)=O | [N-]=C=O.C(C)[NH+](CC)CC.C(CCCCCCCCCCC)N>>C(CCCCCCCCCCC)NC(=O)N | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].[C:14](=[N-:15])=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH2:15])=[O:16] | CCCCCCCCCCCCN.[N-]=C=O | CCCCCCCCCCCCNC(N)=O | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | fec8ce0db817cb9adf4794b3c5ae318c150decedadcebfebfdf328f25035cc8e | 4cf759e067568cc19d6858be8959598bd5316ab2ab31ad8bd54dcb75f9008a64 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[N-;H0;D1:4]=[C;H0;D2;+0:5]=[O;D1;H0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[NH2;D1;+0:4])=[O;D1;H0:6] | null | [] | null | null | 24 | HOUR | 14.1 g of dodecylamine (0.076 mol) dissolved in 20 ml of chloroform were added dropwise at room temperature with stirring to 100 ml of a solution of 10 g of triethylammonium isocyanate (0.069 mol) in chloroform, prepared according to Example 1. After completion of the addition, the mixture was subsequently stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Urea | null | null | null | null | C(Cl)(Cl)Cl | null | 24 | CCCCCCCCCCCCN.[N-]=C=O>C(Cl)(Cl)Cl>CCCCCCCCCCCCNC(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-26e9cd6443ee4b97a309ce9dc3dbdef8 | CN1CCCC1=O.NCCN.[N-]=C=O>>NC(=O)NCCNC(N)=O | C(CN)N.[N-]=C=O.CN1C(CCC1)=O>>C(CNC(=O)N)NC(=O)N | C[N:9]1CCC[C:8]1=[O:10].[NH2:4][CH2:5][CH2:6][NH2:7].[N-:1]=[C:2]=[O:3]>>[NH2:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][C:8]([NH2:9])=[O:10] | CN1CCCC1=O.NCCN.[N-]=C=O | NC(=O)NCCNC(N)=O | null | null | null | Acylation | OtherReaction | 2efad4ea4a1121c37bb39638d410230c9d1a1c77ba696ac1e25eef30dd987541 | 8cbc7b37abe41435ec5cf68add2d69d8e3a37c171dc02737548783ea182dfec6 | null | C-[N;H0;D3;+0:1]1-C-C-C-[C;H0;D3;+0:2]-1=[O;D1;H0:3].[N-;H0;D1:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[NH2;D1;+0:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 24 | HOUR | 1.88 g of ethylenediamine (0.031 mol) were added dropwise at room temperature with stirring to 100 ml of a solution of 10 g of triethylammonum isocyanate (0.069 mol) in 100 ml of N-methylpyrrolidone, prepared according to the procedure described in example 1. After stirring at room temperature for 24 hours, the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Primary amine | Urea.Urea | C1CC[NH]C1 | null | null | Other | null | null | 24 | CN1CCCC1=O.NCCN.[N-]=C=O>>NC(=O)NCCNC(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-708d04ef70ce40fc929d6ad0b2ca124d | CCCCCCCCCCCCCCCCCCS.CN1CCCC1=O>>CCCCCCCCCCCCCCCCCCSC(N)=O | C(CCCCCCCCCCCCCCCCC)S.CN1C(CCC1)=O>>C(N)(SCCCCCCCCCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][SH:19].C[N:21]1CCC[C:20]1=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19][C:20]([N... | CCCCCCCCCCCCCCCCCCS.CN1CCCC1=O | CCCCCCCCCCCCCCCCCCSC(N)=O | null | null | null | Acylation | OtherReaction | a70866c63b7b54ba7c2787885997ec190749b75aa5b80e249358347801022ac5 | 0ab955a5e6cea8ebd0db5bdf3ed34fbfdf14dbc1d37769d97c6058ae7d4a56ac | null | C-[N;H0;D3;+0:1]1-C-C-C-[C;H0;D3;+0:2]-1=[O;D1;H0:3].[C:4]-[C:5]-[SH;D1;+0:6]>>[C:4]-[C:5]-[S;H0;D2;+0:6]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | 60 | [{"value": 60.0, "product": "C(N)(SCCCCCCCCCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described in Example 17, but using 63 g of 1-octadecylmercaptan (0.22 mol) dissolved in 30 ml of N-methylpyrrolidone, S-octadecyl thiocarbamate was obtained in a yield of 60% of theory.