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-c34472859da14a81bfe0f74e60f15c43 | ord-7ae0e0d6eee14518a7fd74bd58b37184 | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CO3>>CCN1C(=O)Cc2cc3c(cc21)C(=O)CO3 | CN1C(CC=2C=C3C(=CC12)C(CO3)=O)=O.C1(=CC=CC=C1)N1C(CC=2C=C3C(=CC12)C(CO3)=O)=O.C(CC)N1C(CC=2C=C3C(=CC12)C(CO3)=O)=O.C(C)(C)N1C(CC=2C=C3C(=CC12)C(CO3)=O)=O>>C(C)N1C(CC=2C=C3C(=CC12)C(CO3)=O)=O | C[CH2:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]21)[C:13](=[O:14])[CH2:15][O:16]3>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]21)[C:13](=[O:14])[CH2:15][O:16]3 | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CO3 | CCN1C(=O)Cc2cc3c(cc21)C(=O)CO3 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2cc3c(cc2N1)C(=O)CO3 | C-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5]>>[CH3;D1;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | null | [] | null | null | null | null | Starting with the requisite 1-substituted-5-hydroxyoxindole and following the procedures of Preparation B, 5-methyl-3,6-dioxo-2,3,6,7-tetrahydro-furo[2,3-f]indole, 5-phenyl-3,6-dioxo-2,3,6,7-tetrahydro-furo[2,3-f]indole, 5-n-propyl-3,6-dioxo-2,3,6,7-tetrahydro-furo[2,3-f]indole and 5-i-propyl-3,6-dioxo-2,3,6,7-tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1c2c(cc3c1[NH]CC3)OCC2 | Other | null | null | null | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CO3>>CCN1C(=O)Cc2cc3c(cc21)C(=O)CO3 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9348e8713c0c4212ad097a63dc69aec5 | CCN1C(=O)Cc2cc(O)ccc21.O=C1OCc2ccccc21>>CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21 | C1(=O)OCC2=CC=CC=C12.[OH-].[Na+].C(C)N1C(CC2=CC(=CC=C12)O)=O.C1(=O)OCC2=CC=CC=C12.[Na]>>C(C)N1C(CC2=CC(=CC=C12)OCC1=C(C=CC=C1)C(=O)O)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([OH:10])[cH:21][cH:22][c:23]21.[CH2:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18](=[O:19])[O:20]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18](=[O:19])[OH:20])[cH:21][cH:22][c:23... | CCN1C(=O)Cc2cc(O)ccc21.O=C1OCc2ccccc21 | CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f21303708c71e0e563353cda5908cd8ac465d35d59a41fbab7d6ddbbe6349edd | 21d21cdde7da913d6c26924b0599dc44ab5b72da5d27d2ccdab271b427d7f895 | O=C1Cc2cc(OCc3ccccc3)ccc2N1 | [O;D1;H0:1]=[C:2]1-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:7]:[c:5](-[CH2;D2;+0:4]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:6] | 24 | [{"value": 24.0, "product": "C(C)N1C(CC2=CC(=CC=C12)OCC1=C(C=CC=C1)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 2.24 g. (54.3 mmoles) of sodium hydroxide in 450 ml. of methanol was added 9.63 g. (54.3 mmoles) of 1-ethyl-5-hydroxyoxindole and the resulting solution concentrated in vacuo to dryness at 65° C. The residual sodium salt was mixed with 10.7 g. (79.8 mmoles) of phthalide and the mixture heated one hour ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Carboxylic acid.Ether | c1ccc2c(c1)COC2 | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | null | CO | null | 0.333333 | CCN1C(=O)Cc2cc(O)ccc21.O=C1OCc2ccccc21>CO>CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-78eb1b01c201482c9ed2107391d60ee0 | CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21>>CCN1C(=O)Cc2cc3c(cc21)C(=O)c1ccccc1CO3 | C(C)N1C(CC2=CC(=CC=C12)OCC1=C(C=CC=C1)C(=O)O)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)N1C(CC2=CC3=C(C=C12)C(C1=C(CO3)C=CC=C1)=O)=O | O[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[CH2:21][O:22][c:9]1[cH:8][c:7]2[c:12]([cH:11][cH:10]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH2:6]2>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]21)[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[CH2:21][O:22]3 | CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21 | CCN1C(=O)Cc2cc3c(cc21)C(=O)c1ccccc1CO3 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 7935df99f57c38836f856fde526960ba32b3827ec6ff4bc125a18a621954898d | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1Cc2cc3c(cc2N1)C(=O)c1ccccc1CO3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[c:7]:[c:8]:[cH;D2;+0:9]:[c:10](-[#8:11]):[c:12]>>[#7:6]-[c:7]:[c:8]:[c;H0;D3;+0:9](:[c:10](:[c:12])-[#8:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 69 | [{"value": 69.0, "product": "C(C)N1C(CC2=CC3=C(C=C12)C(C1=C(CO3)C=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 30 | MINUTE | To a suspension of 5.0 g. (16.1 mmoles) of 1-ethyl-5-(2-carboxybenzyloxy)oxindole in 100 ml. of methylene chloride was added 3.34 g. (16.1 mmoles) of phosphorous pentachloride and the reaction mixture allowed to stir 30 minutes at 25° C. The reaction mixture was cooled to -15° C. and 8.56 g. (64.4 mmoles) of aluminum c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)COc1cc3c(cc1C2)[NH]CC3 | c1ccc2c(c1)COc1cc3c(cc1C2)[NH]CC3 | HO- | C(Cl)Cl | 25 | 0.5 | CCN1C(=O)Cc2cc(OCc3ccccc3C(=O)O)ccc21>C(Cl)Cl>CCN1C(=O)Cc2cc3c(cc21)C(=O)c1ccccc1CO3 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a50eb5ef4b044940b36cdcd5b2485d70 | CCN1C(=O)Cc2cc(C(=O)c3ccc(Cl)cc3)ccc21>>CCN1C(=O)Cc2cc(C(=O)c3ccccc3)ccc21 | C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=C(C=C1)C#N)=O)=O.C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=C(C=C1)Cl)=O)=O.C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=C(C=C1)F)=O)=O.C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=C(C=C1)C)=O)=O>>C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=CC=C1)=O)=O | Cl[c:15]1[cH:14][cH:13][c:12]([C:10]([c:9]2[cH:8][c:7]3[c:20]([cH:19][cH:18]2)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH2:6]3)=[O:11])[cH:17][cH:16]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]21 | CCN1C(=O)Cc2cc(C(=O)c3ccc(Cl)cc3)ccc21 | CCN1C(=O)Cc2cc(C(=O)c3ccccc3)ccc21 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | null | null | In a similar manner were prepared 1-ethyl-5-(4-chlorobenzoyl)oxindole, m.p. 154°-156° C.; 1-ethyl-5-(4-fluorobenzoyl)oxindole, m.p. 110°-120° C.; 1-ethyl-5-(4-methylbenzoyl)oxindole, m.p. 169°-170° C.; 1-ethyl-5-(4-cyanobenzoyl)oxindole, m.p. 163°-168° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | Other | null | null | null | CCN1C(=O)Cc2cc(C(=O)c3ccc(Cl)cc3)ccc21>>CCN1C(=O)Cc2cc(C(=O)c3ccccc3)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ee6eca94548940528bfcb2b9ba4a3f66 | CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(C)cc3)ccc21.CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(Cl)cc3)ccc21>>CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3ccccc3)cc21 | C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=C(C=C1)Cl)=O)C(=O)OC)=O.C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=C(C=C1)F)=O)C(=O)OC)=O.C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=C(C=C1)C)=O)C(=O)OC)=O>>C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=CC=C1)=O)C(=O)OCC)=O | COC(=O)C1C(=O)N([CH2:2][CH3:1])c2ccc(C(=O)c3ccc(C)cc3)cc21.C[O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[N:9]([CH2:10][CH3:11])[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21](Cl)[cH:22][cH:23]3)[cH:24][c:25]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[N:9]([CH2:10][CH3:11])[c:12]2[cH:13][cH... | CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(C)cc3)ccc21.CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(Cl)cc3)ccc21 | CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3ccccc3)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e58c1a31f7d4456098f3e815060006df4e5ab5a4e74f63a6b905c058dc512ba | f61992a73db59a96e2af6c5df578d82275140f2decb128b170ec41635c944c37 | O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 | C-O-C(=O)-C1-C(=O)-N(-[CH2;D2;+0:1]-[C;D1;H3:2])-c2:c:c:c(-C(=O)-c3:c:c:c(-C):c:c:3):c:c:2-1.C-[O;H0;D2;+0:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7](=[O;D1;H0:8])-[#7:9].Cl-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7:9]-[C:7](=[O;D1;H0:8])-[C:6]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:3]-[CH2;D2;+0:1]-[C;D1;H3:2].[c:12]:[c:11]... | null | [] | null | null | null | null | In a similar manner were prepared methyl 1-ethyl-5-(4-chlorobenzoyl)oxindole-3-carboxylate, m.p. 115°-118° C.; methyl 1-ethyl-5-(4-fluorobenzoyl)oxindole-3-carboxylate, m.p. 90°-100° C. (dec.); and methyl 1-ethyl-5-(4-methylbenzoyl)oxindole-3carboxylate, m.p. 110°-115° C.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester.Ester.Tertiary amide | Ester | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | null | null | null | CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(C)cc3)ccc21.CCN1C(=O)C(C(=O)OC)c2cc(C(=O)c3ccc(Cl)cc3)ccc21>>CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3ccccc3)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1f33ee33022f4f018069c6a43e80935c | CCOC(=O)OCC.O=C1Cc2cccc(C(=O)c3ccccc3)c2N1>>CCOC(=O)C1C(=O)Nc2c(C(=O)c3ccccc3)cccc21 | [H-].[Na+].C(C1=CC=CC=C1)(=O)C=1C=CC=C2CC(NC12)=O.C(OCC)(OCC)=O>>C(C1=CC=CC=C1)(=O)C=1C=CC=C2C(C(NC12)=O)C(=O)OCC | CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:6]1[C:7](=[O:8])[NH:9][c:10]2[c:11]([C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21][cH:22][c:23]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[NH:9][c:10]2[c:11]([C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21][cH:22][... | CCOC(=O)OCC.O=C1Cc2cccc(C(=O)c3ccccc3)c2N1 | CCOC(=O)C1C(=O)Nc2c(C(=O)c3ccccc3)cccc21 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 721d55f19cb5b62629e77e19cfc72834655f439ba3d32741f1f4c0950d8a1673 | 372f84de287e46e8e402e2fc0f416c45846439cb3eb957465fe2464b708bdd7f | O=C1Cc2cccc(C(=O)c3ccccc3)c2N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:11]1-[C:6](=[O;D1;H0:5])-[#7:7]-[c:8]:[c:9]-1:[c:10] | null | [] | null | null | 10 | MINUTE | To a slurry of 365 mg. of sodium hydride in 8 ml. of dimethylformamide at 0° C. was gradually added 1.0 g. (4.22 mmoles) of 7-benzoyloxindole, and the mixture allowed to stir for 10 minutes in an ice bath. Diethyl carbonate (1.53 g., 12.7 mmoles) was added and the reaction mixture allowed to stir at ice bath temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester | Ester | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | CN(C=O)C | null | 0.166667 | CCOC(=O)OCC.O=C1Cc2cccc(C(=O)c3ccccc3)c2N1>CN(C=O)C>CCOC(=O)C1C(=O)Nc2c(C(=O)c3ccccc3)cccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a6f8d127e254415abb12a1c578177af2 | COS(=O)(=O)OC.O=C(c1ccccc1)c1cccc2cc[nH]c12>>Cn1ccc2cccc(C(=O)c3ccccc3)c21 | C(C1=CC=CC=C1)(=O)C=1C=CC=C2C=CNC12.S(=O)(=O)(OC)OC.[OH-].[K+]>>CN1C=CC2=CC=CC(=C12)C(C1=CC=CC=C1)=O | COS(=O)(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]12 | COS(=O)(=O)OC.O=C(c1ccccc1)c1cccc2cc[nH]c12 | Cn1ccc2cccc(C(=O)c3ccccc3)c21 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-methylation | c2bda2fbb06213c29acc2045d067c49348fae7bc571364c7a1fb308b93abd461 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C(c1ccccc1)c1cccc2cc[nH]c12 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]:[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c:5]:1:[c:4]-[C:3]=[O;D1;H0:2] | null | [] | null | null | null | null | A mixture of 8.57 g. (38.8 mmoles) of 7-benzoylindole, 5.38 g. (42.7 mmoles) of dimethyl sulfate and 5.12 g. of 85% potassium hydroxide in 40 ml. of acetone was heated to reflux for 75 minutes. The mixture was poured into 500 ml. of water and extracted with methylene chloride. The organic phase was separated, dried and... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1cccc2cc[nH]c12 | c1cccc2cc[nH]c12.c1ccccc1 | HO- | CC(=O)C | null | null | COS(=O)(=O)OC.O=C(c1ccccc1)c1cccc2cc[nH]c12>CC(=O)C>Cn1ccc2cccc(C(=O)c3ccccc3)c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7ded635e61e945f4a0db18fb65a9836c | Cn1ccc2cccc(C(=O)c3ccccc3)c21>>CN1C(=O)Cc2cccc(C(=O)c3ccccc3)c21 | ClN1C(CCC1=O)=O.CN1C=CC2=CC=CC(=C12)C(C1=CC=CC=C1)=O.C(Cl)Cl.ClN1C(CCC1=O)=O>>CN1C(CC2=CC=CC(=C12)C(C1=CC=CC=C1)=O)=O | [CH3:1][n:2]1[cH:3][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]12>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]21 | Cn1ccc2cccc(C(=O)c3ccccc3)c21 | CN1C(=O)Cc2cccc(C(=O)c3ccccc3)c21 | null | null | C(C)OCC.C(Cl)Cl | Functional Group Addition | OtherReaction | 9421d0de478924c3f28b678cdc3687b51449ddae349f811f724ee66a22c24e4d | 50fc2e78ddfbbfcfc29ddaa613cfaa7af8fd0f53e2947c6f55dc01337a9fe6a8 | O=C1Cc2cccc(C(=O)c3ccccc3)c2N1 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8]-[C:9]=[O;D1;H0:10]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;D1;H0:11])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-1:[c:8]-[C:9]=[O;D1;H0:10] | null | [] | 80 | CELSIUS | 90 | MINUTE | To a solution of 6.17 g. (26.25 mmoles) of 1-methyl-7-benzoylindole in 62 ml. of methylene chloride was added 3.58 g. (26.25 mmoles) of 98% N-chlorosuccinimide and the mixture allowed to stir for 90 minutes. An additional 720 mg. of N-chlorosuccinimide was added and stirring continued for 2 hours. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amide | c1cccc2cc[nH]c12 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | Other | C(C)OCC.C(Cl)Cl | 80 | 1.5 | Cn1ccc2cccc(C(=O)c3ccccc3)c21>C(C)OCC.C(Cl)Cl>CN1C(=O)Cc2cccc(C(=O)c3ccccc3)c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5604f5c0dd1d41f8a7d85e82cb744736 | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1>>CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | ClC1=C(C=C(C(=O)C2=CC=CC=C2)C=C1)[N+](=O)[O-].[Na].C(C)O.C(CC(=O)OCC)(=O)OCC>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)C(C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1[N+:26](=[O:27])[O-:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[... | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1 | CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | null | null | C(Cl)Cl | C-C Coupling | Hurtley reaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | O=C(c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[C:9](=[O;D1;H0:10])-[#8:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | To a solution of sodium ethoxide, formed by reacting 4.6 g. (0.2 mole) of sodium metal with 200 ml. of ethanol, at 0° C. was added 32 g. (0.2 mole) of diethyl malonate followed by 26.1 g. (0.1 mole) of 4-chloro-3-nitrobenzophenone. The mixture was allowed to stir at room temperature for 2 hours and was then poured into... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-abaea9c2d3f2432c870e6577b3d1cda8 | CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>>O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)C(C(=O)OCC)C(=O)OCC.Cl>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)O | CCOC(=O)[CH:4]([C:2](=[O:1])[O:3]CC)[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | null | null | O1CCOCC1 | Reduction | OtherReaction | 5ba27bafcd96d74a94be636caed9361c02821d71f9ddac00396de4e018da642b | 6d9edf77f3bf4688cdf5f5c3ccf062016b04f2e19a67399a3ca7c7e8d575cc5a | O=C(c1ccccc1)c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C)-[c:5](:[c:6]):[c:7]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | 95 | [{"value": 95.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 14 g. (36.3 mmoles) of diethyl 2-nitro-4-benzoylphenylmalonate, 300 ml. of 4N hydrochloric acid and 300 ml. of dioxane was heated to reflux for 10 hours. The reaction mixture was concentrated in vacuo and the crude product was triturated with hot methylene chloride, 9.88 g. (95% yield), m.p. 168°-170° C.
C... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCOCC1 | null | null | CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>O1CCOCC1>O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8411be17b00746ffb2f51551e59ed3fe | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)O.C(C)N(CC)CC.C(C)OC(=O)Cl.COCCOC>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC | O=C(Cl)O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[N+:21](=[O... | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | null | null | [Cl-].[Na+].O.C(C)OCC.C(C)O | Heteroatom Alkylation and Arylation | Ketonization by decarboxylation of acid halides | 206d5ec09ce643b803adbcf860b4078b98a030d6380c33850f0abd3ec7da7984 | 8388f1b1aad516c0093910cf7e0a1fba12f038b873168f29f87df716614f8df9 | O=C(c1ccccc1)c1ccccc1 | Cl-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | 94 | [{"value": 94.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 5 | MINUTE | To a solution of 13.8 g. (48.4 mmoles) of 2-nitro-4-benzoylphenylacetic acid in 150 ml. of 1,2-dimethoxyethane at 15° C. was added 5.87 g. (58.1 mmole) of triethylamine. After 5 minutes 5.75 g. (53.2 mmoles) of ethylchloroformate was added and the reaction mixture allowed to stir at 10° C. for 15 minutes. Ethanol (15 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | [Cl-].[Na+].O.C(C)OCC.C(C)O | 10 | 0.083333 | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>[Cl-].[Na+].O.C(C)OCC.C(C)O>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1e64bb0ed27a45a192c577b88d76914b | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1N | [N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC>>NC1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC | O=[N+:21]([O-])[c:20]1[c:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[NH2:21] | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1N | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 14 g. (44.7 mmoles) of ethyl 2-nitro-4-benzoylphenylacetate in 225 ml. of ethanol was added 15 g. of wet Raney nickel and the mixture heated to reflux for 1.5 hours. The mixture was filtered and the filtrate concentrated to give a residual oil which was induced to crystallize by trituration with diethy... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>[Ni].C(C)O>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f93f16fd73a54719b902bafab24a70cd | CCCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21>>CCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21 | C(C1=CC=CC=C1)(=O)C1=CC=C2CC(NC2=C1)=O.CN1C(CC2=CC=C(C=C12)C(C1=CC=CC=C1)=O)=O.C(CC)N1C(CC2=CC=C(C=C12)C(C1=CC=CC=C1)=O)=O.C(C)(C)N1C(CC2=CC=C(C=C12)C(C1=CC=CC=C1)=O)=O>>C(C)N1C(CC2=CC=C(C=C12)C(C1=CC=CC=C1)=O)=O | C[CH2:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]21>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]21 | CCCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21 | CCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2ccc(C(=O)c3ccccc3)cc2N1 | C-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5]>>[CH3;D1;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | null | [] | null | null | null | null | Starting with 6-benzoyloxindole and the appropriate dialkyl sulfate and employing the procedure of Preparation G6, 1-methyl-6-benzoyloxindole, 1-n-propyl-6-benzoyloxindole and 1-i-propyl-6-benzoyloxindole are prepared.
Conditions: See reaction.notes.procedure_details.
