dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81005d9a5e474ae9811ee087317133f2 | C1CNCCN1.ClCCCCc1ccc(Cl)cc1>>Clc1ccc(CCCCN2CCNCC2)cc1 | ClC1=CC=C(C=C1)CCCCCl.N1CCNCC1>>ClC1=CC=C(C=C1)CCCCN1CCNCC1 | [NH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.Cl[CH2:9][CH2:8][CH2:7][CH2:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:17][cH:16]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[cH:16][cH:17]1 | C1CNCCN1.ClCCCCc1ccc(Cl)cc1 | Clc1ccc(CCCCN2CCNCC2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCCCN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 46.3 | [{"value": 46.3, "product": "ClC1=CC=C(C=C1)CCCCN1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 26.4 g of 4-(4-chlorophenyl)butyl chloride, 86.1 g of anhydrous piperazine and 250 ml of reagent ethanol was refluxed overnight. Solvent was evaporated from the product and the residue was chromatographed twice on silica with the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1). The first chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HCl | C(C)O | null | null | C1CNCCN1.ClCCCCc1ccc(Cl)cc1>C(C)O>Clc1ccc(CCCCN2CCNCC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-13fda9fea57447eebddeaa653b8ac3a5 | CCOC(=O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1.Cl.Cl>>Cl.Cl.O=C(O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 | Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)OCC)C=C1.[OH-].[Na+]>>Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)O)C=C1 | CC[O:7][C:6](=[O:5])[CH:8]([CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][N:20]([CH2:21][c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)[CH2:29][CH2:30]2)[CH2:31][CH2:32]1)[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1.[ClH:2].[ClH:4]>>[ClH:2].[ClH:4].[O:5]=[C:6]([OH:7])[CH:8]([CH... | CCOC(=O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1.Cl.Cl | Cl.Cl.O=C(O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 16eb0e22715fadede32e44259800ac2375ae7dbc609f9ec677d59917bae07bec | b51da43dbb7140dac708518f8dbf83c5b067214819134afdb3f427285d08d6f8 | c1ccc(CCN2CCN(CCCN3CCN(Cc4ccccc4)CC3)CC2)cc1 | C-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] | 172 | [{"value": 40.0, "product": "Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 172.0, "product": "Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 340 mg of 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride in 10 ml of ethanol was treated with 1 ml of aqueous 5M sodium hydroxide and heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1.Cl.Cl>C(C)O>Cl.Cl.O=C(O)C(CN1CCN(CCCN2CCN(Cc3ccc(Cl)cc3)CC2)CC1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6991b219f52b4e25941ed6cba7871dad | CI.COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC>>COc1ccc(-c2cc(=O)n(C)c(C)n2)cc1OC | O.CC(C)([O-])C.[K+].CI.COC=1C=C(C=CC1OC)C1=CC(NC(=N1)C)=O>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)C)C)=O | I[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[O:10])[nH:11][c:13]([CH3:14])[n:15]2)[cH:16][c:17]1[O:18][CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[O:10])[n:11]([CH3:12])[c:13]([CH3:14])[n:15]2)[cH:16][c:17]1[O:18][CH3:19] | CI.COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC | COc1ccc(-c2cc(=O)n(C)c(C)n2)cc1OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8b8b604c36c54bca847ea1bd1b7840d48f065047e5c951a27f860631728323c9 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1cc(-c2ccccc2)nc[nH]1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](=[O;D1;H0:8]):[nH;D2;+0:9]:1>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](=[O;D1;H0:8]):[n;H0;D3;+0:9]:1-[CH3;D1;+0:1] | 65.3 | [{"value": 65.3, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 3,4-dihydro-6-(3,4 dimethoxyphenyl)-2-methylpyrimidin-4-one (2.0 g) in N,N-dimethylformamide (20 ml) were added potassium tert.butoxide (1.08 g) and methyl iodide (1.0 ml), and stirred at ambient temperature for an hour. Resulting mixture was poured into water, and extracted with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncn1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HI | CN(C=O)C | null | null | CI.COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC>CN(C=O)C>COc1ccc(-c2cc(=O)n(C)c(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6d50e5f7c65748e8bdcac9917b03d8e2 | COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC.O=P(Cl)(Cl)Cl>>COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(NC(=N1)C)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C | O=[c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH3:18])[cH:15]2)[n:14][c:12]([CH3:13])[nH:11]1.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([Cl:10])[n:11][c:12]([CH3:13])[n:14]2)[cH:15][c:16]1[O:17][CH3:18] | COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC.O=P(Cl)(Cl)Cl | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC | null | null | null | Functional Group Interconversion | OtherReaction | ab990d4cf4e29f4bfc1eed19f85a157586116cba28cf7e047e67e704b97886a0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ccncn2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[#7;a:6]:[c:7](-[C;D1;H3:8]):[nH;D2;+0:9]:1>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:4](-[c:5]):[c:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:9]:1 | null | [] | null | null | 2 | HOUR | A suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidin-4-one (2.4 g) in phosphorus oxychloride (20 ml) was refluxed for 2 hours, and evaporated. To the residue were added aqueous sodium bicarbonate solution and chloroform, and stirred at ambient temperature for 2 hours. The organic layer was obtained and... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncn1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | 2 | COc1ccc(-c2cc(=O)[nH]c(C)n2)cc1OC.O=P(Cl)(Cl)Cl>>COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5c3a5a99c48944198bf063c01ea01967 | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.Nc1ccccn1>>COc1ccc(-c2cc(=O)n3ccccc3n2)cc1OC | C(C1=CC(OC)=C(OC)C=C1)(=O)CC(=O)OCC.NC1=NC=CC=C1>>COC=1C=C(C=CC1OC)C=1N=C2N(C(C1)=O)C=CC=C2 | CCO[C:9]([CH2:8][C:7](=O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18]1)=[O:10].[n:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[NH2:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[O:10])[n:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2)[cH:18][c:19]1[O:20][CH3:21] | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.Nc1ccccn1 | COc1ccc(-c2cc(=O)n3ccccc3n2)cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 18aaa9c9f1fc97f1276b7f3d8d51ea2f879273fca2a44162cb2a6bbc6598427f | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | O=c1cc(-c2ccccc2)nc2ccccn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[n;H0;D2;+0:13]:[c:14]:[c:15]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[n;H0;D2;+0:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1:... | 150.8 | [{"value": 150.8, "product": "COC=1C=C(C=CC1OC)C=1N=C2N(C(C1)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | Ethyl veratroylacetate (4.5 g) was added dropwise under stirring at 60°-70° C. to a suspension of 2-aminopyridine (0.84 g) in polyphosphoric acid (13.7 g). The reaction mixture was stirred at 100° C. for 3 hrs and poured into ice-water (50 ml). The aqueous solution was extracted with chloroform, washed with water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | c1ccncc1 | c1ccn2ccccc2n1 | c1ccccc1.c1ccn2ccccc2n1 | HO- | null | 100 | 3 | CCOC(=O)CC(=O)c1ccc(OC)c(OC)c1.Nc1ccccn1>>COc1ccc(-c2cc(=O)n3ccccc3n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53723e478eea4102a066bd715aecef75 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=O)[nH]2)cc1OC.O=P(Cl)(Cl)Cl>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(N(C(N1)=O)C)=NC1=C(C=C(C=C1C)C)C.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC | O=[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25]2)[nH:24]1.O=P(Cl)(Cl)[Cl:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=O)[nH]2)cc1OC.O=P(Cl)(Cl)Cl | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | null | null | null | Functional Group Interconversion | OtherReaction | ab990d4cf4e29f4bfc1eed19f85a157586116cba28cf7e047e67e704b97886a0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(N=c2cc(-c3ccccc3)nc[nH]2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[c:5]):[c:6]:[c:7]:[#7;a:8]:1-[C;D1;H3:9]>>[C;D1;H3:9]-[#7;a:8]1:[c:7]:[c:6]:[c:4](-[c:5]):[n;H0;D2;+0:3]:[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | To 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)-2-(1H)pyrimidone (5.0 g) was added phosphorus oxychloride (50 ml). The mixture was refluxed for 7 hours and evaporated under reduced pressure. The resulting syrup was triturated in a mixture of ice and water, neutralized with aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncn1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=O)[nH]2)cc1OC.O=P(Cl)(Cl)Cl>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-be3baba0a63e43b69785207ba89bb350 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC>>COC=1C=C(C=CC1OC)C1=CC(N(C=N1)C)=NC1=C(C=C(C=C1C)C)C | Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]2)[n:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC | null | [Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 76895d15d2d466b89a30aacc2ef4edbb246f8c7b092db05f2443e4acbf4f85b3 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(N=c2cc(-c3ccccc3)nc[nH]2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 26.3 | [{"value": 26.3, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C=N1)C)=NC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.5 g) in ethanol (20 ml) was added 10%-palladium on carbon (0.8 g). The mixture was stirred under hydrogen (1 atm) for 40 minutes. After removal of the catalist by filtration, the filtrate was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Other | [Pd].C(C)O | null | 0.666667 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>[Pd].C(C)O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1bd4c3ba7a204a948c9a3d8d4191dea3 | CNCc1ccccc1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.CNCC1=CC=CC=C1>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N(CC1=CC=CC=C1)C)C)=NC1=C(C=C(C=C1C)C)C | [NH:23]([CH3:24])[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[cH:33]2)[n:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]... | CNCc1ccccc1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC | null | null | C(Cl)(Cl)Cl.C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CNc2nc(-c3ccccc3)cc(=Nc3ccccc3)[nH]2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C:9]-[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.5 g) in ethanol (15 ml) was added N-methylbenzylamine (1.47 ml). The mixture was refluxed for 5 hours. The resulting suspension was dissolved in chloroform, washed with brine, dried over magnesium sulfat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)(Cl)Cl.C(C)O | null | null | CNCc1ccccc1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>C(Cl)(Cl)Cl.C(C)O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dc411ea16f934b7bbc3fdf11d0029adc | C1CNCCN1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.N1CCNCC1>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCNCC1)C)=NC1=C(C=C(C=C1C)C)C | [NH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1.Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30]2)[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12... | C1CNCCN1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N=c2cc(-c3ccccc3)nc(N3CCNCC3)[nH]2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 57.3 | [{"value": 57.3, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCNCC1)C)=NC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.07 g) in ethanol (10 ml) was added piperazine (0.70 g). The mixture was refluxed for 3 hours, cooled to ambient temperature. The mixture was evaporated, and the residue was dissolved in chloroform and wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | c1cncnc1.C1C[NH]CCN1 | c1ccccc1.c1cncnc1.c1ccccc1.C1C[NH]CCN1 | HCl | C(C)O | null | null | C1CNCCN1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>C(C)O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9fe523c9c62a46dba0a4c75868ed88c4 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NN>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NN)n2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.O.NN>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NN)C)=NC1=C(C=C(C=C1C)C)C | Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26]2)[n:25]1.[NH2:23][NH2:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NN | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NN)n2)cc1OC | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a2442d505c92c8b71e523800797f0037c976f9785f57388464f754ec52db04ac | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccc(N=c2cc(-c3ccccc3)nc[nH]2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[N;D1;H2:7]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (10.0 g) in chloroform (100 ml) was added hydrazine hydrate (3.66 ml). The mixture was refluxed for 6 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on silica gel using... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NN>C(Cl)(Cl)Cl>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NN)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-354ca21a83634760aedd88119171dfa2 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NNC=O>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.C(=O)NN>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NNC=O)C)=NC1=C(C=C(C=C1C)C)C | Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28]2)[n:27]1.[NH2:23][NH:24][CH:25]=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NNC=O | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 05c8b509fbd3209f3d5e9d92885ea58a32d461019bf8f0b9c82cd4b4f5a05883 | cc5a5df08bac6de192cb68c75e5cdf4d844dc944903b8c20fd785c59a832562d | c1ccc(N=c2cc(-c3ccccc3)nc[nH]2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[NH2;D1;+0:7]-[#7:8]-[C:9]=[O;D1;H0:10]>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[#7:8]-[C:9]=[O;D1;H0:10]):[#7;a:2]:[c:3] | 26.4 | [{"value": 26.4, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NNC=O)C)=NC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (3.0 g) in chloroform (15 ml) was added formylhydrazine (1.36 g). The mixture was refluxed for 6 hours and cooled to ambient temperature. The resulting precipitates were filtered off and the filtrate was ev... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aromatic halide | Acylhydrazine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.NNC=O>C(Cl)(Cl)Cl>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dd36e74f535546a1be9f4ec4be1e5354 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC.O=C(Cl)c1ccc(F)cc1>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCN(C(=O)c4ccc(F)cc4)CC3)n2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCNCC1)C)=NC1=C(C=C(C=C1C)C)C.C(C)N(CC)CC.FC1=CC=C(C(=O)Cl)C=C1>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCN(CC1)C(C1=CC=C(C=C1)F)=O)C)=NC1=C(C=C(C=C1C)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH3:19])[n:20]([CH3:21])[c:22]([N:23]3[CH2:24][CH2:25][NH:26][CH2:36][CH2:37]3)[n:38]2)[cH:39][c:40]1[O:41][CH3:42].Cl[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1>>[CH3:1][O:2]... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC.O=C(Cl)c1ccc(F)cc1 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCN(C(=O)c4ccc(F)cc4)CC3)n2)cc1OC | null | null | O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCN(c2nc(-c3ccccc3)cc(=Nc3ccccc3)[nH]2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine (0.31 g) in tetrahydrofuran (10 ml) were added triethylamine (0.11 ml) and 4-fluorobenzoyl chloride (0.69 ml). The mixture was stirred at ambient temperature for an hour and the reaction was quench... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.c1cncnc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | O1CCCC1 | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC.O=C(Cl)c1ccc(F)cc1>O1CCCC1>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCN(C(=O)c4ccc(F)cc4)CC3)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9337e50ccd674af7a4a11996c30facfa | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nncn23)cc1OC | [OH-].[Na+].COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NNC=O)C)=NC1=C(C=C(C=C1C)C)C>>COC=1C=C(C=CC1OC)C1=CC(N(C=2N1C=NN2)C)=NC2=C(C=C(C=C2C)C)C | O=[CH:25][NH:24][NH:23][c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]2)[n:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nncn23)cc1OC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 431839368101cfcce4d54ee04001eea953337f68e32efd7aa6636f10cde15a56 | 3b74dccb5e8d79d411c67bfc6a766c6c6d6e4c42e46457114e1be0efa665abb5 | c1ccc(N=c2cc(-c3ccccc3)n3cnnc3[nH]2)cc1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[NH;D2;+0:3]-[c:4]1:[n;H0;D2;+0:5]:[c:6](-[c:7]):[c:8]:[c:9]:[#7;a:10]:1-[C;D1;H3:11]>>[C;D1;H3:11]-[#7;a:10]1:[c:9]:[c:8]:[c:6](-[c:7]):[n;H0;D3;+0:5]2:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[c:4]:1:2 | 83.8 | [{"value": 83.8, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C=2N1C=NN2)C)=NC2=C(C=C(C=C2C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 2 | HOUR | The mixture of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-(2-formylhydrazino)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (0.81 g) and polyphosphoric acid (8.2 g, 116% as phosphoric acid) was stirred at 110° C. for 2 hours and cooled to ambient temperature. The reaction mixture was poured into water and neutralized wi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | null | c1cncnc1 | c1cnc2nncn2c1 | c1ccccc1.c1ccccc1.c1cnc2nncn2c1 | HO- | O | 110 | 2 | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(NNC=O)n2)cc1OC>O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nncn23)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-40ed55c10e9f410d8fb8ab45b4b32b5c | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.[N-]=[N+]=[N-]>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nnnn23)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.