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-c3a75813d0b24864aa4f7cd526efd6aa | ord-de7f9117544941b58fe05a3b6a6abcd9 | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>>O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C(=O)O)C=C3)=O.C(C(=O)Cl)(=O)Cl.CN(C=O)C>>FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C(=O)Cl)C=C3)=O | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]4[nH:18][cH:19][c:20]-3[c:21]2=[O:22])[cH:23][cH:24]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]4[nH:18][cH:19][c:20]-3[c:21]2=... | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | 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] | 99 | [{"value": 99.0, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C(=O)Cl)C=C3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 3 | HOUR | To a suspension of finely ground 4-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoic acid (1.1 g. 3.4 mmol) in dichloromethane (6 ml) was added oxalyl chloride (2.4 ml, 29 mmol) followed by a drop of dimethyl formamide. The mixture was stirred under nitrogen at 45° C. for 3 h. The solvent was removed in... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | HCl | ClCCl | 45 | 3 | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>ClCCl>O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0a9987fba804406a5ad7e3620f944c8 | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>>CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1.Cl | FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C(=O)Cl)C=C3)=O.CN(CCCN)C>>Cl.CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7].[C:8](=[O:9])([c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]4[cH:18][cH:19][cH:20][c:21]([F:22])[c:23]4[nH:24][cH:25][c:26]-3[c:27]2=[O:28])[cH:29][cH:30]1)[Cl:31]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]... | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1.Cl | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[Cl;H0;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9].[ClH;D0;+0:4] | 53 | [{"value": 53.0, "product": "Cl.CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.6, "product": "Cl.CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a partial solution of 4-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoyl chloride (0.1 g, 0.3 mmol) in tetrahydrofurane (5 ml) under nitrogen was added a solution of 3-dimethylamino-propyl amine (0.03 g, 0.3 mmol) in tetrahydrofurane. The mixture was stirred at rt for 90 minutes. The solvent was rem... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | null | O1CCCC1 | null | 1.5 | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>O1CCCC1>CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c9731bb3eec402c862e43f2dccd3054 | CCOC(=O)COC#N.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>>CCOC(=O)CNC(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | O.O(C#N)CC(=O)OCC.NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.CN(C=O)C>>C(C)OC(CNC(=O)NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:9][C:8]#[N:7].[NH2:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[n:16][c:17]3[c:18]4[cH:19][cH:20][cH:21][c:22]([F:23])[c:24]4[nH:25][cH:26][c:27]-3[c:28]2=[O:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[n:... | CCOC(=O)COC#N.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | CCOC(=O)CNC(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d3fa590c406383703a06396aa0a74d0ff12812878c20f7c6d1c9b72857232ec5 | e0e6e17835ffb90ed25d1370bd81769d9371700d8697fc8bf30fa3f2251d1c16 | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[C;H0;D2;+0:7]#[N;H0;D1;+0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[NH;D2;+0:8]-[C;H0;D3;+0:7](=[O;H0;D1;+0:6])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | 16 | HOUR | Ethyl cyanatoacetate (31 mg, 0.24 mmol) was added in one portion to a stirred solution of 2-(4-aminophenyl)-6-fluoro-2,5-dihydropyrazolo[4,3-c]quinolin-3-one (intermediate 2) (50 mg, 0.17 mmol) in N,N-dimethylformamide (2 ml) and the mixture stirred at room temperature for 16 h. Water (1 ml) was then added to the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Nitrile.Primary amine | Ester.Urea | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | null | null | null | 16 | CCOC(=O)COC#N.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>>CCOC(=O)CNC(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd748a9264b7496b92cc25c146887dc5 | COC(=O)C#N.O=C1CCSc2ccccc21>>COC(=O)C1CSc2ccccc2C1=O | S1CCC(C2=CC=CC=C12)=O.[Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].CCCCCC.C(#N)C(=O)OC>>O=C1C(CSC2=CC=CC=C12)C(=O)OC | N#C[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][S:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][S:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)C#N.O=C1CCSc2ccccc21 | COC(=O)C1CSc2ccccc2C1=O | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 3f5e1dab2b9ef219d58e7426e20576645bbd1219860adff413bd963c90326325 | ea62efa90ef3cfb13125a23e62e9e1787aa2a0b0ee48c8a61b3326a3bda24134 | O=C1CCSc2ccccc21 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[#16:9]-[c:10]:[c:11]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[#16:9]-[c:10]:[c:11]-[C:6]-1=[O;D1;H0:5] | 42 | [{"value": 42.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | Dry tetrahydrofuran (60 ml) was cooled under nitrogen atmosphere to −50 to −60° C. 1M Lithium bis(trimethylsily)amide solution in hexane (56 ml, 56 mmol) was added. The temperature was kept at −50 to −60° C. and thiochroman-4-one was added dropwise over 20 min. Stirring was continued at low temperature for 60 min. Meth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Ketone.Ester | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | Other | O1CCCC1 | null | 1 | COC(=O)C#N.O=C1CCSc2ccccc21>O1CCCC1>COC(=O)C1CSc2ccccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c02072ef1c74c44a9c0d13dfd9d66f4 | O=C(O)c1ccc(N2N=C3c4ccccc4SCC3C2=O)cc1>>O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 | O.O=C1C2C(=NN1C1=CC=C(C(=O)O)C=C1)C=1C=CC=CC1SC2.C1(=C(C(=O)C(=O)C(=C1Cl)Cl)Cl)Cl>>O=C1C=2C(=NN1C1=CC=C(C(=O)O)C=C1)C=1C=CC=CC1SC2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[N:9]=[C:10]3[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[S:17][CH2:18][CH:19]3[C:20]2=[O:21])[cH:22][cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[s:17][cH:18][c:19]-3[c:20]2=[O:21])[cH:22][cH:23]1 | O=C(O)c1ccc(N2N=C3c4ccccc4SCC3C2=O)cc1 | O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 | null | null | CS(=O)C | Miscellaneous | OtherReaction | b54080b6cee2de4ba45f1f1c5e85b56fa423cf6d6c29328f1c24155da83e50e1 | 54f05125c5e4f16b58b7c0463d2268ccbc57ca95bcd8d4cbe5653d15b69e77ad | O=c1c2csc3ccccc3c-2nn1-c1ccccc1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH;D3;+0:3]2-[CH2;D2;+0:4]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9])-[C;H0;D3;+0:10]-2=[N;H0;D2;+0:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[c;H0;D3;+0:3]2:[cH;D2;+0:4]:[s;H0;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:10]-2:[n;H... | 92.2 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Crude 4-(3-Oxo-3a,4-dihydro-3H-thiochromeno[4,3-c]pyrazol-2-yl)-benzoic acid (250 mg, 0.77 mmol) was dissolved in dimethyl sulphoxide (6 ml). O-Chloranil (189 mg, 0.77 mmol) was added and the mixture was stirred at room temperature overnight. Water (20 ml) was added and the solids were collected by filtration and washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Monosulfide | null | c1ccc2c(c1)SCC1C[NH]N=C21 | c1ccc2c(c1)scc1cnnc12 | c1ccccc1.c1ccc2c(c1)scc1cnnc12 | null | CS(=O)C | null | 8 | O=C(O)c1ccc(N2N=C3c4ccccc4SCC3C2=O)cc1>CS(=O)C>O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4bc137e7d1804b629cef2ec91fc0bb15 | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1>>CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(N(C)C)=[N+](C)C.O=C1C=2C(=NN1C1=CC=C(C(=O)O)C=C1)C=1C=CC=CC1SC2.C(C)(C)N(CC)C(C)C.CN(CCCN)C>>CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(C1=O)=CSC=1C=CC=CC12)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[s:23][cH:24][c:25]-3[c:26]2=[O:27])[cH:28][cH:29]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c... | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 | CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 | null | null | CC(=O)N(C)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1c2csc3ccccc3c-2nn1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | 4-(3-oxothiochromeno[4,3-c]pyrazol-2(3H)-yl)benzoic acid (55 mg, 0.17 mmol) was suspended in anhydrous dimethyl acetamide (1 ml). Diisopropyl-ethyl amine (46.5 mg, 0.36 mmol, 62μl) was added followed by 3-dimethylaminopropylamine (17.5 mg, 0.17 mmol) and [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammoniu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)scc1cnnc12 | HO- | CC(=O)N(C)C | null | 4 | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1>CC(=O)N(C)C>CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4scc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7cd3c411adac4a7fa21536a15e530d0e | C=CC(=O)O.Fc1ccccc1S>>O=C(O)CCSc1ccccc1F | Cl.C(C=C)(=O)O.FC1=C(C=CC=C1)S.C(C)N(CC)CC>>FC1=C(C=CC=C1)SCCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH2:5].[SH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[F:13]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[F:13] | C=CC(=O)O.Fc1ccccc1S | O=C(O)CCSc1ccccc1F | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | thia-Michael addition | 9c1714ade80d0bfd6c4747e19bbd5e181aebdd6e70fcf1c4b03944a726aeaf5d | ff275b76dc1ff1d0f3afaf057f654852a0a807709b71c50992bfc9df07afc001 | c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:4]=[C:3](-[O;D1;H1:5])-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 54 | [{"value": 54.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.6, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-Fluorothiophenol (5.0 g, 39 mmol) was dissolved in tetrahydrofuran (50 ml) under a nitrogen atmosphere. Triethylamine (3.94 g, 5.33 ml, 85.8 mmol) was added. Acrylic acid (2.81 g, 2.67 ml, 39 mmol) was dissolved in tetrahydrofuran and added dropwise to the reaction solution over 2 h at room temperature. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Vinyl | Monosulfide | null | null | c1ccccc1 | null | O1CCCC1 | null | 8 | C=CC(=O)O.Fc1ccccc1S>O1CCCC1>O=C(O)CCSc1ccccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0ed496bc0d24e5ea9c582b5cb459602 | O=C(O)CCSc1ccccc1F>>O=C1CCSc2c(F)cccc21 | FC1=C(C=CC=C1)SCCC(=O)O>>FC=1C=CC=C2C(CCSC12)=O | O[C:2](=[O:1])[CH2:3][CH2:4][S:5][c:6]1[c:7]([F:8])[cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][S:5][c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]21 | O=C(O)CCSc1ccccc1F | O=C1CCSc2c(F)cccc21 | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 2b3e47a7492da189595533ae2c2253a30a5eb1f4c16186cb22b5c4ebaba9bbba | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCSc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#16:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[#16:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10] | 58 | [{"value": 58.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 3 | HOUR | 3-[(2-Fluorophenyl)sulfanyl]propanoic acid (4.0 g, 20 mmol) was mixed with concentrated sulphuric acid (20 ml) at 0–5° C. The reaction solution was stirred at 0 to 5° C. for 3 h then allowed to warm up to room temperature overnight. The mixture was quenched dropwise into ice to give a white suspension. The aqueous phas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HO- | S(O)(O)(=O)=O | 2.5 | 3 | O=C(O)CCSc1ccccc1F>S(O)(O)(=O)=O>O=C1CCSc2c(F)cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-849badeab25e42c8b3d493e2813469e2 | COC(=O)C#N.O=C1CCSc2c(F)cccc21>>COC(=O)C1CSc2c(F)cccc2C1=O | [Cl-].[NH4+].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(#N)C(=O)OC.FC=1C=CC=C2C(CCSC12)=O>>FC=1C=CC=C2C(C(CSC12)C(=O)OC)=O | N#C[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][S:7][c:8]2[c:9]([F:10])[cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][S:7][c:8]2[c:9]([F:10])[cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16] | COC(=O)C#N.O=C1CCSc2c(F)cccc21 | COC(=O)C1CSc2c(F)cccc2C1=O | null | null | O1CCCC1.O.CCCCCC | C-C Coupling | OtherReaction | 3f5e1dab2b9ef219d58e7426e20576645bbd1219860adff413bd963c90326325 | ea62efa90ef3cfb13125a23e62e9e1787aa2a0b0ee48c8a61b3326a3bda24134 | O=C1CCSc2ccccc21 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[#16:9]-[c:10]:[c:11]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[#16:9]-[c:10]:[c:11]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | 1M Lithium hexamethyldisilazide solution in hexane (13.2 ml) was dissolved in anhydrous tetrahydrofuran (20 ml) under nitrogen atmosphere. The solution was cooled to −78° C. 8-Fluoro-2,3-dihydro-4H-thiochromen-4-one (2.00 g, 11 mmol) was dissolved in tetrahydrofuran (40 ml), the solution was transferred to the dropping... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Ketone.Ester | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | Other | O1CCCC1.O.CCCCCC | -78 | 2 | COC(=O)C#N.O=C1CCSc2c(F)cccc21>O1CCCC1.O.CCCCCC>COC(=O)C1CSc2c(F)cccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-849c69306ec241d49b259195912ecea5 | COC(=O)C1CSc2c(F)cccc2C1=O.NNc1ccc(C(=O)O)cc1>>O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 | FC=1C=CC=C2C(C(CSC12)C(=O)OC)=O.N(N)C1=CC=C(C(=O)O)C=C1.C(C)(=O)O>>FC1=CC=CC2=C1SC=C1C2=NN(C1=O)C1=CC=C(C(=O)O)C=C1 | CO[C:21]([CH:20]1[C:10](=O)[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[S:18][CH2:19]1)=[O:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][NH2:9])[cH:23][cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]4[s:18][cH:19][c:20]-3[c:21]2=[O:22]... | COC(=O)C1CSc2c(F)cccc2C1=O.NNc1ccc(C(=O)O)cc1 | O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 0a103335ebcf29bf85a9dd659e53557f54e3dfd714c998dc25bfbdea06ab977b | b73272fe514a017930912c98f85fb1ccc55aa3f60622ec45b0daa39338a9b767 | O=c1c2csc3ccccc3c-2nn1-c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9])-[C;H0;D3;+0:10]-1=O.[NH2;D1;+0:11]-[NH;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[c;H0;D3;+0:3]2:[cH;D2;+0:4]:[s;H0;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:10]-2:[n... | 10.3 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.3, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 8-fluoro-4-oxothiochromane-3-carboxylate (1.19 g, 4.95 mmol) and 4-hydrazinobenzoic acid (755 mg, 4.95 mmol) were mixed with glacial acetic acid (10 ml). The mixture was heated to reflux for 4 h. Excess acetic acid was removed under vacuum to give an orange oil. Ethyl acetate (10 ml) was added and the mixture so... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Monosulfide | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)scc1cnnc12 | c1ccccc1.c1ccc2c(c1)scc1cnnc12 | HO- | C(C)(=O)OCC | null | null | COC(=O)C1CSc2c(F)cccc2C1=O.NNc1ccc(C(=O)O)cc1>C(C)(=O)OCC>O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7211bc94ac1349c49ceee66c042b8421 | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1>>CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 | CN(CCCN)C.C(C)(C)N(CC)C(C)C.FC1=CC=CC2=C1SC=C1C2=NN(C1=O)C1=CC=C(C(=O)O)C=C1.