Workup: are prepared | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | Other | null | null | null | CCCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21>>CCN1C(=O)Cc2ccc(C(=O)c3ccccc3)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0f9f5c833f7c431ea73c55a1b90f4562 | CCN1C(=O)Cc2ccccc21.O=C(Cl)c1cccs1>>CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21 | C(C)N1C(CC2=CC=CC=C12)=O.C1(=CC=CS1)C(=O)Cl.[N+](=O)([O-])C1=CC=CC=C1.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=CS1)=O)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][cH:17][cH:18][c:19]21.Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][s:16]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][s:16]3)[cH:17][cH:18][c:19]21 | CCN1C(=O)Cc2ccccc21.O=C(Cl)c1cccs1 | CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21 | null | null | O | C-C Coupling | Friedel-Crafts acylation | 37a2530cc6d758d25de657026256944e4a168864dcf474b7a67e6159b195e35e | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C1Cc2cc(C(=O)c3cccs3)ccc2N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[#16;a:5]:[c:6])-[c;H0;D3;+0:9](:[c:8]:[c:7]):[c:10]:[c:11] | 47.7 | [{"value": 47.7, "product": "C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=CS1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a mixture of 27.3 g. (19.9 mmoles) of 2-thenoyl chloride, 30 ml. of nitrobenzene and 32.95 g. of aluminum chloride was gradually added 10 g. (62 mmoles) of 1-ethyloxindole, and the resulting reaction mixture heated at 100° C. for 75 minutes. The reaction was cooled to room temperature and poured into 2 l. of ice and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.c1ccsc1 | HCl | O | 100 | null | CCN1C(=O)Cc2ccccc21.O=C(Cl)c1cccs1>O>CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6c036ba3d462477b81ac6470a4fae0ac | CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21.CCOC(=O)OCC>>CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3cccs3)cc21 | [Na].C(OCC)(OCC)=O.Cl.C(C)N1C(CC2=CC(=CC=C12)C(C1=CC=CS1)=O)=O>>C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=CS1)=O)C(=O)OCC)=O | [CH2:6]1[C:7](=[O:8])[N:9]([CH2:10][CH3:11])[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][cH:21][s:22]3)[cH:23][c:24]21.CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[N:9]([CH2:10][CH3:11])[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][cH:2... | CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21.CCOC(=O)OCC | CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3cccs3)cc21 | null | null | [Cl-].[Na+].O.C(Cl)Cl.C(C)O | C-C Coupling | OtherReaction | daecb5cf9be12a733a144b7f36385c4c17aca1fd57533281c5fc8af929bacfa3 | 372f84de287e46e8e402e2fc0f416c45846439cb3eb957465fe2464b708bdd7f | O=C1Cc2cc(C(=O)c3cccs3)ccc2N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[#7:6]1-[c:7]:[c:8](:[c:9])-[CH2;D2;+0:10]-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[c:7]:[c:8](:[c:9])-[CH;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:11]-1=[O;D1;H0:12] | 54.4 | [{"value": 54.4, "product": "C(C)N1C(C(C2=CC(=CC=C12)C(C1=CC=CS1)=O)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To sodium ethoxide, formed by adding 2 g. of sodium metal to 58 ml. of ethanol, at 0° C. was added 7.84 g. (28.9 mmoles) of 1-ethyl-5-(2-thenoyl)oxindole followed by 10.24 g. (86.8 mmoles) of diethyl carbonate, and the reaction heated to 65° C. for 2 hours. The reaction mixture was poured into a cold mixture of 250 ml.... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester | Ester | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.c1ccsc1 | HO- | [Cl-].[Na+].O.C(Cl)Cl.C(C)O | null | null | CCN1C(=O)Cc2cc(C(=O)c3cccs3)ccc21.CCOC(=O)OCC>[Cl-].[Na+].O.C(Cl)Cl.C(C)O>CCOC(=O)C1C(=O)N(CC)c2ccc(C(=O)c3cccs3)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ed0a6be47d0f43868578a84df4a040f4 | CC(=O)c1cccc2cc[nH]c12>>CC(=O)c1cccc2c1NC(=O)C2 | C(C)(=O)C=1C=CC=C2C=CNC12.ClN1C(CCC1=O)=O>>C(C)(=O)C=1C=CC=C2CC(NC12)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[nH:10][cH:11][cH:13]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][C:11](=[O:12])[CH2:13]2 | CC(=O)c1cccc2cc[nH]c12 | CC(=O)c1cccc2c1NC(=O)C2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 136cc2105001896d6ef82a4943195e7c94fb000783a68436a71163bad1641769 | cb67d131d33f5fb619561a09ccc5b9198eb9f1fa70b65db3001f270fbc3c1385 | O=C1Cc2ccccc2N1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[nH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:1:[c:10]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:9](:[c:10])-[CH2;D2;+0:8]-[C;H0;D3;+0:7](=[O;D1;H0:11])-[NH;D2;+0:6]-1 | 65 | [{"value": 65.0, "product": "C(C)(=O)C=1C=CC=C2CC(NC12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 12.57 g. (79 mmoles) of 7-acetylindole in 187 ml. of methylene chloride was added 11.07 g. (82.9 mmoles) of N-chlorosuccinimide and the reaction allowed to stir at room temperature for 2 hours. The solvent was removed in vacuo and the residue treated with 155 ml. of acetic acid and heated to 80° C. Pho... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amide | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C(Cl)Cl | null | 2 | CC(=O)c1cccc2cc[nH]c12>C(Cl)Cl>CC(=O)c1cccc2c1NC(=O)C2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-48aae4233540416d98923fe7e4089d35 | CC(=O)Cl.CCN1C(=O)Cc2ccccc21>>CCN1C(=O)Cc2cc(C(C)=O)ccc21 | C(C)(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-].[N+](=O)([O-])C1=CC=CC=C1.C(C)N1C(CC2=CC=CC=C12)=O>>C(C)N1C(CC2=CC(=CC=C12)C(C)=O)=O | Cl[C:10]([CH3:11])=[O:12].[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][cH:13][cH:14][c:15]21>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([C:10]([CH3:11])=[O:12])[cH:13][cH:14][c:15]21 | CC(=O)Cl.CCN1C(=O)Cc2ccccc21 | CCN1C(=O)Cc2cc(C(C)=O)ccc21 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 37a2530cc6d758d25de657026256944e4a168864dcf474b7a67e6159b195e35e | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C1Cc2ccccc2N1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 57.3 | [{"value": 57.3, "product": "C(C)N1C(CC2=CC(=CC=C12)C(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 1 | HOUR | To a mixture of 29.25 g. (0.373 mole) of acetyl chloride and 65.9 g. of aluminum chloride in 60 ml. of nitrobenzene was added gradually 20.0 (0.124 mole) of 1-ethyloxindole. The reaction warmed to about 45° C. with an evolution of gas. After stirring for one hour the reaction was heated to 100° C. for one hour and allo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | null | 45 | 1 | CC(=O)Cl.CCN1C(=O)Cc2ccccc21>>CCN1C(=O)Cc2cc(C(C)=O)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2333e378c2734299a79c3437e8a673e9 | CCOC(=O)C1C(=O)Nc2ccc(C3(CC(C)(C)C)OCCO3)cc21.CCOC(=O)C1C(=O)Nc2ccc(C3(Cc4ccccc4)OCCO3)cc21>>CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21 | C(CCCC)C1(OCCO1)N1C(C(C2=CC=CC=C12)C(=O)[O-])=O.C(C)(C)C1(OCCO1)C=1C=C2C(C(NC2=CC1)=O)C(=O)OCC.C(C(C)(C)C)C1(OCCO1)C=1C=C2C(C(NC2=CC1)=O)C(=O)OCC.C(C1=CC=CC=C1)C1(OCCO1)C=1C=C2C(C(NC2=CC1)=O)C(=O)OCC>>C(C)N1C(C(C2=CC(=CC=C12)C1(OCCO1)C)C(=O)OCC)=O | CC(C)(C)[CH2:17][C:16]1([c:15]2[cH:14][cH:13][c:12]3[c:23]([cH:22]2)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[NH:9]3)[O:18][CH2:19][CH2:20][O:21]1.O=C1Nc2ccc(C3(Cc4ccccc4)OCCO3)cc2C1C(=O)O[CH2:10][CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[N:9]([CH2:10][CH3:11])[c:12]2[cH:13][cH:14][c:15]... | CCOC(=O)C1C(=O)Nc2ccc(C3(CC(C)(C)C)OCCO3)cc21.CCOC(=O)C1C(=O)Nc2ccc(C3(Cc4ccccc4)OCCO3)cc21 | CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 68ffac97ad97c1d1b125c3215850141e5bf055194a909e3fddb93754a19f9c68 | 641b3a52a3ce7cce5fa1a0bdeff3809471e5cc12821fe2535237f40a8e085b77 | O=C1Cc2cc(C3OCCO3)ccc2N1 | C-C(-C)(-C)-[CH2;D2;+0:1]-[C:2]1(-[c:3])-[#8:4]-[C:5]-[C:6]-[#8:7]-1.[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[c:12]:[c:13](:[c:14])-[NH;D2;+0:15]-[C:16]-1=[O;D1;H0:17].O=C1-N-c2:c:c:c(-C3(-C-c4:c:c:c:c:c:4)-O-C-C-O-3):c:c:2-C-1-C(=O)-O-[CH2;D2;+0:18]-[C;D1;H3:19]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[c:12]:[c:13](:[c:14])-... | null | [] | null | null | null | null | Similarly, were prepared ethyl 5-(2-n-pentyl-4,5-dihydro-1,3-dioxol-2-yl-oxindole-3-carboxylate, ethyl 5-(2-isopropyl-4,5-dihydro-1,3-dioxol-2-yl)oxindole-3-carboxylate, ethyl 5-(2-neopentyl-4,5-dihydro-1,3-dioxol-2-yl)oxindole-3-carboxylate and ethyl 5-(2-benzyl-4,5-dihydro-1,3-dioxol-2-yl)oxindole-3-carboxylate.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Secondary amide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2.c1ccccc1.C1COCO1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.C1COCO1 | HO- | null | null | null | CCOC(=O)C1C(=O)Nc2ccc(C3(CC(C)(C)C)OCCO3)cc21.CCOC(=O)C1C(=O)Nc2ccc(C3(Cc4ccccc4)OCCO3)cc21>>CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c6ed2039e2c4495fabe7eb2147326cbe | CCN1C(=O)Cc2ccccc21.O=C(Cl)C1CC1>>CCN1C(=O)Cc2cc(C(=O)C3CC3)ccc21 | C(C)N1C(CC2=CC=CC=C12)=O.C1(CC1)C(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)N1C(CC2=CC(=CC=C12)C(=O)C1CC1)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][cH:15][cH:16][c:17]21.Cl[C:10](=[O:11])[CH:12]1[CH2:13][CH2:14]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[CH:12]3[CH2:13][CH2:14]3)[cH:15][cH:16][c:17]21 | CCN1C(=O)Cc2ccccc21.O=C(Cl)C1CC1 | CCN1C(=O)Cc2cc(C(=O)C3CC3)ccc21 | null | null | C(=S)=S | C-C Coupling | Friedel-Crafts acylation | 37a2530cc6d758d25de657026256944e4a168864dcf474b7a67e6159b195e35e | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C1Cc2cc(C(=O)C3CC3)ccc2N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]1-[C:4]-[C:5]-1)-[c;H0;D3;+0:8](:[c:7]:[c:6]):[c:9]:[c:10] | null | [] | null | null | null | null | In a manner similar to Preparation J1., 10 g. (62 mmoles) of 1-ethyloxindole, 7.2 ml. (78.8 mmoles) of cyclopropylcarbonyl chloride and 51 g. (380 mmoles) of aluminum chloride in 200 ml. of carbon disulfide gave 3.75 of the desired product.
Conditions: See reaction.notes.procedure_details.
Workup: In a manner similar t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.C1CC1 | HCl | C(=S)=S | null | null | CCN1C(=O)Cc2ccccc21.O=C(Cl)C1CC1>C(=S)=S>CCN1C(=O)Cc2cc(C(=O)C3CC3)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-46717d15a606428ab609af8026fb6e88 | O=CN1CCN(O)CC1>>Cl.ON1CCNCC1 | ON1CCN(CC1)C=O.Cl>>Cl.Cl.ON1CCNCC1 | O=C[N:7]1[CH2:6][CH2:5][N:4]([OH:3])[CH2:9][CH2:8]1>>[ClH:2].[OH:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1 | O=CN1CCN(O)CC1 | Cl.ON1CCNCC1 | null | null | null | Miscellaneous | Hydrogenolysis of tertiary amines | abc455bb69403792bf9841fab59edb14ba4f0017b2457c05cb2faebc856192f3 | 5ba542a97dd3ca917dd84dc29c99ae9b05b6ca96dbd806e22774484cf1a34b59 | C1CNCCN1 | O=C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | That is, 1-formylpiperazine (IV) is reacted with ethyl acrylate to give a compound (V), and the resulting compound is treated with an oxidizing agent (e.g. hydrogen peroxide) preferably in the presence of a catalyst (e.g. sodium tungstate) to give 4-hydroxy-1-formylpiperazine (VI). The compound (VI) is hydrolyzed with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | Other | null | null | null | O=CN1CCN(O)CC1>>Cl.ON1CCNCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-01666c198ac543a5af6a980a234f5f81 | C=CC(=O)OCC.O=CN1CCNCC1>>CCOC(=O)CCN1CCN(C=O)CC1 | C(C=C)(=O)OCC.C(=O)N1CCNCC1>>C(C)OC(=O)CCN1CCN(CC1)C=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH:8]1[CH2:9][CH2:10][N:11]([CH:12]=[O:13])[CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([CH:12]=[O:13])[CH2:14][CH2:15]1 | C=CC(=O)OCC.O=CN1CCNCC1 | CCOC(=O)CCN1CCN(C=O)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 707b1f11502796eb2c382b3a49134b17cd8ecebd387395e0d95dfd094ef61441 | e6898c28c2a6b7f7f5b5322689c9c6b3b6ad3dd52268b1e45ad4c4843df05f7d | C1CNCCN1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:1]-[C:2]-[C:3]-1 | 96.6 | [{"value": 96.6, "product": "C(C)OC(=O)CCN1CCN(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | Ethyl acrylate (326 g) and chloroform (2 liters) are added to 1-formylpiperazine (320 g) and the mixture is stirred at room temperature for 3 days. The solvent is evaporated under reduced pressure to yield crude 4-ethoxycarbonylethyl-1-formylpiperazine (580 g) as an orange oil.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ester.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | null | C(Cl)(Cl)Cl | null | 72 | C=CC(=O)OCC.O=CN1CCNCC1>C(Cl)(Cl)Cl>CCOC(=O)CCN1CCN(C=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-328e456a645b482dab330921de96d6eb | CCOC(=O)CCN1CCN(C=O)CC1.OO>>O=CN1CCN(O)CC1 | C(C)OC(=O)CCN1CCN(CC1)C=O.OO.C(C)(=O)OCC>>C(=O)N1CCN(CC1)O | CCOC(=O)CC[N:6]1[CH2:5][CH2:4][N:3]([CH:2]=[O:1])[CH2:9][CH2:8]1.O[OH:7]>>[O:1]=[CH:2][N:3]1[CH2:4][CH2:5][N:6]([OH:7])[CH2:8][CH2:9]1 | CCOC(=O)CCN1CCN(C=O)CC1.OO | O=CN1CCN(O)CC1 | null | O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+] | O | Miscellaneous | OtherReaction | f61f1ead11306a3c72d27db686150a08e39436f12e7dd2146adbe290779f65e7 | aa516334e1f5e5872deacc19615eecdbb5dc25b6cc137b0def0181bdbe8e9b16 | C1CNCCN1 | C-C-O-C(=O)-C-C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[OH;D1;+0:7]>>[OH;D1;+0:7]-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | 1 | HOUR | The crude 4-ethoxycarbonylethyl-1-formylpiperazine (114 g) prepared as described above is dissolved in water (500 ml) and sodium tungstate dihydrate (7.25 g) is added to the solution. At a temperature of 30°-35° C., 31% hydrogen peroxide (82 ml) is added dropwise to the solution and the mixture is stirred for one hour.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine.Peroxide | Tertiary amine | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HO- | O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+].O | null | 1 | CCOC(=O)CCN1CCN(C=O)CC1.OO>O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+].O>O=CN1CCN(O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-25f1f144415f414cb9f09abd371778aa | O=CN1CCN(O)CC1>>Cl.ON1CCNCC1 | C(=O)N1CCN(CC1)O.Cl>>Cl.Cl.ON1CCNCC1 | O=C[N:7]1[CH2:6][CH2:5][N:4]([OH:3])[CH2:9][CH2:8]1>>[ClH:2].[OH:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1 | O=CN1CCN(O)CC1 | Cl.ON1CCNCC1 | null | null | null | Miscellaneous | Hydrogenolysis of tertiary amines | abc455bb69403792bf9841fab59edb14ba4f0017b2457c05cb2faebc856192f3 | 5ba542a97dd3ca917dd84dc29c99ae9b05b6ca96dbd806e22774484cf1a34b59 | C1CNCCN1 | O=C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 20 | MINUTE | To 1-formyl-4-hydroxypiperazine (5.0 g) is added 3N hydrochloric acid (50 ml) and the mixture is heated at 77°-87° C. with stirring for 20 minutes and water is removed from the mixture under reduced pressure to yield a pale yellow residue. After washing with ethanol, the residue is crystallized from a mixture of water ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | Other | null | null | 0.333333 | O=CN1CCN(O)CC1>>Cl.ON1CCNCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c4d9b52229434296a6515c724df8955a | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)O)C=C(C(=C1F)F)F.S(=O)(Cl)Cl>>FC1=C(C(=O)Cl)C=C(C(=C1F)F)F | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13] | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl | O=C(Cl)c1cc(F)c(F)c(F)c1F | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 7 | HOUR | Dimethylformamide (0.6 ml) is added to a mixture of 2,3,4,5-tetrafluorobenzoic acid (100 g) and thionyl chloride (135 ml), and the mixture is heated under reflux with stirring for 7 hours. The reaction mixture is condensed under vacuum to yield crude 2,3,4,5-tetrafluorobenzoyl chloride as a pale yellow oily residue (11... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 7 | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl>CN(C=O)C>O=C(Cl)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b5ace2c0388b4fd4bd544e41a8368eb1 | COC(=O)CC#N.O=C(Cl)c1cc(F)c(F)c(F)c1F>>COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F | C(Cl)Cl.C(#N)CC(=O)OC.[H-].[Na+].FC1=C(C(=O)Cl)C=C(C(=C1F)F)F>>C(#N)C(C(=O)OC)=C(C1=C(C(=C(C(=C1)F)F)F)F)O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]#[N:7].Cl[C:8](=[O:9])[c:10]1[cH:11][c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]1[F:19]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([C:6]#[N:7])=[C:8]([OH:9])[c:10]1[cH:11][c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]1[F:19] | COC(=O)CC#N.O=C(Cl)c1cc(F)c(F)c(F)c1F | COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | f22bf4bd29a538c485db316cbbd94db17505fee3aa09d75c884caebfdf6b2db2 | 57de51b87df028965b3733716f6a5af13774928604e0a70938cf8aa603006c92 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](-[C:11]#[N;D1;H0:12])=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[c:3](:[c:4]):[c:5] | 86.1 | [{"value": 86.1, "product": "C(#N)C(C(=O)OC)=C(C1=C(C(=C(C(=C1)F)F)F)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Methyl cyanoacetate (51.1 g) is added dropwise to a suspension of sodium hydride (43.3 g, in oil, 55-65 w/w %) in dry tetrahydrofuran (600 ml) while maintaining the internal temperature between 15° C. and 20° C. on an ice bath. To the reaction mixture is added dropwise the crude 2,3,4,5-tetrafluorobenzoyl chloride (110... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | Ester.Enol | null | null | c1ccccc1 | HCl | O1CCCC1 | null | 0.5 | COC(=O)CC#N.O=C(Cl)c1cc(F)c(F)c(F)c1F>O1CCCC1>COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-70fee91471c449a7acd7cc2f16112696 | COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F>>N#CCC(=O)c1cc(F)c(F)c(F)c1F | C(#N)C(C(=O)OC)=C(C1=C(C(=C(C(=C1)F)F)F)F)O.[Na].Cl>>FC1=C(C(=O)CC#N)C=C(C(=C1F)F)F | COC(=O)[C:3]([C:2]#[N:1])=[C:4]([OH:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([F:13])[c:14]1[F:15]>>[N:1]#[C:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([F:13])[c:14]1[F:15] | COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F | N#CCC(=O)c1cc(F)c(F)c(F)c1F | null | null | O | Miscellaneous | OtherReaction | 84e91df2c29a101a8e0cb0cda224ad7db5467f6b1b82326b7656b0a0e254ee97 | b97d7a7a56802d612b922595e8951096e922e99492fe423fd0e3eb3c3adb9cb5 | c1ccccc1 | C-O-C(=O)-[C;H0;D3;+0:1](-[C:2]#[N;D1;H0:3])=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[c:6](:[c:7]):[c:8]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6](:[c:7]):[c:8] | 88.9 | [{"value": 88.9, "product": "FC1=C(C(=O)CC#N)C=C(C(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | Methyl 2-cyano-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)acrylate (75.1 g) is added to a solution of sodium hydroxyde (110 g) in water (1.1 liter) and the mixture is stirred at room temperature for 26 hours. To the reaction mixture is added ice (1.3 Kg) and conc. HCl. After 1 hour, the precipitate is filtered and washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Enol | Ketone | null | null | c1ccccc1 | HO- | O | null | 26 | COC(=O)C(C#N)=C(O)c1cc(F)c(F)c(F)c1F>O>N#CCC(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f4e9bacf1cdc4752baaef28e79f8c8f7 | CCOC([O-])[O-].N#CCC(=O)c1cc(F)c(F)c(F)c1F>>CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)CC#N)C=C(C(=C1F)F)F.C(OCC)([O-])[O-].C(C)(=O)OC(C)=O>>C(C)OC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O | [O-][CH:4]([O-])[O:3][CH2:2][CH3:1].