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aliphatic thiol | Primary amide.Monosulfide | C1CC[NH]C1 | null | null | Other | null | null | null | CCCCCCCCCCCCCCCCCCS.CN1CCCC1=O>>CCCCCCCCCCCCCCCCCCSC(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f8135fc2ea3458ea13011035828fec5 | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.C[C@H](O)C(=O)O>>CC(O)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)[C@](C(=O)O)(O)C.C([C@@H](O)C)(=O)O.C(C)(C)N(C(O)=NC(C)C)CC1=CC=CC=C1>>C(C(O)C)(=O)OCC1=CC=CC=C1 | CC(C)N=C(O)N(C(C)C)[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][C@H:2]([OH:3])[C:4](=[O:5])[OH:6]>>[CH3:1][CH:2]([OH:3])[C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.C[C@H](O)C(=O)O | CC(O)C(=O)OCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8ba133f06c4c0df103dfa8d83a3ae1c8f954a895eb15a5679d75dae29435b369 | 99f5e58a6f94b05681979232ec71674baa8e98488f497e30fe94f5f9a191f8d9 | c1ccccc1 | C-C(-C)-N=C(-O)-N(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-C(-C)-C.[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95 | [{"value": 95.0, "product": "C(C(O)C)(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 10 | MINUTE | Construction of Benzyl-L-lactic Acid. L-Lactic acid (9 g, 100 mmol) is added to N,N'-diisopropylbenzylisourea (23.3 g, 100 mmol) with stirring. The mixture becomes very viscous within 10 min and is stirred intermittently for 1 h. The volume is then increased to 200 mL with THF, and the mixture stirred for 48 h at room ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Ester | null | null | c1ccccc1 | HO- | C1CCOC1 | -15 | 0.166667 | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.C[C@H](O)C(=O)O>C1CCOC1>CC(O)C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c317f14cf624df39c513f9852247f2b | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.O=C(O)CO>>O=C(CO)OCc1ccccc1 | C(C1=CC=CC=C1)C(C(=O)O)O.C(CO)(=O)O.C(C)(C)N(C(O)=NC(C)C)CC1=CC=CC=C1>>C(CO)(=O)OCC1=CC=CC=C1 | CC(C)N=C(O)N(C(C)C)[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[O:1]=[C:2]([CH2:3][OH:4])[OH:5]>>[O:1]=[C:2]([CH2:3][OH:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.O=C(O)CO | O=C(CO)OCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8ba133f06c4c0df103dfa8d83a3ae1c8f954a895eb15a5679d75dae29435b369 | 99f5e58a6f94b05681979232ec71674baa8e98488f497e30fe94f5f9a191f8d9 | c1ccccc1 | C-C(-C)-N=C(-O)-N(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-C(-C)-C.[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | -15 | CELSIUS | 1 | HOUR | Construction of Benzyl-glycolic Acid. Glycolic acid (7.69,100 mmols) is added to N,N'-diisopropylbenzylisourea (23.39,100 mmols) with stirring for 1 hour. The volume is then increased to 200 mL with THF, and the mixture stirred for 48 h at room temperature. After cooling the mixture to -15° C., the diisopropylurea is r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Ester | null | null | c1ccccc1 | HO- | C1CCOC1 | -15 | 1 | CC(C)N=C(O)N(Cc1ccccc1)C(C)C.O=C(O)CO>C1CCOC1>O=C(CO)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-306e2fc44682415ab97ed11fe0b4fe4d | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | OC1=CC=C(C(=O)O)C=C1.[N+](=O)([O-])C1=CC=C(C=C1)N=C=O.[N+](=O)([O-])C1=CC=C(C=C1)N=C=O.OC1=CC=C(C(=O)O)C=C1>>OC1=CC=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1 | O=C(O)[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1 | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | null | [O-]CC.