[N-]=[N+]=[N-].[Na+]>>COC=1C=C(C=CC1OC)C1=CC(N(C=2N1N=NN2)C)=NC2=C(C=C(C=C2C)C)C | Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]2)[n:26]1.[N-:23]=[N+:25]=[N-:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15](... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.[N-]=[N+]=[N-] | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nnnn23)cc1OC | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 182b450bde9095fb43b75c5f7dae591bd7226c7b2a645b31f895fc1854549ce7 | 155f764f095c8454a4ad08aaa42f1abcb15d5bc1d4f122e4bcc624dd834362f2 | c1ccc(N=c2cc(-c3ccccc3)n3nnnc3[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c:3](-[c:4]):[c:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8].[N-;H0;D1:9]=[N+;H0;D2:10]=[N-;H0;D1:11]>>[C;D1;H3:8]-[#7;a:7]1:[c:6]:[c:5]:[c:3](-[c:4]):[n;H0;D3;+0:2]2:[n;H0;D2;+0:10]:[n;H0;D2;+0:11]:[n;H0;D2;+0:9]:[c;H0;D3;+0:1]:1:2 | 78.9 | [{"value": 78.9, "product": "COC=1C=C(C=CC1OC)C1=CC(N(C=2N1N=NN2)C)=NC2=C(C=C(C=C2C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in a mixture of methanol (9 ml) and water (1.5 ml) was added sodium azide (0.163 g). The mixture was stirred at 50° to 55° C. for an hour. After removal of the solvent, the residue was washed with w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1cnc2nnnn2c1 | c1ccccc1.c1ccccc1.c1cnc2nnnn2c1 | Other | CO.O | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC.[N-]=[N+]=[N-]>CO.O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c3nnnn23)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-19fb07c87ee04a17a744052b6bbc4bb6 | CI.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=NCc3ccccc3)n2C)cc1OC | COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N(CC1=CC=CC=C1)C)C)=NC1=C(C=C(C=C1C)C)C.CI>>C(C1=CC=CC=C1)N=C1N(C(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC)C | I[CH3:32].C[N:23]([c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[cH:33]2)[n:31]1)[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](... | CI.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=NCc3ccccc3)n2C)cc1OC | null | null | O1CCCC1 | Protection | OtherReaction | bb846def72593a9f2b9f55a622fdbbce35e1d4c3fc05f325df7e2d85a38af78c | 7619bfad8694b1a7e31b76c15f0caec637d52eb79098b20fc98b9e0e51bc2db0 | c1ccc(CN=c2[nH]c(-c3ccccc3)cc(=Nc3ccccc3)[nH]2)cc1 | C-[N;H0;D3;+0:1](-[C:2]-[c:3])-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c:6](-[c:7]):[c:8]:[c:9]:[#7;a:10]:1-[C;D1;H3:11].I-[CH3;D1;+0:12]>>[C;D1;H3:11]-[#7;a:10]1:[c:9]:[c:8]:[c:6](-[c:7]):[n;H0;D3;+0:5](-[CH3;D1;+0:12]):[c;H0;D3;+0:4]:1=[N;H0;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | To a solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(N-methyl-N-benzylamino)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in tetrahydrofuran (20 ml) was added methyl iodide (2.58 ml). The solution was refluxed for 10 hours and cooled to ambient temperature. The reaction mixture was evaporated in vacuo a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HI | O1CCCC1 | null | null | CI.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N(C)Cc3ccccc3)n2)cc1OC>O1CCCC1>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(=NCc3ccccc3)n2C)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c718f36c041c43afbe95ad940fc057c9 | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(N)c(C)c1>>COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C.CC1=C(N)C(=CC(=C1)C)C>>COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)NC1=C(C=C(C=C1C)C)C | Cl[c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]2)[n:23][c:21]([CH3:22])[n:20]1.[NH2:10][c:11]1[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]1[CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([NH:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[... | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(N)c(C)c1 | COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(-c3ccccc3)ncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](-[c:7]):[c:8]:1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:8]:[c:6](-[c:7]):[#7;a:5]:1 | null | [] | 120 | CELSIUS | null | null | The mixture of 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g) and 2,4,6-trimethylaniline (5.3 ml) was stirred at 120° C. for an hour. After cooled, the mixture was triturated with ethyl acetate. The precipitates were collected, and dissolved in chloroform. The solution was washed with aqueous sodium bicarb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | 120 | null | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(N)c(C)c1>>COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7a100c5c6f4546fe8ba2e190fe4324e2 | CI.COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC>>COc1ccc(-c2cc(N(C)c3c(C)cc(C)cc3C)nc(C)n2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)NC1=C(C=C(C=C1C)C)C.CC(C)([O-])C.[K+].CI>>COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)N(C1=C(C=C(C=C1C)C)C)C | I[CH3:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([NH:10][c:12]3[c:13]([CH3:14])[cH:15][c:16]([CH3:17])[cH:18][c:19]3[CH3:20])[n:21][c:22]([CH3:23])[n:24]2)[cH:25][c:26]1[O:27][CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([N:10]([CH3:11])[c:12]3[c:13]([CH3:14])[cH:15][c:16]([CH3:17])[c... | CI.COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | COc1ccc(-c2cc(N(C)c3c(C)cc(C)cc3C)nc(C)n2)cc1OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Nc2cc(-c3ccccc3)ncn2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3](-[NH;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1):[c:11]>>[CH3;D1;+0:1]-[N;H0;D3;+0:4](-[c:3](:[c:2]):[c:11])-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 55.8 | [{"value": 55.8, "product": "COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)N(C1=C(C=C(C=C1C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine (1.0 g) in N,N-dimethylformamide (15 ml) were added potassium tert-butoxide (0.37 g) and methyl iodide (0.34 ml), and the mixture was stirred at ambient temperature for 1.5 hours. Then the mixture was poured into ice-water (200 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HI | CN(C=O)C | null | 1.5 | CI.COc1ccc(-c2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC>CN(C=O)C>COc1ccc(-c2cc(N(C)c3c(C)cc(C)cc3C)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-76ac84f8bfe844fe8d9db859da230bc7 | C1=CCNCC1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CC=CCC3)n2)cc1OC | ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC.N1CCC=CC1>>COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCC=CC1)C)=NC1=C(C=C(C=C1C)C)C | [NH:23]1[CH2:24][CH:25]=[CH:26][CH2:27][CH2:28]1.Cl[c:22]1[n:20]([CH3:21])[c:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30]2)[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12... | C1=CCNCC1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CC=CCC3)n2)cc1OC | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b0012be1b87147a6e6c70481d7758c1e4cea97a075b06c4dc087fc8df8a11b0f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | C1=CCN(c2nc(-c3ccccc3)cc(=Nc3ccccc3)[nH]2)CC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]1-[C:8]=[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:7]-[C:8]=[C:9]-[C:10]-[C:11]-1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.08 g) in ethanol (20 ml) was added 1,2,3,6-tetrahydropyridine (1.38 ml), and refluxed for 1.5 hours. The resulting precipitates were collected, dissolved in chloroform, washed with aqueous sodium bicarbo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1=CCNCC1.c1cncnc1 | c1cncnc1.C1=CC[NH]CC1 | c1ccccc1.c1cncnc1.c1ccccc1.C1=CC[NH]CC1 | HCl | C(C)O | null | null | C1=CCNCC1.COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC>C(C)O>COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CC=CCC3)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-49ae6795d91842138a9966c6c26eeb9a | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC>>COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(N(C=N1)C)=NC1=C(C=C(C=C1C)C)C.[BH4-].[Na+]>>COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH3:19])[n:20]([CH3:21])[cH:22][n:23]2)[cH:24][c:25]1[O:26][CH3:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[CH:8][C:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH3:1... | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC | COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC | null | null | C(C)O.O | Miscellaneous | OtherReaction | 4f374c10be4b94bcd44017d11f58406012c0e7eb93ed620c56e1e9a043361621 | ffa51f011c8cd2db0fde7a0daaa8ad62d16e443d58d706a838e147f90c7c26cf | C1=C(c2ccccc2)NCNC1=Nc1ccccc1 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12]:1=[#7:13]-[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[CH;D2;+0:11]-[C;H0;D3;+0:12]-1=[#7:13]-[c:... | 58.7 | [{"value": 58.7, "product": "COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.0 g) in a mixture of ethanol (10 ml) and water (10 ml) was added sodium borohydride (1.04 g), and the mixture was stirred under reflux for 1.5 hours. After removal of the organic solvent, the mixture was suspende... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine.Tertiary amine | c1cncnc1 | C1=CNC[NH]C1 | c1ccccc1.C1=CNC[NH]C1.c1ccccc1 | null | C(C)O.O | null | null | COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)cn2)cc1OC>C(C)O.O>COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3616968c1a0f4c4397905a7c8fdd4da3 | CC(=O)OC(C)=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC>>COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2C(C)=O)cc1OC | O.COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C.C(C)(=O)OC(C)=O>>C(C)(=O)N1CN(C(C=C1C1=CC(=C(C=C1)OC)OC)=NC1=C(C=C(C=C1C)C)C)C | CC(=O)O[C:24]([CH3:25])=[O:26].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[CH:8][C:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH3:19])[N:20]([CH3:21])[CH2:22][NH:23]2)[cH:27][c:28]1[O:29][CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[CH:8][C:9](=[N:10][c:11]3[c:12]([CH3:13])[cH:14][c:... | CC(=O)OC(C)=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC | COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2C(C)=O)cc1OC | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | 37de4a9cab3150129c585744da39af6b1e53621ddee33eb6a0572e9cd7123509 | c7805e0d43d630f03eb7041e49c61c53da3c359404af09cc4ab8902f166d026d | C1=C(c2ccccc2)NCNC1=Nc1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]=[C:5]1-[C:6]=[C:7](-[c:8])-[NH;D2;+0:9]-[C:10]-[#7:11]-1-[C;D1;H3:12]>>[#7:4]=[C:5]1-[C:6]=[C:7](-[c:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:10]-[#7:11]-1-[C;D1;H3:12] | null | [] | null | null | 2.5 | HOUR | To a solution of 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.5 g) in pyridine (5 ml) was added acetic anhydride (1.0 ml), and the mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured into water (150 ml) and extracted with chloroform. The or... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride | Enamine.Tertiary amide | C1=CNC[NH]C1 | C1=C[NH]C[NH]C1 | c1ccccc1.C1=C[NH]C[NH]C1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | 2.5 | CC(=O)OC(C)=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC>N1=CC=CC=C1>COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2C(C)=O)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8713f1a083924a5fa46b8a31925ba557 | COc1ccc(-c2cc(N3CCNCC3)nc(C)n2)cc1OC.NS(=O)(=O)c1cc(C(=O)Cl)c(Cl)cc1Cl>>COc1ccc(-c2cc(N3CCN(C(=O)c4cc(S(N)(=O)=O)c(Cl)cc4Cl)CC3)nc(C)n2)cc1OC | COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)N1CCNCC1.C(C)N(CC)CC.ClC1=C(C(=O)Cl)C=C(C(=C1)Cl)S(N)(=O)=O>>ClC1=C(C(=O)N2CCN(CC2)C2=NC(=NC(=C2)C2=CC(=C(C=C2)OC)OC)C)C=C(C(=C1)Cl)S(N)(=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([N:10]3[CH2:11][CH2:12][NH:13][CH2:28][CH2:29]3)[n:30][c:31]([CH3:32])[n:33]2)[cH:34][c:35]1[O:36][CH3:37].Cl[C:14](=[O:15])[c:16]1[cH:17][c:18]([S:19]([NH2:20])(=[O:21])=[O:22])[c:23]([Cl:24])[cH:25][c:26]1[Cl:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8]... | COc1ccc(-c2cc(N3CCNCC3)nc(C)n2)cc1OC.NS(=O)(=O)c1cc(C(=O)Cl)c(Cl)cc1Cl | COc1ccc(-c2cc(N3CCN(C(=O)c4cc(S(N)(=O)=O)c(Cl)cc4Cl)CC3)nc(C)n2)cc1OC | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCN(c2cc(-c3ccccc3)ncn2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | 71.5 | [{"value": 71.5, "product": "ClC1=C(C(=O)N2CCN(CC2)C2=NC(=NC(=C2)C2=CC(=C(C=C2)OC)OC)C)C=C(C(=C1)Cl)S(N)(=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of 6-(3,4-dimethoxyphenyl)-2-methyl-4-(1-piperazinyl)pyrimidine (0.8 g) in chloroform (10 ml) were added triethylamine (0.39 ml) and 2,4-dichloro-5-sulfamoylbenzoyl chloride (0.74 g), and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was washed with water, dried over ma... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 20 | COc1ccc(-c2cc(N3CCNCC3)nc(C)n2)cc1OC.NS(=O)(=O)c1cc(C(=O)Cl)c(Cl)cc1Cl>C(Cl)(Cl)Cl>COc1ccc(-c2cc(N3CCN(C(=O)c4cc(S(N)(=O)=O)c(Cl)cc4Cl)CC3)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8c0e664d28f44521b67fd86394cabfa0 | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(O)c(C)c1>>COc1ccc(-c2cc(Oc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | O.ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C.CC1=C(C(=CC(=C1)C)C)O.[H-].[Na+]>>COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)OC1=C(C=C(C=C1C)C)C | Cl[c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]2)[n:23][c:21]([CH3:22])[n:20]1.[OH:10][c:11]1[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]1[CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([O:10][c:11]3[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH... | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(O)c(C)c1 | COc1ccc(-c2cc(Oc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2cc(-c3ccccc3)ncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](-[c:7]):[c:8]:1.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:8]:[c:6](-[c:7]):[#7;a:5]:1 | 71.2 | [{"value": 71.2, "product": "COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)OC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 2,4,6-trimethylphenol (1.03 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (60% in oil, 0.30 g), and stirred at ambient temperature for 5 minutes. To the solution was added 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g), and the mixture was stirred at ambient temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CN(C=O)C | null | 0.083333 | COc1ccc(-c2cc(Cl)nc(C)n2)cc1OC.Cc1cc(C)c(O)c(C)c1>CN(C=O)C>COc1ccc(-c2cc(Oc3c(C)cc(C)cc3C)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-917a2479c3f9457d87255a214f0059bb | COc1ccc(-c2cc(Nc3ccc(N)cc3)nc(C)n2)cc1OC.CS(=O)(=O)Cl>>COc1ccc(-c2cc(Nc3ccc(NS(C)(=O)=O)cc3)nc(C)n2)cc1OC | C(Cl)(Cl)Cl.NC1=CC=C(C=C1)NC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C.CS(=O)(=O)Cl.C(C)N(CC)CC>>COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)NC1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([NH2:15])[cH:20][cH:21]3)[n:22][c:23]([CH3:24])[n:25]2)[cH:26][c:27]1[O:28][CH3:29].Cl[S:16]([CH3:17])(=[O:18])=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([NH:15][S:16]([CH3:1... | COc1ccc(-c2cc(Nc3ccc(N)cc3)nc(C)n2)cc1OC.CS(=O)(=O)Cl | COc1ccc(-c2cc(Nc3ccc(NS(C)(=O)=O)cc3)nc(C)n2)cc1OC | null | null | ClCCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(Nc2cc(-c3ccccc3)ncn2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | To a solution of 4-(4-aminophenylamino)-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (1.0 g) in 1,2-dichloroethane (20 ml) were added methanesulfonyl chloride (0.28 ml) and triethylamine (0.83 ml) and the mixture was refluxed for 3 hours. After cooled, chloroform (50 ml) was added thereto, and washed with water. The solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | ClCCCl | null | null | COc1ccc(-c2cc(Nc3ccc(N)cc3)nc(C)n2)cc1OC.CS(=O)(=O)Cl>ClCCCl>COc1ccc(-c2cc(Nc3ccc(NS(C)(=O)=O)cc3)nc(C)n2)cc1OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-31d1c1feda2b47efbe166c7b36ac8cab | CN=C=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC>>CNC(=O)N1CN(C)C(=Nc2c(C)cc(C)cc2C)C=C1c1ccc(OC)c(OC)c1 | O.COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C.CN=C=O>>COC=1C=C(C=CC1OC)C1=CC(N(CN1C(NC)=O)C)=NC1=C(C=C(C=C1C)C)C | [CH3:1][N:2]=[C:3]=[O:4].[NH:5]1[CH2:6][N:7]([CH3:8])[C:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[CH:20]=[C:21]1[c:22]1[cH:23][cH:24][c:25]([O:26][CH3:27])[c:28]([O:29][CH3:30])[cH:31]1>>[CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][N:7]([CH3:8])[C:9](=[N:10][c:11]2[c:12]([CH3:13])[cH:14... | CN=C=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC | CNC(=O)N1CN(C)C(=Nc2c(C)cc(C)cc2C)C=C1c1ccc(OC)c(OC)c1 | null | null | N1=CC=CC=C1 | Acylation | Urea synthesis via isocyanate and secondary amine | 4bb1a24b1b3e8307677a3ae0cb932053af15b5c63dd708805b4efb2d6595c3bc | 6c7af49963b743cdb3f9754761159984e3aaed1b6f471cc88ee43e1a7e18d880 | C1=C(c2ccccc2)NCNC1=Nc1ccccc1 | [#7:1]=[C:2]1-[C:3]=[C:4](-[c:5])-[NH;D2;+0:6]-[C:7]-[#7:8]-1-[C;D1;H3:9].[C;D1;H3:10]-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7:1]=[C:2]1-[C:3]=[C:4](-[c:5])-[N;H0;D3;+0:6](-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C;D1;H3:10])-[C:7]-[#7:8]-1-[C;D1;H3:9] | null | [] | null | null | 3 | HOUR | To a solution of 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in pyridine (10 ml) was added methyl isocyanate (0.18 ml), and the mixture was stirred at ambient temperature for 3 hours. Then the mixture was poured into water (150 ml), and the resultant precipitates... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Isocyanate | Enamine.Urea | C1=CNC[NH]C1 | C1=C[NH]C[NH]C1 | C1=C[NH]C[NH]C1.c1ccccc1.c1ccccc1 | null | N1=CC=CC=C1 | null | 3 | CN=C=O.COc1ccc(C2=CC(=Nc3c(C)cc(C)cc3C)N(C)CN2)cc1OC>N1=CC=CC=C1>CNC(=O)N1CN(C)C(=Nc2c(C)cc(C)cc2C)C=C1c1ccc(OC)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fa8318595eb54ee98aceafd5c8548e7b | CC(=O)c1ccncc1>>O=C(CBr)c1ccncc1 | Br.C(C)(=O)C1=CC=NC=C1>>Br.BrCC(=O)C1=CC=NC=C1 | [O:2]=[C:3]([CH3:4])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[O:2]=[C:3]([CH2:4][Br:5])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CC(=O)c1ccncc1 | O=C(CBr)c1ccncc1 | null | null | C(C)(=O)O | Functional Group Addition | Bromination | bf5c9c3636d0bb082289a8c9a57893f9c01b86491bbac098df6f08165abff331 | 59d1a8eb6d53c009bab8d2eda578b612565fd5477616e626d840161408a683de | c1ccncc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[Br;D1;H0:5]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | A twelve-liter three neck flask fitted with an efficient mechanical stirrer, 250 mL dropping funnel, and internal thermometer was charged with glacial acetic acid (5000 mL), pyridinium bromide perbromide (90%, 830 g, 2.60 mol) and 30% hydrobromic acid in acetic acid (525 mL). After stirring at room temperature for nine... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccncc1 | Other | C(C)(=O)O | null | null | CC(=O)c1ccncc1>C(C)(=O)O>O=C(CBr)c1ccncc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-01fa80306865499fa787ebe5005a2c4f | CC(=O)Nc1ccccc1Cc1nc(-c2ccncc2)cs1>>Nc1ccccc1Cc1nc(-c2ccncc2)cs1 | C(C)(=O)NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1.[OH-].[Na+]>>NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1 | CC(=O)Nc1ccccc1Cc1nc(-c2ccncc2)cs1 | Nc1ccccc1Cc1nc(-c2ccncc2)cs1 | null | null | C(C)O.Cl.O.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 69.5 | [{"value": 65.0, "product": "NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(o-acetamidobenzyl)-4-(4-pyridyl)thiazole (2.30 g, 0.007 mol) in concentrated hydrochloric acid (2 mL) and ethanol (3 mL) was refluxed for 3 hours, allowed to cool, diluted with water (2 mL) and methylene chloride (5 mL), and basified with 2.5N sodium hydroxide. The layers were separated with the aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1cscn1.c1ccncc1 | HO- | C(C)O.Cl.O.C(Cl)Cl | null | null | CC(=O)Nc1ccccc1Cc1nc(-c2ccncc2)cs1>C(C)O.Cl.O.C(Cl)Cl>Nc1ccccc1Cc1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ed73af56968b4454b488f0c1be5537e4 | O=[N+]([O-])O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>>O=[N+]([O-])c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | C([O-])([O-])=O.[Na+].[Na+].[N+](=O)(O)[O-].C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1.S(O)(O)(=O)=O>>[N+](=O)([O-])C1=CC=C(CC=2SC=C(N2)C2=CC=NC=C2)C=C1 | O=[N+:2]([OH:1])[O-:3].[cH:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][n:15][cH:16][cH:17]3)[cH:18][s:19]2)[cH:20][cH:21]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][n:15][cH:16][cH:17]3)[cH:18][s:19]2)[cH:20][cH:21]1 | O=[N+]([O-])O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | O=[N+]([O-])c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | null | null | C(Cl)(Cl)Cl | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | O=[N+;H0;D3:1](-[O;-;D1;H0:2])-[OH;D1;+0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;H0;D1;+0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 85.9 | [{"value": 85.9, "product": "[N+](=O)([O-])C1=CC=C(CC=2SC=C(N2)C2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | A solution of 2-benzyl-4-(4-pyridyl)thiazole (4.50 g, 0.018 mol) in chloroform (25 mL) was added dropwise to concentrated sulfuric acid (15 mL). The resulting mixture was cooled to 10° C. and fuming nitric acid (1.45 g, 0.97 mL) carefully added dropwise such that the reaction temperature did not exceed 40° C. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cscn1.c1ccncc1 | HO- | C(Cl)(Cl)Cl | 10 | null | O=[N+]([O-])O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>C(Cl)(Cl)Cl>O=[N+]([O-])c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-18b8488c6d344783bff5729349d8b2e5 | CCOC=O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>>O=CC(c1ccccc1)c1nc(-c2ccncc2)cs1 | C(=O)OCC.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1.CN(CCN(C)C)C.C(CCC)[Li]>>C1(=CC=CC=C1)C(C=O)C=1SC=C(N1)C1=CC=NC=C1 | CCO[CH:2]=[O:1].[CH2:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][s:20]1>>[O:1]=[CH:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][s:20]1 | CCOC=O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | O=CC(c1ccccc1)c1nc(-c2ccncc2)cs1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 3dc7150b54f968d08b04811ce6d9fd58ce6b1717b4fbd76dbd02e91654c50b43 | 2aa39a25981921b5291a5742361ce4441cd47a0f2b930c869f26329c906b19c5 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].[c:3]:[c:4](-[CH2;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1):[c:11]>>[O;D1;H0:2]=[CH;D2;+0:1]-[CH;D3;+0:5](-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1)-[c:4](:[c:3]):[c:11] | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C(C=O)C=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | To a solution of 2-benzyl-4-(4-pyridyl)thiazole (4.00 g, 0.016 mol) and tetramethylethylenediamine (2.5 mL) in dry tetrahydrofuran (35 mL) at -78° C. under nitrogen atmosphere was added dropwise n-butyl lithium (1.6M in hexane, 11.4 mL). The resulting dark mixture was allowed to stir at -78° C. for 15 minutes, warmed t... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde | null | null | c1ccccc1.c1cscn1.c1ccncc1 | HO- | O1CCCC1 | -78 | 0.25 | CCOC=O.c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>O1CCCC1>O=CC(c1ccccc1)c1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ee8a5d8d7a7843959078967aa73d7741 | NC(=S)C(F)(F)c1ccccc1.O=C(CBr)c1ccncc1>>FC(F)(c1ccccc1)c1nc(-c2ccncc2)cs1 | FC(C(=S)N)(C1=CC=CC=C1)F.Br.BrCC(=O)C1=CC=NC=C1>>FC(C1=CC=CC=C1)(F)C=1SC=C(N1)C1=CC=NC=C1 | [F:1][C:2]([F:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10]([NH2:11])=[S:20].O=[C:12]([c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1)[CH2:19]Br>>[F:1][C:2]([F:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][s:20]1 | NC(=S)C(F)(F)c1ccccc1.O=C(CBr)c1ccncc1 | FC(F)(c1ccccc1)c1nc(-c2ccncc2)cs1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[c:12])-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[S;H0;D1;+0:15]>>[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[c:12])-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]... | 48 | [{"value": 48.0, "product": "FC(C1=CC=CC=C1)(F)C=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "FC(C1=CC=CC=C1)(F)C=1SC=C(N1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,2-difluoro-2-phenylthioacetamide (1.57 g, 0.0092 mol) in 95% ethanol (20 mL) was added α-bromo-4-acetylpyridine hydrobromide (3.20 g, 0.012 mol) and the mixture warmed on a steam bath for thirty minutes. The product was isolated in the usual way and recrystallized from ethyl acetate/hexane to afford ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccncc1 | HBr | C(C)O | null | null | NC(=S)C(F)(F)c1ccccc1.O=C(CBr)c1ccncc1>C(C)O>FC(F)(c1ccccc1)c1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-765591272e9a4caba598731704b65f44 | N#C[S-].O=C(CBr)c1ccncc1>>Oc1nc(-c2ccncc2)cs1 | Br.BrCC(=O)C1=CC=NC=C1.[S-]C#N.[K+].Cl.O>>OC=1SC=C(N1)C1=CC=NC=C1 | [C:2](#[N:3])[S-:12].Br[CH2:11][C:4](=[O:1])[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1>>[OH:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[cH:11][s:12]1 | N#C[S-].O=C(CBr)c1ccncc1 | Oc1nc(-c2ccncc2)cs1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 2537034356e56beddc377f967150ac167f1835fe0d357c9a23a4e3ab118a5498 | cd18c57be94270d5ae64f4c553960798487616fd5806e36b30d128418cd18cca | c1cc(-c2cscn2)ccn1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[N;H0;D1;+0:10]#[C;H0;D2;+0:11]-[S-;H0;D1:12]>>[OH;D1;+0:3]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2):[cH;D2;+0:1]:[s;H0;D2;+0:12]:1 | null | [] | null | null | 5 | HOUR | A mixture of α-bromo-4-acetylpyridine hydrobromide (140.0 g, 0.50 mol) and potassium thiocyanate (53.4 g, 0.55 mol) in absolute ethanol (1500 mL) was heated to reflux for two hours. To the resulting mixture was added concentrated hydrochloric acid (250 mL) and water (500 mL) and reflux continued for five hours. After c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Nitrile | Aromatic alcohol | null | c1cscn1 | c1cscn1.c1ccncc1 | Br- | C(C)O | null | 5 | N#C[S-].O=C(CBr)c1ccncc1>C(C)O>Oc1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6a872e674f0846bc9fa7a078ae69e05f | O=P(Cl)(Cl)Cl.Oc1nc(-c2ccncc2)cs1>>Clc1nc(-c2ccncc2)cs1 | OC=1SC=C(N1)C1=CC=NC=C1.P(=O)(Cl)(Cl)Cl>>ClC=1SC=C(N1)C1=CC=NC=C1 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[cH:11][s:12]1>>[Cl:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[cH:11][s:12]1 | O=P(Cl)(Cl)Cl.Oc1nc(-c2ccncc2)cs1 | Clc1nc(-c2ccncc2)cs1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | c8dfa2501a169ad412b92a30a4df16525460ddbdf84a0b2da53039c0817e89c5 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cc(-c2cscn2)ccn1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 29 | [{"value": 29.0, "product": "ClC=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 2-hydroxy-4-(4-pyridyl)thiazole (17.8 g, 0.10 mol) in phosphorous oxychloride (175 mL) was heated at 140° C. for 48 hours then quenched by carefully pouring onto ice (4000 mL). The resulting mixture was basified with 50% sodium hydroxide to pH 9 and extracted with methylene chloride (5×400 mL). The combine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cscn1 | c1cscn1 | c1cscn1.c1ccncc1 | HCl | null | 140 | null | O=P(Cl)(Cl)Cl.Oc1nc(-c2ccncc2)cs1>>Clc1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-08c4d0217383477aba8f92824c438c38 | Clc1nc(-c2ccncc2)cs1.N#CCc1ccccc1>>N#CC(c1ccccc1)c1nc(-c2ccncc2)cs1 | ClC=1SC=C(N1)C1=CC=NC=C1.C(C1=CC=CC=C1)C#N.[NH2-].[Na+]>>C1(=CC=CC=C1)C(C#N)C=1SC=C(N1)C1=CC=NC=C1 | Cl[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][s:20]1.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[N:1]#[C:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][s:20]1 | Clc1nc(-c2ccncc2)cs1.N#CCc1ccccc1 | N#CC(c1ccccc1)c1nc(-c2ccncc2)cs1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Hurtley reaction | 07198ff39bbbd3f70802b10d0f27ae5abdac590ca6368a58203c62574039710d | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 8.3 | [{"value": 8.0, "product": "C1(=CC=CC=C1)C(C#N)C=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.3, "product": "C1(=CC=CC=C1)C(C#N)C=1SC=C(N1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 2-chloro-4-(4-pyridyl)thiazole (1.00 g, 0.005 mol) and benzylcyanide (1.18 g, 0.010 mol) in dry toluene (10 mL) at 5° C. was added sodamide (400 mg, 0.010 mol) and the mixture heated to 100° C. for 20 minutes. After cooling, the mixture was quenched with water, the layers separated, and the aqueous pha... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1 | c1cscn1 | c1ccccc1.c1cscn1.c1ccncc1 | HCl | C1(=CC=CC=C1)C | 100 | null | Clc1nc(-c2ccncc2)cs1.N#CCc1ccccc1>C1(=CC=CC=C1)C>N#CC(c1ccccc1)c1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fdefa7a16d504159aa72430f307694ae | [O]=[Mn](=[O])(=[O])[O-].c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>>O=C(c1ccccc1)c1nc(-c2ccncc2)cs1 | C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1.[Mn](=O)(=O)(=O)[O-].[K+]>>C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1 | [O]=[Mn](=[O])([O-])=[O:1].[CH2:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1 | [O]=[Mn](=[O])(=[O])[O-].c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | O=C(c1ccccc1)c1nc(-c2ccncc2)cs1 | null | [I-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | C1=CC=CC=C1.O | Heteroatom Alkylation and Arylation | OtherReaction | 7a0b8463d98f4c7b922b16e60aaf09698e9f90cf246a26e079db9b5cbdeab585 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C(c1ccccc1)c1nc(-c2ccncc2)cs1 | [O-]-[Mn](=[O;H0;D1;+0:1])(=[O])=[O].[c:2]:[c:3](-[CH2;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1):[c:10]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:4](-[c:3](:[c:2]):[c:10])-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1 | 18.8 | [{"value": 11.0, "product": "C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.8, "product": "C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 2-benzyl-4-(4-pyridyl)thiazole (3.00 g, 0.01 mol) and potassium permanganate (3.16 g, 0.02 mol) in benzene (30 mL) and water (60 mL) was added tetrahexyl ammonium iodide (0.96 g, 0.02 mol). The biphasic mixture was heated at reflux for 15 hours. After cooling the organic layer was separated and concentr... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | null | null | c1ccccc1.c1cscn1.c1ccncc1 | HO- | [I-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.C1=CC=CC=C1.O | null | null | [O]=[Mn](=[O])(=[O])[O-].c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>[I-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.C1=CC=CC=C1.O>O=C(c1ccccc1)c1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e29bb60d5a354d0d869838cdbf5e9016 | O=C(c1ccccc1)c1nc(-c2ccncc2)cs1>>OC(c1ccccc1)c1nc(-c2ccncc2)cs1 | C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1.[BH4-].[Na+]>>C1(=CC=CC=C1)C(O)C=1SC=C(N1)C1=CC=NC=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][s:19]1 | O=C(c1ccccc1)c1nc(-c2ccncc2)cs1 | OC(c1ccccc1)c1nc(-c2ccncc2)cs1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 45 | [{"value": 45.0, "product": "C1(=CC=CC=C1)C(O)C=1SC=C(N1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.7, "product": "C1(=CC=CC=C1)C(O)C=1SC=C(N1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (675 g, 0.0025 mol) in methanol (40 mL) was added sodium borohydride (300 mg, 0.0079 mol) in portions and the mixture allowed to stir at room temperature for one hour. The reaction mixture was concentrated, diluted with water, and extracted with ether (3×... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1cscn1.c1ccncc1 | null | CO | null | 1 | O=C(c1ccccc1)c1nc(-c2ccncc2)cs1>CO>OC(c1ccccc1)c1nc(-c2ccncc2)cs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c6e1cc3c94154c00aca4659516630175 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>>[O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1 | ClC1=CC(=CC=C1)C(=O)OO.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1.ClC1=CC(=CC=C1)C(=O)OO>>C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-] | [n:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17]2)[cH:18][cH:19]1>>[O-:1][n+:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17]2)[cH:18][cH:19]1 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | [O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(Cc2nc(-c3cc[nH+]cc3)cs2)cc1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4]:[c:5] | 95 | [{"value": 95.0, "product": "C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of m-chloroperbenzoic acid (14.5 g) in dry methylene chloride (150 mL) was added a solution of 2-benzyl-4-(4-pyridyl)thiazole (15.1 g, 0.06 mol) in methylene chloride (125 mL) over thirty minutes. The mixture was allowed to stir overnight at room temperature then an additional portion of m-chloroperbenz... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1cscn1.c1ccccc1 | null | C(Cl)Cl | null | 8 | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1>C(Cl)Cl>[O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c9b3112c5ae24285a00f3026a4e0278d | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1>>Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1 | C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-].P(=O)(Cl)(Cl)Cl>>C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl | O=P(Cl)(Cl)[Cl:1].[O-][n+:19]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][s:7][c:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16]2)[cH:17][cH:18]1>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][s:7][c:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16]2)[cH:17][cH:18][n:19]1 | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1 | Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1 | null | null | null | Miscellaneous | OtherReaction | a7e4b874c7a18ec6b4305e16cc93c9103d77bfb4ce559ead41b2d45f56dcb90f | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc(Cc2nc(-c3ccncc3)cs2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[n;H0;D2;+0:2]:1 | 31 | [{"value": 31.0, "product": "C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.6, "product": "C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide (1.00 g, 0.0037 mol) in phosphorous oxychloride (10.0 g) was warmed on a steam bath overnight. After cooling the reaction mixture was concentrated and the residue treated with an excess of aqueous sodium bicarbonate. The tan precipitate was collected, tak... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1.c1cscn1.c1ccccc1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.[O-][n+]1ccc(-c2csc(Cc3ccccc3)n2)cc1>>Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4003f3bd15224084afa096bd852af473 | Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1>>Cl.Cl.c1ccc(Cc2nc(-c3ccnc(N4CCCCC4)c3)cs2)cc1 | C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl>>Cl.Cl.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)N1CCCCC1 | [Cl:1][c:15]1[n:14][cH:13][cH:12][c:11](-[c:10]2[n:9][c:8]([CH2:7][c:6]3[cH:21][cH:20][cH:19][cH:3][cH:25]3)[s:24][cH:23]2)[cH:22]1>>[ClH:1].[ClH:2].[cH:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[cH:22]3)[cH:23][s:24]2)[cH:25][cH:26... | Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1 | Cl.Cl.c1ccc(Cc2nc(-c3ccnc(N4CCCCC4)c3)cs2)cc1 | null | null | N1CCCCC1 | Aromatic Heterocycle Formation | OtherReaction | 945d16753d2aadbd12dd057f9c2c2495efb877f5d157885b895bc9d035e01a95 | 66db14b78ca39a2323867c26921347f43c8475b8802a3ad393c6e0a64e54f6be | c1ccc(Cc2nc(-c3ccnc(N4CCCCC4)c3)cs2)cc1 | [#16;a:1]:[c:2](-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1):[#7;a:10].[Cl;H0;D1;+0:11]-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[#16;a:1]:[c:2](-[C:3]-[c;H0;D3;+0:4]1:[c:17]:[c:18]:[cH;D2;+0:8]:[c:19]:[cH;D2;+0:9]:1):[#7;a:10].[c:16]:[c:15]:[c;H0;D3;+0:12](-[#7:20... | 73.5 | [{"value": 49.0, "product": "Cl.Cl.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "Cl.Cl.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)N1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-benzyl-4-(2-chloro-4-pyridyl)thiazole (1.00 g, 0.0035 mol) in piperidine (15 mL) was heated to reflux for 16 hours. The reaction mixture was concentrated, taken up in ether (50 mL), filtered through celite, and the filtrate washed with water (2×). The ether layer was dried and concentrated. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1 | c1ccccc1.c1cscn1.c1ccncc1.C1CC[NH]CC1 | Other | N1CCCCC1 | null | null | Clc1cc(-c2csc(Cc3ccccc3)n2)ccn1>N1CCCCC1>Cl.Cl.c1ccc(Cc2nc(-c3ccnc(N4CCCCC4)c3)cs2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d201dac721b14afb8e363997a5e0f3c7 | COC(=O)c1ccncc1OC.COC(C)=O>>COc1cnccc1C(C)=O | COC(C1=C(C=NC=C1)OC)=O.C(C)(=O)OC.Cl.C([O-])(O)=O.[Na+].[Na].[Na]>>COC=1C=NC=CC1C(C)=O | CO[C:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][n:5][cH:6][cH:7]1)=[O:11].COC(=O)[CH3:10]>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[C:9]([CH3:10])=[O:11] | COC(=O)c1ccncc1OC.COC(C)=O | COc1cnccc1C(C)=O | null | null | CO.O | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccncc1 | C-O-C(=O)-[CH3;D1;+0:1].C-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 46.3 | [{"value": 46.0, "product": "COC=1C=NC=CC1C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.3, "product": "COC=1C=NC=CC1C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A dry 50 mL three neck flask fitted with a reflux condenser and internal thermometer was charged with dry methanol (20 mL). Sodium (516 mg, 0.022 mol) was added in portions and after all the sodium had dissolved the methanol was removed by distillation. The resulting sodium methoxide was cooled and a mixture of methyl-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccncc1 | HO- | CO.O | null | null | COC(=O)c1ccncc1OC.COC(C)=O>CO.O>COc1cnccc1C(C)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2cbd4d49833e4296861b4aa4a8ba079b | Br.COc1cnccc1C(C)=O>>COc1cnccc1C(=O)CBr | Br.[NH+]1=CC=CC=C1.Br.COC=1C=NC=CC1C(C)=O>>Br.BrCC(=O)C1=C(C=NC=C1)OC | [BrH:13].[CH3:2][O:3][c:4]1[cH:5][n:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[CH3:12]>>[CH3:2][O:3][c:4]1[cH:5][n:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[CH2:12][Br:13] | Br.COc1cnccc1C(C)=O | COc1cnccc1C(=O)CBr | null | null | C(C)(=O)O | Functional Group Addition | Bromination | bf5c9c3636d0bb082289a8c9a57893f9c01b86491bbac098df6f08165abff331 | 59d1a8eb6d53c009bab8d2eda578b612565fd5477616e626d840161408a683de | c1ccncc1 | [BrH;D0;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 4 | HOUR | A solution of pyridinium hydrobromide perbromide (2.33 g, 0.0073 mol) in acetic acid (20 mL) containing 31% hydrobromic acid in acetic acid (1.85 mL) was stirred at room temperature for four hours. The mixture was cooled to 17° C. and a solution of 3-methoxy-4-acetylpyridine (1.02 g, 0.0062 mol) in acetic acid (5 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccncc1 | null | C(C)(=O)O | null | 4 | Br.COc1cnccc1C(C)=O>C(C)(=O)O>COc1cnccc1C(=O)CBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c74194e3c47f4eb68794e86e6dfaa233 | NN1CC=CCC1.O=C(Cl)Oc1ccccc1>>O=C(NN1CC=CCC1)Oc1ccccc1 | Cl.NN1CCC=CC1.C(C)N(CC)CC.ClC(=O)OC1=CC=CC=C1>>O(C1=CC=CC=C1)C(=O)NN1CCC=CC1 | [NH2:3][N:4]1[CH2:5][CH:6]=[CH:7][CH2:8][CH2:9]1.Cl[C:2](=[O:1])[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([NH:3][N:4]1[CH2:5][CH:6]=[CH:7][CH2:8][CH2:9]1)[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | NN1CC=CCC1.O=C(Cl)Oc1ccccc1 | O=C(NN1CC=CCC1)Oc1ccccc1 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 5be28d87ebf4e99b19d55116b9ee6a2de77dfa39d592d5f1181884aff5e22c5f | 5fd6250903fa66c378faf3ffa4e2360187bf8e16b5a0c6900f15dfbc5082c0be | O=C(NN1CC=CCC1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C:5]=[C:6]-[C:7]-[#7:8](-[NH2;D1;+0:9])-[C:10]>>[C:5]=[C:6]-[C:7]-[#7:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4])-[C:10] | 92.1 | [{"value": 92.1, "product": "O(C1=CC=CC=C1)C(=O)NN1CCC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 4 | HOUR | To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylami-ne (2.024 g) in methylene chloride (60 ml) was added a solution of phenyl chloroformate (1.566 g) in methylene chloride (40 ml) and the mixture was stirred for 4 hours at 5° C. Evaporation of the solvent gave a residue, which wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Acylhydrazine | null | null | C1=CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl | 5 | 4 | NN1CC=CCC1.O=C(Cl)Oc1ccccc1>C(Cl)Cl>O=C(NN1CC=CCC1)Oc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a3795389ab974dca90679ddbd9c6c680 | NN1CC=CCC1.O=C=Nc1ccc(F)cc1>>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | Cl.NN1CCC=CC1.FC1=CC=C(C=C1)N=C=O.[OH-].[Na+]>>FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1 | [NH2:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[NH:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1 | NN1CC=CCC1.O=C=Nc1ccc(F)cc1 | O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | null | null | O.O1CCOCC1 | Acylation | OtherReaction | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | O=C(Nc1ccccc1)NN1CC=CCC1 | [C:1]=[C:2]-[C:3]-[#7:4](-[NH2;D1;+0:5])-[C:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]=[C:2]-[C:3]-[#7:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:6] | 77.6 | [{"value": 77.6, "product": "FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 2 | HOUR | N-Amino-1,2,3,6-tetrahydropyridine hydrochloride (3.42 g) was dissolved in a mixture of dioxane (30 ml) and water (20 ml). The solution was adjusted to pH 7.5 with 1N-aqueous sodium hydroxide and to the resultant mixture was added a solution of 4-fluorophenylisocyanate (0.548 g) in dioxane (5 ml). Then, the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1=CC[NH]CC1 | null | O.O1CCOCC1 | 5 | 2 | NN1CC=CCC1.O=C=Nc1ccc(F)cc1>O.O1CCOCC1>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-15946ac52f84452daf9d7ce6d8f8fe10 | NN1CC=CCC1.O=C=Nc1cccc(F)c1>>O=C(Nc1cccc(F)c1)NN1CC=CCC1 | Cl.NN1CCC=CC1.C(C)N(CC)CC.FC=1C=C(C=CC1)N=C=O>>FC=1C=C(C=CC1)NC(=O)NN1CCC=CC1 | [NH2:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]([F:9])[cH:10]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([F:9])[cH:10]1)[NH:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1 | NN1CC=CCC1.O=C=Nc1cccc(F)c1 | O=C(Nc1cccc(F)c1)NN1CC=CCC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | O=C(Nc1ccccc1)NN1CC=CCC1 | [C:1]=[C:2]-[C:3]-[#7:4](-[NH2;D1;+0:5])-[C:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]=[C:2]-[C:3]-[#7:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:6] | 60.8 | [{"value": 60.8, "product": "FC=1C=C(C=CC1)NC(=O)NN1CCC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.012 g) in dry methylene chloride (40 ml) was added a solution of 3-fluorophenyl isocyanate (1.37 g) in dry methylene chloride under ice-bath cooling. After stirring for one hour, the reaction mixture was evaporated to dryne... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1=CC[NH]CC1 | null | C(Cl)Cl | null | 1 | NN1CC=CCC1.O=C=Nc1cccc(F)c1>C(Cl)Cl>O=C(Nc1cccc(F)c1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2972a999c99c4df9bc9aa7a812034758 | Fc1ccc(N=C=S)cc1.NN1CC=C(c2ccccc2)CC1>>Fc1ccc(NC(=S)NN2CC=C(c3ccccc3)CC2)cc1 | Cl.NN1CCC(=CC1)C1=CC=CC=C1.[OH-].[Na+].FC1=CC=C(C=C1)N=C=S>>FC1=CC=C(C=C1)NC(=S)NN1CCC(=CC1)C1=CC=CC=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[C:7]=[S:8])[cH:22][cH:23]1.[NH2:9][N:10]1[CH2:11][CH:12]=[C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[S:8])[NH:9][N:10]2[CH2:11][CH:12]=[C:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[CH2:20][CH2:21]2)[cH:22][cH:... | Fc1ccc(N=C=S)cc1.NN1CC=C(c2ccccc2)CC1 | Fc1ccc(NC(=S)NN2CC=C(c3ccccc3)CC2)cc1 | null | null | O.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | d20aaa746dc43df2f35648d9419db98ed96f2035bae3684b9a4378845ffa3585 | f7e2fc7ab2c341a9e6af0d77ebfb73e49e2475bed2a1247a7f61366f6427f2cf | S=C(Nc1ccccc1)NN1CC=C(c2ccccc2)CC1 | [C:1]=[C:2]-[C:3]-[#7:4](-[NH2;D1;+0:5])-[C:6].[S;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]=[C:2]-[C:3]-[#7:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[S;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:6] | 64.4 | [{"value": 64.4, "product": "FC1=CC=C(C=C1)NC(=S)NN1CCC(=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a stirred solution of N-amino-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (1.05 g) in a mixture of dioxane (10 ml) and water (5 ml) was added 1N sodium hydroxide solution (5 ml) under ice-bath cooling, and then a solution of 4-fluorophenyl isothiocyanate (1.15 g) in dioxane (5 ml) was added thereto. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isothiocyanate | Hydrazine.Thiourea | null | null | c1ccccc1.C1=CC[NH]CC1.c1ccccc1 | null | O.O1CCOCC1 | null | 5 | Fc1ccc(N=C=S)cc1.NN1CC=C(c2ccccc2)CC1>O.O1CCOCC1>Fc1ccc(NC(=S)NN2CC=C(c3ccccc3)CC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cc5f2343b0b2464494f03f96f151a07a | NN1CC=CCC1.O=C(Nc1ccc(F)cc1)Oc1ccccc1>>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | FC1=CC=C(NC(=O)OC2=CC=CC=C2)C=C1.Cl.NN1CCC=CC1.C(C)N(CC)CC>>FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1 | [NH2:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]2)cc1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[NH:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1 | NN1CC=CCC1.O=C(Nc1ccc(F)cc1)Oc1ccccc1 | O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 836db69d01985cc962fe5c0a07b8b8d48bdfd49ff4000059963792bc5c6f1006 | 0cb77777283c5722e23a892db9f638efc73d17e00759b2f46f68b450e32d1d89 | O=C(Nc1ccccc1)NN1CC=CCC1 | [C:1]=[C:2]-[C:3]-[#7:4](-[NH2;D1;+0:5])-[C:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-O-c1:c:c:c:c:c:1)-[#7:9]-[c:10]>>[C:1]=[C:2]-[C:3]-[#7:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[#7:9]-[c:10])-[C:6] | 45.1 | [{"value": 45.1, "product": "FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-fluoro-N-phenoxycarbonylaniline (2.29 g), N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.02 g) in chloroform (25 ml) was refluxed for 20 hours. After evaporation of chloroform, the residue was extracted with ethyl acetate (100 ml). The extract was washed with water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carbamic ester.Ether | Acylhydrazine | c1ccccc1 | null | c1ccccc1.C1=CC[NH]CC1 | HO- | C(Cl)(Cl)Cl | null | null | NN1CC=CCC1.O=C(Nc1ccc(F)cc1)Oc1ccccc1>C(Cl)(Cl)Cl>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4dac31e8682a4872921ace479cd32233 | O=C(N=[N+]1C=CC=CC1)Nc1ccccc1>>O=C(Nc1ccccc1)NN1CC=CCC1 | C1(=CC=CC=C1)NC(=O)N=[N+]1CC=CC=C1.[BH4-].[Na+].Cl>>C1(=CC=CC=C1)NC(=O)NN1CCC=CC1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]=[N+:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH2:16]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][N:11]1[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16]1 | O=C(N=[N+]1C=CC=CC1)Nc1ccccc1 | O=C(Nc1ccccc1)NN1CC=CCC1 | null | null | C(C)O.O | Functional Group Interconversion | OtherReaction | e9211f4eb8ad1093fdbfa79df9ebf798cf09f13d01237eea98dde61cba4e5c46 | 49e46cfaf3d77e98e969c0bd47c3ecbd1ec0df0bc3c38cf005eb42de5f17a73a | O=C(Nc1ccccc1)NN1CC=CCC1 | [O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[N;H0;D2;+0:5]=[N+;H0;D3:6]1-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[NH;D2;+0:5]-[N;H0;D3;+0:6]1-[C:7]-[CH2;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | 4 | HOUR | To a solution of N-(phenylcarbamoylimino)pyridinium ylide (0.64 g) in a mixture of ethanol (30 ml) and water (10 ml) was added sodium borohydride (0.20 g) at ambient temperature. After being stirred for 4 hours, the reaction mixture was acidified with 1N hydrochloric acid, concentrated to a volume of ca. 15 ml. The cry... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Conjugated diene | Acylhydrazine.Urea | C1=CC[NH+]C=C1 | C1=CC[NH]CC1 | c1ccccc1.C1=CC[NH]CC1 | null | C(C)O.O | null | 4 | O=C(N=[N+]1C=CC=CC1)Nc1ccccc1>C(C)O.O>O=C(Nc1ccccc1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ba8e9518e9a14e998c41606e7292d98b | O=C(N=[N+]1C=CC=CC1)Nc1ccc(F)cc1>>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | O.FC1=CC=C(C=C1)NC(=O)N=[N+]1CC=CC=C1.[BH4-].[Na+].[BH4-].[Na+]>>FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[N:11]=[N+:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH2:17]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[NH:11][N:12]1[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1 | O=C(N=[N+]1C=CC=CC1)Nc1ccc(F)cc1 | O=C(Nc1ccc(F)cc1)NN1CC=CCC1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | e9211f4eb8ad1093fdbfa79df9ebf798cf09f13d01237eea98dde61cba4e5c46 | 49e46cfaf3d77e98e969c0bd47c3ecbd1ec0df0bc3c38cf005eb42de5f17a73a | O=C(Nc1ccccc1)NN1CC=CCC1 | [O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[N;H0;D2;+0:5]=[N+;H0;D3:6]1-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[NH;D2;+0:5]-[N;H0;D3;+0:6]1-[C:7]-[CH2;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | 16 | HOUR | A suspension of N-[[(4-fluorophenyl)carbamoyl]-imino]pyridinium ylide (1.04 g) and sodium borohydride (2.55 g) in ethanol (100 ml) was stirred at ambient temperature for 16 hours. Excess of sodium borohydride was decomposed with water, and the resulting mixture was evaporated. The residue was extracted with chloroform ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Conjugated diene | Acylhydrazine.Urea | C1=CC[NH+]C=C1 | C1=CC[NH]CC1 | c1ccccc1.C1=CC[NH]CC1 | null | C(C)O | null | 16 | O=C(N=[N+]1C=CC=CC1)Nc1ccc(F)cc1>C(C)O>O=C(Nc1ccc(F)cc1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-824d03c3210447cc84bae0d08c4e9730 | COC(=O)c1ccc(NC(=O)NN2CC=CCC2)cc1>>O=C(Nc1ccc(C(=O)O)cc1)NN1CC=CCC1 | COC(=O)C1=CC=C(C=C1)NC(=O)NN1CCC=CC1.[OH-].[Na+]>>C(=O)(O)C1=CC=C(C=C1)NC(=O)NN1CCC=CC1 | C[O:10][C:8]([c:7]1[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[NH:13][N:14]2[CH2:15][CH:16]=[CH:17][CH2:18][CH2:19]2)[cH:12][cH:11]1)=[O:9]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1)[NH:13][N:14]1[CH2:15][CH:16]=[CH:17][CH2:18][CH2:19]1 | COC(=O)c1ccc(NC(=O)NN2CC=CCC2)cc1 | O=C(Nc1ccc(C(=O)O)cc1)NN1CC=CCC1 | null | null | C(Cl)(Cl)Cl.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)NN1CC=CCC1 | 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] | 56.6 | [{"value": 56.6, "product": "C(=O)(O)C1=CC=C(C=C1)NC(=O)NN1CCC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-[[(4-methoxycarbonylphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.21 g) in a mixture of methanol (30 ml) and chloroform (30 ml) was added. 1N sodium hydroxide (10 ml) and the mixture was stirred at ambient temperature for 18 hours. After evaporation of the solvent, the residue was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1=CC[NH]CC1 | Other | C(Cl)(Cl)Cl.CO | null | null | COC(=O)c1ccc(NC(=O)NN2CC=CCC2)cc1>C(Cl)(Cl)Cl.CO>O=C(Nc1ccc(C(=O)O)cc1)NN1CC=CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-10bcb14ff2a94443b04413a0a391e4dc | CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C>>CCOC(=O)[C@H](C[C@@H](O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O>>C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](C[C@@H](O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C@@H:17]([CH3:18])[C:19](=[O:20])[N:21]1[CH2:22][CH2:23][CH2:24][C@H:25]1[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][C@@H:8]([OH:9])[c:10]1[cH:11][... | CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | CCOC(=O)[C@H](C[C@@H](O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | null | [Pd] | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(CNCCCc1ccccc1)N1CCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 13.4 g (30 mmoles) of N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t - butylester are dissolved in 120 ml of ethanol and hydrogenated in the presence of 1.5 g of 10% palladium-on-charcoal catalyst at room temperature. After the uptake of the theoretically needed hydrogen (720 ml), the catalyst ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.C1CC[NH]C1 | null | [Pd].C(C)O | null | null | CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C>[Pd].C(C)O>CCOC(=O)[C@H](C[C@@H](O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f01be8f761ca4562ae3496ae6ef3ae07 | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C>>CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N)C)=O)=O.C(C)OC(\C=C\C(C1=CC=CC=C1)=O)=O.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:16][C@@H:17]([CH3:18])[C:19](=[O:20])[N:21]1[CH2:22][CH2:23][CH2:24][C@H:25]1[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH... | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | aza-Michael addition primary | f23c1d33294f7c2373748c5c22b15927f476391e752421c17b512248b86c26cb | f96ab441d5d582a398da5dd243d1e594dd5722bfce5951b92a99ef0632ea2683 | O=C(CCNCC(=O)N1CCCC1)c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8](-[C;D1;H3:9])-[NH2;D1;+0:10])-[C:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[CH;D2;+0:17]/[C:18](=[O;D1;H0:19])-[c:20]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[C@@H;D3;+0:16](-[CH2;D2;+... | 60 | [{"value": 60.0, "product": "C(\\C=C/C(=O)O)(=O)O.C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "C(\\C=C/C(=O)O)(=O)O.C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O", "details": "... | null | null | null | null | 4.84 g (20 mmoles) of (S)-alanyl-(S)-proline-t-butylester are dissolved in 40 ml of dry benzene and 4.08 g (20 mmoles) of E-ethyl-3-benzoyl-acrylate are added at room temperature under stirring. After one hour stirring at room temperature the solvent is evaporated off under reduced pressure, the residue is dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ketone.Ester.Secondary amine | null | null | c1ccccc1.C1CC[NH]C1 | null | C1=CC=CC=C1 | null | null | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C>C1=CC=CC=C1>CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8a5aa9b39d74e0b898f76e9233cf62f | CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C.CCOC(=O)/C=C/C(=O)c1ccccc1>>CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | C(C)(=O)OCC.C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N)CCCCNC(=O)OC(C)(C)C)=O)=O.C(C)OC(\C=C\C(C1=CC=CC=C1)=O)=O>>C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)CCCCNC(=O)OC(C)(C)C)=O)=O | [NH2:16][C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C:30](=[O:31])[N:32]1[CH2:33][CH2:34][CH2:35][C@H:36]1[C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43].