dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fae1bc17779a4c33ab6bacd79ee3ea5d | CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1>>O=C(O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1 | O=C1C=C(NC=C1OCC1=CC=CC=C1)/C=C/C(=O)OCC.[OH-].[K+]>>O=C1C=C(NC=C1OCC1=CC=CC=C1)/C=C/C(=O)O | CC[O:3][C:2](=[O:1])/[CH:4]=[CH:5]/[c:6]1[cH:7][c:8](=[O:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][nH:20]1>>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][c:8](=[O:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][nH:20]1 | CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1 | O=C(O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc[nH]cc1OCc1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]/[C:5]=[C:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | (E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid, ethyl ester (1.5 g) and 0.29 g of potassium hydroxide were stirred in 30 ml of ethanol for two hours at 50° C. After evaporating the solvent, the residue was dissolved in 100 ml of water and filtered. Hydrochloric acid (2N) was added to the filtr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1>C(C)O>O=C(O)/C=C/c1cc(=O)c(OCc2ccccc2)c[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b1182f573e4048b888b6653ec0ae28f6 | CC(C)(C)OC(=O)NN1CCNC1=O.O=C(Br)CBr>>CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O | O=C1N(CCN1)NC(OC(C)(C)C)=O.N1=CC=CC=C1.BrCC(=O)Br>>BrCC(=O)N1C(N(CC1)NC(OC(C)(C)C)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][N:9]1[CH2:10][CH2:11][NH:12][C:17]1=[O:18].Br[C:13](=[O:14])[CH2:15][Br:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH2:15][Br:16])[C:17]1=[O:18] | CC(C)(C)OC(=O)NN1CCNC1=O.O=C(Br)CBr | CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | c0d7cb275ad2aac32e9deba8fd2a7ffefbc279aaa29e792f49788aaa2d41eb1f | ed2e2a2113014ef864b0a3bd063f004647b373e1f6820e0fdd5587d12a0e8460 | O=C1NCCN1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-1=[O;D1;H0:18]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13](-[#7:12]-[C:10](=[O;D1;H0:11])-[#8:9]-[... | null | [] | 0 | CELSIUS | null | null | N-(2-Oxo-1-imidazolidinyl)carbamic acid, 1,1-dimethylethyl ester (12.0 g, 0.06 mmol) was dissolved in dichloromethane (75 ml) containing pyridine (5.2 g, 0.066 mol). The solution was cooled to 0° C. and treated slowly with bromoacetyl bromide (13.3 g, 0.066 mol). The solution was evaporated in vacuo to give a yellow oi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Urea | Urea.Substituted dicarboximide | C1CNC[NH]1 | C1C[NH]C[NH]1 | C1C[NH]C[NH]1 | HBr | ClCCl | 0 | null | CC(C)(C)OC(=O)NN1CCNC1=O.O=C(Br)CBr>ClCCl>CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-71dd9c746bed41b09c643f7528bb9407 | CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O.[I-]>>CC(C)(C)OC(=O)NN1CCN(C(=O)CI)C1=O | BrCC(=O)N1C(N(CC1)NC(OC(C)(C)C)=O)=O.[I-].[Na+]>>ICC(=O)N1C(N(CC1)NC(OC(C)(C)C)=O)=O | Br[CH2:15][C:13]([N:12]1[CH2:11][CH2:10][N:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:17]1=[O:18])=[O:14].[I-:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH2:15][I:16])[C:17]1=[O:18] | CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O.[I-] | CC(C)(C)OC(=O)NN1CCN(C(=O)CI)C1=O | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | O=C1NCCN1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6](=[O;D1;H0:7])-[#7:8].[I-;H0;D0:9]>>[#7:8]-[C:6](=[O;D1;H0:7])-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[I;H0;D1;+0:9])-[C:5] | null | [] | null | null | null | null | N-[3-(Bromoacetyl)-2-oxo-1-imidazolidinyl]carbamic acid, 1,1-dimethylethyl ester (20.9 g, 65 mmol) was dissolved in acetone (250 ml) containing sodium iodide (10.5 g, 70 mmol). The solution was stirred at reflux for three hours and filtered hot through Celite. The solution was evaporated in vacuo to give the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | C1C[NH]C[NH]1 | Br- | CC(=O)C | null | null | CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O.[I-]>CC(=O)C>CC(C)(C)OC(=O)NN1CCN(C(=O)CI)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-acf88472c2ef4cab9331b6f75454c6a6 | C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(NC(=O)OC(C)(C)C)C1=O>>C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(N)C1=O | CC(C)(OC(=O)NN1C(N(CC1)C(COP(=O)(N1[C@H]([C@@H](C1=O)NC(OCC1=CC=CC=C1)=O)C)O)=O)=O)C.[K].C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F.C([O-])(O)=O.[Na+]>>NN1C(N(CC1)C(COP(=O)(N1[C@H]([C@@H](C1=O)NC(OCC1=CC=CC=C1)=O)C)O)=O)=O | CC(C)(C)OC(=O)[NH:29][N:28]1[CH2:27][CH2:26][N:25]([C:23]([CH2:22][O:21][P:18]([N:17]2[C@@H:2]([CH3:1])[C@H:3]([NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[C:15]2=[O:16])(=[O:19])[OH:20])=[O:24])[C:30]1=[O:31]>>[CH3:1][C@H:2]1[C@H:3]([NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:1... | C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(NC(=O)OC(C)(C)C)C1=O | C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(N)C1=O | null | null | O | Reduction | Reduction of primary amides to amines | dd5f1d5939749381406c2645d26610b15255d5a51ca846ff661f45d1c5e951db | b8e1e75e4199725018e8cff61fd2fde98c56b629bbf185579b99364e52c966a1 | O=C(N[C@H]1CN([PH](=O)OCC(=O)N2CCNC2=O)C1=O)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[#7:2]1-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]-1=[O;D1;H0:9]>>[NH2;D1;+0:1]-[#7:2]1-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]-1=[O;D1;H0:9] | null | [] | null | null | 6 | HOUR | (2S-trans)[1-[[2-[3-[[(1,1-Dimethylethoxy)-carbonyl]amino]-2-oxo-1-imidazolidinyl]-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, monopotassium salt (5.9 g, 10 mmol) was treated at 0° C. sequentially with anisole (25 ml) and trifluoroacetic acid (60 ml), and the solution w... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Carbamic ester.Ether.Boc | Acylhydrazine | null | null | C1C[NH]C1.c1ccccc1.C1C[NH]C[NH]1 | HO- | O | null | 6 | C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(NC(=O)OC(C)(C)C)C1=O>O>C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1P(=O)(O)OCC(=O)N1CCN(N)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81dc0c6c46c04f688c9e0a0ed9716418 | CCC1CO1.Nc1ccccc1>>CCC(O)CNc1ccccc1 | NC1=CC=CC=C1.O1CCOCC1.O1CC1CC.[F-].[K+]>>C1(=CC=CC=C1)NCC(CC)O | [CH3:1][CH2:2][CH:3]1[O:4][CH2:5]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CCC1CO1.Nc1ccccc1 | CCC(O)CNc1ccccc1 | null | null | C(Cl)Cl.O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccccc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | Aniline, (102.3 g, 1.1 mole) was added to 50 ml of dioxane, 108 g of 1,2-epoxy butane and 1 g of potassium fluoride in 25 ml of water. The mixture heated to reflux for 30 hours. The mixture was poured into water, taken up in 200 ml of methylene chloride, dried over anhydrous magnesium sulfate and stripped under vacuum.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1 | null | C(Cl)Cl.O | null | null | CCC1CO1.Nc1ccccc1>C(Cl)Cl.O>CCC(O)CNc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2606b9cbf440416d8f3e63a1500dbed7 | CCC(O)CNc1ccc(F)c(C(F)(F)F)c1.O=Cc1cccc(Cl)c1>>CCC1CN(c2ccc(F)c(C(F)(F)F)c2)C(c2cccc(Cl)c2)O1 | ClC=1C=C(C=O)C=CC1.FC(C=1C=C(C=CC1F)NCC(CC)O)(F)F>>ClC=1C=C(C=CC1)C1OC(CN1C1=CC(=C(C=C1)F)C(F)(F)F)CC | [CH3:1][CH2:2][CH:3]([CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[OH:25].O=[CH:17][c:18]1[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]1>>[CH3:1][CH2:2][CH:3]1[CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[CH:17]([c:18]2[cH:19][cH:20][... | CCC(O)CNc1ccc(F)c(C(F)(F)F)c1.O=Cc1cccc(Cl)c1 | CCC1CN(c2ccc(F)c(C(F)(F)F)c2)C(c2cccc(Cl)c2)O1 | null | CS(=O)(=O)O | null | Heteroatom Alkylation and Arylation | OtherReaction | ab3b4f808b07350acfd6d1e85757bbd6baa88d84a0ea16a460bf9c38c0c85e4e | 95793bcca7dfdb9678898541206b5740e40b60c474970e6249c9e5d5ba1d0947 | c1ccc(C2OCCN2c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[C:6]1-[C:8]-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[O;H0;D2;+0:7]-1 | null | [] | null | null | null | null | Meta-chlorobenzaldehyde (2.3 g, 0.016 mole) was combined with 5 g of 1-(3-trifluoromethyl-4-fluorophenylamino)-2-butanol and 3 drops of methane sulfonic acid was added. The mixture was heated on the steam bath for about one hour and stripped on the rotary evaporator. The product, a sticky, thick liquid, was characteriz... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol.Secondary amine | Ether.Tertiary amine | null | C1COC[NH]1 | C1COC[NH]1.c1ccccc1.c1ccccc1 | HO- | CS(=O)(=O)O | null | null | CCC(O)CNc1ccc(F)c(C(F)(F)F)c1.O=Cc1cccc(Cl)c1>CS(=O)(=O)O>CCC1CN(c2ccc(F)c(C(F)(F)F)c2)C(c2cccc(Cl)c2)O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-95fce6ee0fd6497e86db89788ce9af11 | CCC(O)CNc1ccc(Cl)c(C(F)(F)F)c1.N#Cc1cccc(C=O)c1>>CCC1CN(c2ccc(Cl)c(C(F)(F)F)c2)C(c2cccc(C#N)c2)O1 | C(#N)C=1C=C(C=O)C=CC1.FC(C=1C=C(C=CC1Cl)NCC(CC)O)(F)F.O>>C(#N)C=1C=C(C=CC1)C1OC(CN1C1=CC(=C(C=C1)Cl)C(F)(F)F)CC | [CH3:1][CH2:2][CH:3]([CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[OH:26].O=[CH:17][c:18]1[cH:19][cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25]1>>[CH3:1][CH2:2][CH:3]1[CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[CH:17]([c:18]2[cH:19]... | CCC(O)CNc1ccc(Cl)c(C(F)(F)F)c1.N#Cc1cccc(C=O)c1 | CCC1CN(c2ccc(Cl)c(C(F)(F)F)c2)C(c2cccc(C#N)c2)O1 | null | CS(=O)(=O)O | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ab3b4f808b07350acfd6d1e85757bbd6baa88d84a0ea16a460bf9c38c0c85e4e | 95793bcca7dfdb9678898541206b5740e40b60c474970e6249c9e5d5ba1d0947 | c1ccc(C2OCCN2c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[C:6]1-[C:8]-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[O;H0;D2;+0:7]-1 | null | [] | null | null | null | null | Meta-cyanobenzaldehyde (2.1 g, 0.016 mole) was added to 4.3 g of 1-(3-trifluoromethyl-4-chlorophenylamino)-2-butanol in 50 ml of toluene and 2-3 drops of methane sulfonic acid was added. The mixture was refluxed under a modified Dean-Stark apparatus until no more water came off and the mixture was stripped on a rotary ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol.Secondary amine | Ether.Tertiary amine | null | C1COC[NH]1 | C1COC[NH]1.c1ccccc1.c1ccccc1 | HO- | CS(=O)(=O)O.C1(=CC=CC=C1)C | null | null | CCC(O)CNc1ccc(Cl)c(C(F)(F)F)c1.N#Cc1cccc(C=O)c1>CS(=O)(=O)O.C1(=CC=CC=C1)C>CCC1CN(c2ccc(Cl)c(C(F)(F)F)c2)C(c2cccc(C#N)c2)O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d3aa4ef6e7854887855a44c964e29706 | CC(C)(C)C1(COc2ccc(Cl)cc2)CO1.c1nc[nH]n1>>CC(C)(C)C(O)(COc1ccc(Cl)cc1)Cn1cncn1 | ClC1=CC=C(OCC2(OC2)C(C)(C)C)C=C1.N1N=CN=C1.C(C)(=O)OCC>>ClC1=CC=C(OCC(CN2N=CN=C2)(C(C)(C)C)O)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[O:6][CH2:16]1.[nH:17]1[cH:18][n:19][cH:20][n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]([OH:6])([CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[CH2:16][n:17]1[cH:18][n:19][cH:20][n:21]1 | CC(C)(C)C1(COc2ccc(Cl)cc2)CO1.c1nc[nH]n1 | CC(C)(C)C(O)(COc1ccc(Cl)cc1)Cn1cncn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 28a0254009916c6c546927d7927691482e70d5ce5f7580284682740d091ca734 | 64c863766284618c8c914b50974c3faab567499928c69890adf3711c924533f0 | c1ccc(OCCCn2cncn2)cc1 | [#7;a:1]1:[c:2]:[nH;D2;+0:3]:[#7;a:4]:[c:5]:1.[C:6]-[C:7]1(-[C:8])-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:6]-[C:7](-[C:8])(-[OH;D1;+0:10])-[CH2;D2;+0:9]-[n;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[#7;a:1]:[c:2]:1 | 65 | [{"value": 65.0, "product": "ClC1=CC=C(OCC(CN2N=CN=C2)(C(C)(C)C)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.8, "product": "ClC1=CC=C(OCC(CN2N=CN=C2)(C(C)(C)C)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 72.15 g (0.3 mole) of 2-(4-chlorophenoxy-methyl)-2-tert.-butyl-oxirane and 24.15 g (0.35 mole) of 1,2,4-triazole were heated under reflux in 120 ml of ethanol for 48 hours. The mixture was then concentrated, the residue was taken up in 200 ml of ethyl acetate and the ethyl acetate mixture was heated. It was then cooled... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1.c1nc[nH]n1 | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | null | C(C)O | null | null | CC(C)(C)C1(COc2ccc(Cl)cc2)CO1.c1nc[nH]n1>C(C)O>CC(C)(C)C(O)(COc1ccc(Cl)cc1)Cn1cncn1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9a65196066a45deb5cb3baa21f1de1c | CC(C)(C)C(=O)COc1ccc(Cl)cc1.COS(=O)(=O)OC>>CC(C)(C)C1(COc2ccc(Cl)cc2)CO1 | CSC.S(=O)(=O)(OC)OC.ClC1=CC=C(OCC(C(C)(C)C)=O)C=C1.C[O-].[Na+]>>ClC1=CC=C(OCC2(OC2)C(C)(C)C)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5]([CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)=[O:16].COS(=O)(=O)O[CH3:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[CH2:15][O:16]1 | CC(C)(C)C(=O)COc1ccc(Cl)cc1.COS(=O)(=O)OC | CC(C)(C)C1(COc2ccc(Cl)cc2)CO1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 8baa6edb5cd8bf6ac3a159f9a2c83da9850af70751cef9ef728836b2ad75fe75 | 65a8af0997ec9f56fa44fac9e6db8d8aeec07e535d6b4d216a6180693919dc05 | c1ccc(OCC2CO2)cc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[#8:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9]>>[#8:2]-[C:3]-[C;H0;D4;+0:4]1(-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-1 | 84 | [{"value": 84.0, "product": "ClC1=CC=C(OCC2(OC2)C(C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "ClC1=CC=C(OCC2(OC2)C(C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 162 ml (2.2 moles) of dimethyl sulphide in 400 ml of absolute acetonitrile was added to a solution of 189 ml (2.0 moles) of dimethyl sulphate in 1,200 ml of absolute acetonitrile at room temperature. The reaction mixture was stirred overnight at room temperature. 118.8 g (2.2 moles) of sodium methylate we... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ether | null | C1CO1 | c1ccccc1.C1CO1 | HO- | C(C)#N | null | 8 | CC(C)(C)C(=O)COc1ccc(Cl)cc1.COS(=O)(=O)OC>C(C)#N>CC(C)(C)C1(COc2ccc(Cl)cc2)CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-65ac7b4e119c45f7be18d6fb28021e3d | CC(C)(C)C1(C=Cc2ccc(Cl)cc2)CO1.CCO.c1nc[nH]n1>>CC(C)(C)C(O)(C=Cc1ccc(Cl)cc1)Cn1ccnc1 | ClC1=CC=C(C=C1)C=CC1(OC1)C(C)(C)C.N1N=CN=C1.C(C)O>>ClC1=CC=C(C=C1)C=CC(C(C)(C)C)(O)CN1C=NC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1([CH:7]=[CH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[O:6][CH2:16]1.OC[CH3:18].n1[nH:17][cH:21][n:20][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]([OH:6])([CH:7]=[CH:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[CH2:16][n:17]1[cH:18][cH:19][n:20][cH:21]1 | CC(C)(C)C1(C=Cc2ccc(Cl)cc2)CO1.CCO.c1nc[nH]n1 | CC(C)(C)C(O)(C=Cc1ccc(Cl)cc1)Cn1ccnc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5ea3783ebbd7096b13f1a1e72bf7085cb2d74cabf763792337323141dcbf5162 | 02cfabc6df4b8f83999e8e1bd949695f2480f50e3abb598c239092f7460dfe4f | C(=Cc1ccccc1)CCn1ccnc1 | O-C-[CH3;D1;+0:1].[#7;a:2]1:[c:3]:[nH;D2;+0:4]:n:[cH;D2;+0:5]:1.[C:6]-[C:7]1(-[C:8]=[C:9]-[c:10])-[CH2;D2;+0:11]-[O;H0;D2;+0:12]-1>>[C:6]-[C:7](-[OH;D1;+0:12])(-[C:8]=[C:9]-[c:10])-[CH2;D2;+0:11]-[n;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:5]:[cH;D2;+0:1]:1 | 77 | [{"value": 77.0, "product": "ClC1=CC=C(C=C1)C=CC(C(C)(C)C)(O)CN1C=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 17.75 g (0.075 mole) of 2-(4-chlorophenyl-ethenyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol was heated in a bomb tube at 150° C. for 20 hours. The reaction mixture was then concentrated and the crystalline residue was stirred with ether. The solid was then filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Tertiary alcohol | C1CO1.c1nc[nH]n1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HO- | null | null | null | CC(C)(C)C1(C=Cc2ccc(Cl)cc2)CO1.CCO.c1nc[nH]n1>>CC(C)(C)C(O)(C=Cc1ccc(Cl)cc1)Cn1ccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-31a19b8bc9484cb78d47d71464d3b4e3 | CC(C)(C)C1(CCc2ccc(Cl)cc2)CO1.c1nc[nH]n1>>CC(C)(C)C(O)(CCc1ccc(Cl)cc1)Cn1cncn1 | ClC1=CC=C(C=C1)CCC1(OC1)C(C)(C)C.N1N=CN=C1>>ClC1=CC=C(C=C1)CCC(C(C)(C)C)(O)CN1N=CN=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1([CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[O:6][CH2:16]1.[nH:17]1[cH:18][n:19][cH:20][n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]([OH:6])([CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[CH2:16][n:17]1[cH:18][n:19][cH:20][n:21]1 | CC(C)(C)C1(CCc2ccc(Cl)cc2)CO1.c1nc[nH]n1 | CC(C)(C)C(O)(CCc1ccc(Cl)cc1)Cn1cncn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 28a0254009916c6c546927d7927691482e70d5ce5f7580284682740d091ca734 | 64c863766284618c8c914b50974c3faab567499928c69890adf3711c924533f0 | c1ccc(CCCCn2cncn2)cc1 | [#7;a:1]1:[c:2]:[nH;D2;+0:3]:[#7;a:4]:[c:5]:1.[C:6]-[C:7]1(-[C:8])-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:6]-[C:7](-[C:8])(-[OH;D1;+0:10])-[CH2;D2;+0:9]-[n;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[#7;a:1]:[c:2]:1 | 53.3 | [{"value": 53.2, "product": "ClC1=CC=C(C=C1)CCC(C(C)(C)C)(O)CN1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "ClC1=CC=C(C=C1)CCC(C(C)(C)C)(O)CN1N=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 17.9 g (0.075 mole) of 2-(4-chlorophenylethyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol was heated in a bomb tube at 150° C. for 20 hours. The reaction solution was allowed to cool and was concentrated. The residue was dissolved in ether and the solution was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1.c1nc[nH]n1 | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | null | C(C)O | null | null | CC(C)(C)C1(CCc2ccc(Cl)cc2)CO1.c1nc[nH]n1>C(C)O>CC(C)(C)C(O)(CCc1ccc(Cl)cc1)Cn1cncn1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-aa9ed74e9a0d49428bacce5162b0c162 | CC(C)C(C)(N)C(N)=O.CC1=C(C)C(=O)OC1=O>>C/C(C(=O)O)=C(\C)C(=O)NC(C)(C(N)=O)C(C)C | C/C/1=C(/C(=O)OC1=O)\C.NC(C(=O)N)(C(C)C)C>>C/C(/C(=O)NC(C(C)C)(C)C(=O)N)=C(/C(=O)O)\C | [NH2:10][C:11]([CH3:12])([C:13]([NH2:14])=[O:15])[CH:16]([CH3:17])[CH3:18].