[Na+] | O | Acylation | OtherReaction | 0a4f9f839bd76ff42d7022423fd0d57ba4af4e525edf9af136996b41a6d77a9a | 8cd051de7c4ef961c82855c2d4826ac655c3097ad2a955f94089daf3fea36350 | O=C(Nc1ccccc1)c1ccccc1 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 30 | CELSIUS | 24 | MINUTE | p-Hydroxybenzoic acid (59.05 grams, 0.4275 mole), sodium ethoxide catalyst (0.133 gram, 0.225% wt. of the p-hydroxybenzoic acid used) and N,N'-dimethylacetamide solvent (404 grams) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere at 80° C. p-Nitrophenylisocyanate (73.85 gr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Isocyanate | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | [O-]CC.[Na+].O | 30 | 0.4 | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1>[O-]CC.[Na+].O>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dedaac03465d424890205b49f02a8944 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1>>Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 | OC1=CC=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1>>OC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]2)[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]2)[cH:16][cH:17]1 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 23.3 | HOUR | A portion (44.1 grams, 0.1708 mole) of 4-hydroxy-4'-nitrobenzanilide from A. above and ethanol (300 milliliters) are added to a 400 milliliter heavy walled glass bottle then sparged with nitrogen. After removal of air by nitrogen sparaing, Raney nickel catalyst (5.5 grams of a 75% wt. slurry in water at pH 10) is added... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 25 | 23.3 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1>C(C)O>Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b470b03ef0a74e3ea56e7f31c8f25984 | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1>>CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | OC1=CC=C(C=O)C=C1.C(C)(=O)OC(C)=O.[N+](=O)([O-])C1=CC=C(C=C1)CC(=O)O.[OH-].[Na+]>>[N+](=O)([O-])C1=CC=C(C=C1)C(C(=O)O)=CC1=CC=C(C=C1)OC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[CH2:10]([C:11](=[O:12])[OH:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.O=[CH:9][c:8]1[cH:7][cH:6][c:5]([OH:4])[cH:24][cH:23]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:10]([C:11](=[O:12])[OH:13])[c:14]2[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20... | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | null | null | C(C)O.O | C-C Coupling | OtherReaction | 24a5e5e840ab45f5ac71997b75bf9c9458ee729ce4846b47c2e20c66771f0961 | 6c4f18f39f8669eaadd9c3cc600e61ebad6b18d43c79a6714cb972028b541e8a | C(=Cc1ccccc1)c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]:[c:11]:1.[O;D1;H0:12]=[C:13](-[O;D1;H1:14])-[CH2;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:9]-[c:8]1:[c:7]:[c:6]:[c:5](-[CH;D2;+0:4]=[C;H0;D3;+0:15](-[C:13](=[O;D... | null | [] | 60 | CELSIUS | null | null | p-Nitrophenylacetic acid (94.02 grams, 0.519 mole) and 1.038 N sodium hydroxide solution (500 mL) are added to a 1,000 mL beaker and heated with stirring to 60° C. The resultant solution is rotary evaporated under vacuum until final conditions of 110° C. and 1 mm Hg are achieved and maintained for 30 minutes. A portion... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aldehyde.