[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][... | CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C.CCOC(=O)/C=C/C(=O)c1ccccc1 | CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C | null | null | CCOCC.C(C)OCC | Heteroatom Alkylation and Arylation | aza-Michael addition primary | f23c1d33294f7c2373748c5c22b15927f476391e752421c17b512248b86c26cb | f96ab441d5d582a398da5dd243d1e594dd5722bfce5951b92a99ef0632ea2683 | O=C(CCNCC(=O)N1CCCC1)c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8](-[C:9])-[NH2;D1;+0:10])-[C:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[CH;D2;+0:17]/[C:18](=[O;D1;H0:19])-[c:20]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8](-[C:9])-[NH;D2;+0:10]-[C@@H;D3;+0:16](-[CH2;D2;+0:17]-[C:18]... | null | [] | null | null | 5 | HOUR | 8.0 g (20 mmoles) of Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester are dissolved in 100 ml of diethyl ether and 4.48 g (22 mmoles) of E-ethyl-3-benzoyl-acrylate are added to the solution. The reaction mixture is stirred at room temperature for 5 hours. After evaporation of the solvent the title product is iso... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ketone.Ester.Secondary amine | null | null | c1ccccc1.C1CC[NH]C1 | null | CCOCC.C(C)OCC | null | 5 | CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C.CCOC(=O)/C=C/C(=O)c1ccccc1>CCOCC.C(C)OCC>CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-97da413a676c4eefa7c6d0c7176edaf1 | C=C(C)C.CCCCOC(=O)CO>>CCCCOC(=O)COC(C)(C)C | CC(C)=C.C(CO)(=O)OCCCC.S(O)(O)(=O)=O>>C(C)(C)(C)OCC(=O)OCCCC | [C:10]([CH3:11])(=[CH2:12])[CH3:13].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][O:9][C:10]([CH3:11])([CH3:12])[CH3:13] | C=C(C)C.CCCCOC(=O)CO | CCCCOC(=O)COC(C)(C)C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f7c7da7c78eb65b9b2c8f63d0f16c4d5887e45e01ac1a9ea608f777c535e8cd7 | d7c87de309863ac8797e1e336d1d5992291f9ca863376e68ebcf1e8fd5f0e442 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[OH;D1;+0:10]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[O;H0;D2;+0:10]-[C;H0;D4;+0:2](-[C;D1;H3:1])(-[C;D1;H3:3])-[CH3;D1;+0:4] | null | [] | null | null | 3 | DAY | A 500-ml, thick-walled Erlenynmeyer flask equipped with a magnetic stirring bar was cooled to -78° C. (dry iece-acetone bath) and charged with isobutylene (150 ml). Then, n-butyl glycolate (20.0 g, 0.151 mol) and 50 ml of methylene chloride was added along with 1 ml of concentrated sulfuric acid. The cold bath was remo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Vinyl | Ether | null | null | null | null | C(Cl)Cl | null | 72 | C=C(C)C.CCCCOC(=O)CO>C(Cl)Cl>CCCCOC(=O)COC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-683c16909174462faf1b49adbea715f3 | CCCCOC(=O)COC(C)(C)C>>CC(C)(C)OCC(=O)O | C([O-])([O-])=O.[K+].[K+].C(C)(C)(C)OCC(=O)OCCCC>>C(C)(C)(C)OCC(=O)O | CCCC[O:9][C:7]([CH2:6][O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH2:6][C:7](=[O:8])[OH:9] | CCCCOC(=O)COC(C)(C)C | CC(C)(C)OCC(=O)O | null | null | CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-C-C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 0 | CELSIUS | null | null | To 100 ml of a 50:50 (v/v) methanol/water solution containing 14.35 g of potassium carbonate, was added n-butyl 2-tert-butoxyacetate (6.50 g, 0.0346 mol). The mixture was heated at reflux for 17 hours and the volatiles removed on a flash evaporator. The remaining solution was cooled to approximately 0° C. and acidified... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO.O | 0 | null | CCCCOC(=O)COC(C)(C)C>CO.O>CC(C)(C)OCC(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-735fc3dbd8da40b9ad499f1ee9ee5a7e | ClCc1ccc2ccccc2n1.Oc1ccccc1>>c1ccc(OCc2ccc3ccccc3n2)cc1 | ClCC1=NC2=CC=CC=C2C=C1.C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[Na+]>>O(C1=CC=CC=C1)CC1=NC2=CC=CC=C2C=C1 | Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[n:16]1.[cH:1]1[cH:2][cH:3][c:4]([OH:5])[cH:17][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1 | ClCc1ccc2ccccc2n1.Oc1ccccc1 | c1ccc(OCc2ccc3ccccc3n2)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccc3ccccc3n2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | A mixture of 2-chloromethyl quinoline (0.05 mol), phenol (0.055 mol), finely powdered potassium carbonate (0.055 mol), cesium carbonate (0.005 mol) and sodium iodide (0.0025 mol) in acetone was refluxed for about 4 hours. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | CC(=O)C | null | null | ClCc1ccc2ccccc2n1.Oc1ccccc1>CC(=O)C>c1ccc(OCc2ccc3ccccc3n2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-69d6dd0a63e846cc9ea6cbd2d9d2af27 | O=[N+]([O-])c1ccc(O)cc1.Oc1ccccc1>>O=[N+]([O-])c1ccc(OCc2ccc3ccccc3n2)cc1 | C1=CC(=CC=C1[N+](=O)[O-])O.C1(=CC=CC=C1)O>>[N+](=O)([O-])C1=CC=C(OCC2=NC3=CC=CC=C3C=C2)C=C1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:20][cH:21]1.O[c:9]1[cH:11][cH:17][cH:16][cH:15][cH:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2)[cH:20][cH:21]1 | O=[N+]([O-])c1ccc(O)cc1.Oc1ccccc1 | O=[N+]([O-])c1ccc(OCc2ccc3ccccc3n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 46ea60c0a6998c6f5c81dcefe587c0e7eb13f574231f11ea0e6d1812799c5e68 | 055aebb1401c8b073f067057dba15f6b45e1b6d8b27a6d27ee14b797b8e2ceae | c1ccc(OCc2ccc3ccccc3n2)cc1 | O-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:11]1:[#7;a:12]:[c:13]2:[cH;D2;+0:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:14]:2:[c:15]:[cH;D2;+0:2]:1):[c:10] | null | [] | null | null | null | null | This compound was prepared in an identical manner as described in Example 1, except p-nitrophenol was substituted for phenol, m.p. 142°-143° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared in an identical manner | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | null | null | null | null | O=[N+]([O-])c1ccc(O)cc1.Oc1ccccc1>>O=[N+]([O-])c1ccc(OCc2ccc3ccccc3n2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3b691c0f3b274492971e450bdceebda6 | NNc1ccc(F)cc1.O=C1CCCC(=O)C1>>OC1=CC(=NNc2ccc(F)cc2)CCC1 | C1(CC(CCC1)=O)=O.Cl.FC1=CC=C(C=C1)NN.[OH-].[Na+]>>FC1=CC=C(C=C1)NN=C1C=C(CCC1)O | [NH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1.O=[C:4]1[CH2:3][C:2](=[O:1])[CH2:16][CH2:15][CH2:14]1>>[OH:1][C:2]1=[CH:3][C:4](=[N:5][NH:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16]1 | NNc1ccc(F)cc1.O=C1CCCC(=O)C1 | OC1=CC(=NNc2ccc(F)cc2)CCC1 | null | null | O | Acylation | OtherReaction | 4588bc0ac913444b8772115fc2d17c8f8adb352d295d5f09b850098e26b0afb9 | aeed7f7f446135028f4c8b0de72f1d32a303d1e6e825e26d145e859295b3da3e | C1=CC(=NNc2ccccc2)CCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[CH2;D2;+0:7]-1.[NH2;D1;+0:8]-[#7:9]-[c:10]>>[OH;D1;+0:6]-[C;H0;D3;+0:5]1=[CH;D2;+0:7]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[#7:9]-[c:10])-[C:2]-[C:3]-[C:4]-1 | 96.4 | [{"value": 96.4, "product": "FC1=CC=C(C=C1)NN=C1C=C(CCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of 4-fluorophenylhydrazine hydrochloride (50 g) in water (500 ml) was treated with sodium hydroxide (12.3 g) in water (50 ml) and the resultant solution added to solution of cyclohexane-1,3-dione (97%, 35.6 g) in water (300 ml) over 2 h under nitrogen with stirring. After a further 30 min, the precipitate ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Hydrazone.Enol | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HO- | O | null | 0.5 | NNc1ccc(F)cc1.O=C1CCCC(=O)C1>O>OC1=CC(=NNc2ccc(F)cc2)CCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-76b14a9408c64659932b886070897fcf | COS(=O)(=O)OC.O=C1CCCc2[nH]c3ccc(F)cc3c21>>Cn1c2c(c3cc(F)ccc31)C(=O)CCC2 | FC=1C=C2C=3C(CCCC3NC2=CC1)=O.C([O-])([O-])=O.[K+].[K+].COS(=O)(=O)OC>>FC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O | COS(=O)(=O)O[CH3:1].[nH:2]1[c:3]2[c:4]([c:5]3[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]13)[C:12](=[O:13])[CH2:14][CH2:15][CH2:16]2>>[CH3:1][n:2]1[c:3]2[c:4]([c:5]3[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]13)[C:12](=[O:13])[CH2:14][CH2:15][CH2:16]2 | COS(=O)(=O)OC.O=C1CCCc2[nH]c3ccc(F)cc3c21 | Cn1c2c(c3cc(F)ccc31)C(=O)CCC2 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-methylation | 30cbab1101db21674c61864f82b5b188234804a6cfd88c5e783305d37b85c63f | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C1CCCc2[nH]c3ccccc3c21 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[c:3]1:[nH;D2;+0:4]:[c:5](:[c:6]):[c:7]:[c:8]:1-[C:9]=[O;D1;H0:10]>>[C:2]-[c:3]1:[c:8](:[c:7]:[c:5](:[c:6]):[n;H0;D3;+0:4]:1-[CH3;D1;+0:1])-[C:9]=[O;D1;H0:10] | 97.5 | [{"value": 97.5, "product": "FC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The product of Stage (ii) (7.28 g), potassium carbonate (9.90 g), acetone (70 ml), and dimethylsulphate (5.1 ml) were vigorously stirred at room temperature overnight under nitrogen. The mixture was concentrated to one half of its volume and then stirred with water (350 ml) for 30 min. The mixture was filtered off, was... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)CCCC3 | C1CCCc2[nH]c3ccccc3c21 | C1CCCc2[nH]c3ccccc3c21 | HO- | CC(=O)C | null | 0.5 | COS(=O)(=O)OC.O=C1CCCc2[nH]c3ccc(F)cc3c21>CC(=O)C>Cn1c2c(c3cc(F)ccc31)C(=O)CCC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cc2dc59ce3544cd8a5c808b61203bdd1 | NNc1ccc(Br)cc1.O=C1CCCC(=O)C1>>O=C1CCCC(=NNc2ccc(Br)cc2)C1 | Cl.BrC1=CC=C(C=C1)NN.C1(CC(CCC1)=O)=O>>BrC1=CC=C(C=C1)NN=C1CC(CCC1)=O | [NH2:7][NH:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.O=[C:6]1[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:16]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][C:6](=[N:7][NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1 | NNc1ccc(Br)cc1.O=C1CCCC(=O)C1 | O=C1CCCC(=NNc2ccc(Br)cc2)C1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 8fd42c3afb34fc209a626759948c4bd78aa782c38787b900b74e01ff0893a4bd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | O=C1CCCC(=NNc2ccccc2)C1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1.[NH2;D1;+0:8]-[#7:9]-[c:10]>>[O;D1;H0:4]=[C:3]1-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[#7:9]-[c:10])-[C:7]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | A solution of 4-bromophenylhydrazine hydrochloride (2.24 g) and 1,3-cyclohexanedione (1.23 g) in water (60 ml) was stirred at room temperature for 1 h, giving a precipitate. The solid title compound was filtered off and dried (1.63 g). t.l.c (D), Rf 0.35 On cooling a second crop was obtained (0.395 g)
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | O | null | null | NNc1ccc(Br)cc1.O=C1CCCC(=O)C1>O>O=C1CCCC(=NNc2ccc(Br)cc2)C1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-477e144581644ea4bec3777f5ed06716 | O=C1CCCC(=NNc2ccc(Br)cc2)C1>>O=C1CCCc2[nH]c3ccc(Br)cc3c21 | BrC1=CC=C(C=C1)NN=C1CC(CCC1)=O.O>>BrC=1C=C2C=3C(CCCC3NC2=CC1)=O | N([N:7]=[C:6]1[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:15]1)[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[c:15]21 | O=C1CCCC(=NNc2ccc(Br)cc2)C1 | O=C1CCCc2[nH]c3ccc(Br)cc3c21 | null | [Cl-].[Zn+2].[Cl-] | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 5e9560b6cda3347248de8b7acae96ba24659bf5628d876729bf51ef333dea93f | 6158bf86826c5f774a824bd0f476ebd74135d9604cccee336f26a5f9efada43a | O=C1CCCc2[nH]c3ccccc3c21 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6](=[N;H0;D2;+0:7]-N-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:2)-[CH2;D2;+0:14]-1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C:5]-[c;H0;D3;+0:6]2:[nH;D2;+0:7]:[c;H0;D3;+0:8]3:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:3:[c;H0;D3;+0:14]:2-1 | null | [] | null | null | null | null | The product of Stage (i) (1.5 g) was heated under reflux with dry zinc chloride (16 g) in glacial acetic acid (75 ml) for 24 h. The mixture was cooled, poured into water (200 ml), and the resulting solid filtered off and dried (0.95 g). Purification by flash chromatography (E) gave the title compound as a solid (125 mg... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone | Ketone | C1CCCCC1.c1ccccc1 | c1ccc2c3c([nH]c2c1)CCCC3 | c1ccc2c3c([nH]c2c1)CCCC3 | Other | [Cl-].[Zn+2].[Cl-].C(C)(=O)O | null | null | O=C1CCCC(=NNc2ccc(Br)cc2)C1>[Cl-].[Zn+2].[Cl-].C(C)(=O)O>O=C1CCCc2[nH]c3ccc(Br)cc3c21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a26e6327d94044e097c670375d9520d2 | C=O.CNC.Cn1c2c(c3cc(Br)ccc31)C(=O)CCC2>>CN(C)CC1CCc2c(c3cc(Br)ccc3n2C)C1=O | O.C=O.Cl.CNC.BrC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O>>Cl.BrC=1C=C2C=3C(C(CCC3N(C2=CC1)C)CN(C)C)=O | O=[CH2:4].[CH3:1][NH:2][CH3:3].[CH2:5]1[CH2:6][CH2:7][c:8]2[c:9]([c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[n:17]2[CH3:18])[C:19]1=[O:20]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][c:8]2[c:9]([c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[n:17]2[CH3:18])[C:19]1=[O:20] | C=O.CNC.Cn1c2c(c3cc(Br)ccc31)C(=O)CCC2 | CN(C)CC1CCc2c(c3cc(Br)ccc3n2C)C1=O | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | c1a45b1ac40a56543412022e9be077adade507f2494f6aa3371281dd5be7791c | e8784011446fecd0a9b69948eec8f6e670a0f5952d23e21c3e86b629168fc3f8 | O=C1CCCc2[nH]c3ccccc3c21 | O=[CH2;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8]-[C:9]-1.[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[#7;a:2]:[c:3]1:[c:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12])-[C:8]-[C:9]-1 | 67.3 | [{"value": 67.3, "product": "Cl.BrC=1C=C2C=3C(C(CCC3N(C2=CC1)C)CN(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Paraformaldehyde (1.5 g) and dimethylamine hydrochloride (3.75 g) were added to a solution of the product of Stage (iii) (10 g) in acetic acid (70 ml) and then heated to reflux for 8 h. On cooling to ambient temperature the reaction mixture was poured into water (400 ml). The oil which separated out was triturated with... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone.Secondary amine | Ketone.Tertiary amine | C1CCCc2[nH]c3ccccc3c21 | C1[CH]CCc2[nH]c3ccccc3c21 | C1[CH]CCc2[nH]c3ccccc3c21 | HO- | C(C)(=O)O | null | null | C=O.CNC.Cn1c2c(c3cc(Br)ccc31)C(=O)CCC2>C(C)(=O)O>CN(C)CC1CCc2c(c3cc(Br)ccc3n2C)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-313df49ceb1b4c6cb32f2cf23619645d | COc1ccc(NN)cc1.O=C1CCCC(=O)C1>>COc1ccc2[nH]c3c(c2c1)C(=O)CCC3 | C1(CC(CCC1)=O)=O.Cl.COC1=CC=C(C=C1)NN>>COC=1C=C2C=3C(CCCC3NC2=CC1)=O | N[NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:11][cH:10]1.O=[C:8]1[CH2:9][C:12](=[O:13])[CH2:14][CH2:15][CH2:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[C:12](=[O:13])[CH2:14][CH2:15][CH2:16]3 | COc1ccc(NN)cc1.O=C1CCCC(=O)C1 | COc1ccc2[nH]c3c(c2c1)C(=O)CCC3 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 216d1a60c6e7a9cb1b0c8014f08184065b33ea82af906e7694cae36b12f075b9 | 0b5a1886fc2038f5ee65b48e06759bc9de0979200ef7d47d3e0b760c7f7778a8 | O=C1CCCc2[nH]c3ccccc3c21 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:12]=[C:11]1-[C:10]-[C:9]-[C:8]-[c;H0;D3;+0:7]2:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:13]:2-1 | 48.7 | [{"value": 48.7, "product": "COC=1C=C2C=3C(CCCC3NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1,3-Cyclohexanedione (8 g) was added to a solution of 4-methoxyphenylhydrazine hydrochloride (10 g) in ethanol (350 ml) and water (70 ml). The resulting solution was stirred at room temperature for 3 h and then at reflux for 14 h. On cooling to ambient temperature, the reaction mixture was poured into water (3 l) to gi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ketone | c1ccccc1.C1CCCCC1 | c1ccc2c3c([nH]c2c1)CCCC3 | c1ccc2c3c([nH]c2c1)CCCC3 | HO- | C(C)O.O | null | 3 | COc1ccc(NN)cc1.O=C1CCCC(=O)C1>C(C)O.O>COc1ccc2[nH]c3c(c2c1)C(=O)CCC3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1ac4895b46ac455b903ac181d0e5e30d | COS(=O)(=O)OC.COc1ccc2[nH]c3c(c2c1)C(=O)CCC3>>COc1ccc2c(c1)c1c(n2C)CCCC1=O | O.C([O-])([O-])=O.[K+].[K+].COC=1C=C2C=3C(CCCC3NC2=CC1)=O.S(=O)(=O)(OC)OC>>COC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O | COS(=O)(=O)O[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]([nH:11]2)[CH2:13][CH2:14][CH2:15][C:16]1=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]([n:11]2[CH3:12])[CH2:13][CH2:14][CH2:15][C:16]1=[O:17] | COS(=O)(=O)OC.COc1ccc2[nH]c3c(c2c1)C(=O)CCC3 | COc1ccc2c(c1)c1c(n2C)CCCC1=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-methylation | 30cbab1101db21674c61864f82b5b188234804a6cfd88c5e783305d37b85c63f | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C1CCCc2[nH]c3ccccc3c21 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[c:3]1:[nH;D2;+0:4]:[c:5](:[c:6]):[c:7]:[c:8]:1-[C:9]=[O;D1;H0:10]>>[C:2]-[c:3]1:[c:8](:[c:7]:[c:5](:[c:6]):[n;H0;D3;+0:4]:1-[CH3;D1;+0:1])-[C:9]=[O;D1;H0:10] | 78.2 | [{"value": 78.2, "product": "COC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Anhydrous potassium carbonate (2.24 g) was added to a solution of the product of Stage (i) (3 g) in acetone (30 ml) at room temperature and stirred for 30 min. Dimethyl sulphate (1.6 ml) was added and the mixture was heated to reflux for 4 h. The resulting solution was poured into water (150 ml) and the resulting preci... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)CCCC3 | C1CCCc2[nH]c3ccccc3c21 | C1CCCc2[nH]c3ccccc3c21 | HO- | CC(=O)C | null | 0.5 | COS(=O)(=O)OC.COc1ccc2[nH]c3c(c2c1)C(=O)CCC3>CC(=O)C>COc1ccc2c(c1)c1c(n2C)CCCC1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-63297f81bc0d4054a9441052d946e9fe | Nc1ccc(OCc2ccccc2)cc1>>NNc1ccc(OCc2ccccc2)cc1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1.N(=O)[O-].