[CH3:1][C:2]1=[C:6]([CH3:7])[C:8](=[O:9])[O:5][C:3]1=[O:4]>>[CH3:1]/[C:2]([C:3](=[O:4])[OH:5])=[C:6](\[CH3:7])[C:8](=[O:9])[NH:10][C:11]([CH3:12])([C:13]([NH2:14])=[O:15])[CH:16]([CH3:17])[CH3:18] | CC(C)C(C)(N)C(N)=O.CC1=C(C)C(=O)OC1=O | C/C(C(=O)O)=C(\C)C(=O)NC(C)(C(N)=O)C(C)C | null | null | C(Cl)Cl | Protection | OtherReaction | 5eeb1ad872b9f10501b37c5f8eee8f05cbb334b0ab6844e4f6b65e32b076e4ce | d83a5fe7c1575bfa4f6a9dc1cf7406e299c5c7ecfc75f13bc6d348857a70653f | null | [C;D1;H3:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[C:8]-1=[O;D1;H0:9].[C:10]-[C:11](-[C;D1;H3:12])(-[NH2;D1;+0:13])-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]>>[C:10]-[C:11](-[C;D1;H3:12])(-[NH;D2;+0:13]-[C;H0;D3;+0:5](=[O;D1;H0:6])/[C:3](-[C;D1;H3:4])=[C:2](/[C;D1;H3:1])-[C:8](=[O;D1;H0:9])-[O... | 96.3 | [{"value": 96.0, "product": "C/C(/C(=O)NC(C(C)C)(C)C(=O)N)=C(/C(=O)O)\\C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "C/C(/C(=O)NC(C(C)C)(C)C(=O)N)=C(/C(=O)O)\\C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 46 g of dimethylmaleic acid anhydride, 48 g of 2-amino-2,3-dimethylbutyric acid amide and 70 ml of methylene chloride was heated at its boiling point for 15 minutes. After some of the solvent had been distilled off, the residual mixture was stirred with 300 ml of diethyl ether, and the product precipitated... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Secondary amide | C1=CCOC1 | null | null | null | C(Cl)Cl | null | null | CC(C)C(C)(N)C(N)=O.CC1=C(C)C(=O)OC1=O>C(Cl)Cl>C/C(C(=O)O)=C(\C)C(=O)NC(C)(C(N)=O)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1726b250b80e416d94f4df3e349e6e44 | CC(C)C(C)(N)C(N)=O>>CC(C)C(C)([NH-])C(N)=O | NC(C(=O)N)(C(C)C)C.C(C)N(CC)CC.[Cl-].C/C(/C(=O)OCC)=C(\C(=O)[O-])/C>>C(C)OC(\C(=C(\C(=O)[O-])/C)\C)=O.NC(=O)C(C(C)C)(C)[NH-] | [CH3:1][CH:2]([CH3:3])[C:4]([CH3:5])([NH2:6])[C:7]([NH2:8])=[O:9]>>[CH3:1][CH:2]([CH3:3])[C:4]([CH3:5])([NH-:6])[C:7]([NH2:8])=[O:9] | CC(C)C(C)(N)C(N)=O | CC(C)C(C)([NH-])C(N)=O | null | null | C(Cl)Cl | Reduction | OtherReaction | a4dec735d83c6848619f7be0a55460a7c8d55fc3ba038446e1223b4ec7329128 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | null | [C:1]-[C:2](-[C;D1;H3:3])(-[NH2;D1;+0:4])-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]>>[C:1]-[C:2](-[C;D1;H3:3])(-[NH-;D1:4])-[C:5](-[N;D1;H2:6])=[O;D1;H0:7] | 42.3 | [{"value": 41.0, "product": "C(C)OC(\\C(=C(\\C(=O)[O-])/C)\\C)=O.NC(=O)C(C(C)C)(C)[NH-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.3, "product": "C(C)OC(\\C(=C(\\C(=O)[O-])/C)\\C)=O.NC(=O)C(C(C)C)(C)[NH-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 13 g of monoethyl 2,3-dimethylfumarate chloride in 20 ml of methylene chloride was added dropwise, while stirring and cooling with ice, to a solution of 12 g of 2-amino-2,3-dimethyl-butyric acid amide and 12 ml of triethylamine in 80 ml of methylene chloride. The mixture was stirred for 2 hours at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | null | null | null | C(Cl)Cl | null | null | CC(C)C(C)(N)C(N)=O>C(Cl)Cl>CC(C)C(C)([NH-])C(N)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a4c6ac19a65248798aac4e008fbbaf15 | Cc1cc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-]>>Cc1cc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 | NC1=NC(=CC(=C1C#N)C)C.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N=C=O>>C(#N)C=1C(=NC(=CC1C)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7]#[N:8])[c:9]([NH2:10])[n:26]1.[C:11](=[O:12])=[N:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[N+:23](=[O:24])[O-:25]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7]#[N:8])[c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c... | Cc1cc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-] | Cc1cc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ccccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12] | null | [] | null | null | 8 | HOUR | To a stirred suspension of 0.5 g (4.3 mmol) 2-amino-4,6-dimethyl-3-pyridinecarbonitrile [Archiv. Pharm., 288, 174 (1955)] in 20 ml of acetonitrile was added 1.3 g (5.7 mmol) o-nitrobenzenesulfonyl isocyanate. The mixture was then heated to reflux (80°) for four hours followed by stirring at ambient temperature overnigh... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccncc1.c1ccccc1 | null | C(C)#N | null | 8 | Cc1cc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1[N+](=O)[O-]>C(C)#N>Cc1cc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2[N+](=O)[O-])n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-78ad90bd69134387b5703ba1c2246b9a | COc1cc(N)nc(OC)n1.O=[N+]([O-])O>>COc1nc(N)c([N+](=O)[O-])c(OC)n1 | S(O)(O)(=O)=O.COC1=NC(=CC(=N1)N)OC.[N+](=O)(O)[O-]>>COC1=NC(=C(C(=N1)N)[N+](=O)[O-])OC | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:7][c:11]([O:12][CH3:13])[n:14]1.O[N+:8](=[O:9])[O-:10]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[c:7]([N+:8](=[O:9])[O-:10])[c:11]([O:12][CH3:13])[n:14]1 | COc1cc(N)nc(OC)n1.O=[N+]([O-])O | COc1nc(N)c([N+](=O)[O-])c(OC)n1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 17bd7245f9d737a6c07bbf84345ed5d1d53ccf508974b3db72c7e5633e72b7db | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cncnc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[cH;D2;+0:11]:1>>[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[c;H0;D3;+0:11]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | null | null | To a solution of 20 ml of concentrated nitric acid and 16 ml of concentrated sulfuric acid was added 3.9 g (0.025 mmol) of 2,6-dimethoxy-4-pyrimidinamine. The resulting solution was stirred at ambient temperature and pressure for thirty minutes and was then stirred at 50° for fifteen minutes. The solution was then cool... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cncnc1 | c1cncnc1 | c1cncnc1 | HO- | null | null | null | COc1cc(N)nc(OC)n1.O=[N+]([O-])O>>COc1nc(N)c([N+](=O)[O-])c(OC)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9ecd5cb885984a4aae7b8025b84f1e4f | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)c([N+](=O)[O-])c(OC)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)c1[N+](=O)[O-] | COC1=NC(=C(C(=N1)N)[N+](=O)[O-])OC.C(=O)(OC)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=C(C(=N1)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1)[N+](=O)[O-])OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([O:21][CH3:22])[n:23][c:24]([O:25][CH3:26])[c:27]1[N+:28](=[O:29])[O-:30]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[N... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)c([N+](=O)[O-])c(OC)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)c1[N+](=O)[O-] | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ccncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 90.6 | [{"value": 90.6, "product": "COC1=NC(=C(C(=N1)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1)[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 0.2 g (1.0 mmol) of 2,6-dimethoxy-5-nitro-4-pyrimidinamine and 0.6 g (2.4 mmol) of 2-carbomethoxybenzenesulfonyl isocyanate in 15 ml of methylene chloride was stirred at ambient temperature and pressure for 12 hours under anhydrous conditions. The solvent was then evaporated under reduced pressure. The re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(Cl)Cl | null | 12 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)c([N+](=O)[O-])c(OC)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)c1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c4afe691e3a7425cae2c519da2b6103e | Cc1nc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl>>Cc1nc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 | ClC1=C(C=CC=C1)S(=O)(=O)N=C=O.NC1=NC(=NC(=C1C#N)C)C.N12CCN(CC1)CC2>>ClC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=C1C#N)C)C | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]#[N:8])[c:9]([NH2:10])[n:24]1.[C:11](=[O:12])=[N:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Cl:23]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]#[N:8])[c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]... | Cc1nc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl | Cc1nc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ccncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14] | 71.2 | [{"value": 71.2, "product": "ClC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=C1C#N)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 4.35 g of 2-Chlorobenzenesulfonyl isocyanate was dissolved in 10 ml xylenes and 25 ml methylene chloride. To this was added 2.96 g of 4-amino-2,6-dimethyl-5-pyrimidine carbonitrile and a catalytic amount of 1,4-diazabicyclo-[2.2.2]octane. The reaction was stirred under a CaSO4 drying tube for three days. The reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccccc1 | null | C(Cl)Cl | null | 72 | Cc1nc(C)c(C#N)c(N)n1.O=C=NS(=O)(=O)c1ccccc1Cl>C(Cl)Cl>Cc1nc(C)c(C#N)c(NC(=O)NS(=O)(=O)c2ccccc2Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6a5fb342034c427dadbea3f95a18e897 | Cc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl>>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 | NC1=NC(=CC(=N1)C)C.ClC(C1=C(C=CC=C1)S(=O)(=O)N=C=O)Cl>>ClC(C1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)C)C)Cl | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH2:8])[n:24]1.[C:9](=[O:10])=[N:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[CH:21]([Cl:22])[Cl:23]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[O:10])[NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[CH:21]([Cl... | Cc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl | Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 18 | HOUR | 2-(Dichloromethyl)benzenesulfonyl isocyanate, prepared from 10 mmol of sulfonamide as described in the synthesis of Example 1, was treated with acetonitrile and 2-amino-4,6-dimethylpyrimidine (1.23 g). The mixture was stirred at room temperature for 18 hrs, cooled, and filtered to provide 1.08 g of white solid, mp 195°... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccccc1 | null | C(C)#N | null | 18 | Cc1cc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl>C(C)#N>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a13c037be7c241d6a705a7e8083f6b1a | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 | NC1=NC(=NC(=N1)OC)C.ClC(C1=C(C=CC=C1)S(=O)(=O)N=C=O)Cl>>ClC(C1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)C)Cl | [CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:25]1.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[CH:22]([Cl:23])[Cl:24]>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[... | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 18 | HOUR | 2-(Dichloromethyl)benzenesulfonyl isocyanate prepared from 10 mmol of sulfonamide as described in the synthesis of Example 1, was treated with acetonitrile (15 ml) and 2-amino-4-methoxy-6-methyl-1,3,5-triazine (1.40 g). The mixture was stirred for 18 hrs. and filtered. The filtrate was evaporated and recrystallized fro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(C)#N | null | 18 | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(Cl)Cl>C(C)#N>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(Cl)Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e3f81eb409d2431c8e14cd850aef493f | CO.C[O-].NS(=O)(=O)c1ccccc1CCl.O=C=Nc1nc(Cl)nc(Cl)n1>>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)nc(OC)n1 | O.C[O-].[Na+].CO.ClC1=NC(=NC(=N1)Cl)N=C=O.ClCC1=C(C=CC=C1)S(=O)(=O)N>>ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)OC | [CH3:1][OH:2].[O-:23][CH3:24].[NH2:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH2:19][Cl:20].Cl[c:3]1[n:4][c:5]([N:6]=[C:7]=[O:8])[n:21][c:22](Cl)[n:25]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH2:19][Cl:20])[n:... | CO.C[O-].NS(=O)(=O)c1ccccc1CCl.O=C=Nc1nc(Cl)nc(Cl)n1 | COc1nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)nc(OC)n1 | null | null | C(C)#N | Acylation | OtherReaction | 5cdd877a8ea4ad7f77e0b58a5aa98d7b3adfbfbb456325612b5171f9a3531a5c | e436601634444b82a56ec7862cb8244a75bca7f9b265f2a0e3614cb21c0195bb | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6]):[#7;a:7]:[c;H0;D3;+0:8](-Cl):[#7;a:9]:1.[C;D1;H3:10]-[O-;H0;D1:11].[C;D1;H3:12]-[OH;D1;+0:13].[NH2;D1;+0:14]-[#16:15](=[O;D1;H0:16])(=[O;D1;H0:17])-[c:18]>>[C;D1;H3:12]-[O;H0;D2;+0:13]-[c;H0;D3;+0:8]1:[#7;a:9]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-... | null | [] | null | null | 20 | HOUR | A solution of 4,6-dichloro-1,3,5-triazin-2-yl isocyanate (3.10 g, 16.2 mmol) in acetonitrile (15 ml) was contacted with 2-(chloromethyl)benzene sulfonamide (3.34 g, 16.2 mmol) and stirred for 20 hrs at 25°. The mixture was heated at 50° for 2 hrs, cooled and filtered to provide 3.86 g, mp 162°-170°, which was contacted... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Aromatic halide.Isocyanate.Methanol | Sulfonamide.Ether.Ether.Urea | c1ncncn1 | c1ncncn1 | c1ncncn1.c1ccccc1 | HCl | C(C)#N | null | 20 | CO.C[O-].NS(=O)(=O)c1ccccc1CCl.O=C=Nc1nc(Cl)nc(Cl)n1>C(C)#N>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)nc(OC)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7101f12d796b4a7697ca6546a96de61b | COc1cc(OC)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1CCl>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1 | S(=O)(=O)(N=C=O)N=C=O.ClCC1=C(C=CC=C1)S(=O)(=O)N=C=O.C(=O)(Cl)Cl.NC1=NC(=CC(=N1)OC)OC.ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NCCCC>>ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH2:10])[n:25]1.[C:11](=[O:12])=[N:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH2:23][Cl:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c... | COc1cc(OC)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1CCl | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1 | null | N12NCC(CC1)CC2 | C(C)#N.C=1(C(=CC=CC1)C)C | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6])-[NH;D2;+0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13] | 69.6 | [{"value": 69.6, "product": "ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 2-(chloromethyl)-N-(butylaminocarbonyl)benzene sulfonamide (1.33 g, 4.38 mmol) and diazabicyclo[2.2.2]octane (5 mg) in xylene (12 ml) was heated at reflux and contacted in portions with phosgene (1.0 ml. condensed phase). After 2.0 hrs at reflux, the mixture was cooled to room temperature, decanted, and v... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1ccccc1 | null | N12NCC(CC1)CC2.C(C)#N.C=1(C(=CC=CC1)C)C | null | 16 | COc1cc(OC)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1CCl>N12NCC(CC1)CC2.C(C)#N.C=1(C(=CC=CC1)C)C>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-849b814f85c74b4ea52ba55f26ec47fb | C1CCNC1.COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CN2CCCC2)n1.Cl | ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC.N1CCCC1.[K+].[Br-]>>Cl.N1(CCCC1)CC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC | [NH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[CH2:23][Cl:30])[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:1... | C1CCNC1.COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1 | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CN2CCCC2)n1.Cl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1CN1CCCC1 | [C:1]1-[C:2]-[C:3]-[C:4]-[NH;D2;+0:5]-1.[Cl;H0;D1;+0:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[ClH;D0;+0:6].[c:9]:[c:8](-[CH2;D2;+0:7]-[N;H0;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[C:4]-1):[c:10] | null | [] | null | null | 3.5 | HOUR | A slurry of 2-(chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.00 g) in dimethylformamide (5 ml) was contacted with pyrrolidine (0.45 ml) and stirred for 3.5 hrs. Volatiles were removed under vacuum and the residue was taken up in methanol. Solvent was removed and the water (15 ml) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1cncnc1.c1ccccc1.C1CC[NH]C1 | null | CN(C=O)C | null | 3.5 | C1CCNC1.COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCl)n1>CN(C=O)C>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CN2CCCC2)n1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5a26a82ee29e4183bd849568dc3c6a8f | CCc1ccccc1S(=O)(=O)Cl.ClOCl>>CC(Cl)c1ccccc1S(=O)(=O)Cl | C(C)C1=C(C=CC=C1)S(=O)(=O)Cl.O(Cl)Cl>>ClC(C)C1=C(C=CC=C1)S(=O)(=O)Cl | [CH3:1][CH2:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10](=[O:11])(=[O:12])[Cl:13].ClO[Cl:3]>>[CH3:1][CH:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10](=[O:11])(=[O:12])[Cl:13] | CCc1ccccc1S(=O)(=O)Cl.ClOCl | CC(Cl)c1ccccc1S(=O)(=O)Cl | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | c1ccccc1 | Cl-O-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH;D3;+0:3](-[Cl;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | 83.9 | [{"value": 83.9, "product": "ClC(C)C1=C(C=CC=C1)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethylbenzenesulfonyl chloride (obtained by chlorosulfonation of ethylbenzene) (7.78 g) in carbon tetrachloride (5.0 ml) was contacted with a solution of dichlorine monoxide (82 mmol) in carbon tetrachloride (100 ml) and the mixture was heated in a closed system at 50°-60° for 16 hrs. The mixture was dri... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ccccc1 | HCl | C(Cl)(Cl)(Cl)Cl | null | null | CCc1ccccc1S(=O)(=O)Cl.ClOCl>C(Cl)(Cl)(Cl)Cl>CC(Cl)c1ccccc1S(=O)(=O)Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-27141d7cdd0949518f09952f7124156b | N.O=S(=O)(Cl)c1ccccc1CCl>>NS(=O)(=O)c1ccccc1CCl | N.ClCC1=C(C=CC=C1)S(=O)(=O)Cl>>ClCC1=C(C=CC=C1)S(=O)(=O)N | [NH3:1].Cl[S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Cl:12]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Cl:12] | N.O=S(=O)(Cl)c1ccccc1CCl | NS(=O)(=O)c1ccccc1CCl | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 419151dfc49d0719bc8d3fc5b23cdd08248d27df18761ee59c11624194c4c5ab | ae33b93faeb632e8ec1263862cc7a6f628747ed893339f281ddf88c6e380b60a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of ammonia (5.2 ml) in tetrahydrofuran (250 ml) at -70° was contacted rapidly with a solution of 2-(chloromethyl)benzenesulfonyl chloride (21.8 g) in tetrahydrofuran (125 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed under vacuum. The residue was contacted with ethyl acetate a... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | N.O=S(=O)(Cl)c1ccccc1CCl>O1CCCC1>NS(=O)(=O)c1ccccc1CCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81369e951b824169a8227c813fb01c19 | CC(Cl)c1ccccc1S(=O)(=O)Cl.N>>CC(Cl)c1ccccc1S(N)(=O)=O | N.ClC(C)C1=C(C=CC=C1)S(=O)(=O)Cl>>ClC(C)C1=C(C=CC=C1)S(=O)(=O)N | Cl[S:10]([c:9]1[c:4]([CH:2]([CH3:1])[Cl:3])[cH:5][cH:6][cH:7][cH:8]1)(=[O:12])=[O:13].[NH3:11]>>[CH3:1][CH:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10]([NH2:11])(=[O:12])=[O:13] | CC(Cl)c1ccccc1S(=O)(=O)Cl.N | CC(Cl)c1ccccc1S(N)(=O)=O | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 419151dfc49d0719bc8d3fc5b23cdd08248d27df18761ee59c11624194c4c5ab | ae33b93faeb632e8ec1263862cc7a6f628747ed893339f281ddf88c6e380b60a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of ammonia (1.2 ml) in tetrahydrofuran (100 ml) at -70° was contacted rapidly with a solution of 2-(1-chloroethyl)benzenesulfonyl chloride (4.32 g, 18.1 mmol) in tetrahydrofuran (50 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed under reduced pressure. The residue was taken up ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | CC(Cl)c1ccccc1S(=O)(=O)Cl.N>O1CCCC1>CC(Cl)c1ccccc1S(N)(=O)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e0b6a4d4050747dd9fd78e33c2ece435 | N.O=S(=O)(Cl)c1ccccc1CBr>>NS(=O)(=O)c1ccccc1CBr | N.BrCC1=C(C=CC=C1)S(=O)(=O)Cl.BrCC1=CC=C(C=C1)S(=O)(=O)Cl>>BrCC1=C(C=CC=C1)S(=O)(=O)N | [NH3:1].Cl[S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Br:12]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Br:12] | N.O=S(=O)(Cl)c1ccccc1CBr | NS(=O)(=O)c1ccccc1CBr | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 419151dfc49d0719bc8d3fc5b23cdd08248d27df18761ee59c11624194c4c5ab | ae33b93faeb632e8ec1263862cc7a6f628747ed893339f281ddf88c6e380b60a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of ammonia (1.0 ml) in tetrahydrofuran (50 ml) at -78° was contacted dropwise with a solution of a 60/40 mixture of 2-(bromomethyl)benzenesulfonyl chloride/4-(bromomethyl)benzenesulfonyl chloride (4.52 g) in tetrahydrofuran (20 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed in ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | N.O=S(=O)(Cl)c1ccccc1CBr>O1CCCC1>NS(=O)(=O)c1ccccc1CBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eab0fe71e0cc43c3893df4095261d255 | C1CCNC1.NS(=O)(=O)c1ccccc1CCl>>NS(=O)(=O)c1ccccc1CN1CCCC1 | ClCC1=C(C=CC=C1)S(=O)(=O)N.N1CCCC1>>N1(CCCC1)CC1=C(C=CC=C1)S(=O)(=O)N | [NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.Cl[CH2:11][c:10]1[c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:6][cH:7][cH:8][cH:9]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | C1CCNC1.NS(=O)(=O)c1ccccc1CCl | NS(=O)(=O)c1ccccc1CN1CCCC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | 92.8 | [{"value": 92.8, "product": "N1(CCCC1)CC1=C(C=CC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2-(chloromethyl)benzenesulfonamide (2.00 g, 10 mmol) in acetonitrile (20 ml) was contacted with pyrrolidine (1.6 ml, 20 mmol). After 1.0 hr at ambient temperature, the volatiles were removed under vacuum and the residue was treated with water (40 ml) and chilled. The resulting solid was pulverized, filter... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HCl | C(C)#N | null | 1 | C1CCNC1.NS(=O)(=O)c1ccccc1CCl>C(C)#N>NS(=O)(=O)c1ccccc1CN1CCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a1d6ecf5affe4cdc9339c195051b4e6a | CI.NS(=O)(=O)c1ccccc1CN1CCCC1>>CNS(=O)(=O)c1ccccc1CN1CCCC1.[I-] | N1(CCCC1)CC1=C(C=CC=C1)S(=O)(=O)N.CI>>[I-].N1(CCCC1)CC1=C(C=CC=C1)S(=O)(=O)NC | [CH3:1][I:18].[NH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.[I-:18] | CI.NS(=O)(=O)c1ccccc1CN1CCCC1 | CNS(=O)(=O)c1ccccc1CN1CCCC1.[I-] | null | null | C(C)#N | Functional Group Addition | N-alkylation of primary amines with alkyl halides | 976de1015d989c0c5f36a699555d436cf203ed2f06f91b0acbfa101a293d3eeb | 6a5d85c8f0ea70e5fce45998d00e869aa529bdae85ab86c721877b1dc53f883d | c1ccc(CN2CCCC2)cc1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[CH3;D1;+0:1]-[NH;D2;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7].[I-;H0;D0:2] | null | [] | null | null | null | null | A solution of 2-(pyrrolidinomethyl)benzenesulfonamide (0.8 g) in acetonitrile (10 ml) was contacted with methyl iodide (3 ml) and heated to reflux for 2.0 hrs. Solvent was removed and the residue was treated with acetone and ether. The solid was filtered, digested with acetone (20 ml), chilled and collected. There was ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1 | null | C(C)#N | null | null | CI.NS(=O)(=O)c1ccccc1CN1CCCC1>C(C)#N>CNS(=O)(=O)c1ccccc1CN1CCCC1.[I-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-96b36f56b2bf4e2fa59c2f023ae48e35 | CCCCN=C=O.NS(=O)(=O)c1ccccc1CCl>>CCCCNC(=O)NS(=O)(=O)c1ccccc1CCl | ClCC1=C(C=CC=C1)S(=O)(=O)N.C(CCC)N=C=O>>ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[NH2:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[CH2:18][Cl:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[NH:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[CH2:18][Cl:19] | CCCCN=C=O.NS(=O)(=O)c1ccccc1CCl | CCCCNC(=O)NS(=O)(=O)c1ccccc1CCl | null | N12NCC(CC1)CC2 | C=1(C(=CC=CC1)C)C | Acylation | OtherReaction | 5e91197373c0e9b04f4abef28663b2a5340491c55a6757f9a5f8cf7ca2e4aefe | 0fe1082098d61e5130a83440c9351817ede5cdd433bfc65ee308ef6fab351022 | c1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10] | 74.8 | [{"value": 74.8, "product": "ClCC1=C(C=CC=C1)S(=O)(=O)NC(=O)NCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | Sulfonamide.Urea | null | null | c1ccccc1 | null | N12NCC(CC1)CC2.C=1(C(=CC=CC1)C)C | null | null | CCCCN=C=O.NS(=O)(=O)c1ccccc1CCl>N12NCC(CC1)CC2.C=1(C(=CC=CC1)C)C>CCCCNC(=O)NS(=O)(=O)c1ccccc1CCl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d41592ac9b864e5fa8d5045e4e4bc7fb | C=CCc1cc(C)c(OCC2CO2)c(C)c1.CC(=O)OO>>Cc1cc(CC2CO2)cc(C)c1OCC1CO1 | C(C1CO1)OC1=C(C=C(C=C1C)CC=C)C.C(C)(=O)[O-].[Na+].C(C)(=O)OO>>C(C1CO1)OC1=C(C=C(C=C1C)CC1CO1)C | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]=[CH2:7])[cH:9][c:10]([CH3:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1.CC(=O)O[OH:8]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]2[CH2:7][O:8]2)[cH:9][c:10]([CH3:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1 | C=CCc1cc(C)c(OCC2CO2)c(C)c1.CC(=O)OO | Cc1cc(CC2CO2)cc(C)c1OCC1CO1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 173f96f965e916bc74678202d36f5d0142af5230a7d483e540b63ebc1e6f47ae | cf4df6d170df9662664f9744161f06baeb1f4777cb3701fb34820ed0286c62f4 | c1cc(OCC2CO2)ccc1CC1CO1 | C-C(=O)-O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[C:4]-[c:5]>>[c:5]-[C:4]-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[O;H0;D2;+0:1]-1 | 863.5 | [{"value": 863.5, "product": "C(C1CO1)OC1=C(C=C(C=C1C)CC1CO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A 350 ml sulfurating flask equipped with thermometer, stirrer, cooler and drip funnel is charged with 46.30 g (0.21 mole) of 4-allyl-2,6-dimethylphenyl glycidyl ether, 1.93 g of sodium acetate and 160 ml of chloroform, and the batch is heated to 35°-40° C. At this temperature, 52.3 g (0.28 mole) of 40% peracetic acid a... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Ether | null | C1CO1 | c1ccccc1.C1CO1.C1CO1 | HO- | C(Cl)(Cl)Cl | null | 4 | C=CCc1cc(C)c(OCC2CO2)c(C)c1.CC(=O)OO>C(Cl)(Cl)Cl>Cc1cc(CC2CO2)cc(C)c1OCC1CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a2a0d78cbcc499984b40bbe74b117a2 | C=CCc1cc(C)c(OCC2CO2)c(C)c1.OO>>Cc1cc(CC2CO2)cc(C)c1OCC1CO1 | C(C1CO1)OC1=C(C=C(C=C1C)CC=C)C.C(=O)O.OO>>C(C1CO1)OC1=C(C=C(C=C1C)CC1CO1)C | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]=[CH2:7])[cH:9][c:10]([CH3:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1.O[OH:8]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]2[CH2:7][O:8]2)[cH:9][c:10]([CH3:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1 | C=CCc1cc(C)c(OCC2CO2)c(C)c1.OO | Cc1cc(CC2CO2)cc(C)c1OCC1CO1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 173f96f965e916bc74678202d36f5d0142af5230a7d483e540b63ebc1e6f47ae | cf4df6d170df9662664f9744161f06baeb1f4777cb3701fb34820ed0286c62f4 | c1cc(OCC2CO2)ccc1CC1CO1 | O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[C:4]-[c:5]>>[c:5]-[C:4]-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[O;H0;D2;+0:1]-1 | 85.5 | [{"value": 80.5, "product": "C(C1CO1)OC1=C(C=C(C=C1C)CC1CO1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.5, "product": "C(C1CO1)OC1=C(C=C(C=C1C)CC1CO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 350 ml sulfurating flask equipped with thermometer, stirrer, cooler and drip funnel is charged with 21.8 g (0.10 mole) of 4-allyl-2,6-dimethylphenyl glycidyl ether, 10.9 g (0.24 mole) of formic acid and 135 ml of chloroform. At room temperature, 23.2 g (0.47 mole) of hydrogen peroxide are then added dropise over 4 ho... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Ether | null | C1CO1 | c1ccccc1.C1CO1.C1CO1 | HO- | C(Cl)(Cl)Cl | null | null | C=CCc1cc(C)c(OCC2CO2)c(C)c1.OO>C(Cl)(Cl)Cl>Cc1cc(CC2CO2)cc(C)c1OCC1CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-652355d8c729482398cb6fea03dd1456 | C=CCc1cc(Cl)c(OCC2CO2)c(Cl)c1.CC(=O)OO>>Clc1cc(CC2CO2)cc(Cl)c1OCC1CO1 | C(C1CO1)OC1=C(C=C(C=C1Cl)CC=C)Cl.C(C)(=O)OO>>C(C1CO1)OC1=C(C=C(C=C1Cl)CC1CO1)Cl | [Cl:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]=[CH2:7])[cH:9][c:10]([Cl:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1.CC(=O)O[OH:8]>>[Cl:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]2[CH2:7][O:8]2)[cH:9][c:10]([Cl:11])[c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17]1 | C=CCc1cc(Cl)c(OCC2CO2)c(Cl)c1.CC(=O)OO | Clc1cc(CC2CO2)cc(Cl)c1OCC1CO1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 173f96f965e916bc74678202d36f5d0142af5230a7d483e540b63ebc1e6f47ae | cf4df6d170df9662664f9744161f06baeb1f4777cb3701fb34820ed0286c62f4 | c1cc(OCC2CO2)ccc1CC1CO1 | C-C(=O)-O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[C:4]-[c:5]>>[c:5]-[C:4]-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[O;H0;D2;+0:1]-1 | 92.3 | [{"value": 92.3, "product": "C(C1CO1)OC1=C(C=C(C=C1Cl)CC1CO1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "C(C1CO1)OC1=C(C=C(C=C1Cl)CC1CO1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 100 ml sulfurating flask equipped with stirrer, cooler, thermometer and drip funnel is charged with 13.0 g (0.05 mole) of 4-allyl-2,6-dichlorophenyl glycidyl ether in 40 ml of toluene and 0.5 g of sodium acetate. Over 2 hours, 14.0 g (0.07 mole) of 10% peracetic acid are then added dropwise at 30°-50° C. After the dr... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Ether | null | C1CO1 | c1ccccc1.C1CO1.C1CO1 | HO- | C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+] | null | 2 | C=CCc1cc(Cl)c(OCC2CO2)c(Cl)c1.CC(=O)OO>C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+]>Clc1cc(CC2CO2)cc(Cl)c1OCC1CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a11e6358c0444cb68a62cdc6256a2d8a | C=CCc1cc(-c2ccccc2)c(OCC2CO2)c(-c2ccccc2)c1.CC(=O)OO>>c1ccc(-c2cc(CC3CO3)cc(-c3ccccc3)c2OCC2CO2)cc1 | C(C1CO1)OC1=C(C=C(C=C1C1=CC=CC=C1)CC=C)C1=CC=CC=C1.C(C)(=O)OO>>C(C1CO1)OC1=C(C=C(C=C1C1=CC=CC=C1)CC1CO1)C1=CC=CC=C1 | [cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][CH:9]=[CH2:10])[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]2[O:21][CH2:22][CH:23]2[CH2:24][O:25]2)[cH:26][cH:27]1.CC(=O)O[OH:11]>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][CH:9]3[CH2:10][O:11]3)[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17]... | C=CCc1cc(-c2ccccc2)c(OCC2CO2)c(-c2ccccc2)c1.CC(=O)OO | c1ccc(-c2cc(CC3CO3)cc(-c3ccccc3)c2OCC2CO2)cc1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 173f96f965e916bc74678202d36f5d0142af5230a7d483e540b63ebc1e6f47ae | cf4df6d170df9662664f9744161f06baeb1f4777cb3701fb34820ed0286c62f4 | c1ccc(-c2cc(CC3CO3)cc(-c3ccccc3)c2OCC2CO2)cc1 | C-C(=O)-O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[C:4]-[c:5]>>[c:5]-[C:4]-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[O;H0;D2;+0:1]-1 | 86.9 | [{"value": 86.5, "product": "C(C1CO1)OC1=C(C=C(C=C1C1=CC=CC=C1)CC1CO1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "C(C1CO1)OC1=C(C=C(C=C1C1=CC=CC=C1)CC1CO1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 100 ml sulfurating flask equipped with stirrer, cooler, thermometer and drip funnel is charged with 13.7 g (0.04 mole) of 4-allyl-2,6-diphenylphenyl glycidyl ether in 20 ml of toluene and 0.7 g of sodium acetate. Over 2 hours, 9.13 g (0.048 mole) of 40% peracetic acid are added at a temperature in the range from 30° ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Ether | null | C1CO1 | c1ccccc1.c1ccccc1.C1CO1.c1ccccc1.C1CO1 | HO- | C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+] | null | 2 | C=CCc1cc(-c2ccccc2)c(OCC2CO2)c(-c2ccccc2)c1.CC(=O)OO>C1(=CC=CC=C1)C.C(C)(=O)[O-].[Na+]>c1ccc(-c2cc(CC3CO3)cc(-c3ccccc3)c2OCC2CO2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-72f2082343ba44e69fe8adf60a87217c | CCOc1ccc(C(=O)O)c(O)c1.CO>>CCOc1ccc(C(=O)OC)c(O)c1 | Cl.C(C)OC1=CC(=C(C(=O)O)C=C1)O.CO>>C(C)OC1=CC(=C(C(=O)OC)C=C1)O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:12]([OH:13])[cH:14]1.O[CH3:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([OH:13])[cH:14]1 | CCOc1ccc(C(=O)O)c(O)c1.CO | CCOc1ccc(C(=O)OC)c(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccccc1 | O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | 15 | CELSIUS | null | null | Hydrogen chloride was bubbled into a stirred solution of 4-ethoxy-2-hydroxybenzoic acid (10.10 g, 0.554 mol) in methanol (2000 mL) until the solution was saturated. The solution was heated under reflux for 3 days and then cooled to 15° C. This caused the product to crystallize out. The crystals were collected, rinsed w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | 15 | null | CCOc1ccc(C(=O)O)c(O)c1.CO>>CCOc1ccc(C(=O)OC)c(O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f3c65c892c17444ab3d7195abd66c222 | CCOc1ccc(C(=O)OC)c(SC(=O)N(C)C)c1>>CCOc1ccc(C(=O)OC)c(S)c1 | C[O-].[Na+].CN(C(=O)SC1=C(C(=O)OC)C=CC(=C1)OCC)C>>C(C)OC1=CC(=C(C(=O)OC)C=C1)S | CN(C)C(=O)[S:13][c:12]1[c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:14]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([SH:13])[cH:14]1 | CCOc1ccc(C(=O)OC)c(SC(=O)N(C)C)c1 | CCOc1ccc(C(=O)OC)c(S)c1 | null | null | CO | Reduction | OtherReaction | b8de7c0dd998c42f71fbae789bd47547a8833f1078d4106e4c6eaba466ea8b96 | 616235514d65b822291e24d80df126c1e4bd115c2e4fc6cf16de0cb196278e81 | c1ccccc1 | C-N(-C)-C(=O)-[S;H0;D2;+0:1]-[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](-[SH;D1;+0:1]):[c:3] | 86.7 | [{"value": 86.7, "product": "C(C)OC1=CC(=C(C(=O)OC)C=C1)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methanolic sodium methoxide (4.9M, 22.4 mL, 0.11 mol) was added via syringe to a solution of methyl 2-[(dimethylamino)carbonylthio]-4-ethoxybenzoate (crude, ca. 28.3 g, 0.10 mol) in methanol (100 mL) under nitrogen. The reaction mixture was heated at reflux for 30 minutes, then cooled with the aid of a water bath. Rota... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide | Aromatic thiol | null | null | c1ccccc1 | HO- | CO | null | null | CCOc1ccc(C(=O)OC)c(SC(=O)N(C)C)c1>CO>CCOc1ccc(C(=O)OC)c(S)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5b7d4e41ceb24f3f9e9e577756bacd06 | CCOc1ccc(C(=O)OC)c(S(=O)(=O)Cl)c1.N>>CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1 | O.N.ClS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)OCC.O>>NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)OCC | Cl[S:13]([c:12]1[c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:17]1)(=[O:15])=[O:16].[NH3:14]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([S:13]([NH2:14])(=[O:15])=[O:16])[cH:17]1 | CCOc1ccc(C(=O)OC)c(S(=O)(=O)Cl)c1.N | CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1 | null | null | ClCCl | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]-[C:7](-[#8:8])=[O;D1;H0:9].[NH3;D0;+0:10]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:4](-[S;H0;D4;+0:1](-[NH2;D1;+0:10])(=[O;D1;H0:2])=[O;D1;H0:3]):[c:5] | 74.4 | [{"value": 74.4, "product": "NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 30 | MINUTE | Liquified ammonia (4.4 mL, 180 mmol) was added to a stirred solution of methyl 2-(chlorosulfonyl)-4-ethoxybenzoate (22.1 g, 79.3 mmol) in dichloromethane (221 mL) at -70° C. The reaction mixture was allowed to warm to -10° C. and was held at this temperature for 30 minutes. The mixture was then poured into water (221 m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | ClCCl | -10 | 0.5 | CCOc1ccc(C(=O)OC)c(S(=O)(=O)Cl)c1.N>ClCCl>CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-afb1397756f348c8aace29697e67d299 | CCCCN=C=O.CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1>>CCOc1ccc(C(=O)OC)c(S(=O)(=O)N=C=O)c1 | C(=O)(Cl)Cl.NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)OCC.C(CCC)N=C=O>>C(C)OC1=CC(=C(C(=O)OC)C=C1)S(=O)(=O)N=C=O | CCCCN=[C:17]=[O:18].[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([S:13](=[O:14])(=[O:15])[NH2:16])[cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([S:13](=[O:14])(=[O:15])[N:16]=[C:17]=[O:18])[cH:19]1 | CCCCN=C=O.CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1 | CCOc1ccc(C(=O)OC)c(S(=O)(=O)N=C=O)c1 | null | null | null | Functional Group Interconversion | OtherReaction | d6c69f89b87c5c421a628563544ee2b8b0164ec4561bcd29a2cbba0dce4075ac | 5df9e857f75ada60baf9e936007533a18389016451154bd1ed26e91b5babd844 | c1ccccc1 | C-C-C-C-N=[C;H0;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[O;D1;H0:5]=[#16:4](=[O;D1;H0:6])(-[c:7])-[N;H0;D2;+0:3]=[C;H0;D2;+0:1]=[O;D1;H0:2] | 98.4 | [{"value": 98.4, "product": "C(C)OC1=CC(=C(C(=O)OC)C=C1)S(=O)(=O)N=C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 2-(aminosulfonyl)-4-ethoxybenzoate (7.56 g, 29.2 mmol), n-butyl isocyanate (3.29 mL, 29.2 mmol), and 1,4-diaza[2.2.2]bicyclooctane (0.13 g, 1.2 mmol) in mixed xylenes was heated at reflux for 10 minutes. Phosgene was then added at such a rate that the internal temperature stayed at 133° C. or above... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | null | null | null | c1ccccc1 | Other | null | null | null | CCCCN=C=O.CCOc1ccc(C(=O)OC)c(S(N)(=O)=O)c1>>CCOc1ccc(C(=O)OC)c(S(=O)(=O)N=C=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-efea6328e97c41fda837d753a6815718 | COC(=O)c1ccc(SC)cc1[N+](=O)[O-]>>COC(=O)c1ccc(SC)cc1N | CSC1=CC(=C(C(=O)OC)C=C1)[N+](=O)[O-].[H][H]>>NC1=C(C(=O)OC)C=CC(=C1)SC | O=[N+:13]([O-])[c:12]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([S:9][CH3:10])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([S:9][CH3:10])[cH:11][c:12]1[NH2:13] | COC(=O)c1ccc(SC)cc1[N+](=O)[O-] | COC(=O)c1ccc(SC)cc1N | null | [Pt]=S | C(C)(=O)OC | 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] | null | [] | null | null | null | null | A mixture of methyl 4-(methylthio)-2-nitrobenzoate (11.3 g, 49.7 mmol) and 5% platinum sulfide on carbon catalyst (0.7 g) in methyl acetate (40 mL) was hydrogenated at 750 psi and 75° C. until hydrogen uptake ceased. The mixture was filtered through Celite®, and the filtrate solvent was rotary evaporated, leaving methy... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pt]=S.C(C)(=O)OC | null | null | COC(=O)c1ccc(SC)cc1[N+](=O)[O-]>[Pt]=S.C(C)(=O)OC>COC(=O)c1ccc(SC)cc1N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2b6185ff48f74872a4d4707ac892d99d | CCCCN=C=O.COC(=O)c1ccc(SC)cc1S(N)(=O)=O>>COC(=O)c1ccc(SC)cc1S(=O)(=O)N=C=O | C(=O)(Cl)Cl.NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)SC.C(CCC)N=C=O>>N(=C=O)S(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)SC | CCCCN=[C:17]=[O:18].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([S:9][CH3:10])[cH:11][c:12]1[S:13](=[O:14])(=[O:15])[NH2:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([S:9][CH3:10])[cH:11][c:12]1[S:13](=[O:14])(=[O:15])[N:16]=[C:17]=[O:18] | CCCCN=C=O.COC(=O)c1ccc(SC)cc1S(N)(=O)=O | COC(=O)c1ccc(SC)cc1S(=O)(=O)N=C=O | null | null | null | Functional Group Interconversion | OtherReaction | d6c69f89b87c5c421a628563544ee2b8b0164ec4561bcd29a2cbba0dce4075ac | 5df9e857f75ada60baf9e936007533a18389016451154bd1ed26e91b5babd844 | c1ccccc1 | C-C-C-C-N=[C;H0;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[O;D1;H0:5]=[#16:4](=[O;D1;H0:6])(-[c:7])-[N;H0;D2;+0:3]=[C;H0;D2;+0:1]=[O;D1;H0:2] | 111.4 | [{"value": 111.4, "product": "N(=C=O)S(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 2-(aminosulfonyl)-4-(methylthio)benzoate (5.23 g, 20.0 mmol), n-butyl isocyanate (2.25 mL, 20.0 mmol), and 1,4-diaza[2.2.2]bicyclooctane (0.09 g, 0.8 mmol) in mixed xylenes (50 mL) was heated at reflux for 10 minutes. Phosgene was then added at such a rate that the internal temperature stayed at 13... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | null | null | null | c1ccccc1 | Other | null | null | null | CCCCN=C=O.COC(=O)c1ccc(SC)cc1S(N)(=O)=O>>COC(=O)c1ccc(SC)cc1S(=O)(=O)N=C=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-41d0738c14934a8d8d2f0c0151409174 | CCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>>CCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCC)cc3)CN(Nc3ccc(C(=O)OCC)cc3)C2)cc1 | NC1=CC=C(C(=O)OCC)C=C1.N1=C(Cl)N=C(Cl)N=C1Cl.Cl>>C(C)OC(=O)C1=CC=C(NN2CN(CN(C2)NC2=CC=C(C=C2)C(=O)OCC)NC2=CC=C(C=C2)C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:41][cH:38]1.Cl[c:12]1[n:11][c:16](Cl)[n:13][c:19](Cl)[n:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][N:11]2[CH2:12][N:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([C:19](=[O:20])[O:21][CH2:22][CH3:23])[cH:24][cH:25]3)[CH2:26][N:27](... | CCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1 | CCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCC)cc3)CN(Nc3ccc(C(=O)OCC)cc3)C2)cc1 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | ed9b4e3f7d9fcf59802d9282dfba25cd158ad6444611b9c9e892d87f4f4ad2f1 | 89c26d060a9b2ad6ff892ab2cb3f2d3dd04eecda2432a97bc7079f40dd16fe84 | c1ccc(NN2CN(Nc3ccccc3)CN(Nc3ccccc3)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14](-[NH2;D1;+0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[C:18]-[#8:19]-[C;H0;D3;+0:5](=[O;D1;H0:20])-[c:21]1:[c:22]:[cH;D2;+0:3]:[c:23](-[#7:24]-[N;H0... | 97 | [{"value": 97.0, "product": "C(C)OC(=O)C1=CC=C(NN2CN(CN(C2)NC2=CC=C(C=C2)C(=O)OCC)NC2=CC=C(C=C2)C(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 82.6 g of ethyl p-aminobenzoate and 30.75 g of cyanuric chloride in 1,500 ml of xylene were refluxed for 8 hours, hydrogen chloride escaping during this procedure. Thereafter, 1 liter of xylene was added, and the suspension, at 80°-90° C., was washed neutral with saturated sodium bicarbonate solution and then cooled to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Hydrazine.Hydrazine.Hydrazine.Ester.Ester.Ester | c1ccccc1.c1ncncn1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | null | null | CCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>C=1(C(=CC=CC1)C)C>CCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCC)cc3)CN(Nc3ccc(C(=O)OCC)cc3)C2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-848069fa4f1f477c85839d23e4203cc5 | CCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>>CCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)C2)cc1 | NC1=CC=C(C(=O)OCCCCCCCC)C=C1.N1=C(Cl)N=C(Cl)N=C1Cl.Cl>>C(CCCCCCC)OC(=O)C1=CC=C(NN2CN(CN(C2)NC2=CC=C(C=C2)C(=O)OCCCCCCCC)NC2=CC=C(C=C2)C(=O)OCCCCCCCC)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:45]([c:44]1[cH:43][cH:42][c:15]([NH2:16])[cH:59][cH:56]1)=[O:46].Cl[c:10]1[n:17][c:25](Cl)[n:20][c:24](Cl)[n:39]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([NH:16][N:17]2[CH2:18][N:19]([NH:20][... | CCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1 | CCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)C2)cc1 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | ed9b4e3f7d9fcf59802d9282dfba25cd158ad6444611b9c9e892d87f4f4ad2f1 | 89c26d060a9b2ad6ff892ab2cb3f2d3dd04eecda2432a97bc7079f40dd16fe84 | c1ccc(NN2CN(Nc3ccccc3)CN(Nc3ccccc3)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C:19]-[#8:20]-[C;H0;D3;+0:3](=[O;D1;H0:21])-[c;H0;D3;+0:5]1:[c... | null | [] | 90 | CELSIUS | null | null | 75 g of octyl p-aminobenzoate and 18.5 g of cyanuric chloride in 1,000 ml of xylene were heated at 140° C. for 8 hours. After the evolution of hydrogen chloride was complete, the reaction solution was cooled to 90° C., washed twice with saturated sodium bicarbonate solution and once with water and then cooled to room t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Hydrazine.Hydrazine.Hydrazine.Ester.Ester.Ester | c1ccccc1.c1ncncn1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | 90 | null | CCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>C=1(C(=CC=CC1)C)C>CCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCC)cc3)C2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d7ec7c5243894addb439002cd6f1f99a | CCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>>CCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)C2)cc1 | NC1=CC=C(C(=O)OCCCCCCCCCC)C=C1.N1=C(Cl)N=C(Cl)N=C1Cl.Cl>>C(CCCCCCCCC)OC(=O)C1=CC=C(NN2CN(CN(C2)NC2=CC=C(C=C2)C(=O)OCCCCCCCCCC)NC2=CC=C(C=C2)C(=O)OCCCCCCCCCC)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:27]([c:26]1[cH:25][cH:24][c:17]([NH2:18])[cH:65][cH:40]1)=[O:28].Cl[c:12]1[n:19][c:64](Cl)[n:43][c:42](Cl)[n:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([NH:1... | CCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1 | CCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)C2)cc1 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | ed9b4e3f7d9fcf59802d9282dfba25cd158ad6444611b9c9e892d87f4f4ad2f1 | 89c26d060a9b2ad6ff892ab2cb3f2d3dd04eecda2432a97bc7079f40dd16fe84 | c1ccc(NN2CN(Nc3ccccc3)CN(Nc3ccccc3)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C:19]-[#8:20]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c... | null | [] | 90 | CELSIUS | null | null | 83 g of decyl p-aminobenzoate and 18.5 g of cyanuric chloride in 1,000 ml of xylene were heated at 140° C. for 8 hours. After the evolution of hydrogen chloride was complete, the reaction solution was cooled to 90° C., washed twice with saturated sodium bicarbonate solution and once with water, and then cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Hydrazine.Hydrazine.Hydrazine.Ester.Ester.Ester | c1ccccc1.c1ncncn1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | 90 | null | CCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>C=1(C(=CC=CC1)C)C>CCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCC)cc3)C2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6b8bf34c051a47799634f0478cd59831 | CCCCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>>CCCCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)C2)cc1 | N1=C(Cl)N=C(Cl)N=C1Cl.NC1=CC=C(C(=O)OCCCCCCCCCCCC)C=C1.Cl>>C(CCCCCCCCCCC)OC(=O)C1=CC=C(NN2CN(CN(C2)NC2=CC=C(C=C2)C(=O)OCCCCCCCCCCCC)NC2=CC=C(C=C2)C(=O)OCCCCCCCCCCCC)C=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][O:13][C:53]([c:52]1[cH:51][cH:50][c:19]([NH2:20])[cH:71][cH:68]1)=[O:54].Cl[c:14]1[n:21][c:29](Cl)[n:47][c:28](Cl)[n:48]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][O:13][C:14](=[O:15])[... | CCCCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1 | CCCCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)C2)cc1 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | ed9b4e3f7d9fcf59802d9282dfba25cd158ad6444611b9c9e892d87f4f4ad2f1 | 89c26d060a9b2ad6ff892ab2cb3f2d3dd04eecda2432a97bc7079f40dd16fe84 | c1ccc(NN2CN(Nc3ccccc3)CN(Nc3ccccc3)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C:19]-[#8:20]-[C;H0;D3;+0:3](=[O;D1;H0:21])-[c;H0;D3;+0:5](:[c... | null | [] | 80 | CELSIUS | 8 | HOUR | 18.5 g of cyanuric chloride and 92 g of dodecyl p-aminobenzoate in 1,000 ml of xylene were heated at 140° C. until HCl gas was no longer evolved. After 8 hours, the reaction solution was cooled to 80° C., washed twice with saturated sodium bicarbonate solution and once with water, and then cooled to room temperature. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Hydrazine.Hydrazine.Hydrazine.Ester.Ester.Ester | c1ccccc1.c1ncncn1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | c1ccccc1.C1[NH]C[NH]C[NH]1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | 80 | 8 | CCCCCCCCCCCCOC(=O)c1ccc(N)cc1.Clc1nc(Cl)nc(Cl)n1>C=1(C(=CC=CC1)C)C>CCCCCCCCCCCCOC(=O)c1ccc(NN2CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)CN(Nc3ccc(C(=O)OCCCCCCCCCCCC)cc3)C2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-51d04ddc18b345bfacbd8eb04a8a2685 | c1ccc(C2CO2)cc1>>c1ccc(C2CO2)cc1 | C(CCCCCCC\C=C/CCCCCCCC)N.C1C(C2=CC=CC=C2)O1.C1(=CC=CC=C1)C.[B]>>C(CCCCCCC\C=C/CCCCCCCC)N.C1C(C2=CC=CC=C2)O1 | [cH:20]1[cH:21][cH:22][c:23]([CH:24]2[CH2:25][O:26]2)[cH:27][cH:28]1>>[cH:20]1[cH:21][cH:22][c:23]([CH:24]2[CH2:25][O:26]2)[cH:27][cH:28]1 | c1ccc(C2CO2)cc1 | c1ccc(C2CO2)cc1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(C2CO2)cc1 | null | null | [] | null | null | null | null | A sulfurized, boron-containing, heterocyclic compound is prepared by mixing 12 grams of oleylamine, 9.6 grams of styrene oxide and 200 ml of toluene for 30 minutes at room temperature (25° C.) in a single-necked one-liter round-bottomed flask. The flask is placed in a heating mantle and equipped with a water-cooled con... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CO1 | null | O | null | null | c1ccc(C2CO2)cc1>O>c1ccc(C2CO2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-91b5da6b753c4d87a85d7b0c1e08baeb | Nc1ccc(NNC=O)cc1.O=C(O)c1cccc(-n2nnnc2S)c1>>O=CNNc1ccc(NC(=O)c2cccc(-n3nnnc3S)c2)cc1 | C1(CCCCC1)N=C=NC1CCCCC1.C(=O)(O)C=1C=C(C=CC1)N1N=NN=C1S.C(=O)NNC1=CC=C(N)C=C1>>SC1=NN=NN1C1=CC(=CC=C1)C(NC1=CC=C(C=C1)NNC=O)=O | [O:1]=[CH:2][NH:3][NH:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:24][cH:25]1.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16](-[n:17]2[n:18][n:19][n:20][c:21]2[SH:22])[cH:23]1>>[O:1]=[CH:2][NH:3][NH:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16](-[n:17]3[n:18][n:19][n:20][c:21]3[SH:22])[... | Nc1ccc(NNC=O)cc1.O=C(O)c1cccc(-n2nnnc2S)c1 | O=CNNc1ccc(NC(=O)c2cccc(-n3nnnc3S)c2)cc1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccc(-n2cnnn2)c1 | 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] | 25.4 | [{"value": 25.4, "product": "SC1=NN=NN1C1=CC(=CC=C1)C(NC1=CC=C(C=C1)NNC=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | In 50 ml of dimethylformamide were dissolved 11.1 g of 1-(3-carboxyphenyl)-5-mercaptotetrazole and 7.6 g of 4-(2-formylhydrazino)aniline, and a solution of 10.3 g of dicyclohexylcarbodiimide in 10 ml of dimethylformamide was added dropwise to the solution at 0° C. in a nitrogeneous atmosphere over about 30 minutes. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1nnn[nH]1 | HO- | CN(C=O)C | null | 3 | Nc1ccc(NNC=O)cc1.O=C(O)c1cccc(-n2nnnc2S)c1>CN(C=O)C>O=CNNc1ccc(NC(=O)c2cccc(-n3nnnc3S)c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-03c19910184945d28d0037efcffa7194 | O=C(O)CBr.Sc1nnc(S)s1>>O=C(O)CSc1nnc(S)s1 | BrCC(=O)O.SC=1SC(=NN1)S.[OH-].[K+]>>C(=O)(O)CSC=1SC(=NN1)S | Br[CH2:4][C:2](=[O:1])[OH:3].[SH:5][c:6]1[n:7][n:8][c:9]([SH:10])[s:11]1>>[O:1]=[C:2]([OH:3])[CH2:4][S:5][c:6]1[n:7][n:8][c:9]([SH:10])[s:11]1 | O=C(O)CBr.Sc1nnc(S)s1 | O=C(O)CSc1nnc(S)s1 | null | null | O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1nncs1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[SH;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[#7;a:9]:[#7;a:10]:1>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[S;H0;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[#7;a:9]:[#7;a:10]:1 | 86.6 | [{"value": 86.6, "product": "C(=O)(O)CSC=1SC(=NN1)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | In 200 ml of water were dissolved 15.0 g of 2,5-dimercapto-1,3,4-thiadiazole and 69 g of potassium hydroxide, and a solution of 13.9 g of bromoacetic acid in 30 ml of water was added thereto dropwise at room temperature. After the addition, the mixture was stirred at 60° C. for 1 hour, followed by allowing to cool to r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1nncs1 | HBr | O | 60 | 1 | O=C(O)CBr.Sc1nnc(S)s1>O>O=C(O)CSc1nnc(S)s1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ade2fb49e10c41c6b4889a7c288bd378 | O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21>>O=C(O)c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12 | C1=CC2=C(C=C1N=C=S)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O.C([O-])([O-])=O.C1=CC2=C(C=C1N=C=S)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O>>C=1C=CC(=C(C1)C2=C3C=CC(=O)C=C3OC4=C2C=CC(=C4)O)C(=O)O | S=C=N[c:6]1[cH:5][c:4]2[c:9]([cH:8][cH:7]1)[C:10]1([O:3][C:2]2=[O:1])[c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]2[O:18][c:19]2[cH:20][c:21]([OH:22])[cH:23][cH:24][c:25]21>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[c:11]2[cH:12][cH:13][c:14](=[O:15])[cH:16][c:17]-2[o:18][c:19]2[cH:20][c:21]([... | O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21 | O=C(O)c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 2bdf19f895cccba6c6602b312223931295ab2b9d32ef41313b16970e6181726d | e6f7e6efa036edd9dd5bbb1c3bf5fdd9a5ca0cde297a4f028b8d6746b1b615fd | O=c1ccc2c(-c3ccccc3)c3ccccc3oc-2c1 | S=C=N-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c;H0;D3;+0:4](:[c:5]:[c:6]:1)-[C;H0;D4;+0:7]1(-[O;H0;D2;+0:8]-[C:9]-2=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[O;H0;D2;+0:15]-[c;H0;D3;+0:16]2:[c:17]:[c;H0;D3;+0:18](-[OH;D1;+0:19]):[c:20]:[c:21]:[c;H0;D3;+0:22]:2-1>>[O;D1;H0:10]=[C:9](-[OH;D1;+0:8])-[c:3]1:[c:2]:[cH;D2;+0:1]:[... | null | [] | null | null | null | null | Fluoresceinisothiocyanate (FITC) is dissolved in ethanol (5 mg solid/ml). To 2 ml of a 5 mg/ml protein solution from (I), 0.5 ml carbonate buffer (1M NaHCO3 --Na2CO3 buffer pH 9) is added, followed by 50 μl FITC solution. The mixture is shaken well and the free FITC is chromatographically separated from the bound molec... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Aromatic alcohol.Isothiocyanate | Carboxylic acid | c1ccc2c(c1)COC21c2ccccc2Oc2ccccc21 | c1ccccc1.c1ccc2cc3ccccc3oc2c1 | c1ccccc1.c1ccc2cc3ccccc3oc2c1 | Other | C(C)O | null | null | O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21>C(C)O>O=C(O)c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6c256a247ecb4bdb8cf60a7f89a63e98 | CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](N)C(=O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 | [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1.N[C@@H](CC(C)C)C(=O)O.N[C@@H](CC(C)C)C(=O)O>>C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O.[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1 | C[CH:27]([CH2:19][C@@H:20]([C:18](=[O:17])[OH:29])[NH2:32])[CH3:26].C[CH:24](C)[CH2:23][C@H:22]([NH2:21])[C:30]([OH:28])=[O:31].[O:1]=[c:2]1[cH:3][cH:4][n:5]([C@H:6]2[C@H:7]([OH:25])[C@H:8]([OH:9])[C@@H:10]([CH2:11][OH:12])[O:13]2)[c:14](=[O:15])[nH:16]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5]([C@H:6]2[CH2:7][C@H:8]([OH:9])[C@@... | CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](N)C(=O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c4b81035e98988b0bda725ca7fddc63bba64117299484e9ac7ac3e4e4482c668 | 69613725106b233a9d33d53844819b260ebce100f3446af9f0222e8b950247eb | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1.O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-[CH;D3;+0:1](-C)-[C:2]-[C@H;D3;+0:3](-[NH2;D1;+0:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:7].C-[CH;D3;+0:8](-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[C@H;D3;+0:11](-[NH2;D1;+0:12])-[C;H0;D3;+0:13](=[O;D1;H0:14])-[OH;D1;+0:15].