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O.O | 60 | null | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1>C(C)O.O>CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d00a375e72f0484ca91396b30c1a39d9 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1>>O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C(C(=O)O)=CC1=CC=C(C=C1)OC(C)=O.C(C)O.Cl>>[N+](=O)([O-])C1=CC=C(C=C1)C=CC1=CC=C(C=C1)O | CC(=O)[O:14][c:13]1[cH:12][cH:11][c:10]([CH:9]=[C:8](C(=O)O)[c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][cH:17]2)[cH:16][cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | null | null | O | Reduction | OtherReaction | 63d7b9aaad312e5baffeb44abd9c90e266b4780604401c57bad121dfb88a1b0f | cdacdbe1471398702b32f2e73cf8a0e6eb084eb181796c9ace64f43ec88059ea | C(=Cc1ccccc1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C(=O)-[C;H0;D3;+0:5](=[C:6]-[c:7])-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[c:7]-[C:6]=[CH;D2;+0:5]-[c:8](:[c:9]):[c:10] | null | [] | 95 | CELSIUS | null | null | A portion (36.75 grams) of a-p-nitrophenyl-p-acetoxycinnamic acid from A. above, ethanol (300 mL) and concentrated hydrochloric acid (300 mL) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere. Heating commenced and a reflux is achieved at 93° C. Refluxing continued over the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O | 95 | null | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1>O>O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f8a59aa44ce44b84b554ec20435346e3 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1>>Nc1ccc(C=Cc2ccc(O)cc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C=CC1=CC=C(C=C1)O>>OC1=CC=C(C=C1)C=CC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]2)[cH:15][cH:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | Nc1ccc(C=Cc2ccc(O)cc2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=Cc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 28.5 | HOUR | A portion (20.9 grams, 0.0866 mole) of 4-nitro-4'-hydroxystilbene from B. above and ethanol (300 mL) are added to a 400 milliliter heavy walled glass bottle then sparged with nitrogen. After removal of air by nitrogen sparging, Raney nickel catalyst (2.5 grams of a 50% wt. slurry in water at pH 10) is washed one time w... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 25 | 28.5 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1>C(C)O>Nc1ccc(C=Cc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-144d23a00694409eac516557c38a54b0 | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | OC1=CC=C(C(=O)O)C=C1.[N+](=O)([O-])C1=CC=C(C=C1)N=C=O.[N+](=O)([O-])C1=CC=C(C=C1)N=C=O.OC1=CC=C(C(=O)O)C=C1>>OC1=CC=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1 | O=C(O)[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1 | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | null | [O-]CC.[Na+] | O | Acylation | OtherReaction | 0a4f9f839bd76ff42d7022423fd0d57ba4af4e525edf9af136996b41a6d77a9a | 8cd051de7c4ef961c82855c2d4826ac655c3097ad2a955f94089daf3fea36350 | O=C(Nc1ccccc1)c1ccccc1 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 30 | CELSIUS | 24 | MINUTE | p-Hydroxybenzoic acid (59.05 grams, 0.4275 mole), sodium ethoxide catalyst (0.133 gram, 0.225% wt. of the p-hydroxybenzoic acid used) and N,N'-dimethylacetamide solvent (404 grams) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere at 80° C. p-Nitrophenylisocyanate (73.85 gr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Isocyanate | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | [O-]CC.[Na+].O | 30 | 0.4 | O=C(O)c1ccc(O)cc1.O=C=Nc1ccc([N+](=O)[O-])cc1>[O-]CC.