[Na+]>>Cl.C1(=CC=CC=C1)COC1=CC=C(C=C1)NN | [NH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[NH2:2][NH:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | Nc1ccc(OCc2ccccc2)cc1 | NNc1ccc(OCc2ccccc2)cc1 | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccc(COc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | A solution of sodium nitrite (16.1 g) in water was added dropwise over a period of ca 0.75 h to a cold (salt-ice bath) stirred suspension of 4-benzyloxyaniline hydrochloride (50 g) in concentrated hydrochloric acid (120 ml). The temperature was kept between -6° and -12° during the addition and stirring was continued fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1.c1ccccc1 | Other | Cl.O | null | 1 | Nc1ccc(OCc2ccccc2)cc1>Cl.O>NNc1ccc(OCc2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-78fc489b6c4b4be39c7bb6d9b5564ba7 | NNc1ccc(OCc2ccccc2)cc1.O=C1CCCC(=O)C1>>O=C1CCCc2[nH]c3ccc(OCc4ccccc4)cc3c21 | C1(CC(CCC1)=O)=O.Cl.C1(=CC=CC=C1)COC1=CC=C(C=C1)NN>>C1(=CC=CC=C1)COC=1C=C2C=3C(CCCC3NC2=CC1)=O | N[NH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1.O=[C:6]1[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:22]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]4[cH:15][cH:16][cH:17][cH:18][cH:19]4)[cH:20][c:21]3[c:22]21 | NNc1ccc(OCc2ccccc2)cc1.O=C1CCCC(=O)C1 | O=C1CCCc2[nH]c3ccc(OCc4ccccc4)cc3c21 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 216d1a60c6e7a9cb1b0c8014f08184065b33ea82af906e7694cae36b12f075b9 | 0b5a1886fc2038f5ee65b48e06759bc9de0979200ef7d47d3e0b760c7f7778a8 | O=C1CCCc2[nH]c3ccc(OCc4ccccc4)cc3c21 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:12]=[C:11]1-[C:10]-[C:9]-[C:8]-[c;H0;D3;+0:7]2:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:13]:2-1 | 38.4 | [{"value": 38.4, "product": "C1(=CC=CC=C1)COC=1C=C2C=3C(CCCC3NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,3-Cyclohexanedione (3.1 g) and the product of Stage (i) (5.6 g) in ethanol (196 ml) and water (39 ml) was stirred at room temperature for 3 h and then heated to reflux for 14 h. The resulting solution was allowed to cool, poured into water (500 ml) and the precipitate filtered and washed with isopropyl acetate and et... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | Ketone | c1ccccc1.C1CCCCC1 | c1ccc2c3c([nH]c2c1)CCCC3 | c1ccc2c3c([nH]c2c1)CCCC3.c1ccccc1 | HO- | C(C)O.O | null | null | NNc1ccc(OCc2ccccc2)cc1.O=C1CCCC(=O)C1>C(C)O.O>O=C1CCCc2[nH]c3ccc(OCc4ccccc4)cc3c21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f29eda88a35249c99e36ce3a1f68295a | COc1cccc(N)c1>>COc1cccc(NN)c1 | [Sn].Cl.COC=1C=C(N)C=CC1.Cl.N(=O)[O-].[Na+]>>Cl.COC=1C=C(C=CC1)NN | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][NH2:9])[cH:10]1 | COc1cccc(N)c1 | COc1cccc(NN)c1 | null | null | O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 3-methoxyaniline (10 g) in concentrated hydrochloric acid (85 ml) was stirred at ca. 0° and a solution of sodium nitrite (5.75 g) in water (25 ml) was slowly added over a period of 30 min keeping the temperature of the mixture at ca. 0°. After 1 h a solution of tin II chloride dihydrate (59 g) in concen... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | O | null | null | COc1cccc(N)c1>O>COc1cccc(NN)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c419ae0f44f44e4fa86eadeb58039dce | Cn1c2c(c3cc(C#N)ccc31)C(=O)CCC2.O=S(=O)(O)O>>Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2 | CN1C2=CC=C(C=C2C=2C(CCCC12)=O)C#N.S(O)(O)(=O)=O>>CN1C2=CC=C(C=C2C=2C(CCCC12)=O)C(=O)N | [CH3:1][n:2]1[c:3]2[c:4]([c:5]3[cH:6][c:7]([C:8]#[N:9])[cH:11][cH:12][c:13]13)[C:14](=[O:15])[CH2:16][CH2:17][CH2:18]2.O=S(=O)(O)[OH:10]>>[CH3:1][n:2]1[c:3]2[c:4]([c:5]3[cH:6][c:7]([C:8]([NH2:9])=[O:10])[cH:11][cH:12][c:13]13)[C:14](=[O:15])[CH2:16][CH2:17][CH2:18]2 | Cn1c2c(c3cc(C#N)ccc31)C(=O)CCC2.O=S(=O)(O)O | Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | O=C1CCCc2[nH]c3ccccc3c21 | O-S(=O)(=O)-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of the product of Stage (i) cyanonitrile (2.7 g) in concentrated sulphuric acid (30 ml) was heated at 80° for 1 h. The mixture was poured onto ice (ca. 500 g) to precipitate a solid which was filtered, washed with water (3×50 ml) and dried in vacuo to leave a solid (3.1 g). This was extracted with boiling ab... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | C1CCCc2[nH]c3ccccc3c21 | Other | null | null | null | Cn1c2c(c3cc(C#N)ccc31)C(=O)CCC2.O=S(=O)(O)O>>Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-45ebea4005c547ca92a07b1f8fb6a84c | C=O.CNC.Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2>>CN(C)CC1CCc2c(c3cc(C(N)=O)ccc3n2C)C1=O | N.CN1C2=CC=C(C=C2C=2C(CCCC12)=O)C(=O)N.C=O.Cl.CNC>>CN(C)CC1CCC=2N(C3=CC=C(C=C3C2C1=O)C(=O)N)C | O=[CH2:4].[CH3:1][NH:2][CH3:3].[CH2:5]1[CH2:6][CH2:7][c:8]2[c:9]([c:10]3[cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][c:8]2[c:9]([c:10]3[cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22] | C=O.CNC.Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2 | CN(C)CC1CCc2c(c3cc(C(N)=O)ccc3n2C)C1=O | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | c1a45b1ac40a56543412022e9be077adade507f2494f6aa3371281dd5be7791c | e8784011446fecd0a9b69948eec8f6e670a0f5952d23e21c3e86b629168fc3f8 | O=C1CCCc2[nH]c3ccccc3c21 | O=[CH2;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8]-[C:9]-1.[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[#7;a:2]:[c:3]1:[c:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12])-[C:8]-[C:9]-1 | null | [] | null | null | null | null | A mixture of the product of Stage (ii) (1.8 g), paraformaldehyde (0.3 g) and dimethylamine hydrochloride (0.75 g) in acetic acid (14 ml) was heated at 80°-100° under nitrogen for 2 h. The reaction mixture was cooled (20°), evaporated in vacuo and purified by flash chromatography (L) to give a foam. A sample (0.2 g) was... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone.Secondary amine | Ketone.Tertiary amine | C1CCCc2[nH]c3ccccc3c21 | C1[CH]CCc2[nH]c3ccccc3c21 | C1[CH]CCc2[nH]c3ccccc3c21 | HO- | C(C)(=O)O | null | null | C=O.CNC.Cn1c2c(c3cc(C(N)=O)ccc31)C(=O)CCC2>C(C)(=O)O>CN(C)CC1CCc2c(c3cc(C(N)=O)ccc3n2C)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-35e63bd3939a469295f57ada34255d08 | ClCc1coc(-c2ccccc2)n1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1>>O=C1NC(=O)C(Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 | O.OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1.[H-].[Na+].ClCC=1N=C(OC1)C1=CC=CC=C1>>C1(=CC=CC=C1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | Cl[CH2:13][c:14]1[cH:15][o:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1.[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:25][cH:26]2)[S:27]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][o:16][c:17](-[c:18]4[cH:19... | ClCc1coc(-c2ccccc2)n1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1 | O=C1NC(=O)C(Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NC(=O)C(Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1):[c:10] | 56.8 | [{"value": 47.4, "product": "C1(=CC=CC=C1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C1(=CC=CC=C1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (9.4 g) in N,N-dimethylformamide (80 ml) was added 60% sodium hydride in oil (3.4 g), and the mixture was stirred for 30 minutes. Then, a solution of 4-chloromethyl-2-phenyloxazole (9.6 g) in N,N-dimethylformamide (20 ml) was added dropwise thereto at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1CSCN1.c1ccccc1.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | ClCc1coc(-c2ccccc2)n1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1>CN(C=O)C>O=C1NC(=O)C(Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1600130bf31e4d3497fdf571ee839211 | CC1(c2nc(CCl)co2)CCCCC1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1>>CC1(c2nc(COc3ccc(CC4SC(=O)NC4=O)cc3)co2)CCCCC1 | O.[H-].[Na+].OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1.ClCC=1N=C(OC1)C1(CCCCC1)C>>CC1(CCCCC1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | Cl[CH2:6][c:5]1[n:4][c:3]([C:2]2([CH3:1])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[o:23][cH:22]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH:13]2[S:14][C:15](=[O:16])[NH:17][C:18]2=[O:19])[cH:20][cH:21]1>>[CH3:1][C:2]1([c:3]2[n:4][c:5]([CH2:6][O:7][c:8]3[cH:9][cH:10][c:11]([CH2:12][CH:13]4[S:14][C:15](=[O:16])[NH:17][... | CC1(c2nc(CCl)co2)CCCCC1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1 | CC1(c2nc(COc3ccc(CC4SC(=O)NC4=O)cc3)co2)CCCCC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NC(=O)C(Cc2ccc(OCc3coc(C4CCCCC4)n3)cc2)S1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1):[c:10] | null | [] | null | null | 30 | MINUTE | 60% sodium hydride in oil (1.32 g) was added to solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (3.35 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred for 30 minutes. Then, solution of 4-chloromethyl-2-(1-methylcyclohexyl)oxazole (3.85 g) in N,N-dimethylformamide (5 ml) was added dropwise thereto ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cocn1.c1ccccc1.C1CSCN1.C1CCCCC1 | HCl | CN(C=O)C | null | 0.5 | CC1(c2nc(CCl)co2)CCCCC1.O=C1NC(=O)C(Cc2ccc(O)cc2)S1>CN(C=O)C>CC1(c2nc(COc3ccc(CC4SC(=O)NC4=O)cc3)co2)CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b455a0376424e3e96c5ad5aa252a94c | CCO.Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=N)NC2=O)cc1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 | N=C1SC(C(N1)=O)CC1=CC=C(C=C1)OCCC=1N=C(OC1C)C1=CC=CC=C1.Cl.C(C)O>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | CC[OH:24].N=[C:23]1[S:22][CH:21]([CH2:20][c:19]2[cH:18][cH:17][c:16]([O:15][CH2:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:29][cH:28]2)[C:26](=[O:27])[NH:25]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[c... | CCO.Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=N)NC2=O)cc1 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6aaa2f59d7c8f3f887508e59aa8a49bf81aaddba8060243fd1af782ff664b4c8 | 29f3038d9385b8bd5021ff923a1b65cb4a19845f3f77cbeb7ca067f6e83c9c23 | O=C1NC(=O)C(Cc2ccc(OCCc3coc(-c4ccccc4)n3)cc2)S1 | C-C-[OH;D1;+0:1].N=[C;H0;D3;+0:2]1-[#16:3]-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-1>>[O;D1;H0:6]=[C:5]1-[#7:7]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[#16:3]-[C:4]-1 | 95.7 | [{"value": 95.7, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-imino-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-4-thiazolidinone (18.8 g), 2N-HCl (200 ml) and ethanol (200 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogen carbonate, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Monosulfide | Unsubstituted dicarboximide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | Other | null | null | null | CCO.Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=N)NC2=O)cc1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b6234674c5d40d897dae8a634dc35f0 | Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=N)NC2=O)cc1.O=S(=O)(O)O>>Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=O)NC2=O)cc1 | N=C1SC(C(N1)=O)CC1=CC=C(C=C1)OCC=1N=C(OC1C)C1=CC=CC=C1.OS(=O)(=O)O.O1CCOCC1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | N=[C:22]1[S:21][CH:20]([CH2:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:28][cH:27]2)[C:25](=[O:26])[NH:24]1.O=S(=O)(O)[OH:23]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH... | Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=N)NC2=O)cc1.O=S(=O)(O)O | Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=O)NC2=O)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 36e8b3343c3732c812c88deadbd6fc3bb4fcd1410389683a7b04e225d2613a26 | 0035211ca664bab428d64ca2082d0980841c38a6de91749d7754b70d2a7510c1 | O=C1NC(=O)C(Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 | N=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-1.O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4]1-[#7:6]-[C;H0;D3;+0:1](=[O;H0;D1;+0:7])-[#16:2]-[C:3]-1 | 58.8 | [{"value": 58.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone (11.4 g), 1N.H2SO4 (100 ml) and dioxane (100 ml) was stirred at 80° C. for 5 hours, and poured in water. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Unsubstituted dicarboximide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | HO- | O | null | null | Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=N)NC2=O)cc1.O=S(=O)(O)O>O>Cc1oc(-c2ccccc2)nc1COc1ccc(CC2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7107d45708c94d15882a5699664f3c58 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1.O=C1CCC(=O)N1Br>>O=C1NC(=O)C(Cc2ccc(OCCc3nc(-c4ccccc4)oc3CBr)cc2)S1 | BrN1C(CCC1=O)=O.CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrCC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]3[n:16][c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[o:24][c:25]3[CH3:26])[cH:28][cH:29]2)[S:30]1.O=C1CCC(=O)N1[Br:27]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][... | Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1.O=C1CCC(=O)N1Br | O=C1NC(=O)C(Cc2ccc(OCCc3nc(-c4ccccc4)oc3CBr)cc2)S1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | O=C1NC(=O)C(Cc2ccc(OCCc3coc(-c4ccccc4)n3)cc2)S1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:1-[CH3;D1;+0:8]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:8]-[c:7]1:[#8;a:6]:[c:5]:[#7;a:4]:[c:3]:1-[C:2] | null | [] | null | null | null | null | N-Bromosuccinimide (2.75 g) was added portionwise to a solution of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (6.0 g) and α,α'-azobisisobutyronitrile (0.5 g) in carbon tetrachloride(150 ml) under reflux. After refluxing for another 10 minutes, the reaction mixture was washed with water a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | C1CSCN1.c1ccccc1.c1cocn1.c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>O=C1NC(=O)C(Cc2ccc(OCCc3nc(-c4ccccc4)oc3CBr)cc2)S1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d519b00c7e994e338826daf4aa407bae | Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1>>Cc1nc(C(=O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 | C(C)(=O)OC(C)=O.CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)O)C.O>>CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O)C | [CH3:1][c:2]1[n:3][c:4]([CH:5]([OH:6])[CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH:14]3[S:15][C:16](=[O:17])[NH:18][C:19]3=[O:20])[cH:21][cH:22]2)[c:23]([CH3:24])[o:25]1>>[CH3:1][c:2]1[n:3][c:4]([C:5](=[O:6])[CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH:14]3[S:15][C:16](=[O:17])[NH:18][C:19]3=[O:20])[cH:21][... | Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 | Cc1nc(C(=O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1NC(=O)C(Cc2ccc(OCC(=O)c3cocn3)cc2)S1 | [#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[c:9]:1-[C;D1;H3:10]>>[#8:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[c:9]:1-[C;D1;H3:10] | 48.3 | [{"value": 48.3, "product": "CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Acetic anhydride (1.0 ml) was added to a solution of 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (0.5 g) in dimethylsulfoxide (10 ml), and the mixture was allowed to stand overnight and poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1cocn1.c1ccccc1.C1CSCN1 | null | CS(=O)C | null | 8 | Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1>CS(=O)C>Cc1nc(C(=O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-512f61929c254761a4426dca28886965 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1.O=C1CSC(=O)N1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1 | CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=O)C=C1.S1C(NC(C1)=O)=O.N1CCCCC1>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1 | O=[CH:20][c:19]1[cH:18][cH:17][c:16]([O:15][CH2:14][CH2:13][c:12]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[n:11]2)[cH:29][cH:28]1.[CH2:21]1[S:22][C:23](=[O:24])[NH:25][C:26]1=[O:27]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17... | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1.O=C1CSC(=O)N1 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1 | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=O)C(=Cc2ccc(OCCc3coc(-c4ccccc4)n3)cc2)S1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:5]=[C:6]1-[#16:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | 77.1 | [{"value": 76.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (5.0 g), 2,4-thiazolidinedione (3.8 g), piperidine (0.32 ml) and ethanol (100 ml) was stirred under reflux for 5 hours. After cooling, the crystals which separated out were collected by filtration to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]be... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | HO- | C(C)O | null | null | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1.O=C1CSC(=O)N1>C(C)O>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-59eb3a84c5114e449b61d0353ae198d1 | Cc1oc(-c2ccccc2)nc1CCl.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1>>Cc1oc(-c2ccccc2)nc1COc1ccc(C=C2SC(=O)NC2=O)cc1 | O.[H-].[Na+].OC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1.ClCC=1N=C(OC1C)C1=CC=CC=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1 | Cl[CH2:13][c:12]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1.[OH:14][c:15]1[cH:16][cH:17][c:18]([CH:19]=[C:20]2[S:21][C:22](=[O:23])[NH:24][C:25]2=[O:26])[cH:27][cH:28]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([... | Cc1oc(-c2ccccc2)nc1CCl.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1 | Cc1oc(-c2ccccc2)nc1COc1ccc(C=C2SC(=O)NC2=O)cc1 | null | null | CN(C=O)C.C(C)(=O)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NC(=O)C(=Cc2ccc(OCc3coc(-c4ccccc4)n3)cc2)S1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 41.6 | [{"value": 40.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.6, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.664 g) in N,N-dimethylformamide (20 ml), and the mixture was stirred for 30 minutes. A solution of 4-chloromethyl-5-methyl-2-phenyloxazole (0.623 g) in N,N-dimethylformamide (10 ml) was added dropwise to the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | HCl | CN(C=O)C.C(C)(=O)O | null | 0.5 | Cc1oc(-c2ccccc2)nc1CCl.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1>CN(C=O)C.C(C)(=O)O>Cc1oc(-c2ccccc2)nc1COc1ccc(C=C2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b11cbb3989ca4572a78c632b845a4b6a | Cc1oc(-c2ccccc2)nc1C(=O)CBr.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1>>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1 | C(C)(=O)O.[H-].[Na+].OC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1.BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O | Br[CH2:15][C:13]([c:12]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1)=[O:14].[OH:16][c:17]1[cH:18][cH:19][c:20]([CH:21]=[C:22]2[S:23][C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH2:15][O:16... | Cc1oc(-c2ccccc2)nc1C(=O)CBr.