[CH2:5]([C:6]#[N:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]1[F:19]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6]#[N:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]1[F:19] | CCOC([O-])[O-].N#CCC(=O)c1cc(F)c(F)c(F)c1F | CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F | null | null | null | C-C Coupling | OtherReaction | 711c36c5b600763b7036ea50a2d0c3d6585c1a1b08993f79370fde60d993af57 | 3cc271b60f7ba314e9e46daac0d281b1143f77f6aaf418b7dc5ffd18c49fa0e9 | c1ccccc1 | [C:1]-[#8:2]-[CH;D3;+0:3](-[O-])-[O-].[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[C:1]-[#8:2]-[CH;D2;+0:3]=[C;H0;D3;+0:6](-[C:5]#[N;D1;H0:4])-[C:7](=[O;D1;H0:8])-[c:9] | 88 | [{"value": 88.0, "product": "C(C)OC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of 2-(2,3,4,5-tetrafluorobenzoyl)acetonitrile (13.1 g), ethyl orthoformate (13.4 g) and acetic anhydride (15.4 g) is heated at 100° C. with stirring for 3 hours. The reaction mixture is concentrated under vacuum to yield an orange brownish oily residue. When the oily residue is allowed to stand at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ketone.Ether | null | null | c1ccccc1 | HO- | null | 100 | 3 | CCOC([O-])[O-].N#CCC(=O)c1cc(F)c(F)c(F)c1F>>CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-18a86dc2dfb6483390cdb8493d259c89 | CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F.NC1CC1>>N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F | C1(CC1)N.C(C)OC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O>>C1(CC1)NC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O | CCO[CH:4]=[C:3]([C:2]#[N:1])[C:9](=[O:10])[c:11]1[cH:12][c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19]1[F:20].[NH2:5][CH:6]1[CH2:7][CH2:8]1>>[N:1]#[C:2][C:3](=[CH:4][NH:5][CH:6]1[CH2:7][CH2:8]1)[C:9](=[O:10])[c:11]1[cH:12][c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19]1[F:20] | CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F.NC1CC1 | N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F | null | null | CCCCCC.C(Cl)(Cl)Cl.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | cd3db327c21c90c24d38808dacb2ed3fbf57044150e5b341d88de9389ff3759d | 54aca1a08d403c8dd5c375df3e63fffc5027b15326b2523cf980a4a251290495 | O=C(C=CNC1CC1)c1ccccc1 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3]#[N;D1;H0:4])-[C:5](=[O;D1;H0:6])-[c:7].[NH2;D1;+0:8]-[C:9]1-[C:10]-[C:11]-1>>[N;D1;H0:4]#[C:3]-[C:2](=[CH;D2;+0:1]-[NH;D2;+0:8]-[C:9]1-[C:10]-[C:11]-1)-[C:5](=[O;D1;H0:6])-[c:7] | 86.5 | [{"value": 86.5, "product": "C1(CC1)NC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of cyclopropylamine (3.3 g) in chloroform (20 ml) is added dropwise to a solution of 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (14.0 g) in chloroform (50 ml) with maintaining the internal temperature between 6° C. and 8° C. by using an ice bath. The mixture is allowed to stand overnight at room te... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Enamine | null | null | C1CC1.c1ccccc1 | HO- | CCCCCC.C(Cl)(Cl)Cl.C(C)O | null | 8 | CCOC=C(C#N)C(=O)c1cc(F)c(F)c(F)c1F.NC1CC1>CCCCCC.C(Cl)(Cl)Cl.C(C)O>N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bb4faac45a8f4f5d8929cdcc7278d10a | N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F>>N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O | C1(CC1)NC=C(C#N)C(C1=C(C(=C(C(=C1)F)F)F)F)=O.[H-].[Na+].CCCCCC>>C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C#N | F[c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[cH:16][c:17]1[C:18]([C:3]([C:2]#[N:1])=[CH:4][NH:5][CH:6]1[CH2:7][CH2:8]1)=[O:19]>>[N:1]#[C:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8]2)[c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[cH:16][c:17]2[c:18]1=[O:19] | N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F | N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 703e9127907030eb316ada2e2c09030fd0ac6e1dbc170e1a86f009de409395a8 | 9ed9f4cbdec0522c6f77820cd35cca9308c396850cfb1263d5d98ab7ce71af7a | O=c1ccn(C2CC2)c2ccccc12 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](-[C:9]#[N;D1;H0:10])=[CH;D2;+0:11]-[NH;D2;+0:12]-[C:13]1-[C:14]-[C:15]-1):[c:16]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1]1:[c:5](:[c:16]):[c;H0;D3;+0:6](=[O;D1;H0:7]):[c;H0;D3;+0:8](-[C:9]#[N;D1;H0:10]):[cH;D2;+0:11]:[n;H0;... | 91.4 | [{"value": 91.4, "product": "C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of 3-cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (12.0 g) in dioxane (60 ml) is added dropwise to a suspension of sodium hydride (1.9 g, in oil, 55-65 w/w%) in dioxane (40 ml) while maitainig the internal temperature between 16° C. and 18° C. on an ice bath. The mixture is stirred for 6 hour... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone | null | c1ccccc1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1 | HF | O1CCOCC1 | null | 6 | N#CC(=CNC1CC1)C(=O)c1cc(F)c(F)c(F)c1F>O1CCOCC1>N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-69a2a105fbf243efb1c35a56bb089878 | CCn1cc(C(=O)O)c(=O)c2cc(F)c(F)c(F)c21.ON1CCNCC1>>CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(O)CC3)c(F)c21 | Cl.Cl.Cl.ON1CCNCC1.C(C)N(CC)CC.C(C)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C(=O)O>>C(C)N1C=C(C(C2=CC(=C(C(=C12)F)N1CCN(CC1)O)F)=O)C(=O)O | F[c:15]1[c:13]([F:14])[cH:12][c:11]2[c:9](=[O:10])[c:5]([C:6](=[O:7])[OH:8])[cH:4][n:3]([CH2:2][CH3:1])[c:25]2[c:23]1[F:24].[NH:16]1[CH2:17][CH2:18][N:19]([OH:20])[CH2:21][CH2:22]1>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[c:11]2[cH:12][c:13]([F:14])[c:15]([N:16]3[CH2:17][CH2:18][N:19]([OH:20]... | CCn1cc(C(=O)O)c(=O)c2cc(F)c(F)c(F)c21.ON1CCNCC1 | CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(O)CC3)c(F)c21 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc[nH]c2cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6](:[#7;a:7](-[C:8]):[c:9]):[c:10]:1-[F;D1;H0:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:8]-[#7;a:7](:[c:9]):[c:6]1:[c:5]:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:10]:1-[F;D1;H0:11] | 81.1 | [{"value": 81.1, "product": "C(C)N1C=C(C(C2=CC(=C(C(=C12)F)N1CCN(CC1)O)F)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 1-Hydroxypiperazine dihydrochloride (3.94 g) (which is prepared in Preparation 1), triethylamine (21 ml) and dimethylsulfoxide (30 ml) are added to 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.07 g), which is prepared according to the procedure described in Japanese Patent First Publication N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HF | O.CS(=O)C | 100 | null | CCn1cc(C(=O)O)c(=O)c2cc(F)c(F)c(F)c21.ON1CCNCC1>O.CS(=O)C>CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(O)CC3)c(F)c21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-62d5549876a64c209d2645a79fd100cc | O=C(O)c1cn(CCF)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>>O=C(O)c1cn(CCF)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | Cl.Cl.ON1CCNCC1.C(C)N(CC)CC.CN(C=O)C.FC=1C=C2C(C(=CN(C2=C(C1F)F)CCF)C(=O)O)=O>>FC=1C=C2C(C(=CN(C2=C(C1N1CCN(CC1)O)F)CCF)C(=O)O)=O | F[c:13]1[c:11]([F:12])[c:10]2[n:6]([CH2:7][CH2:8][F:9])[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:25](=[O:26])[c:24]2[cH:23][c:21]1[F:22].[NH:14]1[CH2:15][CH2:16][N:17]([OH:18])[CH2:19][CH2:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]([CH2:7][CH2:8][F:9])[c:10]2[c:11]([F:12])[c:13]([N:14]3[CH2:15][CH2:16][N:17]([OH:18])[CH2:19][... | O=C(O)c1cn(CCF)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1 | O=C(O)c1cn(CCF)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc[nH]c2cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:2]:1-[F;D1;H0:3] | 169.4 | [{"value": 169.4, "product": "FC=1C=C2C(C(=CN(C2=C(C1N1CCN(CC1)O)F)CCF)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 1-Hydroxypiperazine dihydrochloride (1.03 g), triethylamine (35.6 g) and dimethylformamide (85 ml) are added to 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (8.5 g), which is prepared by the procedure described in Japanese Patent First Publication No. 30964/1981, and the mixture is sti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HF | C(C)(=O)O | null | 1.5 | O=C(O)c1cn(CCF)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>C(C)(=O)O>O=C(O)c1cn(CCF)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a8128302981244928c282a1627e02429 | O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>>O=C(O)c1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | Cl.Cl.ON1CCNCC1.C(C)N(CC)CC.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C(=O)O>>C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)N1CCN(CC1)O)F)=O)C(=O)O | F[c:13]1[c:11]([F:12])[c:10]2[n:6]([CH:7]3[CH2:8][CH2:9]3)[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:25](=[O:26])[c:24]2[cH:23][c:21]1[F:22].[NH:14]1[CH2:15][CH2:16][N:17]([OH:18])[CH2:19][CH2:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9]2)[c:10]2[c:11]([F:12])[c:13]([N:14]3[CH2:15][CH2:16][N:17]([OH:18])[CH... | O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1 | O=C(O)c1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:2]:1-[F;D1;H0:3] | 71.3 | [{"value": 71.3, "product": "C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)N1CCN(CC1)O)F)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | 1-Hydroxypiperazine dihydrochloride (4.64 g), triethylamine (8.9 g) and dimethylsulfoxide (25 ml) are added to 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (5.0 g), which is prepared according to the procidures described in Japanese Patent First Publication No. 212474/1984, and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | C1CC1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HF | CS(=O)C | 130 | null | O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>CS(=O)C>O=C(O)c1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f0baf9bc98584eac840fbefba23d905c | N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>>N#Cc1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | Cl.Cl.ON1CCNCC1.CS(=O)C.C(C)N(CC)CC.C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C#N>>C(#N)C1=CN(C2=C(C(=C(C=C2C1=O)F)N1CCN(CC1)O)F)C1CC1 | F[c:12]1[c:10]([F:11])[c:9]2[n:5]([CH:6]3[CH2:7][CH2:8]3)[cH:4][c:3]([C:2]#[N:1])[c:24](=[O:25])[c:23]2[cH:22][c:20]1[F:21].[NH:13]1[CH2:14][CH2:15][N:16]([OH:17])[CH2:18][CH2:19]1>>[N:1]#[C:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8]2)[c:9]2[c:10]([F:11])[c:12]([N:13]3[CH2:14][CH2:15][N:16]([OH:17])[CH2:18][CH2:19]3)[c:... | N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1 | N#Cc1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O | null | null | O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn(C2CC2)c2cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:2]:1-[F;D1;H0:3] | 82.1 | [{"value": 82.1, "product": "C(#N)C1=CN(C2=C(C(=C(C=C2C1=O)F)N1CCN(CC1)O)F)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 1-Hydroxypiperazine dihydrochloride (2.45 g) (which is prepared in Preparation 1), dimethylsulfoxide (20 ml) and triethylamine (5.05 g) are added to 1-cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline (2.64 g), which is prepared in Preparation 3, and the mixture is stirred with heating at 100° C. for 4 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | C1CC1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HF | O | 100 | null | N#Cc1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O.ON1CCNCC1>O>N#Cc1cn(C2CC2)c2c(F)c(N3CCN(O)CC3)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-532e171a05b24c8f8683deaabd29dd37 | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C(Cl)C1COc2ccccc2O1>>COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)CC3)cc(N)c2cc1OC.Cl.O | O1C(COC2=C1C=CC=C2)C(=O)Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1.C(C)N(CC)CC>>O.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)C1COC2=C(O1)C=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:24][CH2:25]3)[cH:26][c:27]([NH2:28])[c:29]2[cH:30][c:31]1[O:32][CH3:33].[C:12](=[O:13])([CH:14]1[CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[O:23]1)[Cl:34]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=... | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C(Cl)C1COc2ccccc2O1 | COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)CC3)cc(N)c2cc1OC.Cl.O | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(C1COc2ccccc2O1)N1CCN(c2ccc3ccccc3n2)CC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[#8:7]-[C:8]-[C:9](-[C;H0;D3;+0:10](-[Cl;H0;D1;+0:11])=[O;D1;H0:12])-[#8:13]-[c:14]>>[#8:7]-[C:8]-[C:9](-[C;H0;D3;+0:10](=[O;D1;H0:12])-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:1]-[C:2]-[C:3]-1)-[#8:13]-[c:14].[ClH;D0;+0:11] | 29.4 | [{"value": 29.4, "product": "O.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)C1COC2=C(O1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1,4-benzodioxan-2-carbonyl chloride (0.75 g) in chloroform (10 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.0 g) in chloroform (50 ml) with triethylamine (1.06 g) at 5°-10°. The reaction was stirred at 5°-10° for one hour, then allowed to attain room... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | Other | C(Cl)(Cl)Cl | null | 1 | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C(Cl)C1COc2ccccc2O1>C(Cl)(Cl)Cl>COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)CC3)cc(N)c2cc1OC.Cl.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-198982f308634153beff07d8333f21f7 | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.ClC(Cl)Cl.O=C=Nc1ccccc1>>COc1cc2nc(N3CCN(C(=O)Nc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl | C1(=CC=CC=C1)N=C=O.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1.C(Cl)(Cl)Cl>>Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(NC1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]3)[cH:23][c:24]([NH2:25])[c:26]2[cH:27][c:28]1[O:29][CH3:30].ClC([Cl:31])[Cl:32].[C:12](=[O:13])=[N:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[NH... | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.ClC(Cl)Cl.O=C=Nc1ccccc1 | COc1cc2nc(N3CCN(C(=O)Nc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl | null | null | null | Acylation | OtherReaction | a4718afb2c0943f35a264fb2415cd0e678d48c426ff327cbe6339759a16a8b1e | 7d4b94b6ea3bb8edacd044d6dfa5d957c9b0ccbf79816483ed63a32ff4e79bfb | O=C(Nc1ccccc1)N1CCN(c2ccc3ccccc3n2)CC1 | Cl-C(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[ClH;D0;+0:1].[ClH;D0;+0:2].[O;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:3]-[C:4]-[C:5]-1 | null | [] | null | null | 4 | HOUR | Phenylisocyanate (1.1 g) was added to a stirred suspension of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (0.72 g) in chloroform (25 ml) at room temperature and the reaction mixture was stirred for 4 hours. The mixture was evaporated in vacuo, the residue taken up in methanol-chloroform and treated with ethereal ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Isocyanate.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | 4 | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.ClC(Cl)Cl.O=C=Nc1ccccc1>>COc1cc2nc(N3CCN(C(=O)Nc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d642450138948b08e61b7cdec6f0498 | CN(C)c1ccnc(Cl)n1.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC>>COc1cc2nc(N3CCN(c4nccc(N(C)C)n4)CC3)cc(N)c2cc1OC.Cl.Cl.O.O | NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1.ClC1=NC=CC(=N1)N(C)C>>O.O.Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC=CC(=N1)N(C)C | [c:12]1([Cl:31])[n:13][cH:14][cH:15][c:16]([N:17]([CH3:18])[CH3:19])[n:20]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]3)[cH:23][c:24]([NH2:25])[c:26]2[cH:27][c:28]1[O:29][CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([c:12]4[n:13][cH:14][cH:15][... | CN(C)c1ccnc(Cl)n1.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC | COc1cc2nc(N3CCN(c4nccc(N(C)C)n4)CC3)cc(N)c2cc1OC.Cl.Cl.O.O | null | null | C(CCC)O | Functional Group Addition | OtherReaction | cf0f64e4bd6cdfae23079064f224909d696b97002d77dc75e6ea88901169c3be | 61fffeaa75edcf21f8db97fe82a634291f4dc5c49705965cea81dd0b490dbebd | c1cnc(N2CCN(c3ccc4ccccc4n3)CC2)nc1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[Cl;H0;D1;+0:7]-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[ClH;D0;+0:7].[c:10]:[#7;a:9]:[c;H0;D3;+0:8](-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:1]-[C:2]-[C:3]-1):[#7;a:11]:[c:12] | 25.2 | [{"value": 25.2, "product": "O.O.Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC=CC(=N1)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.26 g) and 2-chloro-4-dimethylaminopyrimidine (0.76 g) in n-butanol (60 ml) were heated under reflux for 16 hours. The mixture was then evaporated in vacuo, the residue partitioned between chloroform and sodium carbonate solution (10%) and the aqueous phase extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1cncnc1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1cncnc1 | Other | C(CCC)O | null | null | CN(C)c1ccnc(Cl)n1.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC>C(CCC)O>COc1cc2nc(N3CCN(c4nccc(N(C)C)n4)CC3)cc(N)c2cc1OC.Cl.Cl.O.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-af56137fa4ef4309b9ed79595c9f42c5 | COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.Oc1ccccc1>>COc1cc2nc(N3CCN(c4ccnc(Oc5ccccc5)n4)CC3)cc(N)c2cc1OC.Cl.Cl | O.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC(=NC=C1)Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC(=NC=C1)Cl.C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+].[I-].[K+].C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC(=NC=C1)OC1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([c:12]4[cH:13][cH:14][n:15][c:16]([Cl:35])[n:24]4)[CH2:25][CH2:26]3)[cH:27][c:28]([NH2:29])[c:30]2[cH:31][c:32]1[O:33][CH3:34].COc1cc2nc(N3CCN(c4ccnc([Cl:36])n4)CC3)cc(N)c2cc1OC.[OH:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH... | COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.Oc1ccccc1 | COc1cc2nc(N3CCN(c4ccnc(Oc5ccccc5)n4)CC3)cc(N)c2cc1OC.Cl.Cl | null | null | C(Cl)Cl.CO.CC(CC(C)=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 891504fe20fb48282f50d9edaf47212380725992ae1be9f0b38f14e29dc28724 | bcf8ea8c8f1f86afe6269c31f8efba14168e73c2f11d3e404eef146780923965 | c1ccc(Oc2nccc(N3CCN(c4ccc5ccccc5n4)CC3)n2)cc1 | C-O-c1:c:c2:n:c(-N3-C-C-N(-c4:c:c:n:c(-[Cl;H0;D1;+0:1]):n:4)-C-C-3):c:c(-N):c:2:c:c:1-O-C.[Cl;H0;D1;+0:2]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[ClH;D0;+0:2].[ClH;D0;+0:1].