[Na+].O>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ae4392ce52324edfb94a96dc192d5fe2 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1>>Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 | OC1=CC=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1>>OC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]2)[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]2)[cH:16][cH:17]1 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1 | Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 23.3 | HOUR | A portion (44.1 grams, 0.1708 mole) of 4-hydroxy-4'-nitrobenzanilide from A. above and ethanol (300 milliliters) are added to a 400 milliliter heavy walled glass bottle then sparged with nitrogen. After removal of air by nitrogen sparaing, Raney nickel catalyst (5.5 grams of a 75% wt. slurry in water at pH 10) is added... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 25 | 23.3 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1>C(C)O>Nc1ccc(NC(=O)c2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f0a6c0c7bd4543d5854a784022e9f21e | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1>>CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | OC1=CC=C(C=O)C=C1.C(C)(=O)OC(C)=O.[N+](=O)([O-])C1=CC=C(C=C1)CC(=O)O.[OH-].[Na+]>>[N+](=O)([O-])C1=CC=C(C=C1)C(C(=O)O)=CC1=CC=C(C=C1)OC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[CH2:10]([C:11](=[O:12])[OH:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.O=[CH:9][c:8]1[cH:7][cH:6][c:5]([OH:4])[cH:24][cH:23]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:10]([C:11](=[O:12])[OH:13])[c:14]2[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20... | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | null | null | C(C)O.O | C-C Coupling | OtherReaction | 24a5e5e840ab45f5ac71997b75bf9c9458ee729ce4846b47c2e20c66771f0961 | 6c4f18f39f8669eaadd9c3cc600e61ebad6b18d43c79a6714cb972028b541e8a | C(=Cc1ccccc1)c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]:[c:11]:1.[O;D1;H0:12]=[C:13](-[O;D1;H1:14])-[CH2;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:9]-[c:8]1:[c:7]:[c:6]:[c:5](-[CH;D2;+0:4]=[C;H0;D3;+0:15](-[C:13](=[O;D... | null | [] | 60 | CELSIUS | null | null | p-Nitrophenylacetic acid (94.02 grams, 0.519 mole) and 1.038 N sodium hydroxide solution (500 mL) are added to a 1,000 mL beaker and heated with stirring to 60° C. The resultant solution is rotary evaporated under vacuum until final conditions of 110° C. and 1 mm Hg are achieved and maintained for 30 minutes. A portion... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aldehyde.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O.O | 60 | null | CC(=O)OC(C)=O.O=C(O)Cc1ccc([N+](=O)[O-])cc1.O=Cc1ccc(O)cc1>C(C)O.O>CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bd2f92a102804b7a9cd611e6967e0025 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1>>O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C(C(=O)O)=CC1=CC=C(C=C1)OC(C)=O.C(C)O.Cl>>[N+](=O)([O-])C1=CC=C(C=C1)C=CC1=CC=C(C=C1)O | CC(=O)[O:14][c:13]1[cH:12][cH:11][c:10]([CH:9]=[C:8](C(=O)O)[c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][cH:17]2)[cH:16][cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | null | null | O | Reduction | OtherReaction | 63d7b9aaad312e5baffeb44abd9c90e266b4780604401c57bad121dfb88a1b0f | cdacdbe1471398702b32f2e73cf8a0e6eb084eb181796c9ace64f43ec88059ea | C(=Cc1ccccc1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C(=O)-[C;H0;D3;+0:5](=[C:6]-[c:7])-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[c:7]-[C:6]=[CH;D2;+0:5]-[c:8](:[c:9]):[c:10] | null | [] | 95 | CELSIUS | null | null | A portion (36.75 grams) of a-p-nitrophenyl-p-acetoxycinnamic acid from A. above, ethanol (300 mL) and concentrated hydrochloric acid (300 mL) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere. Heating commenced and a reflux is achieved at 93° C. Refluxing continued over