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(N(C)C)=[N+](C)C>>CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(C1=O)=CSC=1C(=CC=CC12)F)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]4[cH:18][cH:19][cH:20][c:21]([F:22])[c:23]4[s:24][cH:25][c:26]-3[c:27]2=[O:28])[cH:29][cH:30]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c... | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 | CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 | null | null | CC(=O)N(C)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1c2csc3ccccc3c-2nn1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | 4-(6-Fluoro-3-oxothiochromeno[4,3-c]pyrazol-2(3H)-yl)benzoic acid (41 mg, 0.12 mmol) was dissolved in anhydrous dimethyl-acetamide(1 ml). Diisopropyl-ethyl amine (46 mg, 0.36 mmol, 62 μl) was added followed by [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium hexafluoro phosphate (65 mg, 0.17 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)scc1cnnc12 | HO- | CC(=O)N(C)C | null | 8 | CN(C)CCCN.O=C(O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1>CC(=O)N(C)C>CN(C)CCCNC(=O)c1ccc(-n2nc3c4cccc(F)c4scc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a30e635efc747dabd7838cc8a808026 | COc1cc(N)c(C(=O)O)cc1OC.NC=O>>COc1cc2nc[nH]c(=O)c2cc1OC | COC=1C=C(C(C(=O)O)=CC1OC)N.C(=O)N>>COC=1C=C2C(NC=NC2=CC1OC)=O | O[C:9](=[O:10])[c:11]1[c:5]([NH2:6])[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12]1.O=[CH:7][NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][nH:8][c:9](=[O:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc(N)c(C(=O)O)cc1OC.NC=O | COc1cc2nc[nH]c(=O)c2cc1OC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 5215b2aebdf37498a4d4a87048f2b5a68a2aa2731f8695ccc5897fee02296c51 | 42d7d0d29a255bcbf4fdad9c0b39487d2cf609ac6796e99c9c033d59efbdbdc9 | O=c1[nH]cnc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 18 | [{"value": 18.0, "product": "COC=1C=C2C(NC=NC2=CC1OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 190 | CELSIUS | 3 | HOUR | A mixture of 4,5-dimethoxyanthranilic acid (19.7 g, 100 mmol) and formamide (10 ml) was heated at 190° C. for 5 hours. The mixture was allowed to cool to approximately 80° C. and water (50 ml) was added. The mixture was then allowed to stand at ambient temperature for 3 hours. Collection of the solid by suction filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | O | 190 | 3 | COc1cc(N)c(C(=O)O)cc1OC.NC=O>O>COc1cc2nc[nH]c(=O)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52fa94082cc6450aa658d5bcc31e2e0f | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1OC | CN(C=O)C.COC=1C=C2C(NC=NC2=CC1OC)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OC | O=[c:9]1[nH:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12][c:11]21.O=S(Cl)[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl | COc1cc2ncnc(Cl)c2cc1OC | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 98 | [{"value": 98.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethylformamide (0.2 ml) was added dropwise to a solution of 6,7-dimethoxy-3,4-dihydro-quinazolin-4-one (10.0 g, 48.5 mmol) in thionyl chloride (200 ml) and the reaction was heated at reflux for 6 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-843c3ac7f2d94cf9be1593fb8f68f4b4 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | NC1=C(C(=O)N)C=C(C(=C1)OCC1=CC=CC=C1)OC.CN(C)C=NC=[N+](C)C.[Cl-].C(C)(=O)[O-].[Na+].C(C)(=O)O>>C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 0798449d56bc7e7756a703d33bd60780d26c4986e39e1809e15228456c95135b | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (10 g, 0.04 mol), (prepared according to J Med. Chem. 1977, 20, 146–149), and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | O1CCOCC1 | null | null | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>O1CCOCC1>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2180fb6bfb1f4374a267f228137b431d | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | CN(C=O)C.COC=1C=C2C(NC=NC2=CC1OCC1=CC=CC=C1)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1=CC=CC=C1 | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 90 | [{"value": 90.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (10 g, 0.04 mol), (prepared according to J Med. Chem. 1977, 20, 146–149), and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40883f32ac2e49d894bc6c508a078743 | CC(C)(C)OC(=O)Nc1ccc(N)cc1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)ncnc2cc1OCCCN1CCOCC1.Cl.Cl | C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1>>Cl.Cl.C(=O)(OC(C)(C)C)NC1=CC=C(NC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1 | [NH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:38])[n:22][cH:23][n:24][c:25]2[cH:26][c:27]1[O:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8... | CC(C)(C)OC(=O)Nc1ccc(N)cc1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)ncnc2cc1OCCCN1CCOCC1.Cl.Cl | null | null | C(C)(C)O | Functional Group Addition | Goldberg coupling aryl amine-aryl chloride | c6cd75578a0e012699a72b942ff8ae972025db694d8529f29ae62196b2270816 | 6f78585f8136bfeb64030c4a3c4021c4cf8a554288637e24070b99b83b5f9b48 | c1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13] | 189.4 | [{"value": 95.0, "product": "Cl.Cl.C(=O)(OC(C)(C)C)NC1=CC=C(NC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 189.4, "product": "Cl.Cl.C(=O)(OC(C)(C)C)NC1=CC=C(NC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCOCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(t-butoxycarbonyl) 4-aminoaniline (5.73 g, 27.5 mmol), and 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (8.44 g, 25.0 mmol), in isopropanol (100 ml) was heated at reflux for 3.5 hours before the reaction was allowed to cool to ambient temperature. The solid which had precipitated was collected ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.C1COCC[NH]1 | Other | C(C)(C)O | null | null | CC(C)(C)OC(=O)Nc1ccc(N)cc1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>C(C)(C)O>COc1cc2c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)ncnc2cc1OCCCN1CCOCC1.Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9315e24e2cc145ea9b69ce2304646676 | COc1cc2ncnc(Cl)c2cc1OC.Cc1cc(N)ccc1O>>COc1cc2ncnc(Nc3ccc(O)c(C)c3)c2cc1OC | NC1=CC(=C(C=C1)O)C.Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>OC1=C(C=C(NC2=NC=NC3=CC(=C(C=C23)OC)OC)C=C1)C | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[cH:20][c:19]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[c:16]([CH3:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[c:16]([CH3:17])[cH:18]3)[c:19]2[cH:20][c:21]1[O:22][CH3:23] | COc1cc2ncnc(Cl)c2cc1OC.Cc1cc(N)ccc1O | COc1cc2ncnc(Nc3ccc(O)c(C)c3)c2cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 100.4 | [{"value": 90.0, "product": "OC1=C(C=C(NC2=NC=NC3=CC(=C(C=C23)OC)OC)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.4, "product": "OC1=C(C=C(NC2=NC=NC3=CC(=C(C=C23)OC)OC)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | An analogous reaction to that described in example 17, but starting with 4-amino-2-methylphenol (6.98 g, 56.7 mmol) and 4-chloro-6,7-dimethoxyquinazoline hydrochloride (14.79 g, 56.7 mmol), yielded 4-(4-hydroxy-3-methylanilino)-6,7-dimethoxyquinazoline (17.72 g, 90% yield) as a white solid:
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2ncnc(Cl)c2cc1OC.Cc1cc(N)ccc1O>>COc1cc2ncnc(Nc3ccc(O)c(C)c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d0f46ed66344ababd2968acf69646d1 | Cc1ccnc(C)c1>>Cc1ccnc(CO)c1 | C(CCC)[Li].N1=C(C=C(C=C1)C)C.O1CCCC1>>OCC1=NC=CC(=C1)C | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[cH:9]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][OH:8])[cH:9]1 | Cc1ccnc(C)c1 | Cc1ccnc(CO)c1 | null | null | null | Oxidation | OtherReaction | 36edec4b18ce2c3a7fbeb76481511ea71ce3ba4a327f9e1abe4335c19ec851f6 | 3084524a2724b3ba38ce3a72d459533eef64cd59178be6bea9c6cc1599f7369b | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[O;D1;H1:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 14 | [{"value": 14.0, "product": "OCC1=NC=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | n-Butyllithium (24 ml of a 1.6 N solution in hexanes, 38.4 mmol) was added to a stirred solution of 2,4-lutidine (4.28 g, 40 mmol) in tetrahydrofuran (70 ml) at −70° C. under an inert atmosphere. After 1 hour, air was bubbled through (for 1 hour), methanol (50 ml) was added and the reaction allowed to warm to ambient t... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccncc1 | Other | null | null | 1 | Cc1ccnc(C)c1>>Cc1ccnc(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10cc6fb9e6c1443a9c00431dcefdc644 | Cc1cc([N+](=O)[O-])ccc1F.Cc1ccnc(CO)c1>>Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1 | O.[H-].[Na+].OCC1=NC=CC(=C1)C.FC1=C(C=C(C=C1)[N+](=O)[O-])C>>CC1=CC(=NC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])C | F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][OH:8])[cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[CH3:18])[cH:19]1 | Cc1cc([N+](=O)[O-])ccc1F.Cc1ccnc(CO)c1 | Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1 | null | null | CN1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCc2ccccn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[#7;a:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#7;a:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | 70 | [{"value": 70.0, "product": "CC1=CC(=NC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "CC1=CC(=NC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | n-Butyllithium (24 ml of a 1.6 N solution in hexanes, 38.4 mmol) was added to a stirred solution of 2,4-lutidine (4.28 g, 40 mmol) in tetrahydrofuran (70 ml) at −70° C. under an inert atmosphere. After 1 hour, air was bubbled through (for 1 hour), methanol (50 ml) was added and the reaction allowed to warm to ambient t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HF | CN1CCCC1 | null | 18 | Cc1cc([N+](=O)[O-])ccc1F.Cc1ccnc(CO)c1>CN1CCCC1>Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11cd4acbba344daca3f83b1f8d725a79 | Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1>>Cc1ccnc(COc2ccc(N)cc2C)c1 | CC1=CC(=NC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])C>>CC=1C=C(N)C=CC1OCC1=NC=CC(=C1)C | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][c:6]2[n:5][cH:4][cH:3][c:2]([CH3:1])[cH:17]2)[c:15]([CH3:16])[cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]2[CH3:16])[cH:17]1 | Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1 | Cc1ccnc(COc2ccc(N)cc2C)c1 | null | [Pt] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 63.2 | [{"value": 63.0, "product": "CC=1C=C(N)C=CC1OCC1=NC=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "CC=1C=C(N)C=CC1OCC1=NC=CC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | n-Butyllithium (24 ml of a 1.6 N solution in hexanes, 38.4 mmol) was added to a stirred solution of 2,4-lutidine (4.28 g, 40 mmol) in tetrahydrofuran (70 ml) at −70° C. under an inert atmosphere. After 1 hour, air was bubbled through (for 1 hour), methanol (50 ml) was added and the reaction allowed to warm to ambient t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pt].C(C)O | null | 2 | Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1>[Pt].C(C)O>Cc1ccnc(COc2ccc(N)cc2C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3139add950a241538b1fdd06676b0e95 | COC(=O)C1(C)C=C(OC)C=CN1>>COc1ccnc(CO)c1 | [C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O.[Na+].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=CC(NC=C1)(C)C(=O)OC>>OCC1=NC=CC(=C1)OC | CO[C:8]([C:7]1(C)[NH:6][CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:10]1)=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][OH:9])[cH:10]1 | COC(=O)C1(C)C=C(OC)C=CN1 | COc1ccnc(CO)c1 | null | null | C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | e214d0dac7edc86590150c7ec7e9615b1f4d1464d7c6672345c4d03da25bfbce | 31939348e3671c2efe091cd0d39835c9d512402ac09689f0d7586bbfec0be7a5 | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C;H0;D4;+0:3]1(-C)-[CH;D2;+0:4]=[C;H0;D3;+0:5](-[#8:6]-[C;D1;H3:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[NH;D2;+0:10]-1>>[C;D1;H3:7]-[#8:6]-[c;H0;D3;+0:5]1:[cH;D2;+0:4]:[c;H0;D3;+0:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[n;H0;D2;+0:10]:[cH;D2;+0:9]:[cH;D2;+0:8]:1 | 36 | [{"value": 36.0, "product": "OCC1=NC=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.9, "product": "OCC1=NC=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2-picolinic acid (10.7 g, 87 mmol) in thionyl chloride (50 ml) was heated at reflux for 18 hours before being cooled and evaporated in vacuo. The residue was treated with methanol (25 ml) and then added to a solution of sodium methoxide prepared from sodium (1.0 g, 43 mmol) and methanol (100 ml). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ether | Ether.Primary alcohol | C1=CCNC=C1 | c1ccncc1 | c1ccncc1 | HO- | C(C)OCC | null | 1 | COC(=O)C1(C)C=C(OC)C=CN1>C(C)OCC>COc1ccnc(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a267dfe4796e473a80c2c1022be2cf59 | CCOC(=O)c1ccc(O)c(OC)c1.CS(=O)(=O)OCC(F)(F)F>>CCOC(=O)c1ccc(OCC(F)(F)F)c(OC)c1 | C(C)OCC.C([O-])([O-])=O.[K+].[K+].C(C1=CC(OC)=C(O)C=C1)(=O)OCC.CS(=O)(=O)OCC(F)(F)F>>FC(COC1=C(C=C(C(=O)OCC)C=C1)OC)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:16]([O:17][CH3:18])[cH:19]1.CS(=O)(=O)O[CH2:11][C:12]([F:13])([F:14])[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][C:12]([F:13])([F:14])[F:15])[c:16]([O:17][CH3:18])[cH:19]1 | CCOC(=O)c1ccc(O)c(OC)c1.CS(=O)(=O)OCC(F)(F)F | CCOC(=O)c1ccc(OCC(F)(F)F)c(OC)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[F;D1;H0:3]-[C:2](-[F;D1;H0:4])(-[F;D1;H0:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 52 | [{"value": 52.0, "product": "FC(COC1=C(C=C(C(=O)OCC)C=C1)OC)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "FC(COC1=C(C=C(C(=O)OCC)C=C1)OC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | Potassium carbonate (62.2 g, 450 mmol) was added to a solution of ethyl vanillate (58.9 g, 300 mmol) in dimethylformamide (400 ml) and the reaction heated to 120° C. 2,2,2-Trifluoroethyl methanesulphonate (63.4 g, 360 mmol) was added over 15 minutes and the reaction heated at 120° C. for 15 hours. The reaction was cool... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | c1ccccc1 | MsOH.HO- | CN(C=O)C | 120 | null | CCOC(=O)c1ccc(O)c(OC)c1.CS(=O)(=O)OCC(F)(F)F>CN(C=O)C>CCOC(=O)c1ccc(OCC(F)(F)F)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb55cb51d0694342836c240203e8b7f3 | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1[N+](=O)[O-]>>CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N | COC=1C=C(C(=O)OCC)C(=CC1OCC(F)(F)F)[N+](=O)[O-]>>COC=1C=C(C(=O)OCC)C(=CC1OCC(F)(F)F)N | O=[N+:20]([O-])[c:19]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[NH2:20] | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1[N+](=O)[O-] | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N | null | [Pd] | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 93 | [{"value": 93.0, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCC(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCC(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A suspension of ethyl 3-methoxy-4-(2,2,2-trifluoroethoxy)-6-nitrobenzoate (24.0 g, 74.3 mmol) and 10% palladium on carbon (3.0 g) in a mixture of ethanol (100 ml) and ethyl acetate (750 ml) was stirred under an atmosphere of hydrogen for 18 hours. Removal of the catalyst by filtration, followed by solvent evaporation i... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | 18 | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1[N+](=O)[O-]>[Pd].C(C)(=O)OCC.C(C)O>CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d5317865b9a9429683071815e99f9e03 | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N.NC=O>>COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F | NC1=C(C(=O)OCC)C=C(C(=C1)OCC(F)(F)F)OC.C(=O)N>>COC=1C=C2C(NC=NC2=CC1OCC(F)(F)F)=O | CCO[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][C:16]([F:17])([F:18])[F:19])[cH:12][c:11]1[NH2:10])=[O:7].O=[CH:9][NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][C:16]([F:17])([F:18])[F:19] | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N.NC=O | COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 558d5445f0c25c1dc397039ffc1d62ab1323fa9420a98d9844188fc8b8f58e63 | d6f61cafbdd5f7299eb67523ae66e4a00c7f515735b0b03d65ed431c679d1e30 | O=c1[nH]cnc2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 84 | [{"value": 84.0, "product": "COC=1C=C2C(NC=NC2=CC1OCC(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 175 | CELSIUS | 18 | HOUR | A mixture of ethyl 2-amino-4-(2,2,2-trifluoroethoxy)-5-methoxybenzoate (20.2 g, 69.1 mmol) and formamide (50 ml) was heated at 175° C. for 6 hours. The mixture was allowed to cool to ambient temperature, ethanol (150 ml) was added and the reaction allowed to stand for 18 hours. Collection of the solid which had precipi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | C(C)O | 175 | 18 | CCOC(=O)c1cc(OC)c(OCC(F)(F)F)cc1N.NC=O>C(C)O>COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a78ce87a98a84bd4bb83cc911f6b6dde | COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCC(F)(F)F | CN(C=O)C.COC=1C=C2C(NC=NC2=CC1OCC(F)(F)F)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCC(F)(F)F | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][C:16]([F:17])([F:18])[F:19])[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][C:16]([F:17])([F:18])[F:19] | COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCC(F)(F)F | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 97 | [{"value": 97.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethylformamide (0.1 ml) was added dropwise to a solution of 6-methoxy-7-(2,2,2-trifluoroethoxy)-3,4-dihydroquinazolin-4-one (15.8 g, 57.7 mmol) in thionyl chloride (200 ml) and the reaction was heated at reflux for 6 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was aze... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCC(F)(F)F.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-435ac2340289451286b26b02ee408ad2 | C1COCCN1.ClCCCBr>>ClCCCN1CCOCC1 | N1CCOCC1.BrCCCCl.BrCCCCl>>ClCCCN1CCOCC1 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[CH2:4][CH2:3][CH2:2][Cl:1]>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | C1COCCN1.ClCCCBr | ClCCCN1CCOCC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1COCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#8:4]-[C:5]-[C:6]-1 | 49 | [{"value": 49.0, "product": "ClCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "ClCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of morpholine (261 ml, 3.00 mol) and 1-bromo-3-chloropropane (148 ml, 1.50 mol) in toluene (900 ml) was stirred for 18 hours at ambient temperature. Additional 1-bromo-3-chloropropane (25 ml, 0.25 mol) was added, the reaction was stirred for a further 1 hour and then filtered to remove the precipitated solid ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HBr | C1(=CC=CC=C1)C | null | 18 | C1COCCN1.ClCCCBr>C1(=CC=CC=C1)C>ClCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8be430819dbb4a75bfe5bbc25789aab5 | CCOC(=O)c1ccc(O)c(OC)c1.ClCCCN1CCOCC1>>CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1 | ClCCCN1CCOCC1.C(C1=CC(OC)=C(O)C=C1)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C(C(=O)OCC)C=CC1OCCCN1CCOCC1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:20]([O:21][CH3:22])[cH:23]1.Cl[CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[c:20]([O:21][CH3:... | CCOC(=O)c1ccc(O)c(OC)c1.ClCCCN1CCOCC1 | CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCN2CCOCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 100 | [{"value": 100.0, "product": "COC=1C=C(C(=O)OCC)C=CC1OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "COC=1C=C(C(=O)OCC)C=CC1OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | N-(3-Chloropropyl)morpholine (90 g, 0.55 mol) was added dropwise, over 30 minutes, to a solution of ethyl vanillate (98 g, 0.50 mol) and powdered potassium carbonate (104 g, 0.75 mol) in dimethylformamide (300 ml) at 80° C. The reaction was heated at 80° C. for 90 minutes, cooled to ambient temperature, filtered and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1COCC[NH]1 | HCl | CN(C=O)C | 80 | null | CCOC(=O)c1ccc(O)c(OC)c1.ClCCCN1CCOCC1>CN(C=O)C>CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2add9ebfbf024e819ea7f340e75950e4 | CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1.O=[N+]([O-])O>>CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-] | COC=1C=C(C(=O)OCC)C=CC1OCCCN1CCOCC1.S(O)(O)(=O)=O.[N+](=O)(O)[O-]>>COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[cH:22][cH:23]1.O[N+:24](=[O:25])[O-:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19]... | CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1.O=[N+]([O-])O | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-] | null | null | ClCCl.O.C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(OCCCN2CCOCC2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:11]:[c:12] | 161.8 | [{"value": 86.0, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 161.8, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated sulphuric acid (110 ml) and concentrated nitric acid (19.0 ml, 0.289 mol) were added cautiously, over a 50 minute period, to a two-phase system containing a stirred solution of ethyl 3-methoxy-4-(3-morpholinopropoxy)benzoate (76.5 g, 0.237 mol) in dichloromethane (600 ml), acetic acid (300 ml) and water (7... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCC[NH]1 | HO- | ClCCl.O.C(C)(=O)O | null | null | CCOC(=O)c1ccc(OCCCN2CCOCC2)c(OC)c1.O=[N+]([O-])O>ClCCl.O.C(C)(=O)O>CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e775ad05f214a308776e9dbbbd2beae | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-]>>CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N | COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)[N+](=O)[O-]>>COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)N | O=[N+:24]([O-])[c:23]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][... | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-] | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N | null | [Pd] | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCCCN2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 100.4 | [{"value": 100.0, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.4, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A suspension of ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate (132.2 g, 359 mmol) and 10% palladium on carbon (3.0 g) in a mixture of ethanol (200 ml) and ethyl acetate (2000 ml) was stirred under an atmosphere of hydrogen for 18 hours. Removal of the catalyst by filtration, followed by solvent evaporation in... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | 18 | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1[N+](=O)[O-]>[Pd].C(C)(=O)OCC.C(C)O>CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-df02568b306e4b00b5f95b85ecf630db | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N.NC=O>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 | COC=1C=C(C(=O)OCC)C(=CC1OCCCN1CCOCC1)N.C(=O)N>>COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O | CCO[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[cH:12][c:11]1[NH2:10])=[O:7].O=[CH:9][NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22]... | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N.NC=O | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 558d5445f0c25c1dc397039ffc1d62ab1323fa9420a98d9844188fc8b8f58e63 | d6f61cafbdd5f7299eb67523ae66e4a00c7f515735b0b03d65ed431c679d1e30 | O=c1[nH]cnc2cc(OCCCN3CCOCC3)ccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 68 | [{"value": 68.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | A solution of ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoate (130 g, 384 mmol) in formamide (280 ml) was heated at 180° C. for 3 hours, during which time a small amount (25 ml) of liquid distilled out of the reaction. The reaction was cooled to 125° C. and the excess formamide was evaporated in vacuo. Triturat... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | null | 125 | null | CCOC(=O)c1cc(OC)c(OCCCN2CCOCC2)cc1N.NC=O>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-531b0617f1c04b48bde5a40121a490f9 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | CN(C=O)C.COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22]... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCOCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 60 | [{"value": 60.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethylformamide (2.0 ml) was added dropwise to a solution of 6-methoxy-7-(3-morpholinopropoxy)-3,4-dihydro-quinazolin-4-one (83.0 g, 261 mmol) in thionyl chloride (700 ml) and the reaction was heated at reflux for 3.5 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo, the residue was taken ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-317c8be1d0594abeac97a3292b5127f9 | COc1cc2nc[nH]c(=O)c2cc1OC.CSCC[C@H](N)C(=O)O>>COc1cc2nc[nH]c(=O)c2cc1OC(C)=O | [OH-].[Na+].COC=1C=C2C(NC=NC2=CC1OC)=O.N[C@@H](CCSC)C(=O)O.O>>C(C)(=O)OC=1C=C2C(NC=NC2=CC1OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][nH:8][c:9](=[O:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15].N[C@@H](CCS[CH3:16])C(O)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][nH:8][c:9](=[O:10])[c:11]2[cH:12][c:13]1[O:14][C:15]([CH3:16])=[O:17] | COc1cc2nc[nH]c(=O)c2cc1OC.CSCC[C@H](N)C(=O)O | COc1cc2nc[nH]c(=O)c2cc1OC(C)=O | null | null | CS(=O)(=O)O | C-C Coupling | OtherReaction | 3b06da3fae32f95a45189e2935fa8587553b2c5cd1a498dbf590b1ce528f905c | 9cb00d8d3217954441d0b4f8c6749015a87dd991589f75a5f47658f24fe005c6 | O=c1[nH]cnc2ccccc12 | N-[C@@H](-C-C-S-[CH3;D1;+0:1])-C(-O)=[O;H0;D1;+0:2].[CH3;D1;+0:3]-[#8:4]-[c:5]>>[CH3;D1;+0:1]-[C;H0;D3;+0:3](=[O;H0;D1;+0:2])-[#8:4]-[c:5] | 57 | [{"value": 57.0, "product": "C(C)(=O)OC=1C=C2C(NC=NC2=CC1OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 6,7-dimethoxy-3,4-dihydroquinazolin-4-one (20.0 g, 97 mmol) and racemic methionine (21.7 g, 146 mmol) in methanesulphonic acid (150 ml) were heated at 100° C. for 5.5 hours and then allowed to cool to ambient temperature over 18 hours. The reaction was poured into cold water (750 ml), the pH of the aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine.Monosulfide | Ester | null | null | c1ccc2ncncc2c1 | Other | CS(=O)(=O)O | 100 | null | COc1cc2nc[nH]c(=O)c2cc1OC.CSCC[C@H](N)C(=O)O>CS(=O)(=O)O>COc1cc2nc[nH]c(=O)c2cc1OC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1471d90fa01040128232ed4bb91f676d | COc1cc2nc[nH]c(=O)c2cc1OC(C)=O.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1OC(C)=O.Cl | CN(C=O)C.C(C)(=O)OC=1C=C2C(NC=NC2=CC1OC)=O.S(=O)(Cl)Cl>>Cl.ClC1=NC=NC2=CC(=C(C=C12)OC(C)=O)OC | O=[c:9]1[nH:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][C:15]([CH3:16])=[O:17])[cH:12][c:11]21.O=S([Cl:10])[Cl:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[O:14][C:15]([CH3:16])=[O:17].[ClH:18] | COc1cc2nc[nH]c(=O)c2cc1OC(C)=O.O=S(Cl)Cl | COc1cc2ncnc(Cl)c2cc1OC(C)=O.Cl | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | O=S(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[ClH;D0;+0:2] | 87 | [{"value": 87.0, "product": "Cl.ClC1=NC=NC2=CC(=C(C=C12)OC(C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethylformamide (0.25 ml) was added dropwise to a solution of 6-acetoxy-7-methoxy-3,4-dihydro-quinazolin-4-one (13.8 g, 59.0 mmol) in thionyl chloride (150 ml) and the reaction was heated at reflux for 1.5 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | null | null | null | COc1cc2nc[nH]c(=O)c2cc1OC(C)=O.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1OC(C)=O.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10b4a1e360fd44fd8067583fd1414ad1 | O=[N+]([O-])c1ccc(F)c(F)c1.OCc1ccccn1>>O=[N+]([O-])c1ccc(OCc2ccccn2)c(F)c1 | OCC1=NC=CC=C1.FC=1C=C(C=CC1F)[N+](=O)[O-]>>N1=C(C=CC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])F | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][c:16]1[F:17].[OH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[c:16]([F:17])[cH:18]1 | O=[N+]([O-])c1ccc(F)c(F)c1.OCc1ccccn1 | O=[N+]([O-])c1ccc(OCc2ccccn2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCc2ccccn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7;a:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#7;a:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 58 | [{"value": 58.0, "product": "N1=C(C=CC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.7, "product": "N1=C(C=CC=C1)COC1=C(C=C(C=C1)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | An analogous reaction to that described in example 42b, but starting with 2-(hydroxymethyl)pyridine (3.50 g, 36 mmol) and 3,4-difluoronitrobenzene (5.00 g, 31.4 mmol), yielded 2-((2-pyridyl)methoxy)-5-nitrofluorobenzene (4.50 g, 58% yield) as a yellow solid. d) An analogous reaction to that described in example 42c, bu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HF | null | null | null | O=[N+]([O-])c1ccc(F)c(F)c1.OCc1ccccn1>>O=[N+]([O-])c1ccc(OCc2ccccn2)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70296c78e31344738708a81a3be49637 | NN.O=C1NC(=O)c2ccccc21>>NCCc1ccc[nH]c1=O | C1(C=2C(C(N1)=O)=CC=CC2)=O.O.NN>>NCCC=1C(NC=CC1)=O | N[NH2:1].O=[C:2]1[NH:8][C:3](=[O:10])[c:4]2[cH:5][cH:6][cH:7]c[c:9]21>>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][nH:8][c:9]1=[O:10] | NN.O=C1NC(=O)c2ccccc21 | NCCc1ccc[nH]c1=O | null | null | ClCCl.CO | C-C Coupling | OtherReaction | 03662bd10049b4ab9b31ad02144021924fa52ff65543d64aab667e5e90135d81 | 308f75b738848e24fb4e299b1496b46700df7b98fa2f71103674d0faeb151880 | O=c1cccc[nH]1 | N-[NH2;D1;+0:1].O=[C;H0;D3;+0:2]1-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6]2:[c:7]:[c:8]:[cH;D2;+0:9]:c:[c;H0;D3;+0:10]:2-1>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:4]-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[nH;D2;+0:3]:[c;H0;D3;+0:10]:1=[O;H0;D1;+0:5] | 55 | [{"value": 55.0, "product": "NCCC=1C(NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 1.2 g (2.5 mmol) of phthalimide 4 in 100 ml of methanol was added 6 ml of hydrazine monohydrate. This was stirred at room temperature overnight upon which the suspension turned into a clear yellow solution. The mixture was concentrated and residue was diluted with water and extracted with chloroform.