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C1NC(=O)C(=Cc2ccc(OCC(=O)c3coc(-c4ccccc4)n3)cc2)S1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#8;a:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:6]:[#8;a:7] | 33.3 | [{"value": 32.3, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.3, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.663 g) in N,N-dimethylformamide (20 ml) and the mixture was stirred for 30 minutes. Then, a solution of 4-bromoacetyl-5-methyl-2-phenyloxazole (0.841 g) in N,N-dimethylformamide (10 ml) was added dropwise to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | HBr | CN(C=O)C | null | 0.5 | Cc1oc(-c2ccccc2)nc1C(=O)CBr.O=C1NC(=O)C(=Cc2ccc(O)cc2)S1>CN(C=O)C>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7c9f173d9c7d4c9db041ee6af88f9112 | Cc1nc(C(=O)COc2ccc(C=C3SC(=O)NC3=O)cc2)c(C)o1>>Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 | C(C)(=O)O.[BH4-].[Na+].CC=1OC(=C(N1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O)C>>CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)O)C | [CH3:1][c:2]1[n:3][c:4]([C:5](=[O:6])[CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([CH:13]=[C:14]3[S:15][C:16](=[O:17])[NH:18][C:19]3=[O:20])[cH:21][cH:22]2)[c:23]([CH3:24])[o:25]1>>[CH3:1][c:2]1[n:3][c:4]([CH:5]([OH:6])[CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH:14]3[S:15][C:16](=[O:17])[NH:18][C:19]3=[O:20])[cH:21][c... | Cc1nc(C(=O)COc2ccc(C=C3SC(=O)NC3=O)cc2)c(C)o1 | Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 | null | null | CO.CN(C=O)C | Reduction | OtherReaction | 26b547225191774776c3b4b00c692cb60cf527f116fdf2c33e3fbd48d27dd217 | ca6bd49afbaeacd83eda3753e609edfcce9407a02a26bc62950bcb3b22cda1d2 | O=C1NC(=O)C(Cc2ccc(OCCc3cocn3)cc2)S1 | [#8:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[c:9]:1-[C;D1;H3:10].[O;D1;H0:11]=[C:12]1-[#16:13]-[C;H0;D3;+0:14](=[CH;D2;+0:15]-[c:16](:[c:17]):[c:18])-[C:19](=[O;D1;H0:20])-[#7:21]-1>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[c:9]:1-[C;D1;H3:10].[O;D1;H0:11]... | 97.5 | [{"value": 97.5, "product": "CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium borohydride (0.16 g) was added to a suspension of 5-{4-[2-(2,5-dimethyl-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.5 g) in methanol-N,N-dimethylformamide (1:1, V.V, 40 ml) under ice-cooling. After stirring under ice-cooling for 20 minutes, the reaction solution was poured into ice-water, and the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Monosulfide | Secondary alcohol.Monosulfide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.C1CSCN1 | null | CO.CN(C=O)C | null | null | Cc1nc(C(=O)COc2ccc(C=C3SC(=O)NC3=O)cc2)c(C)o1>CO.CN(C=O)C>Cc1nc(C(O)COc2ccc(CC3SC(=O)NC3=O)cc2)c(C)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f96237b352604b159d8094b573f7f1e4 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 | CO.CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1.C(C)(=O)O>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([CH:20]=[C:21]2[S:22][C:23](=[O:24])[NH:25][C:26]2=[O:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:1... | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 | null | [Pd] | C(Cl)(Cl)Cl | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NC(=O)C(Cc2ccc(OCCc3coc(-c4ccccc4)n3)cc2)S1 | [O;D1;H0:1]=[C:2]1-[#16:3]-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:1]=[C:2]1-[#16:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | null | [] | 60 | CELSIUS | 3 | HOUR | A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (500 mg), 10% Pd-C (50% wet, 1.0 g) and acetic acid (50 ml) was hydrogenated at 70° C. and at atmospheric pressure for 3 hours. Methanol (20 ml) and chloroform (20 ml) were added to the mixture and the whole was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | null | [Pd].C(Cl)(Cl)Cl | 60 | 3 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=C2SC(=O)NC2=O)cc1>[Pd].C(Cl)(Cl)Cl>Cc1oc(-c2ccccc2)nc1CCOc1ccc(CC2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c8eb97027f2c4870835f040d585e95f1 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1>>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(CC2SC(=O)NC2=O)cc1 | CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O>>CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([CH:21]=[C:22]2[S:23][C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH2:15][O:16][c:17... | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(CC2SC(=O)NC2=O)cc1 | null | [Pd].[Pd] | O1CCOCC1 | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NC(=O)C(Cc2ccc(OCC(=O)c3coc(-c4ccccc4)n3)cc2)S1 | [O;D1;H0:1]=[C:2]1-[#16:3]-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:1]=[C:2]1-[#16:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | null | [] | null | null | 4 | HOUR | A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g), Pd-black (3 g) and dioxane (100 ml) was hydrogenated at 40° C. and at atmospheric pressure. After 4 hours, another Pd-black (3 g) was added and hydrogenation was continued for 4 hours. The catalyst was fi... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | null | [Pd].[Pd].O1CCOCC1 | null | 4 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C=C2SC(=O)NC2=O)cc1>[Pd].[Pd].O1CCOCC1>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(CC2SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7d658abe348645fab4f8f7ddde1e6c72 | CCCC(N)=O.O=C(CCl)CCl>>CCCc1nc(CCl)co1 | C(CCC)(=O)N.ClCC(=O)CCl.C([O-])(O)=O.[Na+]>>ClCC=1N=C(OC1)CCC | [CH3:1][CH2:2][CH2:3][C:4]([NH2:5])=[O:10].O=[C:6]([CH2:7][Cl:8])[CH2:9]Cl>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH2:7][Cl:8])[cH:9][o:10]1 | CCCC(N)=O.O=C(CCl)CCl | CCCc1nc(CCl)co1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | ab1ba96e48a7051990ce9c668ad0397fa94fe4b34eede3db2207f921e4585efd | 5a724a9223d53cbf2bb1ed354a2db350dd6d10aa40058c7a1ca373081e191f17 | c1cocn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3]-[Cl;D1;H0:4].[C:5]-[C:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[O;H0;D1;+0:9]>>[C:5]-[C:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:2](-[C:3]-[Cl;D1;H0:4]):[cH;D2;+0:1]:[o;H0;D2;+0:9]:1 | null | [] | 130 | CELSIUS | null | null | A mixture of butyramide (19.88 g) and 1.3-dichloroacetone (24.14 g) was heated at 130° C. for 1.5 hours. After cooling, the mixture was diluted with water, neutralized with aqueous sodium bicarbonate solution and extracted with ethyl ether. The extract was washed with water, dried (MgSO4) and concentrated. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amide | null | null | c1cocn1 | c1cocn1 | HCl | O | 130 | null | CCCC(N)=O.O=C(CCl)CCl>O>CCCc1nc(CCl)co1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e63f4e4c221e4ca7857dee83451d2403 | CCOC(=O)CC(=O)CCl.NC(=O)c1ccccc1>>CCOC(=O)Cc1coc(-c2ccccc2)n1 | C(C1=CC=CC=C1)(=O)N.ClCC(CC(=O)OCC)=O.C([O-])(O)=O.[Na+]>>C1(=CC=CC=C1)C=1OC=C(N1)CC(=O)OCC | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8]Cl.[O:9]=[C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][o:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]1 | CCOC(=O)CC(=O)CCl.NC(=O)c1ccccc1 | CCOC(=O)Cc1coc(-c2ccccc2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ab1ba96e48a7051990ce9c668ad0397fa94fe4b34eede3db2207f921e4585efd | 5a724a9223d53cbf2bb1ed354a2db350dd6d10aa40058c7a1ca373081e191f17 | c1ccc(-c2ncco2)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[NH2;D1;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[o;H0;D2;+0:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[n;H... | 38 | [{"value": 28.0, "product": "C1(=CC=CC=C1)C=1OC=C(N1)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.0, "product": "C1(=CC=CC=C1)C=1OC=C(N1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amide | null | null | c1cocn1 | c1cocn1.c1ccccc1 | HCl | null | 120 | null | CCOC(=O)CC(=O)CCl.NC(=O)c1ccccc1>>CCOC(=O)Cc1coc(-c2ccccc2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d744f03ba5db41d1bd7902f811b93a8d | CCOC(=O)CC(=O)CCl.NC(=S)C1CCCCC1>>CCOC(=O)Cc1csc(C2CCCCC2)n1 | C1(CCCCC1)C(N)=S.ClCC(CC(=O)OCC)=O>>C1(CCCCC1)C=1SC=C(N1)CC(=O)OCC | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8]Cl.[S:9]=[C:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][s:9][c:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[n:17]1 | CCOC(=O)CC(=O)CCl.NC(=S)C1CCCCC1 | CCOC(=O)Cc1csc(C2CCCCC2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1csc(C2CCCCC2)n1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[C:8]-[C:9](-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[S;H0;D1;+0:12])-[C:13]>>[C:8]-[C:9](-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:2](-[C:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]):[cH;D2;+0:1]:[s;H0;D2;+0:12]:1)-[C:13] | 71.3 | [{"value": 70.9, "product": "C1(CCCCC1)C=1SC=C(N1)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "C1(CCCCC1)C=1SC=C(N1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of cyclohexanethiocarboxamide (5.0 g), ethyl 4-chloroacetoacetate (5.74 g), ethanol (50 ml) was heated under reflux for 1 hour. After dilution with water, mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water, dried (MgSO4), and concentrated. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1.C1CCCCC1 | HCl | C(C)O | null | null | CCOC(=O)CC(=O)CCl.NC(=S)C1CCCCC1>C(C)O>CCOC(=O)Cc1csc(C2CCCCC2)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-55ea6960f61b4354bc71a258ea910ffe | COC(=O)Cc1nc(-c2ccccc2)oc1C>>Cc1oc(-c2ccccc2)nc1CCO | O.CC1=C(N=C(O1)C1=CC=CC=C1)CC(=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)(=O)OCC>>CC1=C(N=C(O1)C1=CC=CC=C1)CCO | CO[C:14]([CH2:13][c:12]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1)=[O:15]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][OH:15] | COC(=O)Cc1nc(-c2ccccc2)oc1C | Cc1oc(-c2ccccc2)nc1CCO | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ncco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4](:[#7;a:5]):[c:6]:[#8;a:7]>>[#7;a:5]:[c:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:6]:[#8;a:7] | 96.5 | [{"value": 96.2, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 5-methyl-2-phenyl-4-oxazoleacetate (54 g) in dry ethyl ether (150 ml) was added dropwise to a stirred, ice-cooled suspension of lithium aluminum hydride (8.8 g) in dry ethyl ether (700 ml) during 1.5 hours. Ethyl acetate (20 ml) was added dropwise thereto with ice-cooling and then water (50 ml) was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cocn1.c1ccccc1 | Other | C(C)OCC | null | null | COC(=O)Cc1nc(-c2ccccc2)oc1C>C(C)OCC>Cc1oc(-c2ccccc2)nc1CCO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2feeb981fa26423a88ce70051e08a909 | Cc1nc(CCO)c(C)o1.O=[N+]([O-])c1ccc(F)cc1>>Cc1nc(CCOc2ccc([N+](=O)[O-])cc2)c(C)o1 | O.CC=1OC(=C(N1)CCO)C.FC1=CC=C(C=C1)[N+](=O)[O-].[H-].[Na+]>>CC=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C | [CH3:1][c:2]1[n:3][c:4]([CH2:5][CH2:6][OH:7])[c:17]([CH3:18])[o:19]1.F[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[n:3][c:4]([CH2:5][CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[c:17]([CH3:18])[o:19]1 | Cc1nc(CCO)c(C)o1.O=[N+]([O-])c1ccc(F)cc1 | Cc1nc(CCOc2ccc([N+](=O)[O-])cc2)c(C)o1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCc2cocn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 87.1 | [{"value": 87.0, "product": "CC=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "CC=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-(2,5-Dimethyl-4-oxazolyl)ethanol (17.0 g) and 4-fluoronitrobenzene (17.0 g) were dissolved in N,N-dimethylformamide (150 ml), and 60% sodium hydride in oil (6.0 g) was added dropwise to the solution under vigorous stirring. After stirring at room temperature for 1 hour, the reaction mixture was poured into water (1 l... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1cocn1.c1ccccc1 | HF | CN(C=O)C | null | 1 | Cc1nc(CCO)c(C)o1.O=[N+]([O-])c1ccc(F)cc1>CN(C=O)C>Cc1nc(CCOc2ccc([N+](=O)[O-])cc2)c(C)o1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fa6b00b25d154a97988b043a2abfac3a | BrBr.CC(=O)c1nc(-c2ccccc2)oc1C>>Cc1oc(-c2ccccc2)nc1C(=O)CBr | C(C)(=O)C=1N=C(OC1C)C1=CC=CC=C1.BrBr.C([O-])(O)=O.[Na+]>>BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1 | Br[Br:16].[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH3:15]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH2:15][Br:16] | BrBr.CC(=O)c1nc(-c2ccccc2)oc1C | Cc1oc(-c2ccccc2)nc1C(=O)CBr | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc(-c2ncco2)cc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[c:3](-[C:4](-[CH3;D1;+0:5])=[O;D1;H0:6]):[c:7]:[#8;a:8]>>[#7;a:2]:[c:3](-[C:4](=[O;D1;H0:6])-[CH2;D2;+0:5]-[Br;H0;D1;+0:1]):[c:7]:[#8;a:8] | 86.8 | [{"value": 86.3, "product": "BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | To a stirred solution of 4-acetyl-5-methyl-2-phenyloxazole (12.0 g) in chloroform (100 ml) was added at 50° C. a solution of bromine (10.5 g) in chloroform (10 ml). The mixture was further heated at 55° C. for 30 minutes and poured into saturated aqueous sodium bicarbonate solution (500 ml). The chloroform layer was se... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1cocn1.c1ccccc1 | HBr | C(Cl)(Cl)Cl | 55 | null | BrBr.CC(=O)c1nc(-c2ccccc2)oc1C>C(Cl)(Cl)Cl>Cc1oc(-c2ccccc2)nc1C(=O)CBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-edc4b3f2acff4e9497253a46d41f09ff | Br.C=CC(=O)OC.Cc1oc(-c2ccccc2)nc1C(O)COc1ccc(N)cc1>>COC(=O)C(Br)Cc1ccc(OCC(O)c2nc(-c3ccccc3)oc2C)cc1 | N(=O)[O-].[Na+].OC(COC1=CC=C(N)C=C1)C=1N=C(OC1C)C1=CC=CC=C1.Br.C(C=C)(=O)OC>>BrC(C(=O)OC)CC1=CC=C(C=C1)OCC(C=1N=C(OC1C)C1=CC=CC=C1)O | [BrH:6].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:7].N[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([OH:15])[c:16]2[n:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[o:25][c:26]2[CH3:27])[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([Br:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([OH:15])[c:16]2[n... | Br.C=CC(=O)OC.Cc1oc(-c2ccccc2)nc1C(O)COc1ccc(N)cc1 | COC(=O)C(Br)Cc1ccc(OCC(O)c2nc(-c3ccccc3)oc2C)cc1 | null | null | CO.O.CC(=O)C | C-C Coupling | OtherReaction | fa6d89a11df1d51d550d71070755be72f9bdb83552839bba404de654836fff02 | 50a9d170f44f15d35e3a7d8ced3592a8de4e6e68b8b82ffc0f15a38f0aee2772 | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[BrH;D0;+0:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[Br;H0;D1;+0:6]-[CH;D3;+0:11](-[CH2;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7] | 98.5 | [{"value": 98.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 15 | MINUTE | 4-[2-Hydroxy-2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]aniline (18.5 g) was dissolved in methanol (50 ml)-acetone (150 ml), and 47% aqueous HBr (41.0 g) was added to the solution. Then, a solution of NaNO2 (4.5 g) in water (10 ml) was added dropwise to the mixture at a temperature of not higher than 5° C. The whole was st... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Secondary halide.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cocn1.c1ccccc1 | Other | CO.O.CC(=O)C | 5 | 0.25 | Br.C=CC(=O)OC.Cc1oc(-c2ccccc2)nc1C(O)COc1ccc(N)cc1>CO.O.CC(=O)C>COC(=O)C(Br)Cc1ccc(OCC(O)c2nc(-c3ccccc3)oc2C)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4df1147214394778b695246102bc2d3e | Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc([N+](=O)[O-])cc1>>Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc(N)cc1 | ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C.C(C)(=O)O>>ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOC1=CC=C(N)C=C1)C | O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]([O:16][CH2:15][CH2:14][c:13]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[Cl:11])[n:12]2)[cH:23][cH:22]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[n:12][c:13]1[CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:22][cH... | Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc([N+](=O)[O-])cc1 | Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc(N)cc1 | null | null | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.6 | [{"value": 97.6, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | Reduced iron (10.6 g) was added portionwise mixture of 4-{2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene (22.9 g), acetic acid (150 ml) and water (50 ml) at 70° C. After stirring at 80° C. for 2 hours, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cocn1.c1ccccc1.c1ccccc1 | Other | O | 80 | 2 | Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc([N+](=O)[O-])cc1>O>Cc1oc(-c2ccccc2Cl)nc1CCOc1ccc(N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a0c3c5e052b64fc395583abf06cf5d36 | Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCOc1ccc([N+](=O)[O-])cc1>>Cc1oc(-c2ccc(O)cc2)nc1CCOc1ccc(N)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C>>OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(N)C=C1)C | O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]([O:16][CH2:15][CH2:14][c:13]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][c:8]([O:9]Cc4ccccc4)[cH:10][cH:11]3)[n:12]2)[cH:23][cH:22]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]2)[n:12][c:13]1[CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([NH2:21... | Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCOc1ccc([N+](=O)[O-])cc1 | Cc1oc(-c2ccc(O)cc2)nc1CCOc1ccc(N)cc1 | null | [Pd] | CO | Reduction | OtherReaction | 9170d0c986a4b23b0014d38a47c7fc9d4706242a2267d3f5bc0d6f66b2394435 | f6fedbf3f30216a140de5c3218dc044b3cb8996afe756cfb2650e812e7cf56ad | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:7]-[c:6](:[c:5]):[c:8] | 80.9 | [{"value": 78.2, "product": "OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(N)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene (10.65 g) in methanol (200 ml) was subjected to a catalytic hydrogenation over 10% Pd-C (50% wet, 4.0 g). After the catalyst was filtered off, the filtrate was concentrated to give 4-{2-[2-(4-hydroxyphenyl)-5-methyl-4-oxazolyl]ethoxy}anil... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group | Aromatic alcohol.Primary amine | c1ccccc1 | null | c1cocn1.c1ccccc1.c1ccccc1 | HO- | [Pd].CO | null | null | Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCOc1ccc([N+](=O)[O-])cc1>[Pd].CO>Cc1oc(-c2ccc(O)cc2)nc1CCOc1ccc(N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-760057bc35304f8ba2f1de1ab245109e | Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2\SC(=O)NC2=O)cc1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2/SC(=O)NC2=O)cc1 | CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\C=C/2\C(NC(S2)=O)=O)C=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\C=C\2/C(NC(S2)=O)=O)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19](/[CH:20]=[C:21]2\[S:22][C:23](=[O:24])[NH:25][C:26]2=[O:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH... | Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2\SC(=O)NC2=O)cc1 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2/SC(=O)NC2=O)cc1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1NC(=O)/C(=C\c2ccc(OCCc3coc(-c4ccccc4)n3)cc2)S1 | null | 20 | [{"value": 20.