the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O | 95 | null | CC(=O)Oc1ccc(C=C(C(=O)O)c2ccc([N+](=O)[O-])cc2)cc1>O>O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0fc77ce97dd941919665786a507204ef | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1>>Nc1ccc(C=Cc2ccc(O)cc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C=CC1=CC=C(C=C1)O>>OC1=CC=C(C=C1)C=CC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]2)[cH:15][cH:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1 | Nc1ccc(C=Cc2ccc(O)cc2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=Cc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 28.5 | HOUR | A portion (20.9 grams, 0.0866 mole) of 4-nitro-4'-hydroxystilbene from B. above and ethanol (300 mL) are added to a 400 milliliter heavy walled glass bottle then sparged with nitrogen. After removal of air by nitrogen sparging, Raney nickel catalyst (2.5 grams of a 50% wt. slurry in water at pH 10) is washed one time w... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 25 | 28.5 | O=[N+]([O-])c1ccc(C=Cc2ccc(O)cc2)cc1>C(C)O>Nc1ccc(C=Cc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e7e3a364972640cab00e95d8a664a41d | CC1(C)CC(N=C=S)CC(C)(C)N1[O]>>CC1(C)CCCC(C)(C)N1[O] | C1=CC(=CC(=C1)NC(=O)CC2=CC=C(C=C2)NC3=NC=NC4=C3N=CN4[C@H]5[C@@H]([C@@H]([C@H](O5)CO)O)O)CC(=O)NCCN.O=C[C@H](O)[C@H](O)[C@H](O)CO.CC1(CC(CC(N1[O])(C)C)N=C=S)C.O.C1=CC(=CC(=C1)NC(=O)CC2=CC=C(C=C2)NC3=NC=NC4=C3N=CN4[C@H]5[C@@H]([C@@H]([C@H](O5)CO)O)O)CC(=O)NCCN>>CC1(CCCC(N1[O])(C)C)C.C1=CC(=CC(=C1)NC(=O)CC2=CC=C(C=C2)NC3=... | S=C=N[CH:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[N:10]([O:11])[C:7]([CH3:8])([CH3:9])[CH2:6]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[N:10]1[O:11] | CC1(C)CC(N=C=S)CC(C)(C)N1[O] | CC1(C)CCCC(C)(C)N1[O] | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | ce96f9dbda9551d9c3bc49f7388aca1ac64720ba7c3b1632614857a0d19192b5 | 4e930e84ca7a4b5a1b2ffdfd0ad5173746b70455a6634f66996611a6644c2fb6 | C1CCNCC1 | S=C=N-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[CH2;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | ADAC, 2 (11.8 mg, 20 umol), was suspended in 0.5 ml DMF and treated with 4-isothiocyanato-TEMPO (2,2,6,6,-tetramethyl-1-piperidinyloxy, free radical (7 mg, Aldrich). After 1 hour 1.5 ml water was added to the solution, and the precipitate was collected, washed with a minimum of MeOH and ether, and recrystallized from D... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | null | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | CN(C)C=O | null | null | CC1(C)CC(N=C=S)CC(C)(C)N1[O]>CN(C)C=O>CC1(C)CCCC(C)(C)N1[O] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9dd9e53838e64349bfafd944e71e35ae | CCCCC(O[SiH](c1ccccc1)c1ccccc1)[C@@H]1O[C@H](n2ccc(N)nc2=O)CS1>>Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1 | C(CCC)C([C@@H]1O[C@@H](CS1)N1C(=O)N=C(N)C=C1)O[SiH](C1=CC=CC=C1)C1=CC=CC=C1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC[C@@H]1O[C@@H](CS1)N1C(=O)N=C(N)C=C1 | CCCC[CH:10]([C@H:9]1[S:8][CH2:7][C@@H:6]([n:5]2[cH:4][cH:3][c:2]([NH2:1])[n:15][c:13]2=[O:14])[O:12]1)[O:11][SiH](c1ccccc1)c1ccccc1>>[NH2:1][c:2]1[cH:3][cH:4][n:5]([C@@H:6]2[CH2:7][S:8][C@H:9]([CH2:10][OH:11])[O:12]2)[c:13](=[O:14])[n:15]1 | CCCCC(O[SiH](c1ccccc1)c1ccccc1)[C@@H]1O[C@H](n2ccc(N)nc2=O)CS1 | Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1 | null | null | C1CCOC1 | Deprotection | OtherReaction | 9aaa703a406e2dc7eac47a2e7fa8489b941730a034828339b6d1cc86fe888dda | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | O=c1ncccn1[C@@H]1CSCO1 | C-C-C-C-[CH;D3;+0:1](-[O;H0;D2;+0:2]-[SiH](-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:3]1-[#16:4]-[C:5]-[C:6]-[#8:7]-1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:3]1-[#16:4]-[C:5]-[C:6]-[#8:7]-1 | 75 | [{"value": 75.0, "product": "OC[C@@H]1O[C@@H](CS1)N1C(=O)N=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "OC[C@@H]1O[C@@H](CS1)N1C(=O)N=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the β anomer 17 (0.15 g, 0.32 mmol) in THF (25 mL) was added tetrabutylammonium fluoride 1M in THF (0.35 mL, 0.35 mmol, 1.1 eq) and the reaction was allowed to stir at room temperature until TLC indicated the disappearance of starting material (30 min). The reaction mixture was concentrated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CSCO1 | Other | C1CCOC1 | null | null | CCCCC(O[SiH](c1ccccc1)c1ccccc1)[C@@H]1O[C@H](n2ccc(N)nc2=O)CS1>C1CCOC1>Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6cab89fbffc94bf8aa8d99d718c666ee | CC(C)(C)C(=O)Cl.Nc1cccc(C(F)(F)F)c1>>CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1 | O.C(C(C)(C)C)(=O)Cl.FC(C=1C=C(N)C=CC1)(F)F.C(C)N(CC)CC>>CC(C(=O)NC1=CC(=CC=C1)C(F)(F)F)(C)C | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1 | CC(C)(C)C(=O)Cl.Nc1cccc(C(F)(F)F)c1 | CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1 | null | null | CCOCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 98.3 | [{"value": 98.0, "product": "CC(C(=O)NC1=CC(=CC=C1)C(F)(F)F)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "CC(C(=O)NC1=CC(=CC=C1)C(F)(F)F)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | A solution of pivaloyl chloride (3.62 g; 30 mmol) in 40 ml dry ether was added dropwise at room temperature to a mixture of 3-trifluoromethyl-aniline (4.83 g, 30 mmol) and triethylamine (4.25 ml, 30.5 mmol). This was stirred at room temperature for a period of 14 hours and then poured into 200 ml water, extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | CCOCC | null | 14 | CC(C)(C)C(=O)Cl.Nc1cccc(C(F)(F)F)c1>CCOCC>CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cf8bc12a322f4aaaa1ba0ed4f8b9cd14 | CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1.CI>>Cc1c(NC(=O)C(C)(C)C)cccc1C(F)(F)F | CC(C(=O)NC1=CC(=CC=C1)C(F)(F)F)(C)C.[Li]CCCC.CI>>CC(C(=O)NC1=C(C(=CC=C1)C(F)(F)F)C)(C)C | [cH:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18].I[CH3:1]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1.CI | Cc1c(NC(=O)C(C)(C)C)cccc1C(F)(F)F | null | null | O1CCCC1 | C-C Coupling | Methylation with MeI_aryl | f457d3624ba90c4fd64ed28171ff7b2f7d20adbdddcd1b7e903999d38e58575c | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccccc1 | I-[CH3;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[#7:10]-[C:11]=[O;D1;H0:12]):[c:13]>>[CH3;D1;+0:1]-[c;H0;D3;+0:8](:[c:6](-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5]):[c:7]):[c:9](-[#7:10]-[C:11]=[O;D1;H0:12]):[c:13] | 80 | [{"value": 80.0, "product": "CC(C(=O)NC1=C(C(=CC=C1)C(F)(F)F)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | A solution of 2,2-dimethyl-3'-trifluoromethyl-propionanilide (6.1 g, 25 mmol) in 100 ml dry tetrahydrofuran was cooled to 0° C. under nitrogen atmosphere and a solution of n-BuLi (1.6M in hexane, 50 ml, 75 mmol) was added dropwise in such a rate that the internal temperature did not rise above 10° C. (about 20 min.) an... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | O1CCCC1 | 5 | null | CC(C)(C)C(=O)Nc1cccc(C(F)(F)F)c1.CI>O1CCCC1>Cc1c(NC(=O)C(C)(C)C)cccc1C(F)(F)F |
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