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Unsubstituted dicarboximide | Primary amine | c1ccc2c(c1)CNC2 | c1cnccc1 | c1cnccc1 | Other | ClCCl.CO | null | 8 | NN.O=C1NC(=O)c2ccccc21>ClCCl.CO>NCCc1ccc[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c30303655a2b4a24becb86513c91bcf9 | CCN(CC)CC.NC1CCN(Cc2ccccc2)CC1.O=C(Cl)OCc1ccccc1>>CCCCCCCCCCCCN | NC1CCN(CC1)CC1=CC=CC=C1.C(C)N(CC)CC.ClC(=O)OCC1=CC=CC=C1>>CCCCCCCCCCCCN | CCN(CC)C[CH3:1].C1C[CH:12]([NH2:13])[CH2:11][CH2:10]N1C[c:7]1[cH:2][cH:3][cH:4][cH:5][cH:6]1.O=C(Cl)OCc1ccc[cH:8][cH:9]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13] | CCN(CC)CC.NC1CCN(Cc2ccccc2)CC1.O=C(Cl)OCc1ccccc1 | CCCCCCCCCCCCN | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 21e9f45c202f89b4c7f3ea9e8916a0233c0d2b6c43e742b89236499ec5df4cfa | b4ef3b86ebd0fc68614170fa576ee7f8bd9b131a1ad54d9d4947eab135b76a2e | null | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-C(=O)-O-C-c1:[cH;D2;+0:2]:[cH;D2;+0:3]:c:c:c:1.[N;D1;H2:4]-[CH;D3;+0:5]1-C-C-N(-C-[c;H0;D3;+0:6]2:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:2)-[CH2;D2;+0:12]-[C:13]-1>>[CH3;D1;+0:1]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0... | 69.3 | [{"value": 69.3, "product": "CCCCCCCCCCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 0° C. solution of 4-amino-1-benzylpiperidine 11 (41.2 g, 216.5 mmol) and triethylamine (51.3 mL, 369 mmol) in 600 mL of tetrahydrofuran was added benzyl chloroformate (31 mL, 217 mmol) dropwise over a period of 30 to 45 min. at such a rate that the reaction temperature was kept between 5° C. and 10° C. After the a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Tertiary amine.Tertiary amine | null | C1CCNCC1.c1ccccc1.c1ccccc1 | null | null | HCl | O1CCCC1 | null | 12 | CCN(CC)CC.NC1CCN(Cc2ccccc2)CC1.O=C(Cl)OCc1ccccc1>O1CCCC1>CCCCCCCCCCCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8959c8c81cd14d269a4648ed8f87ce0e | COc1ccc(C=O)cc1OC.COc1nc(N2CCNCC2)ccc1Br>>COc1ccc(CN2CCN(c3ccc(Br)c(OC)n3)CC2)cc1OC | BrC=1C=CC(=NC1OC)N1CCNCC1.COC=1C=C(C=O)C=CC1OC.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>BrC=1C=CC(=NC1OC)N1CCN(CC1)CC1=CC(=C(C=C1)OC)OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]1.[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([Br:16])[c:17]([O:18][CH3:19])[n:20]2)[CH2:21][CH2:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][c:15]([Br:16])[c:17]([O:18][CH3:19])[... | COc1ccc(C=O)cc1OC.COc1nc(N2CCNCC2)ccc1Br | COc1ccc(CN2CCN(c3ccc(Br)c(OC)n3)CC2)cc1OC | null | C(C)(=O)O | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | reductive amination | 7a1842565a3c73c1d6bba5dccafef60d48e9eaf6e4a0871f60e828bcbdf26fb1 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCN(c3ccccn3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1):[c:4] | null | [] | null | null | null | null | A quantity of 0.1 g (0.4 mmole, 1 eq) of 1-(5-Bromo-6-methoxy-pyridin-2-yl)-piperazine and 0.061 g (0.4 mmole, 1 eq) of 3,4-dimethoxybenzaldehyde is dissolved in 5 mL of anhydrous toluene, and 3 drops of glacial acetic acid is added. An excess of NaBH(OAc)3 is added to the solution and stirred at room temperature under... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | C(C)(=O)O.C1(=CC=CC=C1)C | null | null | COc1ccc(C=O)cc1OC.COc1nc(N2CCNCC2)ccc1Br>C(C)(=O)O.C1(=CC=CC=C1)C>COc1ccc(CN2CCN(c3ccc(Br)c(OC)n3)CC2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0a1f86b44244d6ba10f1cf103692e8a | COc1ccc(C(C)=O)cc1OC.FC(F)(F)c1cc(N2CCNCC2)ccc1Cl>>COc1ccc(C(C)N2CCN(c3ccc(Cl)c(C(F)(F)F)c3)CC2)cc1OC | ClC1=C(C=C(C=C1)N1CCNCC1)C(F)(F)F.CC(=O)C1=CC(=C(C=C1)OC)OC.[BH4-].[Na+]>>ClC1=C(C=C(C=C1)N1CCN(CC1)C(C)C1=CC(=C(C=C1)OC)OC)C(F)(F)F | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26]1)[CH3:8].[NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][c:16... | COc1ccc(C(C)=O)cc1OC.FC(F)(F)c1cc(N2CCNCC2)ccc1Cl | COc1ccc(C(C)N2CCN(c3ccc(Cl)c(C(F)(F)F)c3)CC2)cc1OC | null | CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C | CO | Heteroatom Alkylation and Arylation | reductive amination | d4cc9a2a46f538d7a2ff577eac4d4531ea828578c3aec2ccd0e8c1d501914fc6 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(CN2CCN(c3ccccc3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C;D1;H3:2]-[CH;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | A quantity of 0.17 g (0.6 mmole, 1 eq) of 1-(4-chloro-3-trifluoromethyl-phenyl)-piperazine and 0.1 g (0.6 mmole, 1 eq) of 3,4-dimethoxyacetophenone and 2 mL of Ti(OiPr)4 are warmed to 70° C. for 2 hours. The reaction solution is cooled to room temperature and 20 mL of anhydrous methanol is added followed by 1.0 g of Na... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C.CO | null | 2 | COc1ccc(C(C)=O)cc1OC.FC(F)(F)c1cc(N2CCNCC2)ccc1Cl>CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C.CO>COc1ccc(C(C)N2CCN(c3ccc(Cl)c(C(F)(F)F)c3)CC2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bb7eedc81724abd9e07461551a2da24 | COc1cc(N2CCNCC2)ccc1Br.O=Cc1cnc2ccccc2c1>>COc1cc(N2CCN(C(C)c3cnc4ccccc4c3)CC2)ccc1Br | N1=CC(=CC2=CC=CC=C12)C=O.N1N=NC2=C1C=CC=C2.BrC1=C(C=C(C=C1)N1CCNCC1)OC.C[Mg]Br.C(C)OCC>>BrC1=C(C=C(C=C1)N1CCN(CC1)C(C)C=1C=NC2=CC=CC=C2C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:22][CH2:23]2)[cH:24][cH:25][c:26]1[Br:27].O=[CH:10][c:12]1[cH:13][n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH:10]([CH3:11])[c:12]3[cH:13][n:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[... | COc1cc(N2CCNCC2)ccc1Br.O=Cc1cnc2ccccc2c1 | COc1cc(N2CCN(C(C)c3cnc4ccccc4c3)CC2)ccc1Br | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 66e6667395903ee1c54d8aecc784ece1bccbdcbc9661ebcae0e6a980f9380640 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(N2CCN(Cc3cnc4ccccc4c3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:13]-[CH;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | 60 | CELSIUS | 18 | HOUR | A solution containing 3-quinolinecarboxaldehyde (25 mg, 0.16 mmol, 1.0 equivalents), benzotriazole (19 mg, 0.16 mmol, 1.0 equivalents) and 1-(4-bromo-3-methoxy-phenyl)-piperazine (39 mg, 0.17 mmol, 1.1 equivalents) in ethanol (1 ml) and toluene (2 ml) was heated 20 minutes at 60° C. Solution was concentrated. Residue w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | 60 | 18 | COc1cc(N2CCNCC2)ccc1Br.O=Cc1cnc2ccccc2c1>C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O>COc1cc(N2CCN(C(C)c3cnc4ccccc4c3)CC2)ccc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e708439672104902ad9652f8c150d57e | COc1cc(Br)ccc1Cl.COc1ccc([C@@H](C)N2CCNCC2)cc1OC>>COc1cc(N2CCN([C@H](C)c3ccc(OC)c(OC)c3)CC2)ccc1Cl | CC(C)([O-])C.[K+].COC=1C=C(C=CC1OC)[C@@H](C)N1CCNCC1.BrC=1C=CC(=C(C1)OC)Cl.Cl>>ClC1=C(C=C(C=C1)N1CCN(CC1)[C@H](C)C1=CC(=C(C=C1)OC)OC)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:26]([Cl:27])[cH:25][cH:24]1.[NH:6]1[CH2:7][CH2:8][N:9]([C@H:10]([CH3:11])[c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH3:20])[cH:21]2)[CH2:22][CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C@H:10]([CH3:11])[c:12]3[cH:13][cH:14][c:15]([O:16][CH3:17])[... | COc1cc(Br)ccc1Cl.COc1ccc([C@@H](C)N2CCNCC2)cc1OC | COc1cc(N2CCN([C@H](C)c3ccc(OC)c(OC)c3)CC2)ccc1Cl | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3ccccc3)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 61.7 | [{"value": 53.0, "product": "ClC1=C(C=C(C=C1)N1CCN(CC1)[C@H](C)C1=CC(=C(C=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "ClC1=C(C=C(C=C1)N1CCN(CC1)[C@H](C)C1=CC(=C(C=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A quantity of 4.2 g (17 mmoles, 1 eq) of (R)-1-[1-(3,4-dimethoxy-phenyl)-ethyl]-piperazine and 4.4 g (20 mmoles, 1.2 eq) of 5-Bromo-2-chloro-anisole was dissolved in 110 mL of anhydrous toluene, and the solution is purged with N2 for 20 minutes. To the solution was added 0.33 g (0.5 mmoles, 0.03 eq) of rac-2, 2′-Bis(di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 80 | null | COc1cc(Br)ccc1Cl.COc1ccc([C@@H](C)N2CCNCC2)cc1OC>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>COc1cc(N2CCN([C@H](C)c3ccc(OC)c(OC)c3)CC2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ba6604103bb4174bb8504f5dd723b6b | COC(=O)C(CSCC(=O)c1ccc(OC)c(OC)c1)NC(=O)OC(C)(C)C>>COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1 | COC(C(CSCC(=O)C1=CC(=C(C=C1)OC)OC)NC(=O)OC(C)(C)C)=O.FC(C(=O)O)(F)F.C([O-])(O)=O.[Na+].C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>COC(=O)C1NC(CSC1)C1=CC(=C(C=C1)OC)OC | CC(C)(C)OC(=O)[NH:20][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][S:7][CH2:8][C:9](=O)[c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][S:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19]2)[NH:20]1 | COC(=O)C(CSCC(=O)c1ccc(OC)c(OC)c1)NC(=O)OC(C)(C)C | COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 8fb261716131fb768ea924fd38d1e19554b4bbefd281d07fe864aedc9d8e88cb | 1c4cec4730086d81e4d619e804478e6e78c92525d3d5a05dc2fde7b44b847d30 | c1ccc(C2CSCCN2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[#16:4]-[C:5]-[C;H0;D3;+0:6](=O)-[c:7](:[c:8]):[c:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]>>[C;D1;H3:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C:2]1-[C:3]-[#16:4]-[C:5]-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[NH;D2;+0:1]-1 | 59 | [{"value": 59.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To an ice chilled solution of 2-tert-butoxycarbonylamino-3-[2-(3,4-dimethoxy-phenyl)-2-oxo-ethylsulfanyl]-propionic acid methyl ester (2.00 g, 9.34 mmol, 1.0 equivalents) in dichloromethane (9 ml) was added trifluoroacetic acid (9 ml). The reaction solution was stirred on ice for 4 hours. The solution was concentrated,... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Secondary amine | null | C1CSCCN1 | C1CSCCN1.c1ccccc1 | HO- | ClCCl | null | 4 | COC(=O)C(CSCC(=O)c1ccc(OC)c(OC)c1)NC(=O)OC(C)(C)C>ClCCl>COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98b259cb2faf4ca8837e87a42fc7b395 | COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1.COc1cc(N)ccc1Cl>>COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | C[Al](C)C.COC(=O)C1NC(CSC1)C1=CC(=C(C=C1)OC)OC.ClC1=C(C=C(N)C=C1)OC>>ClC1=C(C=C(C=C1)NC(=O)C1NC(CSC1)C1=CC(=C(C=C1)OC)OC)OC | CO[C:7](=[O:8])[CH:9]1[CH2:10][S:11][CH2:12][CH:13]([c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23]2)[NH:24]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1[Cl:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]2[CH2:10][S:11][CH2:12][CH:13]([c:14]3[cH:15][cH:16][c:17]([O:... | COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1.COc1cc(N)ccc1Cl | COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(Nc1ccccc1)C1CSCC(c2ccccc2)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5])-[C:6]-[#16:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#16:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[#7:4]-[C:5] | 76 | [{"value": 76.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 18 | HOUR | A 2.0M solution of trimethylaluminum (0.39 ml, 0.78 mmol, 3.5 equivalents) was added to a solution of 5-(3,4-dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid methyl ester (67 mg, 0.22 mmol, 1.0 equivalents) and 4-chloro-3-methoxyaniline (106 mg, 0.68 mmol, 3.0 equivalents). The solution was stirred at 50° C. for 18 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1CSCCN1.c1ccccc1 | HO- | null | 50 | 18 | COC(=O)C1CSCC(c2ccc(OC)c(OC)c2)N1.COc1cc(N)ccc1Cl>>COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e5cc19961ba4827bae115bd31489e70 | COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl>>COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | ClC1=C(C=C(C=C1)NC(=O)C1NC(CSC1)C1=CC(=C(C=C1)OC)OC)OC>>ClC1=C(C=C(C=C1)NCC1NC(CSC1)C1=CC(=C(C=C1)OC)OC)OC | O=[C:7]([NH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:26]([Cl:27])[cH:25][cH:24]1)[CH:8]1[CH2:9][S:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]2)[NH:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][CH:8]2[CH2:9][S:10][CH2:11][CH:12]([c:13]3[cH:14][cH:15][c:16]([O:17][CH3:18])[c... | COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(NCC2CSCC(c3ccccc3)N2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4](-[#7:5]-[C:6])-[C:7]-[#16:8]>>[#16:8]-[C:7]-[C:4](-[CH2;D2;+0:1]-[#7:2]-[c:3])-[#7:5]-[C:6] | 95 | [{"value": 95.0, "product": "ClC1=C(C=C(C=C1)NCC1NC(CSC1)C1=CC(=C(C=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To an ice chilled suspension containing 5-(3,4-dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide n(71 mg, 0.17 mmol, 1.0 equivalents) in toluene (1.5 ml) was added a 0.5M solution of alane (1.6 ml, 0.8 mmol, 4.8 equivalents). The reaction was stirred at room temperature for 2 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.C1CSCCN1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | 2 | COc1cc(NC(=O)C2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl>C1(=CC=CC=C1)C>COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e46feeb8a4a04376ae885d905c5c4b2a | CC(Br)Br.COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl>>COc1cc(N2CCN3C(CSCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl | BrC(C)Br.C(C)N(CC)CC.BrC(C)Br.C(C)N(CC)CC.ClC1=C(C=C(C=C1)NCC1NC(CSC1)C1=CC(=C(C=C1)OC)OC)OC.BrC(C)Br.C(C)N(CC)CC>>ClC1=C(C=C(C=C1)N1CC2CSCC(N2CC1)C1=CC(=C(C=C1)OC)OC)OC | Br[CH:8](Br)[CH3:7].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:25][CH:10]2[NH:9][CH:14]([c:15]3[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]3)[CH2:13][S:12][CH2:11]2)[cH:26][cH:27][c:28]1[Cl:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]3[CH:10]([CH2:11][S:12][CH2:13][CH:14]3[c:15]3[cH:1... | CC(Br)Br.COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl | COc1cc(N2CCN3C(CSCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | c17a52e5d43aa1d9cd5a1f06f97c42e464d08975157fe0a3f55e314e9bfaf306 | a4f9aac18aa96dbf899d70608583d8fd7f3c4f3b117366bea2604d063aa01548 | c1ccc(C2CSCC3CN(c4ccccc4)CCN32)cc1 | Br-[CH;D3;+0:1](-Br)-[CH3;D1;+0:2].[c:3]-[C:4]1-[C:5]-[#16:6]-[C:7]-[C:8](-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[NH;D2;+0:14]-1>>[c:3]-[C:4]1-[C:5]-[#16:6]-[C:7]-[C:8]2-[C:9]-[N;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:14]-2-1 | 31.9 | [{"value": 31.9, "product": "ClC1=C(C=C(C=C1)N1CC2CSCC(N2CC1)C1=CC(=C(C=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 4 | HOUR | A solution of (4-chloro-3-methoxy-phenyl)-[5-(3,4-dimethoxy-phenyl)-thiomorpholin-3-ylmethyl]-amine (100 mg, 0.245 mmol, 1.0 equivalents), dibromoethane (0.31 ml, 3.55 mmol, 14.5 equivalents) and triethylamine (0.15 ml, 1.09 mmol, 4.5 equivalents) in dimethylacetamide (2 ml) was heated at 90° C. for 4 hours. Additional... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary amine.Secondary amine | Tertiary amine.Tertiary amine | C1CSCCN1 | C1CN2CCSCC2C[NH]1 | c1ccccc1.C1CN2CCSCC2C[NH]1.c1ccccc1 | HBr | CC(=O)N(C)C | 90 | 4 | CC(Br)Br.COc1cc(NCC2CSCC(c3ccc(OC)c(OC)c3)N2)ccc1Cl>CC(=O)N(C)C>COc1cc(N2CCN3C(CSCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ccf46ede910d40369dee25ac8de4f6cf | COc1ccc(B(O)O)cc1OC.O=C(NCCO)c1cccc(Br)n1>>COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC | OCCNC(=O)C1=NC(=CC=C1)Br.COC=1C=C(C=CC1OC)B(O)O.C(C)O.C(=O)([O-])[O-].[Na+].[Na+]>>OCCNC(=O)C1=NC(=CC=C1)C1=CC(=C(C=C1)OC)OC | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([O:21][CH3:22])[cH:19]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][OH:17])[n:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][OH:17])[n:18]2)[cH:19][c:20]1[O:21][CH3:22] | COc1ccc(B(O)O)cc1OC.O=C(NCCO)c1cccc(Br)n1 | COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC | null | [Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:7]:[c:8] | 69.5 | [{"value": 69.0, "product": "OCCNC(=O)C1=NC(=CC=C1)C1=CC(=C(C=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "OCCNC(=O)C1=NC(=CC=C1)C1=CC(=C(C=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A quantity of 0.25 g (1.0 mmoles, 1 eq) of 6-bromo-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide and 0.28 g (1.5 mmoles, 1.5 eq) of 3,4-dimethoxyphenyl boronic acid are added in 20 mL of ethylene glycol dimethyl ether with 2 ml of ethanol and 2 ml of 2 M Na2CO3. The mixture is purged with N2 for 20 minutes, and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | [Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.COCCOC | 80 | null | COc1ccc(B(O)O)cc1OC.O=C(NCCO)c1cccc(Br)n1>[Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.COCCOC>COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0754a353ee9414ead2818ed353c537a | COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC>>COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC | OCCNC(=O)C1=NC(=CC=C1)C1=CC(=C(C=C1)OC)OC.Cl>>OCCNC(=O)C1NC(CCC1)C1=CC(=C(C=C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][OH:17])[n:18]2)[cH:19][c:20]1[O:21][CH3:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][OH:17])[NH:18]2)[cH:19][c:20]1[O:21][CH3:22] | COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC | COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC | null | [Pt](=O)=O | C(C)O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(C2CCCCN2)cc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[n;H0;D2;+0:15]:1>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH;D3;+0:9](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-... | null | [] | null | null | 8 | HOUR | A quantity of 3.0 g (10 mmoles, 1 eq) of 6-(3,4-dimethoxy-phenyl)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide and 0.23 g (1.0 mmoles, 0.1 eq) of platinum dioxide are added into 35 mL of ethanol and 2.0 ml concentrated HCl. The suspension is hydrogenated under 50 psi of H2 at room temperature overnight. After TLC... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | null | [Pt](=O)=O.C(C)O | null | 8 | COc1ccc(-c2cccc(C(=O)NCCO)n2)cc1OC>[Pt](=O)=O.C(C)O>COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ba9af9d5a2b5441a870843b3f061c6cf | COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC>>COc1ccc(C2CCCC(CNCCO)N2)cc1OC | [O-]S(=O)(=O)[O-].[Mg+2].OCCNC(=O)C1NC(CCC1)C1=CC(=C(C=C1)OC)OC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>COC=1C=C(C=CC1OC)C1CCCC(N1)CNCCO | O=[C:12]([CH:11]1[CH2:10][CH2:9][CH2:8][CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18]2)[NH:17]1)[NH:13][CH2:14][CH2:15][OH:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][NH:13][CH2:14][CH2:15][OH:16])[NH:17]2)[cH:18][c:19]1[O:20][CH3:21] | COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC | COc1ccc(C2CCCC(CNCCO)N2)cc1OC | null | null | O.C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(C2CCCCN2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[C:5])-[#7:6]-[C:7]>>[C:5]-[C:4](-[CH2;D2;+0:1]-[#7:2]-[C:3])-[#7:6]-[C:7] | 101.9 | [{"value": 68.0, "product": "COC=1C=C(C=CC1OC)C1CCCC(N1)CNCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.9, "product": "COC=1C=C(C=CC1OC)C1CCCC(N1)CNCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 1.5 g (5.0 mmoles, 1 eq) of 6-(3,4-Dimethoxy-phenyl)-piperidine-2-carboxylic acid (2-hydroxy-ethyl)-amide in 18 mL of THF is added slowly into 15 mL of 1 M LiAlH4 solution in THF. The reaction is heated at 60° C. under N2 for 6 hours. At that time there is no starting material shown on TLC. Cooled in ice ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.C1CCNCC1 | Other | O.C1CCOC1 | 60 | null | COc1ccc(C2CCCC(C(=O)NCCO)N2)cc1OC>O.C1CCOC1>COc1ccc(C2CCCC(CNCCO)N2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-854a1310fbdb40e5bb98d77d007479bf | CCOC(=O)N=NC(=O)OCC.COc1ccc(C2CCCC(CNCCO)N2)cc1OC>>COc1ccc(C2CCCC3CNCCN32)cc1OC.[NH4+].[OH-] | COC=1C=C(C=CC1OC)C1CCCC(N1)CNCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>[NH4+].[OH-].COC=1C=C(C=CC1OC)C1CCCC2N1CCNC2 | CCOC(=O)[N:21]=NC(=O)[O:22]CC.O[CH2:15][CH2:14][NH:13][CH2:12][CH:11]1[CH2:10][CH2:9][CH2:8][CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[cH:17]2)[NH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:16]23)[cH:17][c:18]1[O:19][CH3:20].[... | CCOC(=O)N=NC(=O)OCC.COc1ccc(C2CCCC(CNCCO)N2)cc1OC | COc1ccc(C2CCCC3CNCCN32)cc1OC.[NH4+].[OH-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 4cc975100256eeb284c00324f9d9c3705e02c5f7ff6f803641e3b753ac272f90 | 8613fd4fe042f0ebb8c19cdf4435b54eded2fa5b8cc5e22bd29bc67fc0f8b53e | c1ccc(C2CCCC3CNCCN32)cc1 | C-C-O-C(=O)-[N;H0;D2;+0:1]=N-C(=O)-[O;H0;D2;+0:2]-C-C.O-[CH2;D2;+0:3]-[C:4]-[#7:5]-[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11])-[C:12]>>[C:8]-[C:7]1-[C:6]-[#7:5]-[C:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:9]-1-[C:10](-[c:11])-[C:12].[NH4+;D0:1].[OH-;D0:2] | 27 | [{"value": 27.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of 3.4 g (11.6 mmoles, 1 eq) of 2-{[6-(3,4-dimethoxy-phenyl)-piperidin-2-ylmethyl]-amino}-ethanol and 0.20 g (17.5 mmoles, 1.5 eq) of triphenyl phosphine in 120 mL of THF, is added 1.9 mL (12.7 mmoles, 1.1 eq) of diethyl azodicarboxylate, and the reaction is stirred at room temperature overnight. At tha... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Primary alcohol.Secondary amine | Tertiary amine | C1CCNCC1 | C1CCN2CCNCC2C1 | c1ccccc1.C1CCN2CCNCC2C1 | HO- | C1CCOC1 | null | 8 | CCOC(=O)N=NC(=O)OCC.COc1ccc(C2CCCC(CNCCO)N2)cc1OC>C1CCOC1>COc1ccc(C2CCCC3CNCCN32)cc1OC.[NH4+].[OH-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-913878cf886e4fed88af97f8d493ec75 | COc1cc(Br)ccc1Cl.COc1ccc(C2CCCC3CNCCN32)cc1OC>>COc1cc(N2CCN3C(CCCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl | COC=1C=C(C=CC1OC)C1CCCC2N1CCNC2.BrC=1C=CC(=C(C1)OC)Cl.CC(C)([O-])C.[K+]>>ClC1=C(C=C(C=C1)N1CC2N(CC1)C(CCC2)C2=CC(=C(C=C2)OC)OC)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:28]([Cl:29])[cH:27][cH:26]1.[NH:6]1[CH2:7][CH2:8][N:9]2[CH:10]([CH2:11][CH2:12][CH2:13][CH:14]2[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]2)[CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]3[CH:10]([CH2:11][CH2:12][CH2:13][CH:14]3[c:15]3[... | COc1cc(Br)ccc1Cl.COc1ccc(C2CCCC3CNCCN32)cc1OC | COc1cc(N2CCN3C(CCCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 42bc18fc6e327c51abf0c17c233ad0e8e8c69664054ccc1eec7570fa43a2138e | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(C2CCCC3CN(c4ccccc4)CCN32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A quantity of 0.85 g (3.0 mmoles, 1 eq) of 6-(3,4-dimethoxy-phenyl)-octahydropyrido[1,2-a]pyrazine and 0.76 g (3.4 mmoles, 1.1 eq) of 5-bromo-2-chloro-anisole is dissolved in 25 mL of anhydrous toluene, and the solution is purged with N2 for 20 min. To the solution is added 0.18 g (0.30 mmoles, 0.10 eq) of rac-2, 2′-Bi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCN2CCNCC2C1 | c1ccccc1.C1CCN2CC[NH]CC2C1 | c1ccccc1.C1CCN2CC[NH]CC2C1.c1ccccc1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 80 | null | COc1cc(Br)ccc1Cl.COc1ccc(C2CCCC3CNCCN32)cc1OC>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>COc1cc(N2CCN3C(CCCC3c3ccc(OC)c(OC)c3)C2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-302383b5d1ae466490342ab67ce79b14 | BrCc1ccccc1.CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)O>>CC(C)(C)OC(=O)N1C(=O)CCC1C(=O)OCc1ccccc1 | C(C)(C)(C)OC(=O)N1[C@@H](CCC1=O)C(=O)O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)N1C(CCC1=O)C(=O)OCC1=CC=CC=C1 | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[O:10])[CH2:11][CH2:12][C@H:13]1[C:14](=[O:15])[OH:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21]... | BrCc1ccccc1.CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)O | CC(C)(C)OC(=O)N1C(=O)CCC1C(=O)OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C1CCC(C(=O)OCc2ccccc2)N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59.1 | [{"value": 59.0, "product": "C(C)(C)(C)OC(=O)N1C(CCC1=O)C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.1, "product": "C(C)(C)(C)OC(=O)N1C(CCC1=O)C(=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | A suspension containing (2S)5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (10.00 g, 0.044 mol, 1.0 equivalent), benzyl bromide (7.88 g, 0.046 mol, 1.05 equivalents), and potassium carbonate (15.20 g, 0.11 mol, 2.5 equivalents) in DMF (200 ml) was allowed to stir at 65° C. overnight. The reaction was allowe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | C1CC[NH]C1.c1ccccc1 | HBr | CN(C)C=O | 65 | 8 | BrCc1ccccc1.CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)O>CN(C)C=O>CC(C)(C)OC(=O)N1C(=O)CCC1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89129204560a4d65af30a3ddcfdac19d | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)OCc1ccccc1.COc1cc[c]([Mg][Br])cc1OC>>COc1ccc(C(=O)CCC(NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC | COC=1C=C(C=CC1OC)[Mg]Br.C(C)(C)(C)OC(=O)N1[C@@H](CCC1=O)C(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(C(CCC(=O)C1=CC(=C(C=C1)OC)OC)NC(=O)OC(C)(C)C)=O | [C:7]1(=[O:8])[CH2:9][CH2:10][C@@H:11]([C:20](=[O:21])[O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[N:12]1[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[Br][Mg][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][CH:... | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)OCc1ccccc1.COc1cc[c]([Mg][Br])cc1OC | COc1ccc(C(=O)CCC(NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 080c2b43d0a0b8f931d6213b8b72dc78f67fa8812b391d600ecdd636d8f3d301 | 9f2c6224204fc882d6f480ccf7ad879a9274e7067e43b7e1ce90a3411c5ff012 | O=C(CCCC(=O)c1ccccc1)OCc1ccccc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C@@H;D3;+0:10]1-[C:11]-[C:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[N;H0;D3;+0:15]-1-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[C;D1;H3:22]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11]-[C:12]-[C;H0;D3;+0:1... | 88 | [{"value": 88.0, "product": "C(C1=CC=CC=C1)OC(C(CCC(=O)C1=CC(=C(C=C1)OC)OC)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of (2S)5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (8.20 g, 0.026 mol, 1.0 equivalent) in anhydrous THF was cooled to 0° C. in an ice bath under N2. A chilled 0.5M solution of 3,4-dimethoxyphenylmagnesium bromide in THF (52.1 mL, 0.026 mol, 1.0 equivalent) was slowly added. The ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Carbamic ester.Substituted dicarboximide | Carbamic ester.Ketone | C1CC[NH]C1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | C1CCOC1 | null | 2 | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1C(=O)OCc1ccccc1.COc1cc[c]([Mg][Br])cc1OC>C1CCOC1>COc1ccc(C(=O)CCC(NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-88e5f4886b544106b08fb0d1153cf862 | COc1ccc(C(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC>>COc1ccc(C2=N[C@H](C(=O)OCc3ccccc3)CC2)cc1OC | C(C1=CC=CC=C1)OC([C@H](CCC(=O)C1=CC(=C(C=C1)OC)OC)NC(=O)OC(C)(C)C)=O.C(=O)(C(F)(F)F)O>>OC(=O)C(F)(F)F.C(C1=CC=CC=C1)OC(=O)[C@H]1N=C(CC1)C1=CC(=C(C=C1)OC)OC | CC(C)(C)OC(=O)[NH:8][C@H:9]([C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[CH2:20][CH2:21][C:7](=O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][C@H:9]([C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:1... | COc1ccc(C(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC | COc1ccc(C2=N[C@H](C(=O)OCc3ccccc3)CC2)cc1OC | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | bf06db3989591852ea9db145104dbc3920fa3e3bda459d735b6db3b71960304d | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C(OCc1ccccc1)[C@@H]1CCC(c2ccccc2)=N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:1]-1 | 91 | [{"value": 91.0, "product": "OC(=O)C(F)(F)F.C(C1=CC=CC=C1)OC(=O)[C@H]1N=C(CC1)C1=CC(=C(C=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2S)2-tert-butoxycarbonylamino-5-(3,4-dimethoxy-phenyl)-5-oxo-pentanoic acid benzyl ester (10.46 g, 0.023 mol) in dichloromethane (150 ml) was cooled to 0° C. in an ice bath. TFA (40 ml) was slowly added to the stirring mixture and the reaction was allowed to warm to room temperature over two hours. The r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=NCCC1 | c1ccccc1.C1=NCCC1.c1ccccc1 | HO- | ClCCl | null | null | COc1ccc(C(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1OC>ClCCl>COc1ccc(C2=N[C@H](C(=O)OCc3ccccc3)CC2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82d2100e72634c39bb308f04cdedd33c | COc1cc(N)ccc1Cl.COc1ccc([C@H]2CC[C@@H](C(=O)O)N2C(=O)OC(C)(C)C)cc1OC>>COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2C(=O)OC(C)(C)C)ccc1Cl | C(C)(C)(C)OC(=O)N1[C@@H](CC[C@@H]1C1=CC(=C(C=C1)OC)OC)C(=O)O.ClC1=C(C=C(N)C=C1)OC.CCN(C(C)C)C(C)C.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F>>C(C)(C)(C)OC(=O)N1[C@@H](CC[C@@H]1C1=CC(=C(C=C1)OC)OC)C(NC1=CC(=C(C=C1)Cl)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:31][cH:32][c:33]1[Cl:34].O[C:7](=[O:8])[C@@H:9]1[CH2:10][CH2:11][C@H:12]([c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]2)[N:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[C@@H:9]2[CH2:10][... | COc1cc(N)ccc1Cl.COc1ccc([C@H]2CC[C@@H](C(=O)O)N2C(=O)OC(C)(C)C)cc1OC | COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2C(=O)OC(C)(C)C)ccc1Cl | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)[C@@H]1CC[C@H](c2ccccc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H... | 100 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1[C@@H](CC[C@@H]1C1=CC(=C(C=C1)OC)OC)C(NC1=CC(=C(C=C1)Cl)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C(C)(C)(C)OC(=O)N1[C@@H](CC[C@@H]1C1=CC(=C(C=C1)OC)OC)C(NC1=CC(=C(C=C1)Cl)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired"... | null | null | 8 | HOUR | A solution of (2S,5R)5-(3,4-dimethoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.50 g, 7.11 mmol, 1.0 equivalent), 4-chloro-3-methoxyaniline (1.12 g, 7.11 mmol, 1.0 equivalent), PyBrop coupling reagent (3.98 g, 8.54 mmol, 1.2 equivalents), and DIEA (1.86 ml, 10.7 mmol, 1.5 equivalents) in dichlorom... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | ClCCl | null | 8 | COc1cc(N)ccc1Cl.COc1ccc([C@H]2CC[C@@H](C(=O)O)N2C(=O)OC(C)(C)C)cc1OC>ClCCl>COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2C(=O)OC(C)(C)C)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-be5af26909e14ae8ae732c45c2af424c | COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2)ccc1Cl>>COc1cc(NC[C@@H]2CC[C@H](C3=CC=CC(OC)(OC)C3)N2)ccc1Cl | ClC1=C(C=C(C=C1)NC(=O)[C@H]1N[C@H](CC1)C1=CC(=C(C=C1)OC)OC)OC.C1CCOC1.C1(=CC=CC=C1)C>>ClC1=C(C=C(C=C1)NC[C@H]1N[C@H](CC1)C=1CC(C=CC1)(OC)OC)OC | O=[C:7]([NH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:25]([Cl:26])[cH:24][cH:23]1)[C@@H:8]1[CH2:9][CH2:10][C@H:11]([c:12]2[cH:13][cH:14][c:15]([O:17][CH3:18])[c:16]([O:19][CH3:20])[cH:21]2)[NH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][C@@H:8]2[CH2:9][CH2:10][C@H:11]([C:12]3=[CH:13][CH:14]=[CH:15][C:16]([O:17][CH3:18]... | COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2)ccc1Cl | COc1cc(NC[C@@H]2CC[C@H](C3=CC=CC(OC)(OC)C3)N2)ccc1Cl | null | null | null | Reduction | OtherReaction | 42907729ce9539517327a3317ef865152d70eb13b6298dab79a9f19adb21a369 | 6113d4b86087fc72521fab67142160242079f55ebd915b93533d21ea0c3fe1be | C1=CCCC([C@H]2CC[C@@H](CNc3ccccc3)N2)=C1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]1-[#7:5]-[C:6](-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[O;H0;D2;+0:11]-[C;D1;H3:12]):[c;H0;D3;+0:13](-[#8:14]-[C;D1;H3:15]):[cH;D2;+0:16]:2)-[C:17]-[C:18]-1>>[C;D1;H3:12]-[O;H0;D2;+0:11]-[C;H0;D4;+0:13]1(-[#8:14]-[C;D1;H3:15])-[CH2;D2;+0:16]-[C;H0;D3;+0:7](-[C:6]... | 67 | [{"value": 67.0, "product": "ClC1=C(C=C(C=C1)NC[C@H]1N[C@H](CC1)C=1CC(C=CC1)(OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | (2S,5R)5-(3,4-Dimethoxy-phenyl)-pyrrolidine-2-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide was dissolved in anhydrous THF and cooled to 0° C. in an ice bath. A 0.5M solution of alane complex in toluene (42.6 ml, 21.3 mmol, 3.0 equivalents) was added slowly and the reaction was allowed to stir and warm to room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide | Ether.Ether.Conjugated diene | c1ccccc1 | C1=CCCC=C1 | c1ccccc1.C1CCNC1.C1=CCCC=C1 | Other | null | 0 | null | COc1cc(NC(=O)[C@@H]2CC[C@H](c3ccc(OC)c(OC)c3)N2)ccc1Cl>>COc1cc(NC[C@@H]2CC[C@H](C3=CC=CC(OC)(OC)C3)N2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52a4e43096c64d72824bb0f4146df619 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(C=O)c(C)c1C>>COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C | CC1=C(C=O)C=CC(=C1C)OC.C(C)(C)(C)OC(=O)N1CCNCC1.N1N=NC2=C1C=CC=C2.C[Mg]Br>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(C)C1=C(C(=C(C=C1)OC)C)C | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([CH3:25])[c:22]1[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[N:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(C=O)c(C)c1C | COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 7a1842565a3c73c1d6bba5dccafef60d48e9eaf6e4a0871f60e828bcbdf26fb1 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCNCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:11]-[CH;D3;+0:1](-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1)-[c:2](:[c:3]):[c:4] | 56 | [{"value": 56.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 2,3-dimethyl 4-methoxy benzaldehyde (1 g, 3.05 mmol), 1 equivalent of piperazine-1-carboxylic acid tert-butyl ester (0.57 g, 3.05 mmol), 1 equivalent of benzotriazole in ethanol was stirred at room temperature for 30 minutes. The solvent was removed and the reaction was dried under vacuum. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | null | C(C)O | null | 0.5 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(C=O)c(C)c1C>C(C)O>COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fee3f409c19c4c92bf946efbde3c383f | COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C>>COc1ccc(C(C)N2CCNCC2)c(C)c1C | C(C)(C)(C)OC(=O)N1CCN(CC1)C(C)C1=C(C(=C(C=C1)OC)C)C.FC(C(=O)O)(F)F>>COC1=C(C(=C(C=C1)C(C)N1CCNCC1)C)C | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:17]([CH3:18])[c:15]2[CH3:16])[CH3:8])[CH2:14][CH2:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[c:15]([CH3:16])[c:17]1[CH3:18] | COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C | COc1ccc(C(C)N2CCNCC2)c(C)c1C | null | null | ClCCl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CN2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[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 | 2 | HOUR | To an ice chilled solution containing 4-[1-(4-methoxy-2,3-dimethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (0.4 g 1.38 mmol) and 10 ml dichloromethane, was added trifluoroacetic acid (2 ml) dropwise. The reaction was stirred at room temperature for 2 hours. The reaction was concentrated. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | ClCCl | null | 2 | COc1ccc(C(C)N2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1C>ClCCl>COc1ccc(C(C)N2CCNCC2)c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-24de49017a5a42adad724ff1a71c63b1 | COc1cc(N2C[C@@H]3CC[C@@H](c4ccc(OC)c(OC)c4)N3C(=O)C2=O)ccc1Cl>>COc1cc(N2CCN3[C@H](CC[C@H]3c3ccc(OC)c(OC)c3)C2)ccc1Cl | ClC1=C(C=C(C=C1)N1C[C@H]2N(C(C1=O)=O)[C@@H](CC2)C2=CC(=C(C=C2)OC)OC)OC.B.C1CCOC1.CO>>ClC1=C(C=C(C=C1)N1C[C@@H]2N(CC1)[C@@H](CC2)C2=CC(=C(C=C2)OC)OC)OC | O=[C:7]1[N:6]([c:5]2[cH:4][c:3]([O:2][CH3:1])[c:27]([Cl:28])[cH:26][cH:25]2)[CH2:24][C@H:10]2[N:9]([C:8]1=O)[C@H:13]([c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23]1)[CH2:12][CH2:11]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]3[C@H:10]([CH2:11][CH2:12][C@H:13]3[c:14]3[cH:15][cH:16... | COc1cc(N2C[C@@H]3CC[C@@H](c4ccc(OC)c(OC)c4)N3C(=O)C2=O)ccc1Cl | COc1cc(N2CCN3[C@H](CC[C@H]3c3ccc(OC)c(OC)c3)C2)ccc1Cl | null | null | C1CCOC1 | Reduction | OtherReaction | c92b2334b2d0c93d61ecf7829bb0b5a5e6074a5d300a1b627ba002642a5dcc3f | 872327d0f5317db5811f770a2ef4e16f48610c72bf7cae5526f2a2a33aa26523 | c1ccc([C@@H]2CC[C@@H]3CN(c4ccccc4)CCN32)cc1 | O=[C;H0;D3;+0:1]1-[#7:2](-[c:3])-[C:4]-[C:5]-[#7:6](-[C:7])-[C;H0;D3;+0:8]-1=O>>[C:7]-[#7:6]1-[C:5]-[C:4]-[#7:2](-[c:3])-[CH2;D2;+0:1]-[CH2;D2;+0:8]-1 | 30.9 | [{"value": 30.9, "product": "ClC1=C(C=C(C=C1)N1C[C@@H]2N(CC1)[C@@H](CC2)C2=CC(=C(C=C2)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.9, "product": "ClC1=C(C=C(C=C1)N1C[C@@H]2N(CC1)[C@@H](CC2)C2=CC(=C(C=C2)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | (±)-cis-2-(4-Chloro-3-methoxy-phenyl)-6-(3,4-dimethoxy-phenyl)-hexahydro-pyrrolo[1,2-a]pyrazine-3,4-dione (49.7 mg, 0.115 mmol) was dissolved in dry THF (10 mL) and BH3.THF (1 mL, 1 mmol) was added dropwise to the mixture, which was then heated at reflux overnight. The solution was cooled to 0° C. and MeOH (2 mL) was a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1C[C@H]2C[NH]CCN2C1 | C1C[C@@H]2C[NH]CCN2C1 | c1ccccc1.C1C[C@@H]2C[NH]CCN2C1.c1ccccc1 | Other | C1CCOC1 | 0 | null | COc1cc(N2C[C@@H]3CC[C@@H](c4ccc(OC)c(OC)c4)N3C(=O)C2=O)ccc1Cl>C1CCOC1>COc1cc(N2CCN3[C@H](CC[C@H]3c3ccc(OC)c(OC)c3)C2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8deb4794e9dc40f1ab3e81c5e63b38a3 | Nc1cc2cn[nH]c2cc1Cl.O=C(O)c1ccccc1NCc1ccncc1>>O=C(Nc1cc2cn[nH]c2cc1Cl)c1ccccc1NCc1ccncc1 | CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C.N1=CC=C(C=C1)CNC1=C(C(=O)O)C=CC=C1.NC=1C=C2C=NNC2=CC1Cl>>ClC1=C(C=C2C=NNC2=C1)NC(C1=C(C=CC=C1)NCC1=CC=NC=C1)=O | [NH2:3][c:4]1[cH:5][c:6]2[cH:7][n:8][nH:9][c:10]2[cH:11][c:12]1[Cl:13].O[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[NH:20][CH2:21][c:22]1[cH:23][cH:24][n:25][cH:26][cH:27]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]2[cH:7][n:8][nH:9][c:10]2[cH:11][c:12]1[Cl:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[NH:20][CH... | Nc1cc2cn[nH]c2cc1Cl.O=C(O)c1ccccc1NCc1ccncc1 | O=C(Nc1cc2cn[nH]c2cc1Cl)c1ccccc1NCc1ccncc1 | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccc2[nH]ncc2c1)c1ccccc1NCc1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 30.2 | [{"value": 30.2, "product": "ClC1=C(C=C2C=NNC2=C1)NC(C1=C(C=CC=C1)NCC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "ClC1=C(C=C2C=NNC2=C1)NC(C1=C(C=CC=C1)NCC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 194 mg (0.85 mmol) of 2-(4-pyridylmethyl)aminobenzoic acid is mixed in 8 ml of dimethylformamide with 283 mg (1.69 mmol) of 5-amino-6-chloroindazole. Under argon and in a moisture-free environment, 215 mg (2.13 mmol) of N-methylmorpholine and 386 mg (1.02 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium h... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2n[nH]cc2c1.c1ccccc1.c1ccncc1 | HO- | O.CN(C=O)C | null | 4 | Nc1cc2cn[nH]c2cc1Cl.O=C(O)c1ccccc1NCc1ccncc1>O.CN(C=O)C>O=C(Nc1cc2cn[nH]c2cc1Cl)c1ccccc1NCc1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-872a222fc12d4d10aafedfb92c226363 | ClCCBr.Oc1ccc2ccccc2c1>>ClCCOc1ccc2ccccc2c1 | C1=C(C=CC2=CC=CC=C12)O.C(=O)([O-])[O-].[K+].[K+].BrCCCl>>C1=C(C=CC2=CC=CC=C12)OCCCl | Br[CH2:3][CH2:2][Cl:1].[OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[Cl:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | ClCCBr.Oc1ccc2ccccc2c1 | ClCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Cl;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of β-naphthol (1 gm, 0.006 mole), anhydrous K2CO3 (10 gm, in excess) and 1-bromo-2-chloroethane (0.6 ml, 0.006 mole) was refluxed in dry acetone (50 ml) for 6 hours. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colorle... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1 | HBr | CC(=O)C | null | null | ClCCBr.Oc1ccc2ccccc2c1>CC(=O)C>ClCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-334d3d2c74964efbacc5b02732ba8a8a | ClCCCBr.Oc1ccc2ccccc2c1>>ClCCCOc1ccc2ccccc2c1 | C1=C(C=CC2=CC=CC=C12)O.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>C1=C(C=CC2=CC=CC=C12)OCCCCl | Br[CH2:4][CH2:3][CH2:2][Cl:1].[OH:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | ClCCCBr.Oc1ccc2ccccc2c1 | ClCCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of β-naphthol (1 gm, 0.006 mole), anhydrous K2CO3 (10 gm, in excess) and 1-bromo-3-chloropropane (0.7 ml, 0.006 mole) was refluxed in dry acetone (50 ml) for 6 hours. Reaction mixture was filtered and filtrate was concentrated to get oily compound which was crystallized with benzene-hexane to give the colorle... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1 | HBr | CC(=O)C | null | null | ClCCCBr.Oc1ccc2ccccc2c1>CC(=O)C>ClCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75b4cf608c3c4ee085a72555b323ce4b | ClCCCCBr.Oc1ccc2ccccc2c1>>ClCCCCOc1ccc2ccccc2c1 | C1=C(C=CC2=CC=CC=C12)O.C(=O)([O-])[O-].[K+].[K+].BrCCCCCl>>C1=C(C=CC2=CC=CC=C12)OCCCCCl | Br[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1].[OH:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1 | ClCCCCBr.Oc1ccc2ccccc2c1 | ClCCCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of β-naphthol (1gm, 0.006 mole), anhydrous K2CO3 (10 gm, in excess) and 1-bromo 4-chlorobutane (0.8 ml, 0.006 mole) was refluxed in dry acetone (50 ml) for 6 hours. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colorles... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1 | HBr | CC(=O)C | null | null | ClCCCCBr.Oc1ccc2ccccc2c1>CC(=O)C>ClCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c27f54bad9cb44dea52e951ac239cabf | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:22][cH:23]1.Cl[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][cH:23]1 | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.42 gm, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c6366e473ff4c269f7ad5920603d475 | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:22][cH:23]1.Cl[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][cH:23]1 | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.42 gm, 0.003 mole) was taken in dry DMF (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CN(C)C=O | 140 | null | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>O.CN(C)C=O>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8297a3a940124a04810cb043346523bc | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>NCCCOc1ccc2ccccc2c1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.C(CC)Br>>C1=C(C=CC2=CC=CC=C12)OCCCN | COc1ccc([NH:1][CH2:2][CH2:3][CH2:4][O:5][c:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15]2)cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | NCCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Reduction | OtherReaction | bd6cc2ddd30b209c36eb43f9e2d163a4da40f8a48bda8b578aa13caf5d4fe5dd | 79272555d5bd71219cf9e8b42c4ac12a30bbf383c58cfbccf49a5a990e3653c1 | c1ccc2ccccc2c1 | C-O-c1:c:c:c(-[NH;D2;+0:1]-[C:2]-[C:3]):c:c:1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A mixture of N-(4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and propyl bromide (0.54ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compound... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2ccccc2c1 | HO- | CC(=O)C | null | null | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>NCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6aa15b9e0d5e4d5689c8e3e7869b00d6 | ClCCOc1ccc2ccccc2c1.NCc1ccccc1>>c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>C(C1=CC=CC=C1)NCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[cH:19]2)[cH:20][cH:21]1 | ClCCOc1ccc2ccccc2c1.NCc1ccccc1 | c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and benzyl amine (0.38 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | ClCCOc1ccc2ccccc2c1.NCc1ccccc1>O.CS(=O)C>c1ccc(CNCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc70e18baee047c6b3a9f591ed865c1a | COc1ccc(N)cc1.ClCCOc1ccc2ccccc2c1>>COc1ccc(NCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>COC1=CC=C(C=C1)NCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:21][cH:22]1.Cl[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[cH:20]2)[cH:21][cH:22]1 | COc1ccc(N)cc1.ClCCOc1ccc2ccccc2c1 | COc1ccc(NCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 145 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.45 gm, 0.003 mole) was taken in dry dimethylsulphoxide (DMSO, 40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 145° C. for 7 hrs. The reaction was completed as checked by T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 145 | null | COc1ccc(N)cc1.ClCCOc1ccc2ccccc2c1>O.CS(=O)C>COc1ccc(NCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0ba771660de423884499ae8eb049417 | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:22][cH:23]1.Cl[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][cH:23]1 | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 135 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.42 gm, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 135° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 135 | null | COc1ccc(N)cc1.