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\\C=C\\2/C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\\C=C\\2/C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (Z)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (200 mg) in acetonitrile (750 ml), in a quartz tube under a stream of nitrogen, was irradiated by a 300 W high-pressure mercury lamp for 3 hours. The solvent was distilled off, and the resulting crystals were chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cocn1.c1ccccc1.c1ccccc1.C1CSCN1 | null | C(C)#N | null | null | Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2\SC(=O)NC2=O)cc1>C(C)#N>Cc1oc(-c2ccccc2)nc1CCOc1ccc(/C=C2/SC(=O)NC2=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ef7d7d2ba1b7436d9bffae2309e59136 | Cc1oc(-c2ccccc2)nc1CCO.N#Cc1ccc(F)cc1>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1 | CC1=C(N=C(O1)C1=CC=CC=C1)CCO.FC1=CC=C(C#N)C=C1.[H-].[Na+].C(C)(=O)O>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C#N)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][OH:15].F[c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1 | Cc1oc(-c2ccccc2)nc1CCO.N#Cc1ccc(F)cc1 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 77.9 | [{"value": 77.5, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol (6.0 g) and 4-fluorobenzonitrile (5.4 g) were dissolved in tetrahydrofurane (70 ml ), and 60% sodium hydride in oil (1.4 g) was added to the solution under ice-cooling with vigorous stirring. The reaction mixture was stirred at room temperature for 18 hours and poured into ice-co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1cocn1.c1ccccc1.c1ccccc1 | HF | O1CCCC1 | null | 18 | Cc1oc(-c2ccccc2)nc1CCO.N#Cc1ccc(F)cc1>O1CCCC1>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-02ae9b80d0de45e4bc6c27c8e8753812 | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1.O=CO>>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1 | CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C#N)C=C1.C(=O)O>>CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=O)C=C1 | N#[C:20][c:19]1[cH:18][cH:17][c:16]([O:15][CH2:14][CH2:13][c:12]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[n:11]2)[cH:23][cH:22]1.OC=[O:21]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([CH:20]=[O:21])[cH:22][cH:23... | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1.O=CO | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1 | null | [Ni] | null | Miscellaneous | OtherReaction | dd48b99193436fbe7b6cc0a1621b6770f60b9def12aae5a3798f5538fe569c97 | 0897ec40f28c09937bcdbb0203ea69433f1817427a4cf5fff67c67ea215ea2af | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C=[O;H0;D1;+0:5]>>[O;H0;D1;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 78.5 | [{"value": 78.5, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile (6.5 g), Raney nickel alloy (6.5 g) and 70% formic acid (100 ml) was heated under reflux for 2 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Aldehyde | null | null | c1cocn1.c1ccccc1.c1ccccc1 | HO- | [Ni] | null | null | Cc1oc(-c2ccccc2)nc1CCOc1ccc(C#N)cc1.O=CO>[Ni]>Cc1oc(-c2ccccc2)nc1CCOc1ccc(C=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-87fabac48c9340eaa4907ce30b7c5b7e | Cc1oc(-c2ccccc2)nc1CCl.O=Cc1ccc(O)cc1>>Cc1oc(-c2ccccc2)nc1COc1ccc(C=O)cc1 | ClCC=1N=C(OC1C)C1=CC=CC=C1.OC1=CC=C(C=O)C=C1.C([O-])([O-])=O.[K+].[K+]>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=O)C=C1 | Cl[CH2:13][c:12]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1.[OH:14][c:15]1[cH:16][cH:17][c:18]([CH:19]=[O:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([CH:19]=[O:20])[cH:21][cH:22]1 | Cc1oc(-c2ccccc2)nc1CCl.O=Cc1ccc(O)cc1 | Cc1oc(-c2ccccc2)nc1COc1ccc(C=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2coc(-c3ccccc3)n2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 100.1 | [{"value": 99.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (3.12 g), 4-hydroxybenzaldehyde (1.83 g), potassium carbonate (2.28 g) and dimethylformaide (40 ml) was stirred under heating at 110° C. for 1 hour. The reaction solution was poured into ice-cold water, and the crystals which separated out were collected by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cocn1.c1ccccc1.c1ccccc1 | HCl | null | 110 | null | Cc1oc(-c2ccccc2)nc1CCl.O=Cc1ccc(O)cc1>>Cc1oc(-c2ccccc2)nc1COc1ccc(C=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8196817410144b5adfdc7884be60b1f | Cc1oc(-c2ccccc2)nc1C(=O)CBr.N#Cc1ccc(O)cc1>>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1 | BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1.C(#N)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O | Br[CH2:15][C:13]([c:12]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1)=[O:14].[OH:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23][cH:24]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[N:22])[... | Cc1oc(-c2ccccc2)nc1C(=O)CBr.N#Cc1ccc(O)cc1 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1 | null | null | C(C)C(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1coc(-c2ccccc2)n1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#8;a:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:6]:[#8;a:7] | 79.2 | [{"value": 78.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-bromoacetyl-5-methyl-2-phenyloxazole (7.0 g), p-cyanophenol (3.0 g), potassium carbonate (6.9 g) and methyl ethyl ketone (100 ml) was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and water (100 ml)-ether (100 ml) was added to the residue. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1cocn1.c1ccccc1.c1ccccc1 | HBr | C(C)C(=O)C | null | null | Cc1oc(-c2ccccc2)nc1C(=O)CBr.N#Cc1ccc(O)cc1>C(C)C(=O)C>Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f9a930e708d48b38d38a3a790caddee | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1>>Cc1cccc(-c2nc(C(O)COc3ccc(C#N)cc3)co2)c1 | O.[BH4-].[Na+].CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O.CN(C=O)C>>OC(COC1=CC=C(C#N)C=C1)C=1N=C(OC1)C1=CC=CC(=C1)C | [CH3:1][c:22]1[c:9]([C:10](=[O:11])[CH2:12][O:13][c:14]2[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]2)[n:8][c:7](-[c:6]2[cH:5][cH:4][cH:3][cH:2][cH:24]2)[o:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]([CH:10]([OH:11])[CH2:12][O:13][c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]3)[cH:22][o:... | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1 | Cc1cccc(-c2nc(C(O)COc3ccc(C#N)cc3)co2)c1 | null | null | CO | Miscellaneous | OtherReaction | ec9ef35050ba6985dceafd1b0dd2e08e66adecacf64ee5cef48bcba0b8c2eb13 | 65c0f1e474134afe581396038c9eec1081d3cf2c66a067b33a419661521d5253 | c1ccc(OCCc2coc(-c3ccccc3)n2)cc1 | [#8:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7](-[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]):[#8;a:13]:[c;H0;D3;+0:14]:1-[CH3;D1;+0:15]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7](-[c:8]:[c:9]:[c;H0;D3;+0:10](-[CH3;D1;+0:15]):[c:11]:[c:12]):[#8;a:13]:[cH;D2;+0:14]:1 | 92.7 | [{"value": 92.7, "product": "OC(COC1=CC=C(C#N)C=C1)C=1N=C(OC1)C1=CC=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium borohydride (0.654 mg) was added to a suspension of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzonitrile (5.5 g) in methanol (100 ml)-N,N-dimethylformamide (50 ml), followed by stirring at room temperature for 1 hour. The reaction solution was poured into water and the crystals which separated out were c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1cocn1.c1ccccc1 | c1ccccc1.c1cocn1 | c1ccccc1.c1cocn1.c1ccccc1 | null | CO | null | 1 | Cc1oc(-c2ccccc2)nc1C(=O)COc1ccc(C#N)cc1>CO>Cc1cccc(-c2nc(C(O)COc3ccc(C#N)cc3)co2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-af833aac68e84efd9b9b7fe09d4bd9be | CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.O=C(Cl)Cl>>CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(N)=O)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O.N1=CC=CC=C1.C(=O)(Cl)Cl>>C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[S:5])[CH2:6][CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]([c:20]1[OH:21])[C:25](=[O:26])[O:27][CH2:28]2.Cl[C:22](Cl)=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[S:5])[CH2:6][CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:16]([C... | CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.O=C(Cl)Cl | CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(N)=O)C(=O)OC2 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 7a500c53e0c90ddb616b1d9844a25d18752778458f7cf9b6b4d76c7f92fd6ed9 | 1c930fd1a8ef596a25a9e8b02e0d655be711516e36782a4da179eb27706d6367 | O=C1OCc2ccccc21 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[N;D1;H2:10])=[O;D1;H0:2]):[c:9] | null | [] | 25 | CELSIUS | 8 | HOUR | To a solution of 500 mgs of ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate in 10 ml of benzene cooled in an ice bath was added 0.1 ml of pyridine and 6 ml of a 12.5% solution of phosgene in benzene. The solution was stirred at 25° C. overnight, the precipitate fi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic alcohol | Carbamic ester | null | null | c1ccc2c(c1)COC2 | Other | C1=CC=CC=C1 | 25 | 8 | CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.O=C(Cl)Cl>C1=CC=CC=C1>CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(N)=O)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-06f8abb82a5a4632b3979237b8ea745a | CC(=O)Cl.CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | Cl.C(C)(=O)Cl.OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O.N1=CC=CC=C1>>C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O | Cl[C:22]([CH3:23])=[O:24].[CH3:1][CH2:2][O:3][C:4](=[S:5])[CH2:6][CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]([c:20]1[OH:21])[C:25](=[O:26])[O:27][CH2:28]2>>[CH3:1][CH2:2][O:3][C:4](=[S:5])[CH2:6][CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:... | CC(=O)Cl.CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | null | null | C(C)#N | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C1OCc2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:10] | null | [] | null | null | 2 | HOUR | To a solution of 1.6 g of ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate in 120 ml of acetonitrile at 0° C. was added 0.74 ml of pyridine followed by 1.0 ml of acetyl chloride. After stirring for 2 hours the reaction mixture was poured into dilute hydrochloric ac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccc2c(c1)COC2 | HCl | C(C)#N | null | 2 | CC(=O)Cl.CCOC(=S)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>C(C)#N>CCOC(=S)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-12d70a69c7f449f5ae68d848a00b2a04 | CCC(C)(C)N(CC(C)O)CC(C)O>>CC(O)CN(CC(C)O)C(C)(C)C | C(C)(C)(CC)N(CC(C)O)CC(C)O.CN(CC(C)O)CC(C)O.C(C)N(CCO)CCO.C1(CCCCC1)N(CCO)CCO.C(C)C(CO)(CO)CN(C)C>>C(C)(C)(C)N(CC(C)O)CC(C)O | C[CH2:12][C:10]([N:5]([CH2:4][CH:2]([CH3:1])[OH:3])[CH2:6][CH:7]([CH3:8])[OH:9])([CH3:11])[CH3:13]>>[CH3:1][CH:2]([OH:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[OH:9])[C:10]([CH3:11])([CH3:12])[CH3:13] | CCC(C)(C)N(CC(C)O)CC(C)O | CC(O)CN(CC(C)O)C(C)(C)C | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | C-[CH2;D2;+0:1]-[C:2](-[#7:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[#7:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH3;D1;+0:1] | null | [] | null | null | null | null | 4-methyl-4-azaheptane-2,6-diol; 3-ethyl-3-azapentane-1,5-diol; 2-ethyl-2-dimethylamino methyl-propane-1,3-diol; 4-tertiary-pentyl-4-azaheptane-2,6-diol; 3-cyclohexyl-3-azapentane-1,5-diol, 3-tert-butylmethyl-3-azapentandiol-1,5, 3-tert.-pentyl-3-aza-pentandiol-1,
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | null | null | null | CCC(C)(C)N(CC(C)O)CC(C)O>>CC(O)CN(CC(C)O)C(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d3765d8579c44d02900e70b0d80879d8 | NCC(=O)O>>N[C@@H](CO)C(=O)O | N[C@@H](C)C(=O)O.NCC(=O)O>>N[C@@H](C)C(=O)O.N[C@@H](CO)C(=O)O | [NH2:7][CH2:8][C:9]([OH:10])=[O:12]>>[NH2:7][C@@H:8]([CH2:9][OH:10])[C:11](=[O:12])[OH:13] | NCC(=O)O | N[C@@H](CO)C(=O)O | null | null | null | Miscellaneous | OtherReaction | d54900f1356837c174b3eeb6cbc2b621e135319d6041351be853c1167cd23743 | 1549656c215892ebd462c7613d543b17758149df09075464e8621349b5d875a1 | null | [N;D1;H2:1]-[CH2;D2;+0:2]-[C;H0;D3;+0:3](-[O;D1;H1:4])=[O;H0;D1;+0:5]>>[N;D1;H2:1]-[C@@H;D3;+0:2](-[CH2;D2;+0:3]-[O;D1;H1:4])-[C:6](-[O;D1;H1:7])=[O;H0;D1;+0:5] | null | [] | null | null | null | null | The formation of Z--Ala--SerOH is obtained by the same process as that described in Example 1.a, but using 1.1 mmol of lyophilised hydrated serine in place of cysteine and 1 mmol of alanine protected by Z and activated in place of glycine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Primary alcohol | null | null | null | Other | null | null | null | NCC(=O)O>>N[C@@H](CO)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf52adeae66d476a983fab8d71fb9ecb | NCC(=O)O.N[C@@H](Cc1ccccc1)C(=O)O>>N[C@@H](CO)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O | N[C@@H](CC1=CC=CC=C1)C(=O)O.NCC(=O)O>>N[C@@H](CC1=CC=CC=C1)C(=O)O.N[C@@H](CO)C(=O)O | [NH2:1][CH2:2][C:5](=[O:4])[OH:7].[cH:3]1[cH:14][cH:13][cH:12][c:11]([CH2:10][C@H:9]([NH2:8])[C:17](=[O:18])[OH:19])[cH:16]1>>[NH2:1][C@@H:2]([CH2:3][OH:4])[C:5](=[O:6])[OH:7].[NH2:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[OH:19] | NCC(=O)O.N[C@@H](Cc1ccccc1)C(=O)O | N[C@@H](CO)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O | null | null | null | Functional Group Addition | OtherReaction | 5a66d4356692e54cf9fcd759ba1d12014645afb8472fb23f4af88e0490fc2174 | 8bef335d6c9b133d83ab31f379ef16b0942b457354d7c276c44766310ad7bc65 | c1ccccc1 | [C:1]-[c:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.[N;D1;H2:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10](-[O;D1;H1:11])=[O;H0;D1;+0:12]>>[C:1]-[c:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[c:13]:[cH;D2;+0:7]:1.[N;D1;H2:8]-[C@@H;D3;+0:9](-[CH2;D2;+0:6]-[OH;D1;+0:12])-[C;H0;D3;+0:10](=[O;D1;H0:14])-[O;D1;H1:11] | null | [] | null | null | null | null | The formation of t-Boc--Phe--SerOH is obtained by the same process, but using 1.1 mmol of lyophilised hydrated serine in place of cysteine and 1 mmol of phenylalanine protected by t-Box and activated in place of glycine.
Conditions: See reaction.notes.procedure_details.
Workup: The formation of t-Boc--Phe--SerOH is obt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | null | null | null | NCC(=O)O.N[C@@H](Cc1ccccc1)C(=O)O>>N[C@@H](CO)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a1e36e97f3014b5da163378c10482c4e | CO[Si](CCl)(OC)OC.N>>CO[Si](CNC[Si](OC)(OC)OC)(OC)OC | ClC[Si](OC)(OC)OC.N>>CO[Si](OC)(OC)CNC[Si](OC)(OC)OC | Cl[CH2:4][Si:3]([O:2][CH3:1])([O:8][CH3:9])[O:10][CH3:6].[NH3:5]>>[CH3:1][O:2][Si:3]([CH2:4][NH:5][CH2:6][Si:7]([O:8][CH3:9])([O:10][CH3:11])[O:12][CH3:13])([O:14][CH3:15])[O:16][CH3:17] | CO[Si](CCl)(OC)OC.N | CO[Si](CNC[Si](OC)(OC)OC)(OC)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1335a9c1e2702a43d3ccb5f36bfc0b3138ddbb4a919a4c95f579ac993d7757c7 | 373af52b4c18c2e5a54f2808d22ea3932e713b2d052f1f79fd95307522b6ab74 | null | Cl-[CH2;D2;+0:1]-[Si;H0;D4;+0:2](-[#8:3]-[C;D1;H3:4])(-[O;H0;D2;+0:5]-[CH3;D1;+0:6])-[O;H0;D2;+0:7]-[C;D1;H3:8].[NH3;D0;+0:9]>>[#8:10]-[#14:11](-[CH2;D2;+0:6]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[Si;H0;D4;+0:2](-[#8:12]-[C;D1;H3:13])(-[#8:14]-[C;D1;H3:15])-[#8:3]-[C;D1;H3:4])(-[O;H0;D2;+0:5]-[C;D1;H3:16])-[O;H0;D2;+0:7]-[C;D1;H... | null | [] | 100 | CELSIUS | null | null | Chloromethyltrimethoxysilane (50.0 g., 0.29 mole) and ammonia (98.6 g., 5.80 mole) were charged to a 300 ml. stainless steel pressure vessel. The mixture was heated to 100° C. at 800 psi pressure for 8 hours and then cooled. The mixture was filtered. The crude product was distilled at 60° C. and 0.2 mm Hg pressure to p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Silyl protective group | Secondary amine.Silyl protective group.Silyl protective group | null | null | null | null | null | 100 | null | CO[Si](CCl)(OC)OC.N>>CO[Si](CNC[Si](OC)(OC)OC)(OC)OC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8f9ba23024a24c68b03865b18a945605 | COC(=O)c1cc(N)cc(C(=O)OC)c1.O=C(O)Cc1ccccc1O>>COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1 | [OH-].COC(=O)C1=CC(=CC(=C1)N)C(=O)OC.N(=O)[O-].[Na+].OC1=C(C=CC=C1)CC(=O)O>>COC(=O)C=1C=C(C=C(C1)C(=O)OC)N=NC=1C=CC(=C(C1)CC(=O)O)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27]1.[cH:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([CH2:16][C:17](=[O:18])[OH:19])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]=[N:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([CH2:16][C:17](=[O:18])[OH:19])[cH... | COC(=O)c1cc(N)cc(C(=O)OC)c1.O=C(O)Cc1ccccc1O | COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1 | null | null | C(C)(=O)O.[OH-].[Na+].Cl.O | Functional Group Addition | OtherReaction | 4dfa1e0075917e3f76a2c771d85af2eb7328e8c1dacc2fef053ab9d7871727bb | 369e32a405523c63be3b198dc14b1fa8567bb17806d598f8dc85ecca177f9307 | c1ccc(N=Nc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[c:5]:[c:6]:[c;H0;D3;+0:7](-[#7:10]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8]:[c:9] | null | [] | 80 | CELSIUS | null | null | 20.9 g of dimethyl-5-amino-benzene-1,3-dicarboxylate was dissolved in 20 ml of concentrated hydrochloric acid in 200 ml of ice water. The solution was diazotized with 7 g of sodium nitrite dissolved in 30 ml of water. 30.4 g of 2-hydroxy-phenylacetic acid was dissolved in 200 ml of water and 24 g of sodium hydroxide. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O.[OH-].[Na+].Cl.O | 80 | null | COC(=O)c1cc(N)cc(C(=O)OC)c1.O=C(O)Cc1ccccc1O>C(C)(=O)O.[OH-].[Na+].Cl.O>COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1 |
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