[c:7]:[#7;a:6]:[c;H0;D3;+0:3](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:4]:[c:5] | 125.3 | [{"value": 125.3, "product": "Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C1=NC(=NC=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-2-[4-(2-chloropyrimidin-4-yl)piperazin-1-yl]-6,7-dimethoxyquinoline hemihydrate (0.32 g), phenol (0.15 g), anhydrous potassium carbonate (0.22 g) and potassium iodide (catalytic trace) in 4-methyl-2-pentanone (125 ml) were stirred under reflux for 18 hours. Further portions of phenol, anhydrous potassium carbon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Aromatic alcohol.Primary amine.Tertiary amine.Tertiary amine | Ether | c1cncnc1.c1ccc2ncccc2c1.C1CNCCN1.c1cncnc1 | c1cncnc1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1cncnc1.c1ccccc1 | HO- | C(Cl)Cl.CO.CC(CC(C)=O)C | null | null | COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(c4ccnc(Cl)n4)CC3)cc(N)c2cc1OC.Oc1ccccc1>C(Cl)Cl.CO.CC(CC(C)=O)C>COc1cc2nc(N3CCN(c4ccnc(Oc5ccccc5)n4)CC3)cc(N)c2cc1OC.Cl.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ec640823db72462fa4795bf7a610d3a2 | CCOCC.COc1cc(C#N)c(N=C(C)N2CCN(Cc3ccccc3)CC2)cc1OC.ClCCl.[OH-]>>COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl.Cl.Cl.O.O.O | CCOCC.[OH-].[Na+].C(Cl)Cl.C(C1=CC=CC=C1)N1CCN(CC1)C(C)=NC1=C(C=C(C(=C1)OC)OC)C#N>>O.Cl.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)CC1=CC=CC=C1.O.O.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)CC1=CC=CC=C1.Cl.Cl | [CH2:5]([CH3:21])[O:30][CH2:31][CH3:54].[CH3:1][O:2][c:3]1[cH:4][c:50]([C:7]#[N:6])[c:33]([N:34]=[C:35]([N:11]2[CH2:37][CH2:38][N:39]([CH2:40][c:41]3[cH:42][cH:43][cH:44][cH:45][cH:46]3)[CH2:47][CH2:48]2)[CH3:49])[cH:32][c:26]1[O:27][CH3:28].[CH2:22]([Cl:57])[Cl:58].[OH-:63]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N... | CCOCC.COc1cc(C#N)c(N=C(C)N2CCN(Cc3ccccc3)CC2)cc1OC.ClCCl.[OH-] | COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl.Cl.Cl.O.O.O | null | [Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-] | CC(=O)N(C)C | Aromatic Heterocycle Formation | OtherReaction | ab233ec0d7d94d46b9dd0034a225e3f4bdc5fb47f953556d959d9a3a011b206f | 32f78d8800e2835b218096e4ee28773ecc2c562bd760cd7c531da98722d796fa | c1ccc(CN2CCN(c3ccc4ccccc4n3)CC2)cc1.c1ccc(CN2CCN(c3ccc4ccccc4n3)CC2)cc1 | [#8:1]-[c:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c;H0;D3;+0:7](-[N;H0;D2;+0:8]=[C;H0;D3;+0:9](-[CH3;D1;+0:10])-[N;H0;D3;+0:11]2-[CH2;D2;+0:12]-[C:13]-[#7:14](-[C:15])-[C:16]-[CH2;D2;+0:17]-2):[cH;D2;+0:18]:[c;H0;D3;+0:19]:1-[#8:20]-[C;D1;H3:21].[CH3;D1;+0:22]-[CH2;D2;+0:23]-[O;H0;D2;+0:24]-[CH... | null | [] | null | null | 5 | MINUTE | N-[1-(4-Benzylpiperazin-1-yl)ethylidene]-2-cyano-4,5-dimethoxyaniline (13.5 g) and zinc chloride (4.86 g) in dimethylacetamide (90 ml) were stirred under reflux for 21/2 hours; further zinc chloride (0.5, 0.2 g) was added after 1/2 and 11/2 hours respectively. The mixture was cooled, treated with ether (700 ml, 2×100 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether.Nitrile.Tertiary amine | Ether.Ether.Ether.Primary amine.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | c1ccccc1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | [Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-].CC(=O)N(C)C | null | 0.083333 | CCOCC.COc1cc(C#N)c(N=C(C)N2CCN(Cc3ccccc3)CC2)cc1OC.ClCCl.[OH-]>[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-].CC(=O)N(C)C>COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC.Cl.Cl.Cl.Cl.O.O.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fa614c7f062d48ed87b80d5478f2ae51 | CC(C)COC(=O)Cl.CCN(CC)CC.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C([O-])[O-]>>COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.Cl.Cl.O.O.O | C(C(C)C)OC(=O)Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1.C(C)N(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>>O.Cl.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)OCC(C)C.O.O.NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)OCC(C)C.Cl | [C:40](=[O:41])([O:42][CH2:43][CH:44]([CH3:45])[CH3:46])[Cl:57].[CH2:10]([N:11]([CH2:15][CH3:16])[CH2:35][CH3:49])[CH3:17].[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:38][NH:39][CH2:47][CH2:48]3)[cH:21][c:22]([NH2:23])[c:24]2[cH:25][c:26]1[O:27][CH3:28].[C:12](=[O:13])([O-:14])[O-:55]>>[CH3:1][O:2][c:3]1... | CC(C)COC(=O)Cl.CCN(CC)CC.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C([O-])[O-] | COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.Cl.Cl.O.O.O | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | fa76263da35443f8bf78cba078c706f0410ef1379faa3a8097f293723beaa61c | 715091dbf7a3df325f02ad1f4c4bcfa1f7437b7764173014a1bd45489d9d2cbd | c1ccc2nc(N3CCNCC3)ccc2c1.c1ccc2nc(N3CCNCC3)ccc2c1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH2;D2;+0:6]-[CH3;D1;+0:7].[C:8]-[#8:9]-[C;H0;D3;+0:10](-[Cl;H0;D1;+0:11])=[O;D1;H0:12].[O-;H0;D1:13]-[C;H0;D3;+0:14](-[O-;H0;D1:15])=[O;D1;H0:16].[c:17]:[c:18](-[N;H0;D3;+0:19]1-[CH2;D2;+0:20]-[C:21]-[NH;D2;+0:22]-[CH2;D2;+0:23]-[CH2;D2;+0:24]-1... | null | [] | null | null | 1 | HOUR | A solution of isobutylchloroformate (0.11 g) in chloroform (5 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-[piperazin-1-yl]quinoline (0.21 g) in chloroform (15 ml) with triethylamine (0.22 g) at 10°. The solution was then stirred at room temperature for 1 hour and sodium carbonate solution (1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine.Tertiary amine.Tertiary amine | Carbamic ester.Carbamic ester.Ether.Ether.Ether.Ether.Primary amine.Tertiary amine.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | null | C(Cl)(Cl)Cl | null | 1 | CC(C)COC(=O)Cl.CCN(CC)CC.COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC.O=C([O-])[O-]>C(Cl)(Cl)Cl>COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.COc1cc2nc(N3CCN(C(=O)OCC(C)C)CC3)cc(N)c2cc1OC.Cl.Cl.O.O.O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a0355ae516294cdf811e5110b87ff144 | COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC>>COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC | NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)CC1=CC=CC=C1.C(Cl)(Cl)Cl>>NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1 | c1ccc(C[N:11]2[CH2:10][CH2:9][N:8]([c:7]3[n:6][c:5]4[cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18][c:17]4[c:15]([NH2:16])[cH:14]3)[CH2:13][CH2:12]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[cH:14][c:15]([NH2:16])[c:17]2[cH:18][c:19]1[O:20][CH3:21] | COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC | COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC | null | [Pd] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | 59cf17273403d7d0f70b28df645477a441335974f2f780a5ce92ce8530bb9352 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc2nc(N3CCNCC3)ccc2c1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1>>[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | 51.2 | [{"value": 51.2, "product": "NC1=CC(=NC2=CC(=C(C=C12)OC)OC)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-6,7-dimethoxy-2-(4-benzylpiperazin-1-yl)quinoline (6.2 g) in ethanol (300 ml) with 5% Pd/C catalyst was stirred at 50° under an atmosphere of hydrogen (50 p.s.i.) for 20 hours. The mixture was cooled, chloroform (100 ml) added and the solution filtered through "Solkafloc". The solid was washed with chloroform-m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2ncccc2c1.C1C[NH]CCN1 | Other | [Pd].C(C)O | null | null | COc1cc2nc(N3CCN(Cc4ccccc4)CC3)cc(N)c2cc1OC>[Pd].C(C)O>COc1cc2nc(N3CCNCC3)cc(N)c2cc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7f3c58d3a0fe422b8570827c7f859b85 | CC(=O)N(C)C.COc1cc(N)c(C#N)cc1OC>>COc1cc(C#N)c(N=C(C)N(C)C)cc1OC | P(=O)(Cl)(Cl)Cl.CC(=O)N(C)C.C(#N)C1=C(N)C=C(C(=C1)OC)OC>>CN(C(C)=NC1=C(C=C(C(=C1)OC)OC)C#N)C | O=[C:10]([CH3:11])[N:12]([CH3:13])[CH3:14].[CH3:1][O:2][c:3]1[cH:4][c:8]([NH2:9])[c:5]([C:6]#[N:7])[cH:15][c:16]1[O:17][CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[c:8]([N:9]=[C:10]([CH3:11])[N:12]([CH3:13])[CH3:14])[cH:15][c:16]1[O:17][CH3:18] | CC(=O)N(C)C.COc1cc(N)c(C#N)cc1OC | COc1cc(C#N)c(N=C(C)N(C)C)cc1OC | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 534e1d5d44557dd3fcb59753c46d2d629ada073f8686b214456bf3a7f8fb6e73 | b9d219f0674c4c56492b0e55f3afda0e6dc263a5614af120d7a27809c687708b | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#8:6]-[c:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[C:10]#[N;D1;H0:11]):[c;H0;D3;+0:12](-[NH2;D1;+0:13]):[cH;D2;+0:14]:[c:15]:1-[#8:16]>>[#8:6]-[c:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:12](-[N;H0;D2;+0:13]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5]):[c;H... | null | [] | null | null | 5 | MINUTE | Phosphorous oxychloride (1.0 ml) was added to a stirred solution of dimethylacetamide (2.8 ml) in chloroform (10 ml) at room temperature. The mixture was stirred for 5 minutes, 2-cyano-4,5-dimethoxyaniline (1.78 g) added and the reaction stirred under reflux for 4 hours. The mixture was cooled, poured onto ice and extr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 0.083333 | CC(=O)N(C)C.COc1cc(N)c(C#N)cc1OC>C(Cl)(Cl)Cl>COc1cc(C#N)c(N=C(C)N(C)C)cc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-507428f38ed1419e9879ff1a9c9112c9 | CI.CN(C)C=O.O=C(O)c1ccc2ccccc2c1O>>COC(=O)c1ccc2ccccc2c1OC | [Cl-].[Na+].[OH-].[K+].OC1=C(C=CC2=CC=CC=C12)C(=O)O.CN(C=O)C.CI>>COC1=C(C=CC2=CC=CC=C12)C(=O)OC | I[CH3:16].CN(C=O)[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[O:15][CH3:16] | CI.CN(C)C=O.O=C(O)c1ccc2ccccc2c1O | COC(=O)c1ccc2ccccc2c1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4e302a5c4b5749a27005cfac332d21a67cd4b03cabc4b79c56523042a9f3f68a | 11e44eaefaffcf2f4bedaafd68334cfa44459302a483454fd2d2ec963968ffac | c1ccc2ccccc2c1 | C-N(-[CH3;D1;+0:1])-C=O.I-[CH3;D1;+0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[CH3;D1;+0:2]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:4](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | 50 | CELSIUS | 15 | MINUTE | Over a 15 minute period, 149 g. (2.7 moles) of ground potassium hydroxide is added to 180 g. (0.96 mole) of 1-hydroxy-2-naphthoic acid in 2.5 l. of dimethylformamide (during the course of which the temperature rises to 32° C.). The reaction mixture is stirred at 20°-25° C. for 16 hours and at 50° C. for 2 hours and coo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Aromatic alcohol | Ester.Ether | null | null | c1ccc2ccccc2c1 | HI | null | 50 | 0.25 | CI.CN(C)C=O.O=C(O)c1ccc2ccccc2c1O>>COC(=O)c1ccc2ccccc2c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b4078077fd54f96b9eda5ab91aab09d | COS(=O)(=O)OC.Oc1cc(O)c2ccccc2c1>>COc1cc(OC)c2ccccc2c1 | OC1=CC(=CC2=CC=CC=C12)O.[OH-].[Na+].O.C(C)O.S(=O)(=O)(OC)OC>>COC1=CC(=CC2=CC=CC=C12)OC | O=S(=O)(O[CH3:1])O[CH3:7].[OH:2][c:3]1[cH:4][c:5]([OH:6])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | COS(=O)(=O)OC.Oc1cc(O)c2ccccc2c1 | COc1cc(OC)c2ccccc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fb1095592b840fd614706aea5353046ecf68855980b5ab9c0a4590b6d3f34f57 | b56a881cca53d645d3ea21c88aa2f444e6fbc0455e71d7569115c4e79d3bc912 | c1ccc2ccccc2c1 | O=S(=O)(-O-[CH3;D1;+0:1])-O-[CH3;D1;+0:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[CH3;D1;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH3;D1;+0:2]):[c:9] | null | [] | null | null | 16 | HOUR | A solution of 32.1 g. (0.801 mole) of sodium hydroxide in 80.3 ml. of water and 96 g. (0.763 mole) of dimethyl sulfate are simultaneously added over a period of 30-45 minutes to g. (0.312 mole) of 1,3-dihydroxynaphthalene in 250 ml. of absolute ethanol stirred at -5°-0° C., the former being added slightly faster than t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | null | c1ccc2ccccc2c1 | HO- | null | null | 16 | COS(=O)(=O)OC.Oc1cc(O)c2ccccc2c1>>COc1cc(OC)c2ccccc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b57714566b3445cac696860cd5a5062 | COc1cc2ccccc2c(OC)c1C(=O)O.O=C(Cl)C(=O)Cl>>COc1cc2ccccc2c(OC)c1C(=O)Cl | COC1=C(C(=CC2=CC=CC=C12)OC)C(=O)O.C(C(=O)Cl)(=O)Cl>>COC1=C(C(=CC2=CC=CC=C12)OC)C(=O)Cl | O[C:15]([c:14]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]1[O:12][CH3:13])=[O:16].O=C(Cl)C(=O)[Cl:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]([O:12][CH3:13])[c:14]1[C:15](=[O:16])[Cl:17] | COc1cc2ccccc2c(OC)c1C(=O)O.O=C(Cl)C(=O)Cl | COc1cc2ccccc2c(OC)c1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2ccccc2c1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | The product is prepared from 9.28 g. (40 mmoles) of 1,3-dimethoxy-2-naphthoic acid and 10.15 g. (80 mmoles) of oxalyl chloride by the process of Step 3 of Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: The product is prepared from 9.28 g | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccc2ccccc2c1 | HCl | null | null | null | COc1cc2ccccc2c(OC)c1C(=O)O.O=C(Cl)C(=O)Cl>>COc1cc2ccccc2c(OC)c1C(=O)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c9f4eec8dc214ef3935fee8057c9c631 | CCOC(=O)C=Cc1ccccc1Br>>OCC=Cc1ccccc1Br | BrC1=C(C=CC(=O)OCC)C=CC=C1.[H-].C(C(C)C)[Al+]CC(C)C>>BrC1=C(C=CCO)C=CC=C1 | CCO[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11]>>[OH:1][CH2:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11] | CCOC(=O)C=Cc1ccccc1Br | OCC=Cc1ccccc1Br | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4]-[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:3]=[C:4]-[c:5] | 61 | [{"value": 61.0, "product": "BrC1=C(C=CCO)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "BrC1=C(C=CCO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl o-bromocinnamate (66.3 g; 260 mM) was dissolved in 750 ml of anhydrous toluene under nitrogen in a three-neck round bottom flask equipped with addition funnel and condensor. A toluene solution of diisobutylaluminum hydride (520 mM; 1.53M) was transferred via canula to the addition funnel and then added dropwise t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)C=Cc1ccccc1Br>C1(=CC=CC=C1)C>OCC=Cc1ccccc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4d20c03e2dff4b738e0fc10793862dea | BrP(Br)Br.OCC=Cc1ccccc1Br>>BrCC=Cc1ccccc1Br | P(Br)(Br)Br.BrC1=C(C=CCO)C=CC=C1>>BrC1=C(C=CCBr)C=CC=C1 | BrP(Br)[Br:1].O[CH2:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11]>>[Br:1][CH2:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11] | BrP(Br)Br.OCC=Cc1ccccc1Br | BrCC=Cc1ccccc1Br | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]=[C:4]-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]=[C:4]-[c:5] | 85 | [{"value": 85.0, "product": "BrC1=C(C=CCBr)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | All of the o-bromocinnamylalcohol (159 mM) from Step A was dissolved in 300 ml of carbon tetrachloride under nitrogen and chilled to 0°. Then 100 ml of carbon tetrachloride containing phosphorous tribromide (5.62 ml; 59.8 mM) was added dropwise. After stirring at 0° for an additional hour the reaction was poured into i... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)(Cl)Cl | null | null | BrP(Br)Br.OCC=Cc1ccccc1Br>C(Cl)(Cl)(Cl)Cl>BrCC=Cc1ccccc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-22514b66bb5342db90650b3aca2f05ce | Oc1cc2c(cc1CC=Cc1ccccc1Br)OCC2>>N#Cc1ccccc1C=CCc1cc2c(cc1O)CCO2 | BrC1=C(C=CCC2=CC3=C(CCO3)C=C2O)C=CC=C1.CN1C(CCC1)=O>>C(#N)C1=C(C=CCC2=CC3=C(CCO3)C=C2O)C=CC=C1 | Br[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[CH:10][CH2:11][c:12]1[cH:13][c:14]2[c:15]([cH:16][c:17]1[OH:18])[CH2:19][CH2:20][O:21]2>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[CH:10][CH2:11][c:12]1[cH:13][c:14]2[c:15]([cH:16][c:17]1[OH:18])[CH2:19][CH2:20][O:21]2 | Oc1cc2c(cc1CC=Cc1ccccc1Br)OCC2 | N#Cc1ccccc1C=CCc1cc2c(cc1O)CCO2 | null | null | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | C(=Cc1ccccc1)Cc1ccc2c(c1)OCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[C:6]-[C:7]):[c:8]>>[C:7]-[C:6]=[C:5]-[c:4](:[c:8]):[c;H0;D3;+0:1](-[C:9]#[N;D1;H0:10]):[c:2]:[c:3] | null | [] | null | null | null | null | 6-(o-Bromocinnamyl)-2,3-dihydro-5-hydroxybenzofuran (1.49 g; 4.5 mM) and cuprous cyanide (1.37 g; 15.3 mM) were suspended in 18 ml of anhydrous N-methyl-2-pyrollidinone. Nitrogen was bubbled through this suspension for approximately 15 minutes and the reaction mixture was then heated to 175° under nitrogen for 2 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | Br- | null | null | null | Oc1cc2c(cc1CC=Cc1ccccc1Br)OCC2>>N#Cc1ccccc1C=CCc1cc2c(cc1O)CCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3a2ff8bc69784dcdb5e774b7ec2951ea | C#CCBr.Oc1ccc(O)cc1>>C#CCOc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C([O-])([O-])=O.[K+].[K+].C(C#C)Br>>C(C#C)OC1=CC=C(C=C1)O | Br[CH2:3][C:2]#[CH:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | C#CCBr.Oc1ccc(O)cc1 | C#CCOc1ccc(O)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Hydroquinone (49.6 g; 450 mM) was dissolved in 700 ml of anhydrous acetone in a two liter, 3-necked, round bottom flask equipped with reflux condensor, air stirrer and nitrogen bubbler. Potassium carbonate (65.6 g; 460 mM) was ground finely and then added to the reaction followed by propargylbromide (53.6 g; 450 mM). T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | C#CCBr.Oc1ccc(O)cc1>CC(=O)C>C#CCOc1ccc(O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-df11ba087625413d92e76cfa78b4056e | Oc1ccc2c(c1)C=CCO2>>Oc1ccc2c(c1)CCCO2 | OC=1C=CC2=C(C=CCO2)C1>>OC=1C=CC2=C(CCCO2)C1 | [OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH:8]=[CH:9][CH2:10][O:11]2>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH2:10][O:11]2 | Oc1ccc2c(c1)C=CCO2 | Oc1ccc2c(c1)CCCO2 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | C1=CC=CC=C1 | Reduction | Hydrogenation (double to single) | 361af49d0d15997eaf6fdfce5f3b2616fe65ac041cc34e887141379258f1ed41 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(c1)CCCO2 | [c:1]:[c:2]1:[c:3]-[#8:4]-[C:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-1>>[c:1]:[c:2]1:[c:3]-[#8:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1 | 93 | [{"value": 93.0, "product": "OC=1C=CC2=C(CCCO2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "OC=1C=CC2=C(CCCO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | The 6-hydroxybenzopyran (1.5 g; 10 mM) was dissolved in 100 ml of anhydrous benzene along with Wilkinson's catalyst (280 mgs; 0.30 mM). This hydrogenation bottle containing this reaction mixture was first flushed with nitrogen and then with hydrogen. The bottle was pressurized to 40 psi in a Paar shaker and agitated fo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2OC1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh].C1=CC=CC=C1 | null | 0.666667 | Oc1ccc2c(c1)C=CCO2>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh].C1=CC=CC=C1>Oc1ccc2c(c1)CCCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d8ad2a321edc48a8b945d42f8ba7f345 | COC(=O)C=Cc1cccc(OC)c1>>COc1cccc(C=CCO)c1 | [H-].C(C(C)C)[Al+]CC(C)C.COC=1C=C(C=CC(=O)OC)C=CC1.