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1e4717643944f04b05d68febe48cea9 | COc1ccc(N)cc1.ClCCCCOc1ccc2ccccc2c1>>COc1ccc(NCCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>COC1=CC=C(C=C1)NCCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:23][cH:24]1.Cl[CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[cH:22]2... | COc1ccc(N)cc1.ClCCCCOc1ccc2ccccc2c1 | COc1ccc(NCCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 130 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.4 gm, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 130° C. for 7 hrs. and the reaction was completed as checked by TLC. Reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 130 | null | COc1ccc(N)cc1.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>COc1ccc(NCCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b5dae56ffa342f4b1bec6b0e9c69b52 | ClCCOc1ccc2ccccc2c1.NCc1ccccc1>>c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>C(C1=CC=CC=C1)NCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[cH:19]2)[cH:20][cH:21]1 | ClCCOc1ccc2ccccc2c1.NCc1ccccc1 | c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and benzyl amine (0.38 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | ClCCOc1ccc2ccccc2c1.NCc1ccccc1>O.CS(=O)C>c1ccc(CNCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ad4f3d5f1eb4c0894cae60ad0a95936 | ClCCCOc1ccc2ccccc2c1.NCc1ccccc1>>c1ccc(CNCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(C1=CC=CC=C1)NCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:21][cH:22]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[cH:20]2)[cH:21][cH:22]1 | ClCCCOc1ccc2ccccc2c1.NCc1ccccc1 | c1ccc(CNCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and benzyl amine (0.36 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 6 hrs. and the reaction was completed as checked by TLC. Reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | ClCCCOc1ccc2ccccc2c1.NCc1ccccc1>O.CS(=O)C>c1ccc(CNCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ede520b1da234a4faea4ad902d89bfcb | ClCCCCOc1ccc2ccccc2c1.NCc1ccccc1>>c1ccc(CNCCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(C1=CC=CC=C1)NCCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][c... | ClCCCCOc1ccc2ccccc2c1.NCc1ccccc1 | c1ccc(CNCCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | 150 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and benzylamine (0.34 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 5 hrs. and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 150 | null | ClCCCCOc1ccc2ccccc2c1.NCc1ccccc1>O.CS(=O)C>c1ccc(CNCCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a88f068295e44a0826659c21b8f3605 | ClCCOc1ccc2ccccc2c1.NC1CCCCC1>>c1ccc2cc(OCCNC3CCCCC3)ccc2c1 | C([O-])([O-])=O.[K+].[K+].C1(CCCCC1)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>C1(CCCCC1)NCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:9][CH2:8][O:7][c:6]1[cH:5][c:4]2[cH:3][cH:2][cH:1][cH:20][c:19]2[cH:18][cH:17]1.[NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]([O:7][CH2:8][CH2:9][NH:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[cH:20]1 | ClCCOc1ccc2ccccc2c1.NC1CCCCC1 | c1ccc2cc(OCCNC3CCCCC3)ccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2cc(OCCNC3CCCCC3)ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])-[C:7] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and cyclohexylamine (0.32 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloro ethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1.C1CCCCC1 | HCl | O.CS(=O)C | 140 | null | ClCCOc1ccc2ccccc2c1.NC1CCCCC1>O.CS(=O)C>c1ccc2cc(OCCNC3CCCCC3)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ebfa2a55d911477f9e169e9be028ddb7 | ClCCCOc1ccc2ccccc2c1.NC1CCCCC1>>c1ccc2cc(OCCCNC3CCCCC3)ccc2c1 | C([O-])([O-])=O.[K+].[K+].C1(CCCCC1)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C1(CCCCC1)NCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:10][CH2:9][CH2:8][O:7][c:6]1[cH:5][c:4]2[cH:3][cH:2][cH:1][cH:21][c:20]2[cH:19][cH:18]1.[NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19][c:20]2[cH:21]1 | ClCCCOc1ccc2ccccc2c1.NC1CCCCC1 | c1ccc2cc(OCCCNC3CCCCC3)ccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2cc(OCCCNC3CCCCC3)ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and cyclohexylamine (0.29 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1.C1CCCCC1 | HCl | O.CS(=O)C | 140 | null | ClCCCOc1ccc2ccccc2c1.NC1CCCCC1>O.CS(=O)C>c1ccc2cc(OCCCNC3CCCCC3)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d26b68af0fc4534abf38b5d89464753 | ClCCCCOc1ccc2ccccc2c1.NC1CCCCC1>>CC(CCNC1CCCCC1)Oc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C1(CCCCC1)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C1(CCCCC1)NCCC(C)OC1=CC2=CC=CC=C2C=C1 | Cl[CH2:1][CH2:4][CH2:3][CH2:2][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1.[NH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH:2]([CH2:3][CH2:4][NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1 | ClCCCCOc1ccc2ccccc2c1.NC1CCCCC1 | CC(CCNC1CCCCC1)Oc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b600a81df87bea1685df54aaf8b30bd23674e9b7dd2a3cc8662e71bd3684ebef | d995b0d46e4aacf6b403d700b3e57edde7ae1aa34d450d1418ad3604b33a8a71 | c1ccc2cc(OCCCNC3CCCCC3)ccc2c1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-[#8:5]-[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[CH2;D2;+0:2]-[C:3]-[CH;D3;+0:4](-[CH3;D1;+0:1])-[#8:5]-[c:6])-[C:10] | null | [] | 150 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and cyclohexylamine (0.28 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 5 hrs and the reaction was completed as checked by TLC. Reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Ether.Secondary amine | null | null | C1CCCCC1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 150 | null | ClCCCCOc1ccc2ccccc2c1.NC1CCCCC1>O.CS(=O)C>CC(CCNC1CCCCC1)Oc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-50a3b7481f7245e08b80179a6c14c38b | CCCCC(CC)CN.ClCCOc1ccc2ccccc2c1>>CCCCC(CC)CNCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(C)C(CN)CCCC.C1=C(C=CC2=CC=CC=C12)OCCCl>>C(C)C(CNCCOC1=CC2=CC=CC=C2C=C1)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH2:9].Cl[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1 | CCCCC(CC)CN.ClCCOc1ccc2ccccc2c1 | CCCCC(CC)CNCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 2-ethyl n-hexylamine (0.37 ml, 0.003 mole) was taken in dry DMSO(40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. React... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCC(CC)CN.ClCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCC(CC)CNCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8791a47137a4489b86340d1a667d0da7 | CCCCC(CC)CN.ClCCCOc1ccc2ccccc2c1>>CCCCC(CC)CNCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(C)C(CN)CCCC.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(C)C(CNCCCOC1=CC2=CC=CC=C2C=C1)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH2:9].Cl[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][... | CCCCC(CC)CN.ClCCCOc1ccc2ccccc2c1 | CCCCC(CC)CNCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 2-ethyl-n-hexylamine (0.35 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCC(CC)CN.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCC(CC)CNCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e82c47d51844dcf87ffb1f9d87321d5 | CCCCC(CC)CN.ClCCCCOc1ccc2ccccc2c1>>CCCCC(CC)CNCCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(C)C(CN)CCCC.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(C)C(CNCCCCOC1=CC2=CC=CC=C2C=C1)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH2:9].Cl[CH2:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20... | CCCCC(CC)CN.ClCCCCOc1ccc2ccccc2c1 | CCCCC(CC)CNCCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 2-ethyl-n-hexylamine (0.33 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCC(CC)CN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCC(CC)CNCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75300d78ff744fbdbf03028d1cea250e | CCCCCCCCCCCCN.ClCCCOc1ccc2ccccc2c1>>CCCCCCCCCCCCNCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCCCCCCCCCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(CCCCCCCCCCC)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].Cl[CH2:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][... | CCCCCCCCCCCCN.ClCCCOc1ccc2ccccc2c1 | CCCCCCCCCCCCNCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-dodecylamine (0.51 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCCCCCCCCCN.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCCCCCCCCCNCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6d91696f5b474ac78bdd9d7fc336a7a0 | CCCCCCCCCCCCN.ClCCCCOc1ccc2ccccc2c1>>CCCCCCCCCCCCNCCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCCCCCCCCCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(CCCCCCCCCCC)NCCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].Cl[CH2:14][CH2:15][CH2:16][CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][... | CCCCCCCCCCCCN.ClCCCCOc1ccc2ccccc2c1 | CCCCCCCCCCCCNCCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 150 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-dodecylamine (0.48 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 8 hrs and the reaction was completed as checked by TLC. Reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 150 | null | CCCCCCCCCCCCN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCCCCCCCCCNCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c862ba0c653749aab182a8023ae75593 | CC(C)CCN.ClCCOc1ccc2ccccc2c1>>CC(C)CCNCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CC(C)C)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>C(CC(C)C)NCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH2:6].Cl[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1 | CC(C)CCN.ClCCOc1ccc2ccccc2c1 | CC(C)CCNCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and isoamylamine (0.24 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 6 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CC(C)CCN.ClCCOc1ccc2ccccc2c1>O.CS(=O)C>CC(C)CCNCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1a55cd73fce4f19a47d33a5d5d31392 | CC(C)CCN.ClCCCCOc1ccc2ccccc2c1>>CC(C)CCNCCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CC(C)C)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(CC(C)C)NCCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH2:6].Cl[CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1 | CC(C)CCN.ClCCCCOc1ccc2ccccc2c1 | CC(C)CCNCCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and isoamylamine (0.21 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CC(C)CCN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CC(C)CCNCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41c68876c5e943088c6dc928e9621008 | ClCCOc1ccc2ccccc2c1.NCCCc1ccccc1>>c1ccc(CCCNCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCCN.C1=C(C=CC2=CC=CC=C12)OCCCl>>C1(=CC=CC=C1)CCCNCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH2:8])[cH:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][c... | ClCCOc1ccc2ccccc2c1.NCCCc1ccccc1 | c1ccc(CCCNCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCCNCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 150 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 3-phenylpropylamine (0.47 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 6 hrs and the reaction was completed as checked by TLC. React... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 150 | null | ClCCOc1ccc2ccccc2c1.NCCCc1ccccc1>O.CS(=O)C>c1ccc(CCCNCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f08dd98c57df4068864f8171af8f0cf3 | ClCCCOc1ccc2ccccc2c1.NCCCc1ccccc1>>c1ccc(CCCNCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCCN.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C1(=CC=CC=C1)CCCNCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH2:8])[cH:23][cH:24]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[c... | ClCCCOc1ccc2ccccc2c1.NCCCc1ccccc1 | c1ccc(CCCNCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCCNCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 150 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 3-phenylpropylamine (0.44 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 7 hrs and the reaction was completed as checked by TLC. Reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 150 | null | ClCCCOc1ccc2ccccc2c1.NCCCc1ccccc1>O.CS(=O)C>c1ccc(CCCNCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4732845dcb994dd2967780f7cdb7a7c9 | ClCCCCOc1ccc2ccccc2c1.NCCCc1ccccc1>>c1ccc(CCCNCCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCCN.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C1(=CC=CC=C1)CCCNCCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[cH:23]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH2:8])[cH:24][cH:25]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20]... | ClCCCCOc1ccc2ccccc2c1.NCCCc1ccccc1 | c1ccc(CCCNCCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCCNCCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 145 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 3-phenylpropylamine (0.42 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 145° C. for 7 hrs and the reaction was completed as checked by TLC. React... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 145 | null | ClCCCCOc1ccc2ccccc2c1.NCCCc1ccccc1>O.CS(=O)C>c1ccc(CCCNCCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-666043bb3b4c49b583eaa97ec264d731 | CCCCCCCCN.ClCCOc1ccc2ccccc2c1>>CCCCCCCCNCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCCCCCC)N.C1=C(C=CC2=CC=CC=C12)OCCCl>>C(CCCCCCC)NCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].Cl[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1 | CCCCCCCCN.ClCCOc1ccc2ccccc2c1 | CCCCCCCCNCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-octylamine (0.37 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCCCCCN.ClCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCCCCCNCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1bf0c8ca6614d2d9469a700579bf704 | CCCCCCCCN.ClCCCOc1ccc2ccccc2c1>>CCCCCCCCNCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCCCCCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(CCCCCCC)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].Cl[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:... | CCCCCCCCN.ClCCCOc1ccc2ccccc2c1 | CCCCCCCCNCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-octylamine (0.35 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 6 hrs and the reaction was completed as checked by TLC. Reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCCCCCN.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCCCCCNCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9bff22f4c0924063a2d2a6d97eb21165 | CCCCCCCCN.ClCCCCOc1ccc2ccccc2c1>>CCCCCCCCNCCC(C)Oc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCCCCCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(CCCCCCC)NCCC(C)OC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].Cl[CH2:10][CH2:11][CH2:13][CH2:12][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH:12]([CH3:13])[O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20]... | CCCCCCCCN.ClCCCCOc1ccc2ccccc2c1 | CCCCCCCCNCCC(C)Oc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b600a81df87bea1685df54aaf8b30bd23674e9b7dd2a3cc8662e71bd3684ebef | d995b0d46e4aacf6b403d700b3e57edde7ae1aa34d450d1418ad3604b33a8a71 | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[#8:5]-[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH;D3;+0:4](-[CH3;D1;+0:3])-[#8:5]-[c:6] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-octylamine (0.33 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Ether.Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCCCCCN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCCCCCNCCC(C)Oc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-534a0f1c23614f0d8bd825d6f36911c4 | CCCCN.ClCCCCOc1ccc2ccccc2c1>>CCCCNCCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(CCC)NCCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].Cl[CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1 | CCCCN.ClCCCCOc1ccc2ccccc2c1 | CCCCNCCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-butylamine (0.32 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 8 hrs and the reaction was completed as checked by TLC. Reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCCN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCNCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecd6745b85834cb7aedc1c85943beb78 | CCCN.ClCCCCOc1ccc2ccccc2c1>>CCCNCCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CC)N.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C(CC)NCCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][NH2:4].Cl[CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1 | CCCN.ClCCCCOc1ccc2ccccc2c1 | CCCNCCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-propyl amine (0.26 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | CCCN.ClCCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCNCCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1a84167fdfa4a05958f2dc9d7eb359b | ClCCCCOc1ccc2ccccc2c1.NCCc1ccccc1>>CCC(CNCCc1ccccc1)Oc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCN.C1=C(C=CC2=CC=CC=C12)OCCCCCl>>C1(=CC=CC=C1)CCNCC(CC)OC1=CC2=CC=CC=C2C=C1 | Cl[CH2:4][CH2:1][CH2:2][CH2:3][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[cH:24]1.[NH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH2:2][CH:3]([CH2:4][NH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH... | ClCCCCOc1ccc2ccccc2c1.NCCc1ccccc1 | CCC(CNCCc1ccccc1)Oc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b600a81df87bea1685df54aaf8b30bd23674e9b7dd2a3cc8662e71bd3684ebef | d995b0d46e4aacf6b403d700b3e57edde7ae1aa34d450d1418ad3604b33a8a71 | c1ccc(CCNCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-[#8:5]-[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[CH;D3;+0:4](-[#8:5]-[c:6])-[C:3]-[CH3;D1;+0:2] | null | [] | 140 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and phenylethylamine (0.4 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 8 hrs and the reaction was completed as checked by TLC. Reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Ether.Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 140 | null | ClCCCCOc1ccc2ccccc2c1.NCCc1ccccc1>O.CS(=O)C>CCC(CNCCc1ccccc1)Oc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11b1fe37bbbc49e2a48c308a8d40ee1c | CCCCN.ClCCCOc1ccc2ccccc2c1>>CCCCNCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CCC)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(CCC)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].Cl[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1 | CCCCN.ClCCCOc1ccc2ccccc2c1 | CCCCNCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 135 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-butylamine (0.34 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 135° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 135 | null | CCCCN.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCCNCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3102b1a1d544a3ebb6092b02e0c3ca2 | CCCN.ClCCCOc1ccc2ccccc2c1>>CCCNCCCOc1ccc2ccccc2c1 | C([O-])([O-])=O.[K+].[K+].C(CC)N.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C(CC)NCCCOC1=CC2=CC=CC=C2C=C1 | [CH3:1][CH2:2][CH2:3][NH2:4].Cl[CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[cH:18]1>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[cH:18]1 | CCCN.ClCCCOc1ccc2ccccc2c1 | CCCNCCCOc1ccc2ccccc2c1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 145 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and n-propylamine (0.28 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 145° C. for 8 hrs and the reaction was completed as checked by TLC. Reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 145 | null | CCCN.ClCCCOc1ccc2ccccc2c1>O.CS(=O)C>CCCNCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-971ce324064948c4830c7e2b7b24e9f7 | ClCCCOc1ccc2ccccc2c1.NCCc1ccccc1>>c1ccc(CCNCCCOc2ccc3ccccc3c2)cc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)CCN.C1=C(C=CC2=CC=CC=C12)OCCCCl>>C1(=CC=CC=C1)CCNCCCOC1=CC2=CC=CC=C2C=C1 | Cl[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][NH2:7])[cH:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[cH:22][c... | ClCCCOc1ccc2ccccc2c1.NCCc1ccccc1 | c1ccc(CCNCCCOc2ccc3ccccc3c2)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCNCCCOc2ccc3ccccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | 145 | CELSIUS | null | null | A mixture of anhydrous potassium carbonate (10 gm, in excess) and 2-phenylethylamine (0.51 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 145° C. for 7 hrs and the reaction was completed as checked by TLC. React... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HCl | O.CS(=O)C | 145 | null | ClCCCOc1ccc2ccccc2c1.NCCc1ccccc1>O.CS(=O)C>c1ccc(CCNCCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5c41d7fab414a0c80ca766a87813d22 | CI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>COc1ccc(N(C)CCCOc2ccc3ccccc3c2)cc1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.CI>>COC1=CC=C(C=C1)N(C)CCCOC1=CC2=CC=CC=C2C=C1 | I[CH3:8].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[cH:22]2)[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH3:8])[CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[cH:22]2)... | CI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | COc1ccc(N(C)CCCOc2ccc3ccccc3c2)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of (4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and methyl iodide (0.49 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compound w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2ccccc2c1 | HI | CC(=O)C | null | null | CI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>COc1ccc(N(C)CCCOc2ccc3ccccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7a8b54195494acfa10a4169a5ff2089 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>NCCCOc1ccc2ccccc2c1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.C(C)Br>>C1=C(C=CC2=CC=CC=C12)OCCCN | COc1ccc([NH:1][CH2:2][CH2:3][CH2:4][O:5][c:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15]2)cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | NCCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Reduction | OtherReaction | bd6cc2ddd30b209c36eb43f9e2d163a4da40f8a48bda8b578aa13caf5d4fe5dd | 79272555d5bd71219cf9e8b42c4ac12a30bbf383c58cfbccf49a5a990e3653c1 | c1ccc2ccccc2c1 | C-O-c1:c:c:c(-[NH;D2;+0:1]-[C:2]-[C:3]):c:c:1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A mixture of N-(4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and ethyl bromide(0.52 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compound ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2ccccc2c1 | HO- | CC(=O)C | null | null | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>NCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9831cd3ecab94533a34687b31311ae20 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>NCCCOc1ccc2ccccc2c1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.C(CC)Br>>C1=C(C=CC2=CC=CC=C12)OCCCN | COc1ccc([NH:1][CH2:2][CH2:3][CH2:4][O:5][c:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15]2)cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | NCCCOc1ccc2ccccc2c1 | null | null | CC(=O)C | Reduction | OtherReaction | bd6cc2ddd30b209c36eb43f9e2d163a4da40f8a48bda8b578aa13caf5d4fe5dd | 79272555d5bd71219cf9e8b42c4ac12a30bbf383c58cfbccf49a5a990e3653c1 | c1ccc2ccccc2c1 | C-O-c1:c:c:c(-[NH;D2;+0:1]-[C:2]-[C:3]):c:c:1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A mixture of N-(4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and propyl bromide (0.54 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compoun... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2ccccc2c1 | HO- | CC(=O)C | null | null | COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>NCCCOc1ccc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9aff86da42f3474f91f2aca17137269e | CCCCI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>CCCCN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.C(CCC)I>>COC1=CC=C(C=C1)N(CCCC)CCCOC1=CC2=CC=CC=C2C=C1 | I[CH2:4][CH2:3][CH2:2][CH3:1].[NH:5]([CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1)[c:20]1[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[c... | CCCCI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | CCCCN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | A mixture of N-(4-methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine (0.5 gm, 0.002 mole) and butyl iodide(1 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compound whic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2ccccc2c1.c1ccccc1 | HI | CC(=O)C | null | null | CCCCI.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>CCCCN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de5caab12b234d198645976888681713 | CCOC(=O)CBr.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>>CCOC(=O)CN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 | COC1=CC=C(C=C1)NCCCOC1=CC2=CC=CC=C2C=C1.BrCC(=O)OCC>>C(C)OC(CN(C1=CC=C(C=C1)OC)CCCOC1=CC2=CC=CC=C2C=C1)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[cH:21]1)[c:22]1[cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH... | CCOC(=O)CBr.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1 | CCOC(=O)CN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0aa79e0969c91fcc78d2e2c57a034d94cf8ba395b1aac7787417752a9d5314e2 | e09591825c4808efe257024fb4bbe3690a7cda9ee664fef9727988761bae5b4a | c1ccc(NCCCOc2ccc3ccccc3c2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C:7]-[C:6])-[c:9](:[c:10]):[c:11] | 96 | [{"value": 96.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (4-methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine (0.5 gm, 0.002 mole) and ethyl bromoacetate (0.62 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 10 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get the oily c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester.Tertiary amine | null | null | c1ccc2ccccc2c1.c1ccccc1 | HBr | CC(=O)C | null | null | CCOC(=O)CBr.COc1ccc(NCCCOc2ccc3ccccc3c2)cc1>CC(=O)C>CCOC(=O)CN(CCCOc1ccc2ccccc2c1)c1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20916a283f7b4e35ae8b97c1acc5e84b | COc1ccc(N)cc1.ClCCCOc1ccc2ccc(OCCCCl)cc2c1>>COc1ccc(NCCCOc2ccc3ccc(OCCCNc4ccc(OC)cc4)cc3c2)cc1 | ClCCCOC1=CC2=CC(=CC=C2C=C1)OCCCCl.COC1=CC=C(C=C1)N>>COC1=CC=C(C=C1)NCCCOC1=CC2=CC(=CC=C2C=C1)OCCCNC1=CC=C(C=C1)OC | [cH:4]1[cH:5][c:6]([NH2:7])[cH:35][cH:30][c:27]1[O:28][CH3:29].Cl[CH2:3][CH2:21][CH2:10][O:11][c:12]1[cH:26][cH:14][c:15]2[cH:16][cH:17][c:18]([O:2][CH2:1][CH2:9][CH2:8]Cl)[cH:32][c:33]2[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([O:19... | COc1ccc(N)cc1.ClCCCOc1ccc2ccc(OCCCCl)cc2c1 | COc1ccc(NCCCOc2ccc3ccc(OCCCNc4ccc(OC)cc4)cc3c2)cc1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | c5a6acf2a9d145fae494c59c817cbad6ce41356c70dafa4e9410e44578c4a1ba | e0bd9dacf65ab682499fd530e948686e7eb66ed45de4d8b873b0b4f10b43569a | c1ccc(NCCCOc2ccc3ccc(OCCCNc4ccccc4)cc3c2)cc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[#8:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]2:[c:8]:[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-Cl):[c:14]:[c:15]:[c:16]:2:[cH;D2;+0:17]:[cH;D2;+0:18]:1.[C;D1;H3:19]-[#8:20]-[c;H0;D3;+0:21]1:[cH;D2;+0:22]:[cH;D2;+0:23]:[c:24](-[NH2;D1;+0:25]):[c:26]:[c... | null | [] | 140 | CELSIUS | null | null | A mixture of 2,7-bis(3-chloropropyloxy)naphthalene (1 gm, 0.003 mole) and p-anisidine (1.17 gm, 0.005 mole) were taken in 60 ml dry DMSO. It was refluxed at 140° C. for 12 hrs the completion of the reaction was checked by TLC. The reaction mixture was poured into distilled water (80 ml) and extracted with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether.Ether.Primary amine | Ether.Ether.Ether.Ether.Secondary amine.Secondary amine | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | null | CS(=O)C | 140 | null | COc1ccc(N)cc1.ClCCCOc1ccc2ccc(OCCCCl)cc2c1>CS(=O)C>COc1ccc(NCCCOc2ccc3ccc(OCCCNc4ccc(OC)cc4)cc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8602afcfcfc34702adeae4b8cb6b6cad | COc1ccc(N)cc1.ClCCCOc1ccc2cc(OCCCCl)ccc2c1>>COc1ccc(NCCCOc2ccc3cc(OCCCNc4ccc(OC)cc4)ccc3c2)cc1 | ClCCCOC1=CC2=CC=C(C=C2C=C1)OCCCCl.COC1=CC=C(C=C1)N>>COC1=CC=C(C=C1)NCCCOC1=CC2=CC=C(C=C2C=C1)OCCCNC1=CC=C(C=C1)OC | [cH:4]1[cH:5][c:6]([NH2:7])[cH:35][cH:29][c:26]1[O:27][CH3:28].Cl[CH2:8][CH2:1][CH2:3][O:2][c:17]1[cH:16][c:15]2[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:30][CH2:23]Cl)[cH:34][c:33]2[cH:32][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][c:17]([O:18][CH2:... | COc1ccc(N)cc1.ClCCCOc1ccc2cc(OCCCCl)ccc2c1 | COc1ccc(NCCCOc2ccc3cc(OCCCNc4ccc(OC)cc4)ccc3c2)cc1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | c5a6acf2a9d145fae494c59c817cbad6ce41356c70dafa4e9410e44578c4a1ba | e0bd9dacf65ab682499fd530e948686e7eb66ed45de4d8b873b0b4f10b43569a | c1ccc(NCCCOc2ccc3cc(OCCCNc4ccccc4)ccc3c2)cc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[#8:4]-[c:5].Cl-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[C;D1;H3:15]-[#8:16]-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[cH;D2;+0:19]:[c:20](-[NH2;D1;+0:21]):[c:22]:[cH;D2;+0:23]:1>>[CH3;D1;+0:7]-[O;H0;D2;+0:9]-[c;H0;D3;+0:8... | null | [] | 140 | CELSIUS | null | null | A mixture of 2,6-bis(3-chloropropyloxy)naphthalene(1 gm, 0.003 mole) and p-anisidine(1.17 gm, 0.005 mole) was taken in 60 ml dry DMSO. It was refluxed at 140° C. for 12 hrs. The completion of the reaction was checked by TLC. The reaction mixture was poured into distilled water (80 ml) and extracted with ethyl acetate t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether.Ether.Primary amine | Ether.Ether.Ether.Ether.Secondary amine.Secondary amine | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | null | CS(=O)C | 140 | null | COc1ccc(N)cc1.ClCCCOc1ccc2cc(OCCCCl)ccc2c1>CS(=O)C>COc1ccc(NCCCOc2ccc3cc(OCCCNc4ccc(OC)cc4)ccc3c2)cc1 |
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