[#7;a:16]-[C:17]1-[#8:18]-[C:19]-[C:20](-[O;D1;H1:21])-[C@H;D3;+0:22]-1-[OH;D1;+0:23]>>[#7;a:16]-[C:... | null | [] | null | null | null | null | Urd-uridine; Leu-L-leucine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Secondary alcohol.Primary amine.Primary amine | Ether.Primary alcohol.Secondary alcohol | C1CCOC1 | C1CCOC1.c1ccncn1.C1CCOC1 | c1ccncn1.C1CCOC1.c1ccncn1.C1CCOC1 | Other | null | null | null | CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](N)C(=O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a74d48ae4860473095f955cf805e25c4 | Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>Cc1cn2c(nc1=O)O[C@H]1C[C@H]2O[C@@H]1CO | [C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1.ClC(C(F)(F)N(CC)CC)F.C(C)O>>CC1=CN2[C@H]3C[C@@H]([C@H](O3)CO)OC2=NC1=O | O=[c:5]1[n:4]([C@H:12]2[CH2:11][C@H:10]([OH:9])[C@@H:14]([CH2:15][OH:16])[O:13]2)[cH:3][c:2]([CH3:1])[c:7](=[O:8])[nH:6]1>>[CH3:1][c:2]1[cH:3][n:4]2[c:5]([n:6][c:7]1=[O:8])[O:9][C@H:10]1[CH2:11][C@H:12]2[O:13][C@@H:14]1[CH2:15][OH:16] | Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | Cc1cn2c(nc1=O)O[C@H]1C[C@H]2O[C@@H]1CO | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 7216ae954245743aa450156cb863eb127cb9ec1e3bba6623b2e49580a2a0c455 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | O=c1ccn2c(n1)O[C@@H]1CO[C@@H]2C1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](=[O;D1;H0:4]):[c:5]:[c:6]:[#7;a:7]:1-[C:8]1-[#8:9]-[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]-1>>[O;D1;H0:4]=[c:3]1:[c:5]:[c:6]:[#7;a:7]2:[c;H0;D3;+0:1](:[n;H0;D2;+0:2]:1)-[O;H0;D2;+0:12]-[C:11]1-[C:13]-[C:8]-2-[#8:9]-[C:10]-1 | 60.3 | [{"value": 60.3, "product": "CC1=CN2[C@H]3C[C@@H]([C@H](O3)CO)OC2=NC1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "CC1=CN2[C@H]3C[C@@H]([C@H](O3)CO)OC2=NC1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Thymidine (85.4 g; 0.353 mol) was dissolved in 500 mL dry DMF (dimethyl formamide) and added to N-(2-chloro-1,1,2-trifluoroethyl)diethylamine (100.3 g; 0.529 mol) [prepared according to the method of D. E. Ayer, J. Med. Chem. 6, 608 (1963)]. This solution was heated at 70° C. for 30 minutes then poured into 950 mL etha... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | c1cncnc1 | c1cnc2n(c1)[C@H]1C[C@@H](CO1)O2 | c1cnc2n(c1)[C@H]1C[C@@H](CO1)O2 | HO- | CN(C=O)C | 70 | null | Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>CN(C=O)C>Cc1cn2c(nc1=O)O[C@H]1C[C@H]2O[C@@H]1CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-74fbee929e784564bd98215859d583b0 | C#CCCC(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21>>C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | C(CCC)[Li].C(CCC#C)(=O)Cl.N1=CC=CC2=C1NC1=C(C(N2)=O)C=CC=C1>>O=C(CCC#C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | Cl[C:5]([CH2:4][CH2:3][C:2]#[CH:1])=[O:6].[NH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21>>[CH:1]#[C:2][CH2:3][CH2:4][C:5](=[O:6])[N:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21 | C#CCCC(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21 | C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | null | CCCCCC.C(C)(=O)OCC.O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | 46c0938aafd554a4057df12dbebe677cf04009fa5bed51927bc1d071fff7b2b6 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1Nc2cccnc2Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]#[C;D1;H1:6].[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[#7;a:12]:[c:13])-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]-1>>[C;D1;H1:6]#[C:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[c:11](:[#7;a:12]:[c:13]):[c:10]-[#7:9]-[C:8](=[O;D1;H0:7])-[c:17]:[c:15]-1:[c:16] | null | [] | 30 | CELSIUS | 30 | MINUTE | 22.4 ml of a 1.6 molar solution of n-butyl-lithium in n-hexane are added dropwise with stirring, at 0° C., to a suspension of 3.7 g (0.017 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 150 ml of absolute tetrahydrofuran. After it has all been added, the mixture is stirred for a further 30 minutes and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CNc1cccnc1N2 | c1ccc2c(c1)CNc1cccnc1[NH]2 | c1ccc2c(c1)CNc1cccnc1[NH]2 | HCl | CCCCCC.C(C)(=O)OCC.O1CCCC1 | 30 | 0.5 | C#CCCC(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21>CCCCCC.C(C)(=O)OCC.O1CCCC1>C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-da6aacba240a48b7804ec076824d5006 | C#CCN.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>>C#CCNC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | C(C#C)N.ClC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2.C(C)N(CC)CC>>C(C#C)NC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | [CH:1]#[C:2][CH2:3][NH2:4].Cl[C:5](=[O:6])[N:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21>>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21 | C#CCN.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21 | C#CCNC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C1Nc2cccnc2Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[c:5]:[#7;a:6].[C;D1;H1:7]#[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:6]:[c:5]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8]#[C;D1;H1:7])-[c:4] | null | [] | 40 | CELSIUS | 30 | MINUTE | 5.5 g (0.1 mol) of propargylamine were added dropwise with stirring at ambient temperature to a suspension of 27.3 g (0.1 mol) of 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 10.0 g (0.1 mol) of triethylamine in 500 ml of chloroform, whereupon the temperature rises to 35° C. The mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccc2c(c1)CNc1cccnc1[NH]2 | HCl | C(Cl)(Cl)Cl | 40 | 0.5 | C#CCN.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>C(Cl)(Cl)Cl>C#CCNC(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-40ce053f6f454522aede5b77a4a32553 | C#CCNC.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>>C#CCN(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | ClC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2.CNCC#C>>CN(C(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2)CC#C | [CH:1]#[C:2][CH2:3][NH:4][CH3:5].Cl[C:6](=[O:7])[N:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][cH:21][n:22][c:23]21>>[CH:1]#[C:2][CH2:3][N:4]([CH3:5])[C:6](=[O:7])[N:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][cH:21][n:22][c:23]21 | C#CCNC.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21 | C#CCN(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 21141392b95d6b95cd118c7c0b595c90f08886f6a08d558238622ce18df3aa9b | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C1Nc2cccnc2Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[c:5]:[#7;a:6].[C;D1;H1:7]#[C:8]-[C:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[#7;a:6]:[c:5]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C:9]-[C:8]#[C;D1;H1:7])-[c:4] | null | [] | null | null | null | null | Analogously to Example C, using 27.3 g (0.1 mol) of 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 7.0 g (0.1 mol) of N-methyl-propargylamine, 27 g (88% of theory) of the desired compound are obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | null | null | c1ccc2c(c1)CNc1cccnc1[NH]2 | HCl | null | null | null | C#CCNC.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>>C#CCN(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b62934e97d654247b2961e7c9f60d869 | C#CCO.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>>C#CCOC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | C(CCC)[Li].C(C#C)O.ClC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2>>C(C#C)OC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | [CH:1]#[C:2][CH2:3][OH:4].Cl[C:5](=[O:6])[N:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21>>[CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[N:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21 | C#CCO.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21 | C#CCOC(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | null | CCCCCC.O1CCCC1 | Protection | Schotten-Baumann to ester | 597fa7ba4ca169ec9e1d3b8730fbab27757ccde00143c31019a679c09b7b2b7f | 562b6a5118cb63cbe5ff058f35135dc3f085de8b8ec7fa4ac4de518324eb826a | O=C1Nc2cccnc2Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[c:5]:[#7;a:6].[C;D1;H1:7]#[C:8]-[C:9]-[OH;D1;+0:10]>>[#7;a:6]:[c:5]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9]-[C:8]#[C;D1;H1:7])-[c:4] | null | [] | null | null | 30 | MINUTE | At 15° to 20° C., 3.08 g (0.048 mol) of n-butyl-lithium in 30 ml of n-hexane are added dropwise to a solution of 2.24 g (0.04 mol) of propargyl alcohol in 120 ml of tetrahydrofuran. After it has all been added, the mixture is stirred for a further 30 minutes at ambient temperature and then mixed with a suspension of 10... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary alcohol | Carbamic ester | null | null | c1ccc2c(c1)CNc1cccnc1[NH]2 | HCl | CCCCCC.O1CCCC1 | null | 0.5 | C#CCO.O=C1Nc2cccnc2N(C(=O)Cl)c2ccccc21>CCCCCC.O1CCCC1>C#CCOC(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7887cac5bd37464998c4050ed1a73ce5 | C#CCBr.CCOC(=O)C(C)C(=O)OCC>>C#CCC(C)(C(=O)OCC)C(=O)OCC | CC(C(=O)OCC)C(=O)OCC.C(C#C)Br.[Br-].[Na+]>>CC(C(=O)OCC)(C(=O)OCC)CC#C | Br[CH2:3][C:2]#[CH:1].[CH:4]([CH3:5])([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15]>>[CH:1]#[C:2][CH2:3][C:4]([CH3:5])([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15] | C#CCBr.CCOC(=O)C(C)C(=O)OCC | C#CCC(C)(C(=O)OCC)C(=O)OCC | null | null | null | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | null | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | null | [] | null | null | null | null | At 35° to 40° to C., with stirring, 174 g (1.0 ml) of diethyl methylmalonate are added dropwise to an alkoxide solution (prepared from 23 g of sodium and 800 ml of absolute ethanol), the mixture is stirred for a further hour and then at 45° C. 130.8 g (1.1 mol) of propargyl bromide are added dropwise. The mixture is re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | null | HBr | null | null | null | C#CCBr.CCOC(=O)C(C)C(=O)OCC>>C#CCC(C)(C(=O)OCC)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f675b34133534fd2ad6348d7c4b67760 | C#CCC(C)(C(=O)OCC)C(=O)OCC>>C#CCC(C)(C(=O)O)C(=O)O | CC(C(=O)OCC)(C(=O)OCC)CC#C.[OH-].[K+]>>CC(C(=O)O)(C(=O)O)CC#C | CC[O:8][C:6]([C:4]([CH2:3][C:2]#[CH:1])([CH3:5])[C:9](=[O:10])[O:11]CC)=[O:7]>>[CH:1]#[C:2][CH2:3][C:4]([CH3:5])([C:6](=[O:7])[OH:8])[C:9](=[O:10])[OH:11] | C#CCC(C)(C(=O)OCC)C(=O)OCC | C#CCC(C)(C(=O)O)C(=O)O | null | null | O.C(C)O | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | null | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | null | null | 2 | HOUR | 187 g (0.88 mol) of diethyl 2-methyl-2-propargyl-malonate are added to a solution of 101 g (1.8 mol) of potassium hydroxide in a mixture of 560 ml of water/ethanol (1:1) and the mixture is refluxed with stirring for 2 hours. After the reaction has ended (monitored by TLC) the mixture is evaporated to dryness in vacuo a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | null | Other | O.C(C)O | null | 2 | C#CCC(C)(C(=O)OCC)C(=O)OCC>O.C(C)O>C#CCC(C)(C(=O)O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-909765aa47fa47b3808e7296f9f062de | C#CCC(C)C(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21>>C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | C(CCC)[Li].N1=CC=CC2=C1NC1=C(C(N2)=O)C=CC=C1.CC(C(=O)Cl)CC#C>>O=C(C(CC#C)C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | Cl[C:6]([CH:4]([CH2:3][C:2]#[CH:1])[CH3:5])=[O:7].[NH:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][cH:21][n:22][c:23]21>>[CH:1]#[C:2][CH2:3][CH:4]([CH3:5])[C:6](=[O:7])[N:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][cH:21][n:22][c:23]... | C#CCC(C)C(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21 | C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | null | CCCCCC.C(C)(=O)OCC.O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | 46c0938aafd554a4057df12dbebe677cf04009fa5bed51927bc1d071fff7b2b6 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1Nc2cccnc2Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C:5]-[C:6]#[C;D1;H1:7].[O;D1;H0:8]=[C:9]1-[#7:10]-[c:11]:[c:12](:[#7;a:13]:[c:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]-1>>[C;D1;H1:7]#[C:6]-[C:5]-[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:15]1-[c:12](:[#7;a:13]:[c:14]):[c:11]-[#7:10]-[C:9](=[O;D1;... | null | [] | null | null | null | null | At 0° to 10° C., with stirring, 416 ml (0.65 mol) of an n-butyl-lithium solution in n-hexane are added dropwise to a suspension of 63 g (0.3 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 1500 ml of absolute tetrahydrofuran. THe mixture is stirred for a further hour at ambient temperature, then cooled... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CNc1cccnc1N2 | c1ccc2c(c1)CNc1cccnc1[NH]2 | c1ccc2c(c1)CNc1cccnc1[NH]2 | HCl | CCCCCC.C(C)(=O)OCC.O1CCCC1 | null | null | C#CCC(C)C(=O)Cl.O=C1Nc2cccnc2Nc2ccccc21>CCCCCC.C(C)(=O)OCC.O1CCCC1>C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-301ed65de99248bebe2bd6e6ac674570 | C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21.C1CCNCC1.C=O>>O=C1Nc2cccnc2N(C(=O)CCC#CCN2CCCCC2)c2ccccc21 | O=C(CCC#C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2.C=O.N1CCCCC1>>O=C(CCC#CCN1CCCCC1)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][n:8][c:9]2[N:10]([C:11](=[O:12])[CH2:13][CH2:14][C:15]#[CH:16])[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21.[NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1.O=[CH2:17]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][n:8][c:9]2[N:10]([C:11](=[O:12])[CH2:13][CH2:14][C:15]#[C:16][CH2... | C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21.C1CCNCC1.C=O | O=C1Nc2cccnc2N(C(=O)CCC#CCN2CCCCC2)c2ccccc21 | null | [Cu]Cl | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1c251f14c75b80b0dd3c8a9f2ea21fcdf95b017bc463f94c2b4be04acef3803b | 7dc88503da2577b71123fe820b1c2cdad87aca8735340a4da3de40929f65c4dd | O=C1Nc2cccnc2N(C(=O)CCC#CCN2CCCCC2)c2ccccc21 | O=[CH2;D1;+0:1].[C:2]-[C:3]#[CH;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:2]-[C:3]#[C;H0;D2;+0:4]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | null | [] | null | null | null | null | A mixture consisting of 9.6 g (0.03 mol) of 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 1.08 g (0.036 mol) of paraformaldehyde, 3.06 g (0.036 mol) of piperidine, 0.2 g of copper(I) chloride and 150 ml of dioxan is refluxed for 1 hour. After the reaction has ended the insoluble constitue... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine.Alkyne | Tertiary amine.Alkyne | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)CNc1cccnc1[NH]2 | HO- | [Cu]Cl.O1CCOCC1 | null | null | C#CCCC(=O)N1c2ccccc2C(=O)Nc2cccnc21.C1CCNCC1.C=O>[Cu]Cl.O1CCOCC1>O=C1Nc2cccnc2N(C(=O)CCC#CCN2CCCCC2)c2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6577de97230742bfbdfb63b5e64d45dc | C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21.C=O.CN1CCNCC1>>CC(CC#CCN1CCN(C)CC1)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | O=C(C(CC#C)C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2.CN1CCNCC1.C(\C=C/C(=O)O)(=O)O.C=O>>O=C(C(CC#CCN1CCN(CC1)C)C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | [CH3:1][CH:2]([CH2:3][C:4]#[CH:5])[C:14](=[O:15])[N:16]1[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[C:23](=[O:24])[NH:25][c:26]2[cH:27][cH:28][cH:29][n:30][c:31]21.O=[CH2:6].[NH:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1>>[CH3:1][CH:2]([CH2:3][C:4]#[C:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]... | C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21.C=O.CN1CCNCC1 | CC(CC#CCN1CCN(C)CC1)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 | null | [Cu]Cl | O.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 258faf155111cceefd44ed14e274394ce1b8b4d98ee6f574efdd5ed2b5325f2d | 7dc88503da2577b71123fe820b1c2cdad87aca8735340a4da3de40929f65c4dd | O=C1Nc2cccnc2N(C(=O)CCC#CCN2CCNCC2)c2ccccc21 | O=[CH2;D1;+0:1].[#7:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[C:8]-[C:9]#[CH;D1;+0:10]>>[C:8]-[C:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:1]-[N;H0;D3;+0:5]1-[C:4]-[C:3]-[#7:2]-[C:7]-[C:6]-1 | null | [] | null | null | 1 | HOUR | A reaction mixture consisting of 36.6 g (0.12 mol) of 5,11-dihydro-11-[1-oxo-2-methyl-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 4 g (0.13 mol) of paraformaldehyde, 13.2 g (0.13 mol) of N-methylpiperazine, 0.2 g of copper(I) chloride and 600 ml of dioxan is refluxed for 2 hours. After the reaction has ended ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine.Alkyne | Tertiary amine.Alkyne | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2c(c1)CNc1cccnc1[NH]2 | HO- | [Cu]Cl.O.O1CCOCC1 | null | 1 | C#CCC(C)C(=O)N1c2ccccc2C(=O)Nc2cccnc21.C=O.CN1CCNCC1>[Cu]Cl.O.O1CCOCC1>CC(CC#CCN1CCN(C)CC1)C(=O)N1c2ccccc2C(=O)Nc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a11989da57094792a3813bfd266f2693 | Cl>>Cl.Cl | O=C(C(CC#CCN1CCN(CC1)C)C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2.Cl>>Cl.Cl.O=C(C(CC#CCN1CCN(CC1)C)C)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 | [ClH:32]>>[ClH:32].[ClH:33] | Cl | Cl.Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 28 g (0.067 mol) of 5,11-dihydro-11-[1-oxo-2-methyl-6-(4-methyl-1-piperazinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one are suspended in 350 ml of absolute ethanol and 45 ml of ethereal hydrochloric acid are added with stirring at boiling temperature. A clear solution is obtained at first, which goes cloudy ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | C(C)O | null | null | Cl>C(C)O>Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-aceb139e08c74474b4660ef26669537f | CC(C)(C)c1cc(CCC(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl>>CC(C)(C)c1cc(CCc2nsc(=O)o2)cc(C(C)(C)C)c1O | OC1=C(C=C(C=C1C(C)(C)C)CCC(=O)N)C(C)(C)C.ClC(=O)SCl>>OC1=C(C=C(C=C1C(C)(C)C)CCC1=NSC(O1)=O)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][CH2:9][C:10]([NH2:11])=[O:15])[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]1[OH:23].Cl[S:12][C:13](Cl)=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][CH2:9][c:10]2[n:11][s:12][c:13](=[O:14])[o:15]2)[cH:16][c:17]([C:18]([CH3:19])([CH3:20]... | CC(C)(C)c1cc(CCC(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl | CC(C)(C)c1cc(CCc2nsc(=O)o2)cc(C(C)(C)C)c1O | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | cf2b908c510698a7414ecaa776babe4f8bc22e2ce68209bffd1e189a5ff20552 | 31356cd529b7c8e4ab7bb0b9ea7ddefab415abb5d70069735affc33ac8027277 | O=c1oc(CCc2ccccc2)ns1 | Cl-[S;H0;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[C:4]-[C:5]-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[O;H0;D1;+0:8]>>[C:4]-[C:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[s;H0;D2;+0:1]:[c;H0;D3;+0:2](=[O;D1;H0:3]):[o;H0;D2;+0:8]:1 | null | [] | 60 | CELSIUS | null | null | A suspension of 13.45 grams of 3-[4-hydroxy-3,5-di- tert-butylphenyl]propionamide in 150 ml of toluene is admixed with 20.22 grams of chlorocarbonyl sulfenyl chloride added dropwise. After heating the reaction mixture at 60° C. for 20 hours, the solvent is removed under reduced pressure. The residue is recrystallized f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Monosulfide | null | null | c1nsco1 | c1ccccc1.c1nsco1 | HCl | C1(=CC=CC=C1)C | 60 | null | CC(C)(C)c1cc(CCC(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl>C1(=CC=CC=C1)C>CC(C)(C)c1cc(CCc2nsc(=O)o2)cc(C(C)(C)C)c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4237d7b249d34c2e8737a3ca18720997 | CC(C)(C)c1cc(C(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl>>CC(C)(C)c1cc(-c2nsc(=O)o2)cc(C(C)(C)C)c1O | OC1=C(C=C(C(=O)N)C=C1C(C)(C)C)C(C)(C)C.ClC(=O)SCl>>OC1=C(C=C(C=C1C(C)(C)C)C1=NSC(O1)=O)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([C:8]([NH2:9])=[O:13])[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]1[OH:21].Cl[S:10][C:11](Cl)=[O:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][s:10][c:11](=[O:12])[o:13]2)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]1[OH:21] | CC(C)(C)c1cc(C(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl | CC(C)(C)c1cc(-c2nsc(=O)o2)cc(C(C)(C)C)c1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | cf2b908c510698a7414ecaa776babe4f8bc22e2ce68209bffd1e189a5ff20552 | 31356cd529b7c8e4ab7bb0b9ea7ddefab415abb5d70069735affc33ac8027277 | O=c1oc(-c2ccccc2)ns1 | Cl-[S;H0;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[O;D1;H0:3]=[c;H0;D3;+0:2]1:[o;H0;D2;+0:6]:[c;H0;D3;+0:5](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:4]:[s;H0;D2;+0:1]:1 | null | [] | null | null | null | null | The procedure of Example 1 is repeated using 3.03 grams of 4-hydroxy-3,5-di-tert-butylbenzamide and 3.18 grams of chlorocarbonylsulfenyl choride. Recrystallization from toluene:heptane (1:1) affords the title compound as a white crystalline solid: mp 155°-157° C. (dec.).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Monosulfide | null | null | c1nsco1 | c1ccccc1.c1nsco1 | HCl | null | null | null | CC(C)(C)c1cc(C(N)=O)cc(C(C)(C)C)c1O.O=C(Cl)SCl>>CC(C)(C)c1cc(-c2nsc(=O)o2)cc(C(C)(C)C)c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e675a8e1c24342e682f05cf2d84ae06b | CN1c2ccccc2C(c2ccccc2F)=NCC1CN.O=C(O)Cc1c[nH]c2ccccc12>>CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)Cc1c[nH]c2ccccc12.O | CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CN.N1C=C(C2=CC=CC=C12)CC(=O)O.Cl.C(C)N=C=NCCCN(C)C>>O.CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(=O)CC2=CNC1=CC=CC=C21 | [CH3:1][N:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])=[N:17][CH2:18][CH:19]1[CH2:20][NH2:21].[C:22](=[O:23])([CH2:24][c:25]1[cH:26][nH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]12)[OH:34]>>[CH3:1][N:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]([c:10]2[cH:11][cH:12][c... | CN1c2ccccc2C(c2ccccc2F)=NCC1CN.O=C(O)Cc1c[nH]c2ccccc12 | CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)Cc1c[nH]c2ccccc12.O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1c[nH]c2ccccc12)NCC1CN=C(c2ccccc2)c2ccccc2N1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:7].[#7:8]-[C:9]-[C:10]-[NH2;D1;+0:11]>>[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:4]-[c:3]:[c:2]:[#7;a:1].[OH2;D0;+0:7] | 71.9 | [{"value": 71.9, "product": "O.CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(=O)CC2=CNC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | According to the method of Example 1, 1-methyl-2-aminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg, 0.88 mmole) and indole-3-acetic acid (154 mg, 0.88 mmole) were combined with 4 ml of dry methylene chloride, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (169 mg, 0.88 mmole) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1=NCC[NH]c2ccccc21.c1ccccc1.c1ccc2[nH]ccc2c1 | null | C(Cl)Cl | null | 8 | CN1c2ccccc2C(c2ccccc2F)=NCC1CN.O=C(O)Cc1c[nH]c2ccccc12>C(Cl)Cl>CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)Cc1c[nH]c2ccccc12.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0bc03ba9e5e2470fbc42b20b354ea151 | CN1c2ccccc2C(c2ccccc2F)=NCC1CCl.Nc1cccc(C(F)(F)F)c1>>CN1c2ccccc2C(c2ccccc2F)=NCC1CNc1cccc(C(F)(F)F)c1 | CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CCl.FC(C=1C=C(N)C=CC1)(F)F.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>>CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC2=CC(=CC=C2)C(F)(F)F | Cl[CH2:20][CH:19]1[N:2]([CH3:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])=[N:17][CH2:18]1.[NH2:21][c:22]1[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]1>>[CH3:1][N:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[... | CN1c2ccccc2C(c2ccccc2F)=NCC1CCl.Nc1cccc(C(F)(F)F)c1 | CN1c2ccccc2C(c2ccccc2F)=NCC1CNc1cccc(C(F)(F)F)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(NCC2CN=C(c3ccccc3)c3ccccc3N2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3]-[#7:4])-[#7:5](-[C;D1;H3:6])-[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7:4]-[C:3]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[#7:5](-[C;D1;H3:6])-[c:7] | null | [] | null | null | null | null | According to the method of Example 5, 1-methyl-2-chloromethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (200 mg, 0.66 mmole) and m-trifluoromethyl aniline (319 mg, 1.97 mmole) were combined in 2 ml of dry N,N-dimethylformamide, and potassium carbonate (273 mg, 1.97 mmole) and sodium iodide (198 mg, 1.32 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1=NCC[NH]c2ccccc21.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | null | CN1c2ccccc2C(c2ccccc2F)=NCC1CCl.Nc1cccc(C(F)(F)F)c1>CN(C=O)C>CN1c2ccccc2C(c2ccccc2F)=NCC1CNc1cccc(C(F)(F)F)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-554210ee51bc42a99644559814429e25 | CC(C)COC(=O)Cl.CN1c2ccccc2C(c2ccccc2F)=NCC1CN>>CC(C)COC(=O)NCC1CN=C(c2ccccc2F)c2ccccc2N1C | CN1CCOCC1.CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CN.ClC(=O)OCC(C)C>>CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(=O)OCC(C)C | Cl[C:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:7].[NH2:8][CH2:9][CH:10]1[CH2:11][N:12]=[C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[F:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[N:27]1[CH3:28]>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][N:12]=[C:13]([c:14]2[cH:15][cH:16][cH:17]... | CC(C)COC(=O)Cl.CN1c2ccccc2C(c2ccccc2F)=NCC1CN | CC(C)COC(=O)NCC1CN=C(c2ccccc2F)c2ccccc2N1C | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc(C2=NCCNc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7:5]-[C:6]-[C:7]-[NH2;D1;+0:8]>>[#7:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 68.2 | [{"value": 68.2, "product": "CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(=O)OCC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Example 1, 1-methyl-2-aminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg, 0.88 mmole) and isobutyl chloroformate (114 μl, 0.88 mmole) were combined with 4 ml of dry methylene chloride, and 97 μl of N-methylmorpholine (0.88 mmole) at -5° C. was added to the mixture. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1=NCC[NH]c2ccccc21 | HCl | C(Cl)Cl | null | null | CC(C)COC(=O)Cl.CN1c2ccccc2C(c2ccccc2F)=NCC1CN>C(Cl)Cl>CC(C)COC(=O)NCC1CN=C(c2ccccc2F)c2ccccc2N1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-83875325c1ee4a0ea07fd297824b70f1 | CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C>>CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.Cl.Cl.Cl.O.O.O | CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(C(CC2=CNC1=CC=CC=C21)NC(=O)OC(C)(C)C)=O.Cl>>O.Cl.Cl.CN1C(CN=C(C2=C1C=CC=C2)C2=C(C=CC=C2)F)CNC(C(CC2=CNC1=CC=CC=C21)N)=O.O.O.CN2C(CN=C(C1=C2C=CC=C1)C1=C(C=CC=C1)F)CNC(C(CC1=CNC2=CC=CC=C12)N)=O.Cl.Cl | [CH3:1][N:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])=[N:17][CH2:18][CH:19]1[CH2:55][NH:56][C:57](=[O:58])[CH:59]([NH:60][C:22](=[O:23])[O:75][C:47]([CH3:20])([CH3:34])[CH3:48])[CH2:61][c:62]1[cH:63][nH:64][c:65]2[cH:66][cH:67][cH:68][cH:69][c:70]12>>[CH3:1][N:2]1[c:3]... | CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C | CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.Cl.Cl.Cl.O.O.O | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 8968ac2f70f8636a6f5d0ecf8299382e98a875ff0d4db68f9dee6e025c153c00 | 196819a33b21068293125ac03c76555aae00bf0dadf1efc47ec526fe42bdb80a | O=C(CCc1c[nH]c2ccccc12)NCC1CN=C(c2ccccc2)c2ccccc2N1.O=C(CCc1c[nH]c2ccccc12)NCC1CN=C(c2ccccc2)c2ccccc2N1 | [C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-[CH3;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#7:13]-[CH2;D2;+0:14]-[CH;D3;+0:15](-[C:16]-[#7:17]=[C:18])-[#7:19](-[C;D1;H3:20])-[c:21]>>[#7:22]-[C:23](-[CH2;D2;+0:14]-[#7:13]-[C:11](=[O;D1;H0:12])-[C:2](-[C:1]... | null | [] | 0 | CELSIUS | null | null | 1-Methyl-2-[2-((1,1-dimethylethoxy)carbonyl)amino-3-(1H-indol-3-yl)propanoyl]aminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (50 mg, 0.08 mmole) was dissolved in 2 ml of ethyl acetate, cooled to 0° C. and treated with hydrogen chloride gas for 1 hour. The solvent and excess hydrogen chloride were remo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Aromatic halide.Substituted imine.Secondary amide.Primary amine.Primary amine.Tertiary amine | C1=NCC[NH]c2ccccc21 | C1=NCC[NH]c2ccccc21.c1ccc2[nH]ccc2c1.C1=NCC[NH]c2ccccc21.c1ccccc1 | C1=NCC[NH]c2ccccc21.c1ccccc1.c1ccc2[nH]ccc2c1.C1=NCC[NH]c2ccccc21.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | C(C)(=O)OCC | 0 | null | CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C>C(C)(=O)OCC>CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.CN1c2ccccc2C(c2ccccc2F)=NCC1CNC(=O)C(N)Cc1c[nH]c2ccccc12.Cl.Cl.Cl.O.O.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7b2385246443417da1587de409a23533 | Oc1ccccc1>>Oc1ccccc1 | CC(C)=C.C1(=CC=CC=C1)O.C(C)(C)(C)C1=C(C=CC=C1)O.C1(=CC=CC=C1)O.C1(=CC=CC=C1)O>>C(C)(C)(C)C1=C(C=CC=C1)O.C1(=CC=CC=C1)O | [OH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[OH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Oc1ccccc1 | Oc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | A mixture of tert-butyl phenol and phenol prepared by alkylating phenol with isobutylene to a C4 /phenol ratio of 0.25 to provide a t-butyl phenol/phenol mixture was flash distilled to remove color. The mixture had an average t-butyl:phenyl ratio of about 0.3 (about 25% phenol:75% t-butyl phenols). 360.7 grams of t-but... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | Oc1ccccc1>>Oc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0eba15b633444881a771df4d2bfbd10e | O=C(Cl)C(=O)Cl.O=C(O)Cc1ccc(Cl)cc1>>O=C(Cl)Cc1ccc(Cl)cc1 | ClC1=CC=C(C=C1)CC(=O)O.C(C(=O)Cl)(=O)Cl>>ClC1=CC=C(C=C1)CC(=O)Cl | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1 | O=C(Cl)C(=O)Cl.O=C(O)Cc1ccc(Cl)cc1 | O=C(Cl)Cc1ccc(Cl)cc1 | null | CN(C=O)C | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | 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]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5] | null | [] | null | null | null | null | 4-Chlorophenylacetic acid (1.7 g, 10 mmol) and oxalyl chloride (2 ml, 23 mmol) were stirred in 100 ml methylene chloride with two drops of dimethylformamide for two hours. The solvent and excess oxalyl chloride were removed under vacuum to give p-chlorophenylacetyl chloride. The 4-chlorophenylacetyl chloride and 4,4,6,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C.C(Cl)Cl | null | null | O=C(Cl)C(=O)Cl.O=C(O)Cc1ccc(Cl)cc1>CN(C=O)C.C(Cl)Cl>O=C(Cl)Cc1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c1dd4451b34a40baa98f4c9107295354 | CC1(C)C(=O)CC(=O)C(C)(C)C1=O.O=C(Cl)Cc1ccc(Cl)cc1>>CC1(C)C(=O)C(C(=O)Cc2ccc(Cl)cc2)C(=O)C(C)(C)C1=O | ClC1=CC=C(C=C1)CC(=O)Cl.CC1(C(CC(C(C1=O)(C)C)=O)=O)C.C(C)N(CC)CC>>ClC1=CC=C(C=C1)CC(=O)C1C(C(C(C(C1=O)(C)C)=O)(C)C)=O | [CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[CH2:6][C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[C:22]1=[O:23].Cl[C:7](=[O:8])[CH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[CH:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[C:17](=[O:18])[C:19]([CH3:20])([... | CC1(C)C(=O)CC(=O)C(C)(C)C1=O.O=C(Cl)Cc1ccc(Cl)cc1 | CC1(C)C(=O)C(C(=O)Cc2ccc(Cl)cc2)C(=O)C(C)(C)C1=O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 44b16f3124d9704735b41660f61a79407d933597f005f0d8a27803cc59b3b159 | d1ef8d6a572be6944eed6d1e50ba23f9d6e95602669b67dac90442aed5304e90 | O=C1CC(=O)C(C(=O)Cc2ccccc2)C(=O)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | 30 | MINUTE | 4-Chlorophenylacetic acid (1.7 g, 10 mmol) and oxalyl chloride (2 ml, 23 mmol) were stirred in 100 ml methylene chloride with two drops of dimethylformamide for two hours. The solvent and excess oxalyl chloride were removed under vacuum to give p-chlorophenylacetyl chloride. The 4-chlorophenylacetyl chloride and 4,4,6,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Ketone | Ketone.Ketone.Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | CC1(C)C(=O)CC(=O)C(C)(C)C1=O.O=C(Cl)Cc1ccc(Cl)cc1>C(Cl)Cl>CC1(C)C(=O)C(C(=O)Cc2ccc(Cl)cc2)C(=O)C(C)(C)C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8b39f025038f42bb9c0a692743fbf1b9 | C=CCCCC.C[Si](C)(C)N=P(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C>>C=CCCCC.C=CCCCCCCCC | C[Si](C)(C)N([Si](C)(C)C)P(=N[Si](C)(C)C)=N[Si](C)(C)C.CCCCC=C>>CCCCCCCCC=C.CCCCC=C | [CH2:4]([CH2:5][CH3:6])[CH2:9][CH:8]=[CH2:7].C[Si](N(P(=N[Si]([CH3:2])([CH3:3])[CH3:12])=N[Si](C)([CH3:1])[CH3:16])[Si]([CH3:11])([CH3:13])[CH3:14])([CH3:10])[CH3:15]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16] | C=CCCCC.C[Si](C)(C)N=P(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | C=CCCCC.C=CCCCCCCCC | null | null | CCCCCCCCC=C | C-C Coupling | OtherReaction | 5c97663cc59484df51d4ae713931f41e24635e8d16b23eeb265c5150810ce2ac | 7089ff7c4563abebd52a1bee7b98fff1f2ed170af78f0e97f731a31027a60280 | null | C-[Si](-[CH3;D1;+0:1])(-[CH3;D1;+0:2])-N=P(=N-[Si](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[CH3;D1;+0:5])-N(-[Si](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8])-[Si](-C)(-[CH3;D1;+0:9])-[CH3;D1;+0:10].[C;D1;H2:11]=[C:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[C:15]-[C;D1;H3:16]>>[C;D1;H2:11]=[C:12]-[CH2;D2;+0:13]-[CH2;D2;+0:9]-[CH2;D2... | null | [] | 0 | CELSIUS | 3 | HOUR | In a glass vessel pre-conditioned by heating under vacuum and filled with argon 0.34 g (1.24 mmol) of bis(cyclooctadiene-1,5)nickel and 0.46 g (1.25 mmol) of bis(trimethylsilyl)amino-bis(trimethylsilylimino)phosphorane were dissolved in 20 ml of decene-1, and the solution was stirred at 0° C. for 3 hours. Then to the g... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Allyl.Silyl protective group.Silyl protective group.Silyl protective group.Silyl protective group | Allyl.Allyl | null | null | null | Other | CCCCCCCCC=C | 0 | 3 | C=CCCCC.C[Si](C)(C)N=P(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C>CCCCCCCCC=C>C=CCCCC.C=CCCCCCCCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ad0a48963d2543e0863f057522180da5 | CC(C)N.ClCCc1cc(Cl)ccc1Sc1ccc(Cl)cc1CCCl>>CC(C)NCCSc1ccc(Cl)cc1.Cl | C(Cl)(Cl)Cl.O.ClCCC1=C(C=CC(=C1)Cl)SC1=C(C=C(C=C1)Cl)CCCl.C(C)(C)N>>Cl.ClC1=CC=C(C=C1)SCCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH2:4].Clc1ccc([S:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[CH2:6][CH2:5]Cl)c(CC[Cl:15])c1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.[ClH:15] | CC(C)N.ClCCc1cc(Cl)ccc1Sc1ccc(Cl)cc1CCCl | CC(C)NCCSc1ccc(Cl)cc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d86d3596d2041492b8d73673891c723ec2c0956e8bb9de7bc8e3a9850977867 | 4858ea9fab1cc5b44bc5feb39f5a6f848b895d40e8e1919c3de421fd1be8a2c4 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[S;H0;D2;+0:7]-c1:c:c:c(-Cl):c:c:1-C-C-[Cl;H0;D1;+0:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[S;H0;D2;+0:7]-[c:6](:[c:9]):[cH;D2;+0:3]:[c:4]:[c:5].[ClH;D0;+... | null | [] | null | null | null | null | A solution of 24.0 g (0.116 mole) chloroethyl-p-chlorophenyl sulfide in 100 ml of isopropylamine was agitated overnight in a stainless steel bomb at 80° C. The reaction mixture was then stripped to dryness and the residue partitioned between water and chloroform. The chloroform layer was extracted with 1N sulfuric acid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Primary amine.Monosulfide | Secondary amine.Monosulfide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | CC(C)N.ClCCc1cc(Cl)ccc1Sc1ccc(Cl)cc1CCCl>>CC(C)NCCSc1ccc(Cl)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1fcdce9b06cf4aeaa6aaa374d1411429 | CC(C)NCCSc1ccc(Cl)cc1>>CC(C)NCCS(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)SCCNC(C)C.B(=O)O[O-].[Na+].[OH-].