[H-].C(C(C)C)[Al+]CC(C)C.Cl.C(C)(=O)OCC.CCCCCC>>COC=1C=C(C=CCO)C=CC1 | CO[C:10]([CH:9]=[CH:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:12]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[CH:9][CH2:10][OH:11])[cH:12]1 | COC(=O)C=Cc1cccc(OC)c1 | COc1cccc(C=CCO)c1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4]-[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:3]=[C:4]-[c:5] | 71 | [{"value": 71.0, "product": "COC=1C=C(C=CCO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | the methyl m-methoxycinnamate was taken up in 50 ml of anhydrous toluene and chilled to -70° under nitrogen. Diisobutylaluminum hydride (54 ml; 83 mM; 1.54M in toluene) was added dropwise through a side-arm addition funnel. Some starting material remained as detected by TLC (35% ethyl acetate/hexane on silica gel) so a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COC(=O)C=Cc1cccc(OC)c1>C1(=CC=CC=C1)C>COc1cccc(C=CCO)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-62976ea3d11749a087501c01286cd7b6 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1Br>>CCOC(=O)C=Cc1ccccc1Br | C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.BrC1=C(C=O)C=CC=C1>>BrC1=C(C=CC(=O)OCC)C=CC=C1 | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Br:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Br:14] | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1Br | CCOC(=O)C=Cc1ccccc1Br | null | null | C(Cl)Cl | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 96 | [{"value": 96.0, "product": "BrC1=C(C=CC(=O)OCC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Carboethoxymethylidene triphenylphosphorane (94 g, 270 mM) was dissolved in 350 ml of methylenechloride under nitrogen. o-Bromobenzaldehyde (31.5 ml; 270 mM) was added via an addition funnel in 125 ml of methylene chloride. The solution was allowed to stand at room temperature overnight and then the solvent was removed... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1Br>C(Cl)Cl>CCOC(=O)C=Cc1ccccc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db6c62ed346343019f2747bac432b479 | COc1ccc(O)c(CC=Cc2ccccc2Br)c1>>COc1ccc(O)c(CC=Cc2ccccc2C#N)c1 | BrC1=C(C=CCC2=C(C=CC(=C2)OC)O)C=CC=C1.CN1C(CCC1)=O>>C(#N)C1=C(C=CCC2=C(C=CC(=C2)OC)O)C=CC=C1 | Br[c:17]1[c:12]([CH:11]=[CH:10][CH2:9][c:8]2[c:6]([OH:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]2)[cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][CH:10]=[CH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]#[N:19])[cH:20]1 | COc1ccc(O)c(CC=Cc2ccccc2Br)c1 | COc1ccc(O)c(CC=Cc2ccccc2C#N)c1 | null | null | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | C(=Cc1ccccc1)Cc1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[C:6]-[C:7]):[c:8]>>[C:7]-[C:6]=[C:5]-[c:4](:[c:8]):[c;H0;D3;+0:1](-[C:9]#[N;D1;H0:10]):[c:2]:[c:3] | 39 | [{"value": 39.0, "product": "C(#N)C1=C(C=CCC2=C(C=CC(=C2)OC)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Cuprous cyanide (1.03 g; 11.5 mM) and 2-(o-bromocinnamyl)-4-methoxyphenol (1.03 g; 3.23 mM) were combined in 12 ml of anhydrous N-methylpyrrolidinone. Nitrogen was bubbled through the resulting suspension for five minutes and it was then heated to 175° under positive nitrogen pressure for 2 hours. The reaction was pour... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | null | null | null | COc1ccc(O)c(CC=Cc2ccccc2Br)c1>>COc1ccc(O)c(CC=Cc2ccccc2C#N)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-574d169d1775494e8913267252cbb8a4 | COc1ccc(O)c(CC=Cc2ccccc2C=O)c1>>COc1ccc(O)c(CC=Cc2ccccc2CO)c1 | [BH4-].[Na+].C(=O)C1=C(C=CCC2=C(C=CC(=C2)OC)O)C=CC=C1>>OCC1=C(C=CCC2=C(C=CC(=C2)OC)O)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][CH:10]=[CH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH:18]=[O:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][CH:10]=[CH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH2:18][OH:19])[cH:20]1 | COc1ccc(O)c(CC=Cc2ccccc2C=O)c1 | COc1ccc(O)c(CC=Cc2ccccc2CO)c1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | C(=Cc1ccccc1)Cc1ccccc1 | [C:1]=[C:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]>>[C:1]=[C:2]-[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7] | null | [] | null | null | 2 | HOUR | Sodium borohydride (35 mg) was added in one portion to a solution of 2-(o-formylcinnamyl)-4-methoxyphenol (240 mg; 0.89 mM) in 5 ml of methanol. The reaction was stirred at room temperature for 2 hours and then the solvent was removed in vacuo. The residue was taken up in 2N aqueous hydrochloric acid and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | CO | null | 2 | COc1ccc(O)c(CC=Cc2ccccc2C=O)c1>CO>COc1ccc(O)c(CC=Cc2ccccc2CO)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ac7a92608b5a4bb997c4e27c74f6fabb | COc1ccc(OCCO)c(C=O)c1>>C=Cc1cc(OC)ccc1OCOC | O1CCCC1.C(CCC)[Li].C(CO)OC1=C(C=O)C=C(C=C1)OC.O1CCCC1>>C(=C)C1=C(C=CC(=C1)OC)OCOC | O=[CH:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:1][OH:13]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][O:13][CH3:14] | COc1ccc(OCCO)c(C=O)c1 | C=Cc1cc(OC)ccc1OCOC | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | null | Functional Group Interconversion | OtherReaction | 789df639e0c7a5021e339fd96942395852748e4604e5d4cf75ff1fe5ad4e953e | c15e62159182f7d24465950a05d8dd0bc849da4dc64fb67b2e3066b578f6abfa | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[OH;D1;+0:8]>>[C;D1;H3:9]-[O;H0;D2;+0:8]-[CH2;D2;+0:6]-[#8:5]-[c:4]:[c:2](-[CH;D2;+0:1]=[CH2;D1;+0:7]):[c:3] | 89 | [{"value": 89.0, "product": "C(=C)C1=C(C=CC(=C1)OC)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of 104 g (0.291 moles) of methyltriphenylphosphonium bromide in 100 ml dry tetrahydrofuran at 0° was added 115 ml (0.275 moles) of 2.4M n-butyllithium and the dark red solution was stirred at 0° for 30 minutes. Then a solution of 38.2 g (0.195 moles) of 2-(3-oxapropyloxy)-5-methoxybenzaldehyde in 100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary alcohol | Ether.Ether.Vinyl | null | null | c1ccccc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | null | 0.5 | COc1ccc(OCCO)c(C=O)c1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>C=Cc1cc(OC)ccc1OCOC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4ba8460c68b34737893bf12d1e09fa88 | C=Cc1cc(OC)ccc1OCOC.OO>>COCOc1ccc(OC)cc1CCO | OO.[OH-].[Na+].C(=C)C1=C(C=CC(=C1)OC)OCOC.B.O1CCCC1>>OCCC1=C(C=CC(=C1)OC)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]1[CH:13]=[CH2:14].O[OH:15]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]1[CH2:13][CH2:14][OH:15] | C=Cc1cc(OC)ccc1OCOC.OO | COCOc1ccc(OC)cc1CCO | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6aaa6688cc4965019d9400c93c20e1d817a445418a6601722f66df7d420427e9 | 4ceb30033bcfd57c382fe05e353b68e7f657859dbacaaa785451a244b2657476 | c1ccccc1 | O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 73 | [{"value": 73.0, "product": "OCCC1=C(C=CC(=C1)OC)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | To a solution of 33.8 g (0.174 moles) of 2-ethenyl-4-methoxy-1-O-methoxymethylphenol in 300 ml of dry tetrahydrofuran at 0° was added 120 ml of a 1.0M borane-tetrahydrofuran solution. The solution was stirred at room temperature for 60 minutes, cooled to 0° and 48 ml of 10% NaOH was added dropwise. Then 41 ml of 30% H2... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Vinyl | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | C=Cc1cc(OC)ccc1OCOC.OO>O1CCCC1>COCOc1ccc(OC)cc1CCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c7319b78311f4d539f78823d48903e7b | CCOC(=O)C1(C=O)CC=CN1C.COc1ccc(OCCO)c(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>>CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C | C(C)OC(=O)C1(N(C=CC1)C)C=O.C(CCC)[Li].[I-].C(CO)OC1=C(C=C(C=C1)OC)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)OCCO)C | O=[CH:9][C:6]1([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH:8]=[CH:24][N:25]1[CH3:26].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][CH2:11][c:12]2[cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18][c:19]2[O:20][CH2:21][CH2:22][OH:23])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]=[CH:10][CH2:11][c:12]2[cH:13][c:14]([O:1... | CCOC(=O)C1(C=O)CC=CN1C.COc1ccc(OCCO)c(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1 | CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C | null | null | O1CCCC1 | C-C Coupling | OtherReaction | fd61f4365204781aa55dc6a426e12655b965921ede43476304c54efa348df474 | a87bb6582611dac4aeb48accc1a0b67d940e7a8afe516102c4d8d984df23a2bb | C(=Cc1cc[nH]c1)Cc1ccccc1 | O=[CH;D2;+0:1]-[C;H0;D4;+0:2]1(-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH2;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[N;H0;D3;+0:10]-1-[C;D1;H3:11].[c:12]-[C:13]-[CH2;D2;+0:14]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[CH;D2;+0:1]=[CH;D2;+... | 85 | [{"value": 85.0, "product": "C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)OCCO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)OCCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 1.6M n-butyllithium (4.0 ml, 6.0 mmol) was added to a suspension of 3.45 g (5.90 mmol) of 2-[2-(3-oxapropyloxy)-5-methoxyphenyl]ethyltriphenylphosphonium iodide in 20 ml of dry tetrahydrofuran at 0°. After 30 minutes a solution of 1.10 g (6.07 mmol) of 2-ethoxycarbonyl-1-methylpyrrole-2-carboxaldehyde in ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ester | Ester | C1=C[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CCOC(=O)C1(C=O)CC=CN1C.COc1ccc(OCCO)c(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>O1CCCC1>CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1235931e06be4737a0c81ac4529fe6e2 | CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C>>CCOC(=O)c1cc(C=CCc2cc(OC)ccc2O)cn1C | C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)OCCO)C>>C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)O)C | OCC[O:20][c:19]1[c:12]([CH2:11][CH:10]=[CH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:22]([CH3:23])[cH:21]2)[cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]=[CH:10][CH2:11][c:12]2[cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18][c:19]2[OH:20])[cH:21][n:22]1[C... | CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C | CCOC(=O)c1cc(C=CCc2cc(OC)ccc2O)cn1C | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 4a66bcf82a2b9b4fffef5c6b6c007d1d0481718dd10228721dcf3aa4deefb7f2 | f78fa56f31fe176e07ba04b30637e2c1222d7496d48126ef057f127f14b0ebb7 | C(=Cc1cc[nH]c1)Cc1ccccc1 | O-C-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 77.3 | [{"value": 77.0, "product": "C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C(C)OC(=O)C=1N(C=C(C1)C=CCC1=C(C=CC(=C1)OC)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1.00 g (2.79 mmol) of 2-ethoxycarbonyl-1-methyl-4-[2-(3-oxapropyloxy)-5-methoxyphenyl]propenylpyrrole in 5 ml of 1:1 aqueous trifluoroacetic acid was stirred at 0° for 1 hour, then at room temperature for 1 hour. The solution was partitioned between ether and water and the ether layer was washed with 3 po... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Aromatic alcohol | null | null | c1cc[nH]c1.c1ccccc1 | HO- | FC(C(=O)O)(F)F | null | 1 | CCOC(=O)c1cc(C=CCc2cc(OC)ccc2OCCO)cn1C>FC(C(=O)O)(F)F>CCOC(=O)c1cc(C=CCc2cc(OC)ccc2O)cn1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-89d964b5325847acaadeeabb191fdf1c | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc(Cl)c1Cl | ClC1=C(C=O)C=CC=C1Cl.FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([Cl:25])[c:26]1[Cl:27]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH:16]([CH3:17])[... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc(Cl)c1Cl | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 38.4 | [{"value": 38.4, "product": "ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 2,3-Dichlorobenzaldehyde (1.75 g, 10 mmoles), methyl 4-fluoro-3-oxobutanoate (1.34 g, 10 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.43 g, 10 mmoles) were heated with stirring at 90° for 2.5 hours. The reaction mixture was dissolved in ethyl acetate and chromatographed on silica eluting with petroleum ether (60°-8... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 2.5 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl>C(C)(=O)OCC>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4827bcb196ef443d97806bbf4f85f6ef | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.Cc1c(C=O)cccc1[N+](=O)[O-]>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1C | CC1=C(C=O)C=CC=C1[N+](=O)[O-].FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>FCC=1NC(=C(C(C1C(=O)OC)C1=C(C(=CC=C1)[N+](=O)[O-])C)C(=O)OC(C)C)C | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[c:28]1[CH3:29]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.Cc1c(C=O)cccc1[N+](=O)[O-] | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 20 | [{"value": 20.0, "product": "FCC=1NC(=C(C(C1C(=O)OC)C1=C(C(=CC=C1)[N+](=O)[O-])C)C(=O)OC(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 2-Methyl-3-nitrobenzaldehyde (1.23 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.07 g, 7.5 mmoles) were heated with stirring at 80° for 2.5 hours. The cooled residue was chromatographed twice on silica eluting first with ethyl acetate/petroleum ether (60°-80... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | 2.5 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.Cc1c(C=O)cccc1[N+](=O)[O-]>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5099b83648494d408f4009e510dc0900 | CC(N)=CC(=O)OC1CCCC1.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl | ClC1=C(C=O)C=CC=C1Cl.FCC(CC(=O)OC)=O.NC(=CC(=O)OC1CCCC1)C>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC1CCCC1)C)CF)C(=O)OC | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:21][c:22]1[cH:23][cH:24][cH:25][c:26]([Cl:27])[c:28]1[Cl:29]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][C... | CC(N)=CC(=O)OC1CCCC1.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | O=C(OC1CCCC1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 28.6 | [{"value": 28.6, "product": "ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC1CCCC1)C)CF)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 2,3-Dichlorobenzaldehyde (1.31 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and cyclopentyl 3-amino-2-butenoate (1.26 g, 7.5 mmoles) were heated at 90° with stirring under nitrogen for 2.5 hours. The reaction mixture was dissolved in ethyl acetate, dried (MgSO4) and the solvent was removed in vacu... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.C1CCCC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 2.5 | CC(N)=CC(=O)OC1CCCC1.COC(=O)CC(=O)CF.O=Cc1cccc(Cl)c1Cl>C(C)(=O)OCC>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ae8bbf4cd8384c3382f6799f2cf7e2e9 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1C(F)(F)F>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1C(F)(F)F | ClC=1C(=C(C=O)C(=CC1)F)C(F)(F)F.FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>ClC=1C(=C(C(=CC1)F)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC)C(F)(F)F | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[c:21]([F:22])[cH:23][cH:24][c:25]([Cl:26])[c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1C(F)(F)F | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 7.5 | [{"value": 7.5, "product": "ClC=1C(=C(C(=CC1)F)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 3-Chloro-6-fluoro-2-(trifluoromethyl)benzaldehyde (1.3 g, 5.7 mmoles), methyl 4-fluoro-3-oxobutanoate (0.77 g, 5.7 mmoles) and 1-methylethyl 3-amino-2-butenoate (0.82 g, 5.7 mmoles) were heated under nitrogen with stirring for 1.5 hours at 90°, followed by 1.5 hours at 100° and then 1 hour at 110°. The cooled reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | 1.5 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1C(F)(F)F>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1C(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3f985ae4fcda40fb9f350a1c1e8e47d8 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc([N+](=O)[O-])c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1Cl | ClC1=C(C=O)C=CC=C1[N+](=O)[O-].FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>ClC1=C(C=CC=C1[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[c:28]1[Cl:29]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][C... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc([N+](=O)[O-])c1Cl | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 42.2 | [{"value": 42.2, "product": "ClC1=C(C=CC=C1[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Chloro-3-nitrobenzaldehyde (1.38 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.06 g, 7.5 mmoles) were heated at 90° for 2.5 hours. The reaction mixture was chromatographed on silica eluting with petroleum ether (60°-80°)/ethyl acetate mixtures. The title c... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | null | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1cccc([N+](=O)[O-])c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bb19e9b64f2446549da75cfab4f3bd94 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)cccc1C(F)(F)F>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)cccc1C(F)(F)F | FC1=C(C=O)C(=CC=C1)C(F)(F)F.FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>FCC=1NC(=C(C(C1C(=O)OC)C1=C(C=CC=C1C(F)(F)F)F)C(=O)OC(C)C)C | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[c:21]([F:22])[cH:23][cH:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:1... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)cccc1C(F)(F)F | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)cccc1C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 3 | [{"value": 3.0, "product": "FCC=1NC(=C(C(C1C(=O)OC)C1=C(C=CC=C1C(F)(F)F)F)C(=O)OC(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Fluoro-6-(trifluoromethyl)benzaldehyde (1.51 g, 7.8 mmoles), methyl 4-fluoro-3-oxobutanoate (1.06 g, 7.8 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.13 g, 7.8 mmoles) were heated at 90° under nitrogen with stirring for 2 hours. The cooled reaction mixture was chromatographed twice; first eluting with toluene/eth... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | 2 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)cccc1C(F)(F)F>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)cccc1C(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e30d54292b834134a4f513af2cb9a96d | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1Cl | ClC1=C(C=O)C(=CC=C1Cl)F.FCC(CC(=O)OC)=O.NC(=CC(=O)OC(C)C)C>>ClC1=C(C(=CC=C1Cl)F)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC | [NH2:9][C:10]([CH3:11])=[CH:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][F:8].O=[CH:19][c:20]1[c:21]([F:22])[cH:23][cH:24][c:25]([Cl:26])[c:27]1[Cl:28]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH:16]([CH... | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1Cl | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C:2]-[F;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[C:18](-[C;D1;H3:19])-[NH2;D1;+0:20]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C;H0;D3;+0:17]1=[C:18](-[C;D1;H3:19])-[NH;D2;+0:20]-[C;H0;D3;+0:1... | 33.8 | [{"value": 33.8, "product": "ClC1=C(C(=CC=C1Cl)F)C1C(=C(NC(=C1C(=O)OC(C)C)C)CF)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 2,3-Dichloro-6-fluorobenzaldehyde (1.44 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.06 g, 7.5 mmoles) were heated at 90° under nitrogen with stirring for 2.5 hours. The cooled reaction mixture was chromatographed on silica eluting with ethyl acetate/methyl... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | null | null | 2.5 | CC(N)=CC(=O)OC(C)C.COC(=O)CC(=O)CF.O=Cc1c(F)ccc(Cl)c1Cl>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC(C)C)C1c1c(F)ccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8868992fd39742ee9646853c3df9c183 | CC(=O)CC(=O)OC1CCCC1.O=Cc1cccc(Cl)c1Cl>>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1 | ClC1=C(C=O)C=CC=C1Cl.O=C(CC(=O)OC1CCCC1)C>>ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1CCCC1)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:14](=[O:15])[O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13]>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13])[C:14](=[O:15])[O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1 | CC(=O)CC(=O)OC1CCCC1.O=Cc1cccc(Cl)c1Cl | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1 | null | N1CCCCC1.C(CCCCC)(=O)O | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | O=C(C=Cc1ccccc1)OC1CCCC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | 109 | [{"value": 109.0, "product": "ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1CCCC1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3-dichlorobenzaldehyde (2.5 g, 14.3 mmoles), cyclopentyl 3-oxobutanoate (2.42 g, 14.3 mmoles), piperidine (8 drops) and hexanoic acid (11 drops) in dry benzene (80 ml) was heated at reflux for 4 hours using a Dean and Stark apparatus. The solution was allowed to cool to room temperature and the solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1.C1CCCC1 | HO- | N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1 | null | null | CC(=O)CC(=O)OC1CCCC1.O=Cc1cccc(Cl)c1Cl>N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a018ff87fe284e27a01f07bd10715329 | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1.COC(=O)C=C(N)CF>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1CCCC1)C(C)=O.NC(=CC(=O)OC)CF>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC1CCCC1)C)CF)C(=O)OC | O=[C:10]([CH3:11])[C:12]([C:13](=[O:14])[O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1)=[CH:21][c:22]1[cH:23][cH:24][cH:25][c:26]([Cl:27])[c:28]1[Cl:29].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH2:7][F:8])[NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH:... | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1.COC(=O)C=C(N)CF | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 7d048f90f3321332f5e78fccf2d783540820d373387de5bf37ed73ac6dddd58a | 4d007b3bedb46cd1f5a6303df894b7569d9c2de73165dd8306c8ba76fe8a45e5 | O=C(OC1CCCC1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:14]-[C:13](-[C:12])=[C;H0... | null | [] | null | null | null | null | A solution of the product of step (a) (5.1 g, 14.3 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (1.9 g, 14.3 mmoles) in dry tert-butanol (25 ml) was heated to 60° (oil bath temperature) for 108 hours. The solution was allowed to cool to room temperature and the solvent removed in vacuo. Chromatography on silica elut... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.C1CCCC1.c1ccccc1 | HO- | C(C)(C)(C)O | null | null | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCCC1.COC(=O)C=C(N)CF>C(C)(C)(C)O>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCCC2)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40d2eb20fccb43b288debf4e7f21a1c3 | CC(=O)CC(=O)OC1CCC1.O=Cc1cccc(Cl)c1Cl>>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1 | ClC1=C(C=O)C=CC=C1Cl.O=C(CC(=O)OC1CCC1)C.C(C)(=O)OCC>>ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1CCC1)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:14](=[O:15])[O:16][CH:17]1[CH2:18][CH2:19][CH2:20]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13]>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13])[C:14](=[O:15])[O:16][CH:17]1[CH2:18][CH2:19][CH2:20]1 | CC(=O)CC(=O)OC1CCC1.O=Cc1cccc(Cl)c1Cl | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1 | null | N1CCCCC1.C(CCCCC)(=O)O | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | O=C(C=Cc1ccccc1)OC1CCC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | null | [] | null | null | null | null | A solution of 2,3-dichlorobenzaldehyde (1.57 g, 8.9 mmoles), cyclobutyl 3-oxobutanoate (1.4 g, 8.9 mmoles), piperidine (8 drops) and hexanoic acid (11 drops) in dry benzene (100 ml) was heated at reflux for 12 hours using a Dean and Stark apparatus. The solution was allowed to cool to room temperature and the solvent r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1.C1CCC1 | HO- | N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1 | null | null | CC(=O)CC(=O)OC1CCC1.O=Cc1cccc(Cl)c1Cl>N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6f215c3459dd4856a60fd10a38793d91 | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1.COC(=O)C=C(N)CF>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCC2)C1c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1CCC1)C(C)=O.NC(=CC(=O)OC)CF>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC1CCC1)C)CF)C(=O)OC | O=[C:10]([CH3:11])[C:12]([C:13](=[O:14])[O:15][CH:16]1[CH2:17][CH2:18][CH2:19]1)=[CH:20][c:21]1[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]1[Cl:28].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH2:7][F:8])[NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH:16]2[CH2... | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1.COC(=O)C=C(N)CF | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCC2)C1c1cccc(Cl)c1Cl | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 7d048f90f3321332f5e78fccf2d783540820d373387de5bf37ed73ac6dddd58a | 4d007b3bedb46cd1f5a6303df894b7569d9c2de73165dd8306c8ba76fe8a45e5 | O=C(OC1CCC1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:14]-[C:13](-[C:12])=[C;H0... | null | [] | null | null | null | null | The product of step (a) (1.7 g, 5.4 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (0.72 g, 5.4 mmoles) were mixed and heated to 95° (oil bath temperature) under an atmosphere of nitrogen for 6 hours. The oil was allowed to cool to room temperature. Chromatography on silica eluting with petroleum ether (60°-80° )/ethy... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.C1CCC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | null | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1CCC1.COC(=O)C=C(N)CF>C(C)(=O)OCC>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2CCC2)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-237a8a17b95a433a9d6231ded81408ce | CC(=O)CC(=O)OC1COC1.O=Cc1cccc(Cl)c1Cl>>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1 | ClC1=C(C=O)C=CC=C1Cl.O=C(CC(=O)OC1COC1)C>>ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1COC1)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:14](=[O:15])[O:16][CH:17]1[CH2:18][O:19][CH2:20]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13]>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13])[C:14](=[O:15])[O:16][CH:17]1[CH2:18][O:19][CH2:20]1 | CC(=O)CC(=O)OC1COC1.O=Cc1cccc(Cl)c1Cl | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1 | null | N1CCCCC1.C(CCCCC)(=O)O | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | O=C(C=Cc1ccccc1)OC1COC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | 121.1 | [{"value": 121.1, "product": "ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1COC1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3-dichlorobenzaldehyde (1.33 g, 7.6 mmoles), 3-oxetanyl 3-oxobutanoate (1.2 g, 7.6 mmoles), piperidine (6 drops) and hexanoic acid (8 drops) in dry benzene (80 ml) was heated at reflux using a Dean and Stark apparatus. The solution was allowed to cool to room temperature and the solvent removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1.C1COC1 | HO- | N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1 | null | null | CC(=O)CC(=O)OC1COC1.O=Cc1cccc(Cl)c1Cl>N1CCCCC1.C(CCCCC)(=O)O.C1=CC=CC=C1>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3c7b27071d2a4a3aac8df5aa0a19735f | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1.COC(=O)C=C(N)CF>>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2COC2)C1c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C=C(C(=O)OC1COC1)C(C)=O.NC(=CC(=O)OC)CF>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)OC1COC1)C)CF)C(=O)OC | O=[C:10]([CH3:11])[C:12]([C:13](=[O:14])[O:15][CH:16]1[CH2:17][O:18][CH2:19]1)=[CH:20][c:21]1[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]1[Cl:28].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH2:7][F:8])[NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH:16]2[CH2:1... | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1.COC(=O)C=C(N)CF | COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2COC2)C1c1cccc(Cl)c1Cl | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 7d048f90f3321332f5e78fccf2d783540820d373387de5bf37ed73ac6dddd58a | 4d007b3bedb46cd1f5a6303df894b7569d9c2de73165dd8306c8ba76fe8a45e5 | O=C(OC1COC1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:14]-[C:13](-[C:12])=[C;H0... | null | [] | null | null | null | null | A solution of the product of step (a) (2.9 g, 7.6 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (1 g, 7.6 mmoles) in dry tert-butanol (20 ml) was heated to 60° (oil bath temperature) for 16 hours. The solution was allowed to cool to room temperature and the solvent removed in vacuo. Chromatography on silica, eluting ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.C1COC1.c1ccccc1 | HO- | C(C)(C)(C)O | null | null | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)OC1COC1.COC(=O)C=C(N)CF>C(C)(C)(C)O>COC(=O)C1=C(CF)NC(C)=C(C(=O)OC2COC2)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ec3d7272ec1a49eebd7fd4a8780aeecc | CC(=O)CC(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.O=Cc1cccc(Cl)c1Cl>>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl | O=C(CC(=O)O[C@H](C(Cl)(Cl)Cl)C1=CC=CC=C1)C.ClC1=C(C=O)C=CC=C1Cl>>ClC1=C(C=CC=C1Cl)C=C(C(=O)O[C@H](C(Cl)(Cl)Cl)C1=CC=CC=C1)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:14](=[O:15])[O:16][C@@H:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:24]([Cl:25])([Cl:26])[Cl:27].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13]>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]1[Cl:13])[C:14](=[O:15])[O:16][C@@H:17]([c:18... | CC(=O)CC(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.O=Cc1cccc(Cl)c1Cl | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl | null | C(CCCCC)(=O)O.N1CCCCC1 | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | O=C(C=Cc1ccccc1)OCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | null | [] | null | null | null | null | (S)-2,2,2-Trichloro-1-phenylethyl 3-oxobutanoate (8.6 g 27.5 mmoles) and 2,3-dichlorobenzaldehyde (4.82 g, 27.5 mmoles) in dry benzene (100 ml) were heated at reflux for 5 hours with hexanoic acid (25 drops) and piperidine (8 drops) in a Dean and Stark apparatus. The solvent was evaporated and the residue dissolved in ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1.c1ccccc1 | HO- | C(CCCCC)(=O)O.N1CCCCC1.C1=CC=CC=C1 | null | null | CC(=O)CC(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.O=Cc1cccc(Cl)c1Cl>C(CCCCC)(=O)O.N1CCCCC1.C1=CC=CC=C1>CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-85f0f7b4499d44979dd6f292fd589555 | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.COC(=O)C=C(N)CF>>COC(=O)C1=C(CF)NC(C)=C(C(=O)O[C@@H](c2ccccc2)C(Cl)(Cl)Cl)C1c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C=C(C(=O)O[C@H](C(Cl)(Cl)Cl)C1=CC=CC=C1)C(C)=O.NC(=CC(=O)OC)CF>>ClC1=C(C=CC=C1Cl)C1C(=C(NC(=C1C(=O)O[C@H](C(Cl)(Cl)Cl)C1=CC=CC=C1)C)CF)C(=O)OC | O=[C:10]([CH3:11])[C:12]([C:13](=[O:14])[O:15][C@@H:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C:23]([Cl:24])([Cl:25])[Cl:26])=[CH:27][c:28]1[cH:29][cH:30][cH:31][c:32]([Cl:33])[c:34]1[Cl:35].[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH2:7][F:8])[NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][F:8])[NH:9][C:10... | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.COC(=O)C=C(N)CF | COC(=O)C1=C(CF)NC(C)=C(C(=O)O[C@@H](c2ccccc2)C(Cl)(Cl)Cl)C1c1cccc(Cl)c1Cl | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 7d048f90f3321332f5e78fccf2d783540820d373387de5bf37ed73ac6dddd58a | 4d007b3bedb46cd1f5a6303df894b7569d9c2de73165dd8306c8ba76fe8a45e5 | O=C(OCc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[NH2;D1;+0:14])=[CH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:14]-[C:13](-[C:12])=[C;H0... | null | [] | null | null | null | null | (S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate (10.8 g, 23 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (3.7 g, 28 mmoles) were heated at 55° in dry tert-butanol (50 ml) for 68 hours. The solvent was removed and the residue purified and separated into single diastereomers by HPLC el... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | C(C)(C)(C)O | null | null | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)O[C@@H](c1ccccc1)C(Cl)(Cl)Cl.COC(=O)C=C(N)CF>C(C)(C)(C)O>COC(=O)C1=C(CF)NC(C)=C(C(=O)O[C@@H](c2ccccc2)C(Cl)(Cl)Cl)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c568eb9ea3b2481a8e9057cadfb1c622 | CCOC(=O)C1=C(C)NC(O)(c2ccc([N+](=O)[O-])cc2)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(c2ccc([N+](=O)[O-])cc2)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | FC(C(=O)OC(C(F)(F)F)=O)(F)F.N1=CC=CC=C1.OC1(NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)C1=CC=C(C=C1)[N+](=O)[O-]>>CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C1=CC=C(C=C1)[N+](=O)[O-] | O[C:10]1([c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2)[NH:9][C:7]([CH3:8])=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:26]([c:27]2[cH:28][cH:29][cH:30][c:31]([N+:32](=[O:33])[O-:34])[cH:35]2)[CH:20]1[C:21](=[O:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][... | CCOC(=O)C1=C(C)NC(O)(c2ccc([N+](=O)[O-])cc2)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(c2ccc([N+](=O)[O-])cc2)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 93f830a227bda5024783b9c11259596149601f6d42d27ad0c5216017b2f38792 | 3335be20dbb472ddf447fdf887d896d62a78a299dab790cc759d6133361682fa | C1=CC(c2ccccc2)C=C(c2ccccc2)N1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[#7:5]-[C:6](-[C;D1;H3:7])=[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])-[C:12](-[c:13])-[CH;D3;+0:14]-1-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18]>>[#8:10]-[C:9](=[O;D1;H0:11])-[C:8]1=[C:6](-[C;D1;H3:7])-[#7:5]-[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])=[C;H0;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#8:17]... | 79.4 | [{"value": 79.4, "product": "CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Trifluoroacetic anhydride (0.65 ml, 4.63 mmoles) was added with stirring to pyridine (0.75 ml, 9.26 mmoles) and diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(4-nitrophenyl)-3,5-pyridinedicarboxylate (2.31 g, 4.63 mmoles) in methylene chloride (60 ml). After stirring for 2.5 hours, the solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary alcohol | Enamine | C1=CNCCC1 | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2.5 | CCOC(=O)C1=C(C)NC(O)(c2ccc([N+](=O)[O-])cc2)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)C1=C(C)NC(c2ccc([N+](=O)[O-])cc2)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b069d5e6788f4a148d76392c428235c7 | CC(=O)OO.CCOC(=O)C1=C(C)NC(SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(S(C)=O)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | C(C)(=O)OO.CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)SC.C([O-])(O)=O.[Na+]>>CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)S(=O)C | CC(=O)O[OH:13].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([S:11][CH3:12])=[C:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[CH:20]1[c:21]1[cH:22][cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([S:11]([CH3:12])=[O:13])=[C:14]([C:... | CC(=O)OO.CCOC(=O)C1=C(C)NC(SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(S(C)=O)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 3f94fa67dce0f9d1622f25c2f6b679e0a2528e6d5c5559b15aed37456745a4b5 | 099322fb111e24ec324e6fad75d493a762ca0cd5af0df8c6f3bfd25c910b45a8 | C1=CC(c2ccccc2)C=CN1 | C-C(=O)-O-[OH;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1=[C:6](-[S;H0;D2;+0:7]-[C;D1;H3:8])-[#7:9]-[C:10]=[C:11]-[C:12]-1>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1=[C:6](-[S;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:1])-[#7:9]-[C:10]=[C:11]-[C:12]-1 | null | [] | null | null | 30 | MINUTE | Peracetic acid (6.8 ml of 1M solution in methanol) was added to a solution of diethyl 1,4-dihydro-2-methyl-6-(methylthio)-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (2.77 g 6.8 mmoles) in methylene chloride (150 ml) at -78°. The reaction mixture was allowed to reach room temperature and was then stirred for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfoxide | null | null | C1=CNC=CC1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.5 | CC(=O)OO.CCOC(=O)C1=C(C)NC(SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)C1=C(C)NC(S(C)=O)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b2c0a48c868439f90ea3bd03ef94952 | CCOC(=O)C1=C(C)NC(C(=O)[O-])=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CNC>>CCOC(=O)C1=C(C)NC(C(=O)N(C)C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | S(=O)(Cl)Cl.CC1=C(C(C(=C(N1)C(=O)[O-])C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.CNC.S(=O)(Cl)Cl>>CN(C(=O)C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)C | [O-][C:11]([C:10]1=[C:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH:22]([c:23]2[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]2)[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:7]([CH3:8])[NH:9]1)=[O:12].[NH:13]([CH3:14])[CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([C:11](=[O:12])[N... | CCOC(=O)C1=C(C)NC(C(=O)[O-])=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CNC | CCOC(=O)C1=C(C)NC(C(=O)N(C)C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | CN(C=O)C | C1=CC=CC=C1.C(Cl)Cl | Acylation | OtherReaction | 4cfceec1aea84a79816c41fae0c81172c18248078f31ae4437446c5821f56e86 | abe2f9e72dd5fcaae131e2f313c58ce84793c9db4899e2929efc0f663f613b41 | C1=CC(c2ccccc2)C=CN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1=[C:5](-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7])-[#7:8]-[C:9]=[C:10]-[C:11]-1.[C;D1;H3:12]-[NH;D2;+0:13]-[C;D1;H3:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1=[C:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:13](-[C;D1;H3:12])-[C;D1;H3:14])-[#7:8]-[C:9]=[C:10]-[C:11]-1 | null | [] | null | null | 30 | MINUTE | Thionyl chloride (0.05 ml) was added to a solution of 3,5-diethyl 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2,3,5-pyridinetricarboxylate (0.25 g, 0.62 mmoles) in methylene chloride (10 ml) containing dimethylformamide (1 drop). After 2 hours at room temperature further thionyl chloride (0.05 ml) was added and the solution... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amide | null | null | C1=CNC=CC1.c1ccccc1 | HO- | CN(C=O)C.C1=CC=CC=C1.C(Cl)Cl | null | 0.5 | CCOC(=O)C1=C(C)NC(C(=O)[O-])=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CNC>CN(C=O)C.C1=CC=CC=C1.C(Cl)Cl>CCOC(=O)C1=C(C)NC(C(=O)N(C)C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ef00e214515242c1ac00fbdfc1de8423 | CCOC(=O)C1=C(C)NC(C#N)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.S>>CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | S.C(#N)C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.C(C)N(CC)CC>>NC(C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)=S | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([C:11]#[N:12])=[C:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[CH:20]1[c:21]1[cH:22][cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29]1.[SH2:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([C:11]([NH2:12])=[S:13])=[C:14]([C:15](=[O... | CCOC(=O)C1=C(C)NC(C#N)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.S | CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e858ca50c8e0f3960e54fda65096a6d38225cbf29ed6c75ac395af3f6ab9ac64 | a539a3f8348860a993f5ad9eafc2817db9cbf8629a0115aa2322cd82053b049e | C1=CC(c2ccccc2)C=CN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1=[C:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7])-[#7:8]-[C:9]=[C:10]-[C:11]-1.[SH2;D0;+0:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1=[C:5](-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[S;H0;D1;+0:12])-[#7:8]-[C:9]=[C:10]-[C:11]-1 | null | [] | null | null | 2 | HOUR | Hydrogen sulphide was bubbled through a solution of diethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (1 g, 2.6 mmoles) in triethylamine (0.36 ml, 2.6 mmoles) and pyridine (20 ml) at room temperature for 2 hours. The solution was degassed with nitrogen and poured into water (300 ml). Afte... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Thioamide | null | null | C1=CNC=CC1.c1ccccc1 | null | N1=CC=CC=C1 | null | 2 | CCOC(=O)C1=C(C)NC(C#N)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.S>N1=CC=CC=C1>CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb6d60be096d4d79b315c7d82172beb9 | CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CI.CI>>CCOC(=O)C1=C(C)NC(C(=N)SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.I | CI.NC(C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)=S.CI>>I.N=C(C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)SC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([C:11]([NH2:12])=[S:13])=[C:15]([C:16](=[O:17])[O:18][CH2:19][CH3:20])[CH:21]1[c:22]1[cH:23][cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30]1.I[CH3:14].C[I:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([C:11](=[NH:12])[S:13][... | CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CI.CI | CCOC(=O)C1=C(C)NC(C(=N)SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.I | null | null | CO | Protection | OtherReaction | 06dd7458eb43e87c49d3d52787be46f27aeb3fb25f53a2d8e52a2834b5e011ba | 95180500517d86b687ef61ad12602310894a8df22a6e282a0c6c3b6fad8199a0 | C1=CC(c2ccccc2)C=CN1 | C-[I;H0;D1;+0:1].I-[CH3;D1;+0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1=[C:7](-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10])-[#7:11]-[C:12]=[C:13]-[C:14]-1>>[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1=[C:7](-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[S;H0;D2;+0:10]-[CH3;D1;+0:2])-[#7:11]-[C:12]=[C:13]-[C:14]-1.[IH;D0;+0:1] | 63.1 | [{"value": 63.1, "product": "I.N=C(C=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | Methyl iodide (0.06 ml, 0.96 mmoles) was added to a solution of diethyl 2-(aminothioxomethyl)-1,4-dihydro- 6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (0.2 g, 0.48 mmoles) in methanol (10 ml). After stirring for 16 hours at room temperature methyl iodide (0.1 ml) was added and the stirring continued for 1 day.... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | null | null | C1=CNC=CC1.c1ccccc1 | HI | CO | null | 24 | CCOC(=O)C1=C(C)NC(C(N)=S)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CI.CI>CO>CCOC(=O)C1=C(C)NC(C(=N)SC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.I |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a5355033654e4c89a95591098884e086 | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.CCOC(=O)CC(=O)CF.N>>CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | FCC(CC(=O)OCC)=O.[N+](=O)([O-])C=1C=C(C=CC1)C=C(C(=O)OCC)C(C)=O.N>>FCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:7]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28]1)[CH3:8].O=[C:10]([CH2:11][F:12])[CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18].[NH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH2:11][F:12])=[C:13]([C:14](=[O:15])[O:16]... | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.CCOC(=O)CC(=O)CF.N | CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e739ce5f803990814cace1d467347eb39a775723a72776a728437a2abef98b85 | 743ed9f09a275222ce9889d1f1fefdd092334fc9474eb16405d5bc3340e47eec | C1=CC(c2ccccc2)C=CN1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].O=[C;H0;D3;+0:12](-[C:13]-[F;D1;H0:14])-[CH2;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19].[NH3;D0;+0:20]>>[C:19]-[#8:18]-[C:16](=[O;D1;H0:17])-[C;H0;D3;+0:15]1=[C;H0;D3;+0:12](-[C:13]-[F;D1;H0:14])-[NH;... | null | [] | null | null | null | null | Ethyl 4-fluoro-3-oxobutanoate (1.45 g, 10 mmoles), ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate (2.63 g, 10 mmoles) and aqueous ammonia (1.1 ml, d 0.88) were heated at reflux in ethanol (15 ml) for 6 hours. The solvent was removed in vacuo and the residue purified by chromatography on silica eluting with petroleum e... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.CCOC(=O)CC(=O)CF.N>C(C)O>CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-22f4db88423c4398b127f4bc8242b287 | CCN(CC)S(F)(F)F.CCOC(=O)C1=C(C)NC(CO)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | OCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.C(C)N(CC)S(F)(F)F.C([O-])(O)=O.[Na+]>>FCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | CCN(CC)S(F)(F)[F:12].O[CH2:11][C:10]1=[C:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[CH:19]([c:20]2[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28]2)[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:7]([CH3:8])[NH:9]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH2:11][F:12])=[C:13]([C:14](=[... | CCN(CC)S(F)(F)F.CCOC(=O)C1=C(C)NC(CO)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | dbbac462603ac033e664af439abb66b6ed7f62a050ec8784cc63432806b53147 | 01bb6897491017986ad23d0ca606d7f8fde10cee91f632739e86b0f2d029f08a | C1=CC(c2ccccc2)C=CN1 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]1=[C:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]=[C:10]-[#7:11]-1>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]1=[C:3](-[CH2;D2;+0:2]-[F;H0;D1;+0:1])-[#7:11]-[C:10]=[C:9]-[C:8]-1 | 15.3 | [{"value": 15.3, "product": "FCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Diethyl 1,4-dihydro-2-(hydroxymethyl)-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (0.1 g, 0.25 mmoles) in dry methylene chloride (5 ml) was added to a stirred solution at -60° of diethylaminosulphur trifluoride (0.068 ml, 0.55 mmoles) in dry methylene chloride (10 ml) over 10 minutes. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine | Primary halide | null | null | C1=CNC=CC1.c1ccccc1 | HF | C(Cl)Cl | null | 2.5 | CCN(CC)S(F)(F)F.CCOC(=O)C1=C(C)NC(CO)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)C1=C(C)NC(CF)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0009ec9b3af2413ebee0890ebe5dcbe1 | CC1(C)OC(=O)CC(=O)O1.O=C(Cl)CF>>COC(=O)CC(=O)CF | FCC(=O)Cl.CC1(OC(CC(O1)=O)=O)C.N1=CC=CC=C1>>FCC(CC(=O)OC)=O | C[C:1]1(C)OC(=O)[CH2:5][C:3](=[O:4])[O:2]1.Cl[C:6](=[O:7])[CH2:8][F:9]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[CH2:8][F:9] | CC1(C)OC(=O)CC(=O)O1.O=C(Cl)CF | COC(=O)CC(=O)CF | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | e5ee695d1d78743b8608798a0e36af6a72f4664706b9ea57fe3da683aa6eeb71 | 0b98f3c92810ed1bd18934df20e2dc11eaf0d97d7f977f2dab53d6a8a4ca8348 | null | C-[C;H0;D4;+0:1]1(-C)-O-C(=O)-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-1.Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-[F;D1;H0:9]>>[CH3;D1;+0:1]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:2]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-[F;D1;H0:9] | 65.4 | [{"value": 65.4, "product": "FCC(CC(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Fluoroacetyl chloride (7.1 g, 73 mmoles) was added dropwise to a stirred solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (10.65 g, 74 mmoles) and pyridine (16.85 ml, 210 mmoles) in methylene chloride (75 ml) keeping the temperature below 10°. After stirring for 16 hours at room temperature the solution was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone.Ester | C1COCOC1 | null | null | HCl | C(Cl)Cl | null | 16 | CC1(C)OC(=O)CC(=O)O1.O=C(Cl)CF>C(Cl)Cl>COC(=O)CC(=O)CF |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-703dd6a1b43d49a5ba396824236d92dc | CCOC(=O)CC(=O)CF.COCCO>>COCCOC(=O)CC(=O)CF | FCC(CC(=O)OCC)=O.COCCO>>FCC(CC(=O)OCCOC)=O | CCO[C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][F:12].[CH3:1][O:2][CH2:3][CH2:4][OH:5]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][F:12] | CCOC(=O)CC(=O)CF.COCCO | COCCOC(=O)CC(=O)CF | null | null | null | Protection | Transesterification | 1adccd25c595429871da3756142c075aac7032d22473ca1588e41d51e1a19040 | a6c84db4df003bced50681f216baba6e759c1d4451f21f814c7bb7ee782a7375 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C:5])=[O;D1;H0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | null | null | Ethyl 4-fluoro-3-oxobutanoate (2.1 g) was heated at reflux in 2-methoxyethanol (10 ml) for 3 hours. The solvent was removed in vacuo and the residue distilled to give the title compound as a colourless oil (1.75 g). Nmr (CDCl3)δ4.9 (d,2H,J-48 Hz), 3.4 (s,3H).
Conditions: See reaction.notes.procedure_details.
Workup: Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | null | HO- | null | null | null | CCOC(=O)CC(=O)CF.COCCO>>COCCOC(=O)CC(=O)CF |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb09f0193b7f4887922c4b589c6703b0 | CC(=O)C1C(=O)OC(C)(C)OC1=O.OC1CCOCC1>>CC(=O)CC(=O)OC1CCOCC1 | O1CCC(CC1)O.C(C)(=O)C1C(OC(OC1=O)(C)C)=O>>O=C(CC(=O)OC1CCOCC1)C | CC1(C)OC(=O)[CH:4]([C:2]([CH3:1])=[O:3])[C:5](=[O:6])O1.[OH:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[O:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | CC(=O)C1C(=O)OC(C)(C)OC1=O.OC1CCOCC1 | CC(=O)CC(=O)OC1CCOCC1 | null | null | C1=CC=CC=C1 | Protection | OtherReaction | 22bab1b8663db362f12d655dbc7b565310e09da82048a25f786a69600a4d62e7 | cc13166926a38bb0e4d6ba71bdfbb137bdf532ee03c6adebb454782d3f41ac9b | C1CCOCC1 | C-C1(-C)-O-C(=O)-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])=[O;D1;H0:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-1.[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4])-[C:10] | null | [] | null | null | null | null | A solution of tetrahydro-4H-pyran-4-ol (1.6 ml, 16.8 mmoles) and 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione (3.0 g, 16.1 mmoles) in dry benzene (50 ml) was heated under reflux for 4 hours. The solvent was removed in vacuo and the residue distilled at 146°-151°/14 mm Hg to afford the title product as a colourless oil, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Secondary alcohol | Ketone.Ester | C1COCOC1 | null | C1CCOCC1 | HO- | C1=CC=CC=C1 | null | null | CC(=O)C1C(=O)OC(C)(C)OC1=O.OC1CCOCC1>C1=CC=CC=C1>CC(=O)CC(=O)OC1CCOCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-faae922f17554e71923cbf62d3b798bf | Nc1ccc(Cl)c(C(F)(F)F)c1>>Fc1ccc(Cl)c(C(F)(F)F)c1 | ClC1=C(C=C(C=C1)N)C(F)(F)F.Cl.N(=O)[O-].[Na+].F[B-](F)(F)F.[H+]>>ClC1=C(C=C(C=C1)F)C(F)(F)F | N[c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1 | Nc1ccc(Cl)c(C(F)(F)F)c1 | Fc1ccc(Cl)c(C(F)(F)F)c1 | null | null | O | Functional Group Interconversion | Primary amine to fluoride | f4fea6a3c7b007f3829d29d893f3499a4094808c0f3b2211f4c3483919a690d8 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[F;D1;H0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 37.8 | [{"value": 37.8, "product": "ClC1=C(C=C(C=C1)F)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-3-(trifluoromethyl)benzenamine (19.5 g, 100 mmoles), water (40 ml) and c.hydrochloric acid (40 ml) were heated with stirring on a steam bath until a white solid formed. The mixture was cooled (ice-salt bath) and a solution of sodium nitrite (7 g, 101 mmoles) in water (15 ml) was added over 15 mins. After stirr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | null | null | Nc1ccc(Cl)c(C(F)(F)F)c1>O>Fc1ccc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1ff3c7bf1efc4f8b9c752f5d2e231c42 | CN(C=O)c1ccccc1.FC(F)(F)c1ccccc1Cl>>O=Cc1cccc(C(F)(F)F)c1Cl | S(O)(O)(=O)=O.C(CCC)[Li].ClC1=C(C=CC=C1)C(F)(F)F.CN(C=O)C1=CC=CC=C1>>ClC1=C(C=O)C=CC=C1C(F)(F)F | CN(c1ccccc1)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]1[Cl:13]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]1[Cl:13] | CN(C=O)c1ccccc1.FC(F)(F)c1ccccc1Cl | O=Cc1cccc(C(F)(F)F)c1Cl | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Cl;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7]:[c:8] | null | [] | null | null | 1.5 | HOUR | Butyl lithium (36.4 ml of 1.6M in hexane) was added to a stirred solution at -65° of 1-chloro-2-(trifluoromethyl)-benzene (10 g) in dry tetrahydrofuran (100 ml) over 20 mins. After stirring for 1.5 hours at -65°, a solution of N-methyl-N-phenylformamide (6.85 ml) in tetrahydrofuran (30 ml) was added over 1 hour. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 1.5 | CN(C=O)c1ccccc1.FC(F)(F)c1ccccc1Cl>O1CCCC1>O=Cc1cccc(C(F)(F)F)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-aa32893fef904f078bce9e10111891da | CN(C=O)c1ccccc1.Fc1ccc(Cl)c(Cl)c1>>O=Cc1c(F)ccc(Cl)c1Cl | C(CCC)[Li].CN(C=O)C1=CC=CC=C1.ClC1=C(C=C(C=C1)F)Cl.S(O)(O)(=O)=O>>ClC1=C(C=O)C(=CC=C1Cl)F | CN(c1ccccc1)[CH:2]=[O:1].[cH:3]1[c:4]([F:5])[cH:6][cH:7][c:8]([Cl:9])[c:10]1[Cl:11]>>[O:1]=[CH:2][c:3]1[c:4]([F:5])[cH:6][cH:7][c:8]([Cl:9])[c:10]1[Cl:11] | CN(C=O)c1ccccc1.Fc1ccc(Cl)c(Cl)c1 | O=Cc1c(F)ccc(Cl)c1Cl | null | null | O1CCCC1.CCOCC | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[F;D1;H0:8]):[c:9]>>[Cl;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7](-[F;D1;H0:8]):[c:9] | null | [] | null | null | 2 | HOUR | Butyl lithium (48 ml of 1.6M in hexane, 52.3 mmoles) was added with stirring over 1.5 hours under nitrogen to a solution of 1,2-dichloro-4-fluorobenzene (7.85 g, 47.6 mmoles) in dry tetrahydrofuran (120 ml) at -68°. The solution was stirred at -68° for 2 hours and then N-methyl-N-phenylformamide (6.48 ml) in dry tetrah... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1.CCOCC | null | 2 | CN(C=O)c1ccccc1.Fc1ccc(Cl)c(Cl)c1>O1CCCC1.CCOCC>O=Cc1c(F)ccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4363dabc83874b53a061e880dad7c775 | CCOC(=O)C=C(C)N.CCOC(=O)CC(=O)C(F)(F)F.O=Cc1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(O)(C(F)(F)F)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=O)C=CC1.NC(=CC(=O)OCC)C.FC(C(CC(=O)OCC)=O)(F)F>>OC1(NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)C(F)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]([CH3:8])[NH2:9].[C:10](=[O:11])([C:12]([F:13])([F:14])[F:15])[CH2:16][C:17](=[O:18])[O:19][CH2:20][CH3:21].O=[CH:22][c:23]1[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([OH:11])([C:12]([F:13])(... | CCOC(=O)C=C(C)N.CCOC(=O)CC(=O)C(F)(F)F.O=Cc1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(O)(C(F)(F)F)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 51ed2f65233f861476c7a5f32499b20b24f7a5b70173b37ee173d6e079a43840 | 244bf3f35e4d960f447d5b670897b04cf089280a3dea697fda8b7a0db0532fdf | C1=CC(c2ccccc2)CCN1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15].[C:16]-[#8:17]-[C:18](=[O;D1;H0:19])-[CH;D2;+0:20]=[C:21](-[C;D1;H3:22])-[NH2;D1;+0:23]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[CH;D3;+0:1](-[c:2... | 21.3 | [{"value": 21.3, "product": "OC1(NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Nitrobenzaldehyde (3.0 g, 20 mmoles), ethyl 3-amino-2-butenoate (2.6 g, 20 mmoles) and ethyl 4,4,4-trifluoro-3-oxobutanoate (2.92 ml, 20 mmoles) were heated at reflux in ethanol (25 ml) for 6 hours. The solvent was removed in vacuo and the residue crystallised by the addition of ether/petroleum ether (60°-80°). The r... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Ester.Ester.Tertiary alcohol | null | C1=CNCCC1 | C1=CNCCC1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C=C(C)N.CCOC(=O)CC(=O)C(F)(F)F.O=Cc1cccc([N+](=O)[O-])c1>C(C)O>CCOC(=O)C1=C(C)NC(O)(C(F)(F)F)C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5b2332c698da4b758551572ce287cd08 | CC1(C)OCC(CO)O1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCC2COC(C)(C)O2)cc1 | O.CC1(OCC(O1)CO)C.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCC1OC(OC1)(C)C)C | [OH:9][CH2:10][CH:11]1[CH2:12][O:13][C:14]([CH3:15])([CH3:16])[O:17]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]2[CH2:12][O:13][C:14]([CH3:15])([CH3:16])[O:17]2)[cH:18][cH:19]1 | CC1(C)OCC(CO)O1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCC2COC(C)(C)O2)cc1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCC1COCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 48 | HOUR | To a solution of 7.2 g of 2,2-dimethyl-1,3-dioxolan-4-ylmethanol in 40 ml of pyridine at 0° C. was added 11.3 g of p-toluenesulfonyl chloride in portions. The solution was kept at 25° C. for 48 hours, then poured into water and extracted with diethyl ether. The organic solution was washed twice with water, once with di... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1COCO1 | HCl | N1=CC=CC=C1 | null | 48 | CC1(C)OCC(CO)O1.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCC2COC(C)(C)O2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-84a23c91a8514930a8775314639b68e3 | CC(C)=O.CC([O-])=S>>CC(=S)OCC1COC(C)(C)O1 | C(C)(=S)[O-].[K+].CC(=O)C>>C(C)(=S)OCC1OC(OC1)(C)C | [CH3:5][C:9]([CH3:6])=[O:8].[CH3:1][C:2](=[S:3])[O-:4]>>[CH3:1][C:2](=[S:3])[O:4][CH2:5][CH:6]1[CH2:7][O:8][C:9]([CH3:10])([CH3:11])[O:12]1 | CC(C)=O.CC([O-])=S | CC(=S)OCC1COC(C)(C)O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3cd4c0712ca17e9febb27fc6202b249f405096038e7724c0e3b44e5f2bbaa5eb | 6231a5108abf1d725e03970c2e32db57351d19b0fef926d73a396dd252cd8267 | C1COCO1 | [C;D1;H3:1]-[C:2](-[O-;H0;D1:3])=[S;D1;H0:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](-[CH3;D1;+0:7])=[O;H0;D1;+0:8]>>[C;D1;H3:9]-[C;H0;D4;+0:6]1(-[C;D1;H3:10])-[#8:11]-[CH;D3;+0:7](-[CH2;D2;+0:5]-[O;H0;D2;+0:3]-[C:2](-[C;D1;H3:1])=[S;D1;H0:4])-[C:12]-[O;H0;D2;+0:8]-1 | null | [] | null | null | null | null | A mixture of 13.3 g of the above product and 7.2 g of potassium thioacetate in 300 ml of acetone was refluxed for 10 hours. The resulting mixture was filtered, most of the solvent evaporated off under vacuum and the remaining solution poured into diethyl ether. The solution was washed with water, the organic solvent re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Thiocarbonyl | Ether.Ether.Ether.Thiocarbonyl | null | C1COCO1 | C1COCO1 | null | null | null | null | CC(C)=O.CC([O-])=S>>CC(=S)OCC1COC(C)(C)O1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cf1a75afa44e49b2a2f9d4faab45e775 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>>C/C=C(\C)CC(C(=O)Cl)c1c(O)c2c(c(C)c1OC)COC2=O | CC1=C2C(=C(C(=C1OC)C/C=C(\C)/CCC(=O)O)O)C(=O)OC2.S(=O)(Cl)Cl.CN(C=O)C.ClCCl>>OC1=C2C(OCC2=C(C(=C1C(C(=O)Cl)C\C(=C\C)\C)OC)C)=O | O[C:7]([CH2:6][CH2:5]/[C:3](=[CH:2]/[CH2:1][c:10]1[c:11]([OH:12])[c:13]2[c:14]([c:15]([CH3:16])[c:17]1[O:18][CH3:19])[CH2:20][O:21][C:22]2=[O:23])[CH3:4])=[O:8].O=S(Cl)[Cl:9]>>[CH3:1]/[CH:2]=[C:3](\[CH3:4])[CH2:5][CH:6]([C:7](=[O:8])[Cl:9])[c:10]1[c:11]([OH:12])[c:13]2[c:14]([c:15]([CH3:16])[c:17]1[O:18][CH3:19])[CH2:2... | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl | C/C=C(\C)CC(C(=O)Cl)c1c(O)c2c(c(C)c1OC)COC2=O | null | null | null | Functional Group Interconversion | OtherReaction | 18293ff8156d0fff985593c3be1a092865940a40da0914949f394875a9d4ed75 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1OCc2ccccc21 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5]/[C:6](-[C;D1;H3:7])=[C:8]/[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[c:11](-[O;D1;H1:12]):[c:13]-[C:14](=[O;D1;H0:15])-[#8:16]):[c:17](-[#8:18]):[c:19]>>[#8:18]-[c:17](:[c:19]):[c;H0;D3;+0:10](-[CH;D3;+0:4](-[C:5]/[C:6](-[C;D1;H3:7])=[C:8]/[CH3;D1;+0:9])-... | null | [] | null | null | null | null | A solution of 500 mgs of mycophenolic acid in 10 ml of dichloromethane containing 0.5 ml of thionyl chloride and 0.05 ml of N.N-dimethylformamide was maintained at 25° C. for 3 hours. The volatile components were then distilled off under vacuum to obtain crude (E)-[1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HCl | null | null | null | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>>C/C=C(\C)CC(C(=O)Cl)c1c(O)c2c(c(C)c1OC)COC2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c5373432472a4323af3eae21f7fcb069 | COc1ccnc(CCl)c1C.Cc1cc2[nH]c(S)nc2c(C)c1OC(F)F>>COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1C | FC(OC1=C(C2=C(NC(=N2)S)C=C1C)C)F.Cl.ClCC1=NC=CC(=C1C)OC.C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl>>FC(OC1=C(C2=C(NC(=N2)SCC2=NC=CC(=C2C)OC)C=C1C)C)F | Cl[CH2:8][c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]1[CH3:26].[SH:9][c:10]1[n:11][c:12]2[c:13]([CH3:14])[c:15]([O:16][CH:17]([F:18])[F:19])[c:20]([CH3:21])[cH:22][c:23]2[nH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S:9][c:10]2[n:11][c:12]3[c:13]([CH3:14])[c:15]([O:16][CH:17]([F:18])[F:19])[c:20]([CH3:... | COc1ccnc(CCl)c1C.Cc1cc2[nH]c(S)nc2c(C)c1OC(F)F | COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1C | null | null | CC(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(CSc2nc3ccccc3[nH]2)nc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2.0 g of 5-difluoromethoxy-4,6-dimethyl-1H-benzimidazole-2-thiol and 1.72 g of 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride are heated in 30 ml of 2-propanol for 4 h to the boil. This gives 3.6 g of the dihydrochloride of the title compound. This is dissolved in water and concentrated hydrochloric acid, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | CC(C)O | null | null | COc1ccnc(CCl)c1C.Cc1cc2[nH]c(S)nc2c(C)c1OC(F)F>CC(C)O>COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6a486ee456c447caa9d39a0cf9c900b2 | COc1cc2[nH]c(S)nc2c(OC(F)F)c1OC.COc1ccnc(CCl)c1C>>COc1ccnc(CSc2nc3c(OC(F)F)c(OC)c(OC)cc3[nH]2)c1C | FC(OC1=C(C(=CC=2NC(=NC21)S)OC)OC)F.Cl.ClCC1=NC=CC(=C1C)OC.[OH-].[Na+]>>FC(OC1=C(C(=CC=2NC(=NC21)SCC2=NC=CC(=C2C)OC)OC)OC)F | [SH:9][c:10]1[n:11][c:12]2[c:13]([O:14][CH:15]([F:16])[F:17])[c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]2[nH:26]1.Cl[CH2:8][c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]1[CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S:9][c:10]2[n:11][c:12]3[c:13]([O:14][CH:15]([F:16])[F:17])[c:18]([O:19][CH... | COc1cc2[nH]c(S)nc2c(OC(F)F)c1OC.COc1ccnc(CCl)c1C | COc1ccnc(CSc2nc3c(OC(F)F)c(OC)c(OC)cc3[nH]2)c1C | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(CSc2nc3ccccc3[nH]2)nc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[#7;a:4]:[c:5] | 87.7 | [{"value": 87.0, "product": "FC(OC1=C(C(=CC=2NC(=NC21)SCC2=NC=CC(=C2C)OC)OC)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "FC(OC1=C(C(=CC=2NC(=NC21)SCC2=NC=CC(=C2C)OC)OC)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of 4-difluoromethoxy-5,6-dimethoxy-1H-benzimidazole-2-thiol, 0.75 g of 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride, 0.3 g of sodium hydroxide, 2 ml of water and 10 ml of ethanol are stirred for 2.5 h at 60° C. The mixture is poured onto 100 ml of water and cooled in an ice bath. This gives 1.3 g (87%)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | O.C(C)O | null | null | COc1cc2[nH]c(S)nc2c(OC(F)F)c1OC.COc1ccnc(CCl)c1C>O.C(C)O>COc1ccnc(CSc2nc3c(OC(F)F)c(OC)c(OC)cc3[nH]2)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2e260586ca2f47d4818b96183895a114 | COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC.O=C(OO)c1cccc(Cl)c1>>COc1ccnc(CS(=O)c2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC | ClC=1C=C(C(=O)OO)C=CC1.FC(OC1=C(C2=C(NC(=N2)SCC2=NC=CC(=C2OC)OC)C=C1C)C)F.C([O-])([O-])=O.[Na+].[Na+].S(=S)(=O)([O-])[O-].[Na+].[Na+]>>FC(OC1=C(C2=C(NC(=N2)S(=O)CC2=NC=CC(=C2OC)OC)C=C1C)C)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S:9][c:11]2[n:12][c:13]3[c:14]([CH3:15])[c:16]([O:17][CH:18]([F:19])[F:20])[c:21]([CH3:22])[cH:23][c:24]3[nH:25]2)[c:26]1[O:27][CH3:28].O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][S:9](=[O:10])[c:11]2[n:12][c:13]3[c:14]([CH3:15])[c:16]([O:... | COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC.O=C(OO)c1cccc(Cl)c1 | COc1ccnc(CS(=O)c2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC | null | null | C(C)N(CC)CC.C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S(Cc1ccccn1)c1nc2ccccc2[nH]1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7;a:2]:[c:3]-[C:4]-[S;H0;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[#7;a:2]:[c:3]-[C:4]-[S;H0;D3;+0:5](=[O;H0;D1;+0:1])-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | null | [] | null | null | 15 | MINUTE | 5 ml of a 0.2N solution of m-chloroperoxybenzoic acid in methylene chloride are added dropwise at -40° C. to a solution of 0.39 g (1 mmol) of 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylthio]-4,6-dimethyl-1H-benzimidazole in 20 ml of methylene chloride, and the mixture is stirred for 15 minutes. 0.5 ml of triet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | C(C)N(CC)CC.C(Cl)Cl | null | 0.25 | COc1ccnc(CSc2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC.O=C(OO)c1cccc(Cl)c1>C(C)N(CC)CC.C(Cl)Cl>COc1ccnc(CS(=O)c2nc3c(C)c(OC(F)F)c(C)cc3[nH]2)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-701b9f38ff994ea8ba273450e05ee229 | COc1ccnc(C(C)Sc2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1.O=C(OO)c1cccc(Cl)c1>>COc1ccnc(C(C)S(=O)c2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1 | ClC=1C=C(C(=O)OO)C=CC1.FC(C(F)F)(OC1=CC2=C(NC(=N2)SC(C)C2=NC=CC(=C2)OC)C=C1)F.C([O-])([O-])=O.[Na+].[Na+]>>FC(C(F)F)(OC1=CC2=C(NC(=N2)S(=O)C(C)C2=NC=CC(=C2)OC)C=C1)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[S:10][c:12]2[n:13][c:14]3[cH:15][c:16]([O:17][C:18]([F:19])([F:20])[CH:21]([F:22])[F:23])[cH:24][cH:25][c:26]3[nH:27]2)[cH:28]1.O=C(O[OH:11])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[S:10](=[O:11])[c:12]2[n:13][c:14]3[cH:15][c:16]([O:... | COc1ccnc(C(C)Sc2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1.O=C(OO)c1cccc(Cl)c1 | COc1ccnc(C(C)S(=O)c2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S(Cc1ccccn1)c1nc2ccccc2[nH]1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[S;H0;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[S;H0;D3;+0:6](=[O;H0;D1;+0:1])-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | 51 | [{"value": 51.0, "product": "FC(C(F)F)(OC1=CC2=C(NC(=N2)S(=O)C(C)C2=NC=CC(=C2)OC)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 2 | HOUR | 9.8 g of 80% m-chloroperoxybenzoic acid in 200 ml of dichloromethane are added dropwise at -65° C. to a solution of 19.5 g of ±-5-(1,1,2,2-tetrafluoroethoxy)-2-{[1-(4-methoxy-2-pyridyl)ethyl]thio}-1H-benzimidazole in 1.5 l of dichloromethane. The reaction mixture is stirred for a further 2 h at -40° C. and then stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | ClCCl | -40 | 2 | COc1ccnc(C(C)Sc2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1.O=C(OO)c1cccc(Cl)c1>ClCCl>COc1ccnc(C(C)S(=O)c2nc3cc(OC(F)(F)C(F)F)ccc3[nH]2)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dd4623601ad14987b7dfd26605bbc2f8 | COc1ccnc(C(C)Cl)c1.FC1(F)Oc2cc3nc(S)[nH]c3cc2O1>>COc1ccnc(C(C)Sc2nc3cc4c(cc3[nH]2)OC(F)(F)O4)c1 | FC1(OC=2C(=CC3=C(N=C(N3)S)C2)O1)F.Cl.ClC(C)C1=NC=CC(=C1)OC.[OH-].[Na+].O>>FC1(OC=2C(=CC3=C(N=C(N3)SC(C)C3=NC=CC(=C3)OC)C2)O1)F | Cl[CH:8]([c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25]1)[CH3:9].[SH:10][c:11]1[nH:12][c:13]2[cH:14][c:15]3[c:16]([cH:17][c:18]2[n:19]1)[O:20][C:21]([F:22])([F:23])[O:24]3>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[S:10][c:11]2[n:12][c:13]3[cH:14][c:15]4[c:16]([cH:17][c:18]3[nH:19]2)[O:20][C:21]([F:22... | COc1ccnc(C(C)Cl)c1.FC1(F)Oc2cc3nc(S)[nH]c3cc2O1 | COc1ccnc(C(C)Sc2nc3cc4c(cc3[nH]2)OC(F)(F)O4)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 4eec551f66f8e4e47b6da30a7309d595f94a891e6c04b9f1225423088e637ca2 | a3f569f776a0416bf64495c7f8687449ddba83060d32c689857c61ee18225a5e | c1ccc(CSc2nc3cc4c(cc3[nH]2)OCO4)nc1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[SH;D1;+0:7]-[c:8]1:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:14]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[S;H0;D2;+0:7]-[c:8]1:[n;H0;D2;+0:14]:[c:12](:[c:13]):[c:10](:[c:11]):[nH;D2;+0:9]:1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 80.5 | [{"value": 80.5, "product": "FC1(OC=2C(=CC3=C(N=C(N3)SC(C)C3=NC=CC(=C3)OC)C2)O1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "FC1(OC=2C(=CC3=C(N=C(N3)SC(C)C3=NC=CC(=C3)OC)C2)O1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4 g of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol, 3.6 g of (±)-2-(1-chloroethyl)-4-methoxy-pyridine hydrochloride, 1.4 g of sodium hydroxide, 3 ml of water and 50 ml of ethanol are stirred for 4 h at 65° C. The reaction mixture is concentrated to dryness, the residue is dissolved in 100 ml of 2N hydroch... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1nc2cc3c(cc2[nH]1)OCO3 | HCl | C(C)O | null | null | COc1ccnc(C(C)Cl)c1.FC1(F)Oc2cc3nc(S)[nH]c3cc2O1>C(C)O>COc1ccnc(C(C)Sc2nc3cc4c(cc3[nH]2)OC(F)(F)O4)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d101888eeef84d72bb71fed974de176a | COc1cnc(CO)cc1OC.O=S(Cl)Cl>>COc1c[nH+]c(CCl)cc1OC.[Cl-] | S(=O)(Cl)Cl.OCC1=NC=C(C(=C1)OC)OC.C1(=CC=CC=C1)C>>[Cl-].ClCC1=[NH+]C=C(C(=C1)OC)OC | O[CH2:7][c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[c:10]([O:11][CH3:12])[cH:9]1.O=S([Cl:8])[Cl:13]>>[CH3:1][O:2][c:3]1[cH:4][nH+:5][c:6]([CH2:7][Cl:8])[cH:9][c:10]1[O:11][CH3:12].[Cl-:13] | COc1cnc(CO)cc1OC.O=S(Cl)Cl | COc1c[nH+]c(CCl)cc1OC.[Cl-] | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | a308d6c4edc1be9f15e6233a958eff3616157dd039c98b9e287f5c5e0bdc9c46 | 9b4091cd4cf205a0767d592c748f58d9aed076d9567056ed2bfdc4af71bd7267 | c1cc[nH+]cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6].O=S(-[Cl;H0;D1;+0:7])-[Cl;H0;D1;+0:8]>>[Cl-;H0;D0:7].[Cl;H0;D1;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[nH+;D2:4]:[c:5]:[c:6] | null | [] | 20 | CELSIUS | 4 | HOUR | 3 ml of thionyl chloride, dissolved in 10 ml of methylene chloride, are added dropwise to a solution, cooled to 0° C., of 5 g of 2-hydroxymethyl-4,5-dimethoxypyridine in 40 ml of methylene chloride in the course of one hour, the reaction mixture is then stirred at 20° C. for 4 hours, during which it becomes red-colored... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | c1ccncc1 | c1cc[n+]cc1 | c1cc[n+]cc1 | Other | C(Cl)Cl | 20 | 4 | COc1cnc(CO)cc1OC.O=S(Cl)Cl>C(Cl)Cl>COc1c[nH+]c(CCl)cc1OC.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b5dd7bb02e464399ad3c8d8c36f93e7b | COc1cc(C)[n+]([O-])cc1OC>>COc1cnc(CO)cc1OC | COC1=CC(=[N+](C=C1OC)[O-])C.C(C)(=O)OC(C)=O>>OCC1=NC=C(C(=C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][n+:5]([O-:8])[c:6]([CH3:7])[cH:9][c:10]1[O:11][CH3:12]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[O:11][CH3:12] | COc1cc(C)[n+]([O-])cc1OC | COc1cnc(CO)cc1OC | null | null | null | Miscellaneous | OtherReaction | 7e561d7afee9600ed6bdb2a097e47ef139bafb1884a12ad7f91414ba01df7b33 | 0607ce9ac404b7f992b14bf13602ccd36eb29bd5911f2b79cc25c0bfd203a764 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-;H0;D1:5]):[c:6]:[c:7]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:6]:[c:7] | 74 | [{"value": 74.0, "product": "OCC1=NC=C(C(=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 45 | MINUTE | 19 g of 4,5-dimethoxy-2-methylpyridine 1-oxide are metered into 60 ml of acetic anhydride, warmed to 80° C., in the course of 30 minutes in a manner such that the temperature does not rise above 100° C. After a further 45 minutes at 85° C., excess acetic anhydride is distilled off in vacuo and the oily dark residue, wh... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | null | null | 80 | 0.75 | COc1cc(C)[n+]([O-])cc1OC>>COc1cnc(CO)cc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6cb98f1b0b3442788680bb6f7d9b6d9a | COc1c[n+]([O-])c(C)cc1[N+](=O)[O-].C[O-]>>COc1cc(C)[n+]([O-])cc1OC | C[O-].[Na+].COC=1C(=CC(=[N+](C1)[O-])C)[N+](=O)[O-].S(O)(O)(=O)=O>>COC1=CC(=[N+](C=C1OC)[O-])C | O=[N+]([O-])[c:3]1[cH:4][c:5]([CH3:6])[n+:7]([O-:8])[cH:9][c:10]1[O:11][CH3:12].[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n+:7]([O-:8])[cH:9][c:10]1[O:11][CH3:12] | COc1c[n+]([O-])c(C)cc1[N+](=O)[O-].C[O-] | COc1cc(C)[n+]([O-])cc1OC | null | null | CO | Functional Group Interconversion | OtherReaction | 27f99d080b738ed3c11247d992420b7c028ad8e0895bb75728d6435304986321 | 5d154e9342b990e3d7c4ce2c6f7cc039bc2f1990cb4cb06dbac9dbddc28572dc | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a;+:5](-[O;-;D1;H0:6]):[c:7]:[c:8]:1-[#8:9].[C;D1;H3:10]-[O-;H0;D1:11]>>[#8:9]-[c:8]1:[c:7]:[#7;a;+:5](-[O;-;D1;H0:6]):[c:3](-[C;D1;H3:4]):[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C;D1;H3:10] | 98 | [{"value": 98.0, "product": "COC1=CC(=[N+](C=C1OC)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 15 | HOUR | 20 ml of a 30% strength sodium methylate solution are added dropwise to a suspension of 16.9 g of 5-methoxy-2-methyl-4-nitropyridine 1-oxide in 170 ml of dry methanol and the mixture is stirred at 20° C. for 15 hours and then at 50° C. for 4 hours. The pH is brought to 7 by careful addition of concentrated sulphuric ac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | Other | CO | 20 | 15 | COc1c[n+]([O-])c(C)cc1[N+](=O)[O-].C[O-]>CO>COc1cc(C)[n+]([O-])cc1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d0f0cffea8547a1bb5473ddff2f25e1 | COc1ccc(C)[n+]([O-])c1.O=[N+]([O-])O>>COc1c[n+]([O-])c(C)cc1[N+](=O)[O-] | COC=1C=CC(=[N+](C1)[O-])C.[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>COC=1C(=CC(=[N+](C1)[O-])C)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][n+:5]([O-:6])[c:7]([CH3:8])[cH:9][cH:10]1.O[N+:11](=[O:12])[O-:13]>>[CH3:1][O:2][c:3]1[cH:4][n+:5]([O-:6])[c:7]([CH3:8])[cH:9][c:10]1[N+:11](=[O:12])[O-:13] | COc1ccc(C)[n+]([O-])c1.O=[N+]([O-])O | COc1c[n+]([O-])c(C)cc1[N+](=O)[O-] | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | ca5f1190ddada94452e11b52ea1eb215875524fe8173f14c45d3608500a1c3bf | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cc[nH+]cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5]1:[c:6]:[#7;a;+:7](-[O;-;D1;H0:8]):[c:9](-[C;D1;H3:10]):[c:11]:[cH;D2;+0:12]:1>>[#8:4]-[c:5]1:[c:6]:[#7;a;+:7](-[O;-;D1;H0:8]):[c:9](-[C;D1;H3:10]):[c:11]:[c;H0;D3;+0:12]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | 87 | [{"value": 87.0, "product": "COC=1C(=CC(=[N+](C1)[O-])C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | 21.2 g of 5-methoxy-2-methylpyridine 1-oxide are metered into 35 ml of 65% strength nitric acid, warmed to 60° C., in a manner such that the temperature of the reaction mixture does not rise above 80° C. The mixture is stirred at 80° C. for 1 hour, a further 13 ml of 100% strength nitric acid are added to bring the rea... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | null | 60 | 1 | COc1ccc(C)[n+]([O-])c1.O=[N+]([O-])O>>COc1c[n+]([O-])c(C)cc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0e53d6247c794354adba0fbdbe5f7b4c | COc1ccc(C)nc1.OO>>COc1ccc(C)[n+]([O-])c1 | OO.COC=1C=CC(=NC1)C>>COC=1C=CC(=[N+](C1)[O-])C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[n:8][cH:10]1.O[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[n+:8]([O-:9])[cH:10]1 | COc1ccc(C)nc1.OO | COc1ccc(C)[n+]([O-])c1 | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | d7f3c84fb751fef5567bc0e84a2e7c0afb271257e8dfb17aa871e038ff1a84c7 | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1cc[nH+]cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | 77 | [{"value": 77.0, "product": "COC=1C=CC(=[N+](C1)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 120 g pf 30% strength hydrogen peroxide solution are added dropwise to a solution of 60.9 g of 5-methoxy-2-methylpyridine in 300 ml of glacial acetic acid at 60° C. in the course of 1 hour and the mixture is subsequently stirred for 3 hours. After destruction of excess percompounds by addition of active manganese dioxi... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | C(C)(=O)O | null | 3 | COc1ccc(C)nc1.OO>C(C)(=O)O>COc1ccc(C)[n+]([O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6c26ef79c3734661a4290cb07892fd55 | CO.Cc1ccc(O)cn1>>COc1ccc(C)nc1 | OC=1C=NC(=CC1)C.[OH-].[K+].CO>>COC=1C=CC(=NC1)C | O[CH3:1].[OH:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[n:8][cH:9]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[n:8][cH:9]1 | CO.Cc1ccc(O)cn1 | COc1ccc(C)nc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 4622e7934dd5328af1014056d8882932e5f303d08f873e671539ebf0ad57f848 | 51e77d0fe280879eec2f84298441067b61501ac5af19ab94008f56517f7456b2 | c1ccncc1 | O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 56 | [{"value": 56.0, "product": "COC=1C=CC(=NC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 15 | HOUR | 150 ml of 3-hydroxy-6-methylpyridine are metered into a solution of 84 g of potassium hydroxide in 400 ml of methanol and 500 ml of dimethyl sulphoxide in the course of one hour. After removal of the methanol on a rotary evaporator, 213 g of methyl iodide, dissolved in 100 ml of dimethyl sulphoxide, are added dropwise,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether | null | null | c1ccncc1 | HO- | CS(=O)C | 20 | 15 | CO.Cc1ccc(O)cn1>CS(=O)C>COc1ccc(C)nc1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.