[Na+]>>ClC1=CC=C(C=C1)S(=O)CCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | CC(C)NCCSc1ccc(Cl)cc1 | CC(C)NCCS(=O)c1ccc(Cl)cc1 | null | null | S(O)(O)(=O)=O | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccccc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:7])-[c:4](:[c:5]):[c:6] | 90.6 | [{"value": 90.6, "product": "ClC1=CC=C(C=C1)S(=O)CCNC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 15.05 g (0.066 mole) of N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine and 12.0 g (0.0779 mole) of sodium perborate in 400 ml of 1M sulfuric acid was stirred at room temperature for about 18 hr. The solution was made basic with 50% sodium hydroxide and the basic solution was extracted with methylene... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1 | null | S(O)(O)(=O)=O | null | null | CC(C)NCCSc1ccc(Cl)cc1>S(O)(O)(=O)=O>CC(C)NCCS(=O)c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a8eb42d4c700427bb2f6aedd4d4b659d | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCCl)c1ccc(Cl)cc1>>O=C1c2ccccc2C(=O)N1CCCS(=O)(=O)c1ccc(Cl)cc1 | ClCCCS(=O)(=O)C1=CC=C(C=C1)Cl.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>ClC1=CC=C(C=C1)S(=O)(=O)CCCN1C(C2=CC=CC=C2C1=O)=O | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1.Cl[CH2:12][CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([... | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCCl)c1ccc(Cl)cc1 | O=C1c2ccccc2C(=O)N1CCCS(=O)(=O)c1ccc(Cl)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1c2ccccc2C(=O)N1CCCS(=O)(=O)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-[C:5]-1=[O;D1;H0:4] | null | [] | null | null | 8 | HOUR | A solution of 17.8 g (0.07 mole) of 1-chloro-3-(p-chlorophenylsulfonyl)propane and 15.2 g (0.082 mole) of potassium phthalimide in 300 ml of dimethylformamide was stirred at 90°-110° C. for 2 hr and then quenched in water. The mixture was extracted with methylene chloride and the methylene chloride layer dried over mag... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | CN(C=O)C | null | 8 | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCCl)c1ccc(Cl)cc1>CN(C=O)C>O=C1c2ccccc2C(=O)N1CCCS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c0e824ff2ea84ee0a559f8efc8f63b92 | CC(C)NCCSc1cccc2ccccc12.[O-]B1OO1>>CC(C)NCCS(=O)c1cccc2ccccc12 | Cl.CC(C)NCCSC1=CC=CC2=CC=CC=C12.B1(OO1)[O-].O.O.O.O.[Na+].[OH-].[Na+]>>Cl.CC(C)NCCS(=O)C1=CC=CC2=CC=CC=C12 | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.O1OB1[O-:8]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CC(C)NCCSc1cccc2ccccc12.[O-]B1OO1 | CC(C)NCCS(=O)c1cccc2ccccc12 | null | null | S(O)(O)(=O)=O | Oxidation | OtherReaction | bebc0a9c46895b64479ca506248015f6e3b2f5ce39f30517ca71f796faa475a6 | 099322fb111e24ec324e6fad75d493a762ca0cd5af0df8c6f3bfd25c910b45a8 | c1ccc2ccccc2c1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[O-;H0;D1:7]-B1-O-O-1>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:7])-[c:4](:[c:5]):[c:6] | 9.1 | [{"value": 9.1, "product": "Cl.CC(C)NCCS(=O)C1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.6, "product": "Cl.CC(C)NCCS(=O)C1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 12.0 g (0.043 mole) of 1-methyl-N-[2-(1-naphthalenylthio)ethyl]ethanamine hydrochloride and 19.7 g (0.028 mole) of sodium perborate tetrahydrate in 500 ml of 2N sulfuric acid was stirred overnight at room temperature. The solution was poured over ice and the mixture was made alkaline with 50% sodium hydro... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfoxide | B1OO1 | null | c1ccc2ccccc2c1 | B | S(O)(O)(=O)=O | null | null | CC(C)NCCSc1cccc2ccccc12.[O-]B1OO1>S(O)(O)(=O)=O>CC(C)NCCS(=O)c1cccc2ccccc12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cc9151e5ad6b4f33b85396bdbeeebe64 | CS(=O)(=O)Cl.OCCSc1ccc(Cl)c(Cl)c1>>CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1 | ClC=1C=C(C=CC1Cl)SCCO.C(C)N(CC)CC.CS(=O)(=O)Cl>>ClC=1C=C(C=CC1Cl)SCCOS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1 | CS(=O)(=O)Cl.OCCSc1ccc(Cl)c(Cl)c1 | CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1 | null | null | C1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 8 | HOUR | To a solution of 117.97 g (0.53 mole) of 2-[(3,4-dichlorophenyl)thio]ethanol (prepared by reacting 3,4-dichlorothiophenol and 2-chloroethanol) and 53.5 g (0.53 mole) of triethylamine in 500 ml of benzene was added dropwise a benzene solution of 60.9 g (0.53 mole) of methanesulfonyl chloride over a one hour period with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1 | HCl | C1=CC=CC=C1 | null | 8 | CS(=O)(=O)Cl.OCCSc1ccc(Cl)c(Cl)c1>C1=CC=CC=C1>CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e9ac2303bc5d496eaac98b7e1bc15dcc | CC(C)N.CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1>>CC(C)NCCSc1ccc(Cl)c(Cl)c1.Cl | ClC=1C=C(C=CC1Cl)SCCOS(=O)(=O)C.C(C)(C)N>>Cl.ClC=1C=C(C=CC1Cl)SCCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH2:4].CS(=O)(=O)O[CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]1.[ClH:16] | CC(C)N.CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1 | CC(C)NCCSc1ccc(Cl)c(Cl)c1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[NH2;D1;+0:7]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:7]-[C:5](-[C;D1;H3:4])-[C;D1;H3:6] | null | [] | null | null | null | null | A solution of 151.46 g (0.548 mole) of methanesulfonic acid[2-[(3,4-dichlorophenyl)thio]ethyl]ester in 100 ml of isopropylamine was heated overnight in a bomb at 100° C. The isopropylamine was removed in a rotary evaporator and the residue partitioned between chloroform and 5% sodium hydroxide. The chloroform was remov... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccccc1 | HO- | null | null | null | CC(C)N.CS(=O)(=O)OCCSc1ccc(Cl)c(Cl)c1>>CC(C)NCCSc1ccc(Cl)c(Cl)c1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ce8e45175ab64e68b2f9eff595f3864a | ClCCCSc1ccccc1.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCSc1ccccc1 | ClCCCSC1=CC=CC=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>C1(=CC=CC=C1)SCCCN1C(C2=CC=CC=C2C1=O)=O | Cl[CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | ClCCCSc1ccccc1.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CCCSc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1c2ccccc2C(=O)N1CCCSc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-[C:5]-1=[O;D1;H0:4] | 63.8 | [{"value": 63.8, "product": "C1(=CC=CC=C1)SCCCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.8, "product": "C1(=CC=CC=C1)SCCCN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 32.86 g (0.177 mole) of 1-chloro-3-(phenylthio)propane and 33.7 g (0.182 mole) of potassium phthalimide in 500 ml of dimethylformamide was stirred at 80° C. for 19 hr. The dimethylformamide was removed in vacuo. The residue was dissolved in methylene chloride and the resulting solution extracted with seve... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | CN(C=O)C | null | null | ClCCCSc1ccccc1.O=C1NC(=O)c2ccccc21>CN(C=O)C>O=C1c2ccccc2C(=O)N1CCCSc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3899e2d65d6d4b47ba44772811d58aca | CC(C)N.O=S(=O)(CCCCl)c1ccccc1>>CC(C)NCCCS(=O)(=O)c1ccccc1.Cl | ClCCCS(=O)(=O)C1=CC=CC=C1.C(C)(C)N>>Cl.CC(C)NCCCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH2:4].[CH2:5]([CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[Cl:17]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[ClH:17] | CC(C)N.O=S(=O)(CCCCl)c1ccccc1 | CC(C)NCCCS(=O)(=O)c1ccccc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[Cl;H0;D1;+0:8]>>[C:5]-[C:6]-[CH2;D2;+0:7]-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3].[ClH;D0;+0:8] | null | [] | null | null | null | null | A solution of 66.55 g (0.3052 mole) of 3-chloropropylphenyl sulfone (prepared by reacting m-chloroperoxybenzoic acid and 3-chloropropyl phenylsulfide in methylene chloride) in 200 ml of isopropylamine was heated at 100° C. overnight in a bomb. The isopropylamine was removed by rotary evaporation and the residue partiti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | null | null | null | CC(C)N.O=S(=O)(CCCCl)c1ccccc1>>CC(C)NCCCS(=O)(=O)c1ccccc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ac7bb16995024c46a7800aead047370a | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1>>CC(C)NCCS(=O)(=O)c1ccc(Cl)c(Cl)c1 | C1(=CC=CC=C1)OC(N(C(C)C)CCS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl)=O>>ClC=1C=C(C=CC1Cl)S(=O)(=O)CCNC(C)C | O=C(Oc1ccccc1)[N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17]1 | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1 | CC(C)NCCS(=O)(=O)c1ccc(Cl)c(Cl)c1 | null | null | Br | Reduction | Hydrogenolysis of tertiary amines | 709a03512f2b36af470a6c002bf594696c9a8d9f4ff0ae82dddda03c8a91a358 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccccc1 | O=C(-O-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](-[C;D1;H3:5])-[C;D1;H3:6] | 32.4 | [{"value": 32.4, "product": "ClC=1C=C(C=CC1Cl)S(=O)(=O)CCNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 44.27 g (0.107 mole of N-[2-[(3,4-dichlorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 300 ml of 48% HBr was heated at reflux for 12 hr. The reaction mixture was cooled to room temperature, made alkaline with 50% sodium hydroxide-ice and extracted with chloroform. The chloroform l... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1 | null | c1ccccc1 | HO- | Br | null | null | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1>Br>CC(C)NCCS(=O)(=O)c1ccc(Cl)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5d2d6d1bd4bb4895b8b561dcce002bb1 | CC(C)(N)CCSc1ccc(F)cc1.O=C(Cl)Oc1ccccc1>>CC(C)N(CCSc1ccc(F)cc1)C(=O)Oc1ccccc1 | ClC(=O)OC1=CC=CC=C1.C(Cl)Cl.FC1=CC=C(C=C1)SCCC(C)(N)C.C(C)N(CC)CC.C(Cl)Cl>>C1(=CC=CC=C1)OC(N(C(C)C)CCSC1=CC=C(C=C1)F)=O | [CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1.Cl[C:15](=[O:16])[O:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[C:15](=[O:16])[O:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c... | CC(C)(N)CCSc1ccc(F)cc1.O=C(Cl)Oc1ccccc1 | CC(C)N(CCSc1ccc(F)cc1)C(=O)Oc1ccccc1 | null | null | null | Protection | OtherReaction | a42633a79ab98a6c6618a6a985c9ef85d612db2a3108c005e1fc58b635172b16 | c7c30c8e119de916171bede109f693a93326df60c194f5e0a34518c63f4ffc24 | O=C(NCCSc1ccccc1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[#16:5]-[C:6]-[CH2;D2;+0:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11]>>[#16:5]-[C:6]-[CH2;D2;+0:7]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4])-[CH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10] | null | [] | null | null | 8 | HOUR | To a solution of 38.5 g (0.15 mole) of N-[2-(4-fluorophenylthio]ethyl-1-methyl-ethanamine and 15.5 g (0.15 mole) of triethylamine in 300 ml of methylene chloride which was cooled in an ice bath was added dropwise with stirring a solution of 23.5 g (0.15 mole) of phenyl chloroformate in 100 ml of methylene chloride over... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester.Ether | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | 8 | CC(C)(N)CCSc1ccc(F)cc1.O=C(Cl)Oc1ccccc1>>CC(C)N(CCSc1ccc(F)cc1)C(=O)Oc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9c7f498abcf44048992767b6acc95b5 | CC(C)N(CCS(=O)(=O)c1ccc(F)cc1)C(=O)Oc1ccccc1.ClCCl>>CC(C)NCCS(=O)(=O)c1ccc(F)cc1.Cl | C1(=CC=CC=C1)OC(N(C(C)C)CCS(=O)(=O)C1=CC=C(C=C1)F)=O.[OH-].[Na+].C(Cl)Cl>>Cl.FC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C | O=C(Oc1ccccc1)[N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.ClC[Cl:17]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[ClH:17] | CC(C)N(CCS(=O)(=O)c1ccc(F)cc1)C(=O)Oc1ccccc1.ClCCl | CC(C)NCCS(=O)(=O)c1ccc(F)cc1.Cl | null | null | CO.Br | Miscellaneous | OtherReaction | 1e3af0eec45bbe3bcf3b649e925407a5e4d014627901b089faf032374572d852 | 3359bcd5552243e6ac1c05029938c325e73803d6c6cb6bada5dcc73b6e54effe | c1ccccc1 | Cl-C-[Cl;H0;D1;+0:1].O=C(-O-c1:c:c:c:c:c:1)-[N;H0;D3;+0:2](-[C:3]-[C:4])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7]>>[C:4]-[C:3]-[NH;D2;+0:2]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7].[ClH;D0;+0:1] | null | [] | null | null | null | null | A solution of 60.25 g (0.165 mole) of N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 400 ml of 48% HBr was heated at reflux for 8 hr. The reaction mixture was cooled with ice and made alkaline with 50% sodium hydroxide. The aqueous phase was extracted with chloroform. The chlorofor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether | Secondary amine | c1ccccc1 | null | c1ccccc1 | HCl | CO.Br | null | null | CC(C)N(CCS(=O)(=O)c1ccc(F)cc1)C(=O)Oc1ccccc1.ClCCl>CO.Br>CC(C)NCCS(=O)(=O)c1ccc(F)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6acd335397af4423ab4dfd5c48ff189b | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCl)c1ccccc1>>O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1 | ClCCS(=O)(=O)C1=CC=CC=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>C1(=CC=CC=C1)S(=O)(=O)CCN1C(C2=CC=CC=C2C1=O)=O | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1.Cl[CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCl)c1ccccc1 | O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-[C:5]-1=[O;D1;H0:4] | 35.7 | [{"value": 35.7, "product": "C1(=CC=CC=C1)S(=O)(=O)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 30.7 g (0.15 mole) of 2-chloroethylphenylsulfone and 69.5 g (0.375 mole) of potassium phthalimide in 600 ml of dimethylformamide was heated overnight at 85° C. The reaction mixture was stripped to dryness and the residue was partitioned between water and chloroform. The chloroform layer was dried and filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | CN(C=O)C | null | null | O=C1NC(=O)c2ccccc21.O=S(=O)(CCCl)c1ccccc1>CN(C=O)C>O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ff66ca3284074b0b8a71d6f999b087a9 | O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1>>NCCS(=O)(=O)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)CCN1C(C2=CC=CC=C2C1=O)=O.O.NN.Cl>>Cl.C1(=CC=CC=C1)S(=O)(=O)CCN | O=C1c2ccccc2C(=O)[N:2]1[CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[NH2:2][CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1 | NCCS(=O)(=O)c1ccccc1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 40.5 | [{"value": 40.5, "product": "Cl.C1(=CC=CC=C1)S(=O)(=O)CCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 32.3 g (0.102 mole) of 2-[2-(phenylsulfonyl)ethyl]-1H-isoindole-1,3-(2H)-dione and 11.8 g (0.2 mole) of 85% hydrazine hydrate in 500 ml of absolute ethanol was refluxed for 6 hr. The reaction mixture was cooled to room temperature, filtered and concentrated. The concentrate was dissolved in chloroform and... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1 | HO- | C(C)O | null | null | O=C1c2ccccc2C(=O)N1CCS(=O)(=O)c1ccccc1>C(C)O>NCCS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fb82c5ce9e9d4fb38a0048e765370c2d | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccc(Cl)cc1)C(=O)Oc1ccccc1>>CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.Cl | C1(=CC=CC=C1)OC(N(C(C)C)CCS(=O)(=O)C1=CC=C(C=C1)Cl)=O.C1(=CC=CC=C1)OC(N(C(C)C)CCS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl)=O>>Cl.ClC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c([Cl:17])c1)C(=O)Oc1ccccc1.O=C(Oc1ccccc1)[N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1.[ClH:17] | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccc(Cl)cc1)C(=O)Oc1ccccc1 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.Cl | null | null | null | Miscellaneous | OtherReaction | 39ab2d8b53fe99c862a1c70f1614b8c6491ecef0516bee7b8c04d8bf4b2a1cdf | 1880bffaf232174b62dff529914e28dcd990da054d75043261a3bbf09bf32805 | c1ccccc1 | C-C(-C)-N(-C-C-S(=O)(=O)-c1:c:c:c(-Cl):c(-[Cl;H0;D1;+0:1]):c:1)-C(=O)-O-c1:c:c:c:c:c:1.O=C(-O-c1:c:c:c:c:c:1)-[N;H0;D3;+0:2](-[C:3]-[C:4])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7]>>[C:4]-[C:3]-[NH;D2;+0:2]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7].[ClH;D0;+0:1] | null | [] | null | null | null | null | When in the procedure of Preparation 29, N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester is substituted for N-[2-[(3,4-dichlorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester, the title compound is obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Carbamic ester.Ether.Ether.Sulfone | Secondary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HCl | null | null | null | CC(C)N(CCS(=O)(=O)c1ccc(Cl)c(Cl)c1)C(=O)Oc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccc(Cl)cc1)C(=O)Oc1ccccc1>>CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ae4c77ae86b04fcaa9012d4cce7a5a3a | CN.O=S(=O)(CCCl)c1ccccc1>>CNCCS(=O)(=O)c1ccccc1 | ClCCS(=O)(=O)C1=CC=CC=C1.CN>>CNCCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][NH2:2].Cl[CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][NH:2][CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CN.O=S(=O)(CCCl)c1ccccc1 | CNCCS(=O)(=O)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[NH2;D1;+0:5]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4] | null | [] | null | null | null | null | A solution of 2-chloroethylphenyl sulfone and a large excess of methylamine (40% solution in water) in acetonitrile is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution is extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HCl | C(C)#N | null | null | CN.O=S(=O)(CCCl)c1ccccc1>C(C)#N>CNCCS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e0ed1f7a66854e2588702449ee9bd2ce | CC(C)N(CCCl)C(C)C.O=C1NC(=O)c2ccccc21>>CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C | Cl.C(C)(C)N(CCCl)C(C)C.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>Cl.CC(C)N(C(C)C)CCN1C(C2=CC=CC=C2C1=O)=O | Cl[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:18]([CH3:19])[CH3:20].[NH:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17])[CH:18]([CH3:19])[CH3:20] | CC(C)N(CCCl)C(C)C.O=C1NC(=O)c2ccccc21 | CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1NC(=O)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5](=[O;D1;H0:4])-[c:10]:[c:9]-[C:7]-1=[O;D1;H0:8] | 62.3 | [{"value": 62.3, "product": "Cl.CC(C)N(C(C)C)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.7, "product": "Cl.CC(C)N(C(C)C)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-diisopropylaminoethyl chloride hydrochloride (40.0 g, 0.2 mole) and potassium phthalimide (74.0 g, 0.4 mole) as stirred overnight at 85° C. in 500 ml of dimethyl formamide. The reaction mixture was stirred to dryness on a rotary evaporator, and the residue was partitioned between chloroform and water. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HCl | CN(C=O)C | null | null | CC(C)N(CCCl)C(C)C.O=C1NC(=O)c2ccccc21>CN(C=O)C>CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d69cadb84c1f457aa9645d6fe5e18d9e | CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C.Cl>>CC(C)N(CCN)C(C)C.Cl | C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl.CC(C)N(C(C)C)CCN1C(C2=CC=CC=C2C1=O)=O.O.NN>>Cl.Cl.CC(C)N(CCN)C(C)C | O=C1c2ccccc2C(=O)[N:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:8]([CH3:9])[CH3:10].[ClH:12]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH2:7])[CH:8]([CH3:9])[CH3:10].[ClH:12] | CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C.Cl | CC(C)N(CCN)C(C)C.Cl | null | null | C(C)O.CO | Miscellaneous | OtherReaction | cd703f280330e7612c3c3b2e3cc2f8f9332381f29a1fd88b2de2a38281774976 | febc1d4b7b44ea3f7762312e158d5ab0fc0ca67ce6d66e23a51e3baafdb353e3 | null | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 8 | HOUR | A solution of 40.54 g (0.148 mole) of 2-[2-[[N,N-bis(1-methylethyl)amino]ethyl]-2H-isoindole-1,3-dione and hydrazine hydrate (85%, 11.8 g, 0.2 mole) in 400 ml of 95% ethanol was heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature while standing overnight. A white solid formed. The... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | null | HO- | C(C)O.CO | null | 8 | CC(C)N(CCN1C(=O)c2ccccc2C1=O)C(C)C.Cl>C(C)O.CO>CC(C)N(CCN)C(C)C.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5b62d5e0639c4fe99fa536f8aadfd356 | CCN(CC)CC.CCOCC.NCCc1ccccc1.O=S(=O)(CCCl)c1ccccc1>>Cl.Cl.O.O=S(=O)(CCNCCc1ccccc1)c1ccccc1.O=S(=O)(CCNCCc1ccccc1)c1ccccc1 | CCOCC.ClCCS(=O)(=O)C1=CC=CC=C1.C(CC1=CC=CC=C1)N.C(C)N(CC)CC>>O.Cl.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.Cl | [CH2:8]([N:9]([CH2:10][CH3:15])[CH2:13][CH3:14])[CH3:16].[O:3]([CH2:12][CH3:11])[CH2:17][CH3:38].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1.[Cl:1][CH2:28][CH2:7][S:5](=[O:6])([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)=[O:26]>>[ClH:1].[ClH:2].[OH2:3].[O:4]=[S:5](=[O:6])([CH2:7][CH2:8][NH:9][CH... | CCN(CC)CC.CCOCC.NCCc1ccccc1.O=S(=O)(CCCl)c1ccccc1 | Cl.Cl.O.O=S(=O)(CCNCCc1ccccc1)c1ccccc1.O=S(=O)(CCNCCc1ccccc1)c1ccccc1 | null | null | C(C)#N.Cl.CO | Aromatic Heterocycle Formation | OtherReaction | 72be0d2e1bf20ce2c679b00c1c160ada3ce336114055468e1a99db416052f9c2 | ea7f51779ce0ba54a18c0e6e9df94f90cd9f6ea9c35213f225da6192c9409911 | O=S(=O)(CCNCCc1ccccc1)c1ccccc1.O=S(=O)(CCNCCc1ccccc1)c1ccccc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH2;D2;+0:6]-[CH3;D1;+0:7].[CH3;D1;+0:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[CH3;D1;+0:12].[C:13]-[C:14]-[NH2;D1;+0:15].[Cl;H0;D1;+0:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-[S;H0;D4;+0:19](=[O;D1;H0:20])(=[O;H0;D1;+0:21])-[c:22](:[c:23]):[c:2... | 89.1 | [{"value": 60.0, "product": "O.Cl.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.1, "product": "O.Cl.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)CCNCCC1=CC=CC=C1.Cl", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 18 | HOUR | A mixture of 70.23 g (0.344 mole) of 2-chloroethylphenylsulfone, 41.92 g (0.343 mole) of phenethylamine and 60 ml of triethylamine in 800 ml of acetonitrile was stirred at room temperature for 18 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine.Tertiary amine.Sulfone | Secondary amine.Secondary amine.Sulfone.Sulfone | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)#N.Cl.CO | null | 18 | CCN(CC)CC.CCOCC.NCCc1ccccc1.O=S(=O)(CCCl)c1ccccc1>C(C)#N.Cl.CO>Cl.Cl.O.O=S(=O)(CCNCCc1ccccc1)c1ccccc1.O=S(=O)(CCNCCc1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-95c3f93212c34abcafd8589c1a2860f7 | CC(C)N.O=S(=O)(CCCCCl)c1ccccc1>>CC(C)NCCCCS(=O)(=O)c1ccccc1.Cl | ClCCCCS(=O)(=O)C1=CC=CC=C1.C(C)(C)N>>Cl.CC(C)NCCCCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH2:4].[CH2:5]([CH2:6][CH2:7][CH2:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[Cl:18]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[ClH:18] | CC(C)N.O=S(=O)(CCCCCl)c1ccccc1 | CC(C)NCCCCS(=O)(=O)c1ccccc1.Cl | null | null | C(Cl)(Cl)Cl.CO | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[Cl;H0;D1;+0:8]>>[C:5]-[C:6]-[CH2;D2;+0:7]-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3].[ClH;D0;+0:8] | 30 | [{"value": 30.0, "product": "Cl.CC(C)NCCCCS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 105.95 g (0.456 mole) [(4-chlorobutyl)sulfonyl]benzene was heated overnight at 75° C. on an autoclave in 200 ml of isopropylamine. The reaction mixture was stripped to dryness. The residue obtained was dissolved in chloroform and the chloroform layer was extracted with water. The chloroform layer was drie... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | C(Cl)(Cl)Cl.CO | null | null | CC(C)N.O=S(=O)(CCCCCl)c1ccccc1>C(Cl)(Cl)Cl.CO>CC(C)NCCCCS(=O)(=O)c1ccccc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7339c7a207114a058f08a02bd2cd46d8 | CC(C)N.ClCCSc1ccccc1>>CC(C)NCCSc1ccccc1.Cl | C1(=CC=CC=C1)SCCCl.[I-].[K+].C(C)(C)N>>Cl.C1(=CC=CC=C1)SCCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH2:4].[CH2:5]([CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[Cl:14]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[ClH:14] | CC(C)N.ClCCSc1ccccc1 | CC(C)NCCSc1ccccc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | [#16:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[#16:1]-[C:2]-[CH2;D2;+0:3]-[NH;D2;+0:8]-[C:6](-[C;D1;H3:5])-[C;D1;H3:7].[ClH;D0;+0:4] | 76.9 | [{"value": 76.9, "product": "Cl.C1(=CC=CC=C1)SCCNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 25 g (0.145 mole) of 2-chloroethyl phenyl sulfide and 1 g (0.006 mole) of potassium iodide in 500 ml of isopropylamine was heated in a bomb at 120° C. for 24 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | null | null | null | CC(C)N.ClCCSc1ccccc1>>CC(C)NCCSc1ccccc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-28031cec7bf3401286c156beffb1ffb3 | CC(C)N.O=S(=O)(CCCl)Cc1ccccc1>>CC(C)NCCS(=O)(=O)Cc1ccccc1 | CCOCC.ClCCS(=O)(=O)CC1=CC=CC=C1.C(C)(C)N.Cl>>Cl.C1(=CC=CC=C1)CS(=O)(=O)CCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH2:4].Cl[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CC(C)N.O=S(=O)(CCCl)Cc1ccccc1 | CC(C)NCCS(=O)(=O)Cc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[NH2;D1;+0:7]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:7]-[C:5](-[C;D1;H3:4])-[C;D1;H3:6] | 65.8 | [{"value": 65.8, "product": "Cl.C1(=CC=CC=C1)CS(=O)(=O)CCNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | A mixture of 51.49 g (0.236 mole) of benzyl 2-chloroethyl sulfone and 600 ml of isopropylamine was stirred at room temperature for 72 hr. The solvent was removed in vacuo, and the residue was partitioned between ether and dilute sodium hydroxide. The ether solution was dried over magnesium sulfate, and the solvent was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HCl | CO | null | 72 | CC(C)N.O=S(=O)(CCCl)Cc1ccccc1>CO>CC(C)NCCS(=O)(=O)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-df95688818af431f92f3b925fa45e917 | CC(C)NCCSc1ccccc1.O.[O-]B1OO1.[OH-]>>CC(C)NCCS(=O)c1ccccc1.O=C(O)/C=C\C(=O)O | Cl.C1(=CC=CC=C1)SCCNC(C)C.B1(OO1)[O-].O.O.O.O.[Na+].[OH-].[Na+]>>C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)S(=O)CCNC(C)C | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[OH2:22].B1([O-:15])[O:8][O:21]1.[OH-:17]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:15]=[C:16]([OH:17])/[CH:18]=[CH:19]\[C:20](=[O:21])[OH:22] | CC(C)NCCSc1ccccc1.O.[O-]B1OO1.[OH-] | CC(C)NCCS(=O)c1ccccc1.O=C(O)/C=C\C(=O)O | null | null | S(O)(O)(=O)=O | Acylation | OtherReaction | 920aba2fc218fc2206abcbec54b771387c85c815425bd4e22ef20c34e9dfd0bd | d5c4df79b25970cc5824026731621baec2947b39fd15cf98f6ca9fecd5262aac | c1ccccc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[O-;H0;D1:7]-B1-[O;H0;D2;+0:8]-[O;H0;D2;+0:9]-1.[OH-;D0:10].[OH2;D0;+0:11]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:9])-[c:4](:[c:5]):[c:6].[O;H0;D1;+0:7]=[C:12](-[OH;D1;+0:10])/[C:13]=[C:14]\[C:15](=[O;H0;D1;+0:8])-[OH;D1;+0:11] | 177.6 | [{"value": 88.3, "product": "C(\\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)S(=O)CCNC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 177.6, "product": "C(\\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)S(=O)CCNC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 15.62 g (0.067 mole) of N-[2-(phenylthio)ethyl]-2-propanamine hydrochloride and 15.62 g (0.101 mole) of sodium perborate tetrahydrate in 300 ml of 2M sulfuric acid was stirred at room temperature for 16 hr. The solution was made basic with 50% sodium hydroxide, and the basic solution was extracted with me... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Carboxylic acid.Carboxylic acid.Sulfoxide | B1OO1 | null | c1ccccc1 | B | S(O)(O)(=O)=O | null | null | CC(C)NCCSc1ccccc1.O.[O-]B1OO1.[OH-]>S(O)(O)(=O)=O>CC(C)NCCS(=O)c1ccccc1.O=C(O)/C=C\C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81ada1811183440c81eed8afb7279bd4 | NCc1ccccc1.O=S(=O)(CCCl)c1ccccc1>>Cl.O=S(=O)(CCNCc1ccccc1)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)CCCl.C(C1=CC=CC=C1)N.C(C)N(CC)CC>>Cl.C1(=CC=CC=C1)S(=O)(=O)CCNCC1=CC=CC=C1 | [NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[Cl:1][CH2:6][CH2:5][S:3](=[O:2])(=[O:4])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[ClH:1].[O:2]=[S:3](=[O:4])([CH2:5][CH2:6][NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | NCc1ccccc1.O=S(=O)(CCCl)c1ccccc1 | Cl.O=S(=O)(CCNCc1ccccc1)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=S(=O)(CCNCc1ccccc1)c1ccccc1 | [#16:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#16:1]-[C:2]-[CH2;D2;+0:3]-[NH;D2;+0:5]-[C:6]-[c:7].[ClH;D0;+0:4] | null | [] | null | null | 64 | HOUR | A mixture of 71.90 g (0.352 mole) of 2-chloroethyl phenyl sulfone, 37.45 g (0.350 mole) of benzylamine and 60 ml of triethylamine in 800 ml of acetonitrile was stirred at room temperature for ≈64 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and dilute sodium hydroxide.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | null | C(C)#N | null | 64 | NCc1ccccc1.O=S(=O)(CCCl)c1ccccc1>C(C)#N>Cl.O=S(=O)(CCNCc1ccccc1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9b6bca417c434762bad8de93b51a34db | OCCCCCl.Sc1ccccc1>>OCCCCSc1ccccc1 | C1(=CC=CC=C1)S.ClCCCCO.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)SCCCCO | Cl[CH2:5][CH2:4][CH2:3][CH2:2][OH:1].[SH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | OCCCCCl.Sc1ccccc1 | OCCCCSc1ccccc1 | null | null | C(Cl)(Cl)Cl.C(OC)COC | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 57.8 | [{"value": 57.8, "product": "C1(=CC=CC=C1)SCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.1, "product": "C1(=CC=CC=C1)SCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of thiophenol (121.2 g, 1.10 mole), 4-chloro-1-butanol (100.0 g, 0.921 mole), and potassium carbonate (138.2 g, 1.0 mole) was heated overnight at gentle reflux in dimethoxyethane. The reaction mixture was filtered and solvent removed by rotary evaporator. The residue obtained was dissolved in chloroform and e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1 | HCl | C(Cl)(Cl)Cl.C(OC)COC | null | null | OCCCCCl.Sc1ccccc1>C(Cl)(Cl)Cl.C(OC)COC>OCCCCSc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9ffe40dfc354894b3753bf7aa940b3d | CCOCCCN.O=S(=O)(CCCl)c1ccccc1>>CCOCCCNCCS(=O)(=O)c1ccccc1 | Cl.C1(=CC=CC=C1)S(=O)(=O)CCCl.C(C)OCCCN.C(C)N(CC)CC>>Cl.C(C)OCCCNCCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][CH2:6][NH2:7].Cl[CH2:8][CH2:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CCOCCCN.O=S(=O)(CCCl)c1ccccc1 | CCOCCCNCCS(=O)(=O)c1ccccc1 | null | null | C(C)#N.CCOCC.CO | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | 63.2 | [{"value": 63.2, "product": "Cl.C(C)OCCCNCCS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "Cl.C(C)OCCCNCCS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 51.4 g (0.253 mole) of 2-chloroethyl phenyl sulfone, 50.2 g (0.417 mole) of 3-ethoxy-1-propanamine, and 33.0 g (0.327 mole) of triethylamine in 400 ml of acetonitrile was stirred at room temperature for 20 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HCl | C(C)#N.CCOCC.CO | null | 20 | CCOCCCN.O=S(=O)(CCCl)c1ccccc1>C(C)#N.CCOCC.CO>CCOCCCNCCS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-712d15a0026748889ba593fd6b6cb891 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.CCO>>CCOc1ccc(S(=O)(=O)CCNC(C)C)cc1 | C(C)O.[H-].[Na+].CS(=O)C.Cl.ClC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C>>Cl.C(C)OC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C | Cl[c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[CH2:11][CH2:12][NH:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[CH2:11][CH2:12][NH:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.CCO | CCOc1ccc(S(=O)(=O)CCNC(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 0.5 | HOUR | To a suspension of 6.6 g of a 60% dispersion of sodium hydride in oil (0.165 mole) in 300 mole of dimethyl sulfoxide was added 7.5 g (0.163 mole) of absolute ethanol. The mixture was stirred at room temperature for 0.5 hr, and 20.8 g (0.080 mole) of N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | 0.5 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.CCO>>CCOc1ccc(S(=O)(=O)CCNC(C)C)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53878bc16b5f4166be999b2b304deda7 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.[OH-]>>CC(C)NCCS(=O)(=O)c1ccc(O)cc1 | Cl.ClC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C.[OH-].[Na+]>>Cl.OC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C | Cl[c:13]1[cH:12][cH:11][c:10]([S:7]([CH2:6][CH2:5][NH:4][CH:2]([CH3:1])[CH3:3])(=[O:8])=[O:9])[cH:16][cH:15]1.[OH-:14]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]1 | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.[OH-] | CC(C)NCCS(=O)(=O)c1ccc(O)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6fb010fda794df3314b587858e2590d87f73768e0e1a88e417db2b55286986bb | 05ba928edd770174a8e0738270a5c99182284743586e41e52e6183b77c44ac41 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH-;D0:6]>>[OH;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | A solution of N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-1-methylethanamine hydrochloride and sodium hydroxide in 500 ml of dimethyl sulfoxide is heated at 95° C. for 2 hrs with stirring. The solvent is removed by rotary evaporation (vacuum pump) and the residue is partitioned between water (pH adjusted to 7 by the addition... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | null | null | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1.[OH-]>CS(=O)C>CC(C)NCCS(=O)(=O)c1ccc(O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bfa7dcd3f23744c99a5e0a575455a555 | CC(C)=O.CC(C)NCCS(=O)(=O)c1ccccc1.CCOC(C)=O.CN(CCN)CCc1ccccc1.O=C(n1ccnc1)n1ccnc1>>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.O | CC(=O)C.C(C)(=O)OCC.C(=O)(N1C=NC=C1)N1C=NC=C1.CN(CCN)CCC1=CC=CC=C1.CC(C)NCCS(=O)(=O)C1=CC=CC=C1>>O.CC(C)N(C(=O)NCCN(CCC1=CC=CC=C1)C)CCS(=O)(=O)C1=CC=CC=C1.CC(C)N(C(=O)NCCN(C)CCC1=CC=CC=C1)CCS(=O)(=O)C1=CC=CC=C1 | [CH3:3][C:32]([CH3:36])=[O:61].[CH3:1][CH:2]([NH:4][CH2:5][CH2:6][S:7](=[O:8])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:39])[CH3:33].[O:9]([C:16](=[O:17])[CH3:40])[CH2:23][CH3:24].[NH2:48][CH2:49][CH2:50][N:51]([CH3:52])[CH2:53][CH2:54][c:55]1[cH:56][cH:57][cH:58][cH:59][cH:60]1.n1[cH:25][cH:26][n:34]([C:46]([n:... | CC(C)=O.CC(C)NCCS(=O)(=O)c1ccccc1.CCOC(C)=O.CN(CCN)CCc1ccccc1.O=C(n1ccnc1)n1ccnc1 | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.O | null | null | CCOCC.O1CCCC1 | Acylation | OtherReaction | 38604cddeaa23064e6198c611ade6a1c7d513a6797da9364a1724eac9cfff159 | b3ee7c51000750bd4fda626e70d203152f4e00e0aa29f7b6c8649bd8159889fd | O=C(NCCNCCc1ccccc1)NCCS(=O)(=O)c1ccccc1.O=C(NCCNCCc1ccccc1)NCCS(=O)(=O)c1ccccc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[NH;D2;+0:4]-[C:5]-[C:6]-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12].[CH3;D1;+0:13]-[C;H0;D3;+0:14](-[CH3;D1;+0:15])=[O;H0;D1;+0:16].[CH3;D1;+0:17]-[CH2;D2;+0:18]-[O;H0;D2;+0:19]-[C;H0;D3;+0:20](-[CH3;D1;+0:21])=[O;D1;H0:22].[C:23]-[C:24]-[NH2;D1;+0:25].... | null | [] | null | null | null | null | A solution of 1,1'-carbonyldiimidazole (8.12 g, 0.05 mole) and N-methyl-N-(2-phenylethyl)-1,2-ethanediamine, 8.0 g (0.0045 mole) in 300 ml of tetrahydrofuran was stirred for 2 hours at room temperature. To the mixture was added 9.37 g (0.0412 mole) of 1-methyl-N-[2-(phenylsulfonyl)ethyl]ethanamine and the reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Secondary amine.Sulfone | Urea.Urea.Tertiary amine.Sulfone.Sulfone | c1c[nH]cn1.c1c[nH]cn1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCOCC.O1CCCC1 | null | null | CC(C)=O.CC(C)NCCS(=O)(=O)c1ccccc1.CCOC(C)=O.CN(CCN)CCc1ccccc1.O=C(n1ccnc1)n1ccnc1>CCOCC.O1CCCC1>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)CCc1ccccc1.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-082c10047ad64187a1aa3f32d4231702 | CC(C)NCCS(=O)(=O)c1ccccc1.CN(CCN)Cc1ccccc1.O=C(n1ccnc1)n1ccnc1>>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)Cc1ccccc1 | [O-][Si](=O)[O-].[Mg+2].CN(CCN)CC1=CC=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.CC(C)NCCS(=O)(=O)C1=CC=CC=C1>>CC(C)N(C(=O)NCCN(CC1=CC=CC=C1)C)CCS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:18][CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.c1cn([C:16](n2ccnc2)=[O:17])cn1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:... | CC(C)NCCS(=O)(=O)c1ccccc1.CN(CCN)Cc1ccccc1.O=C(n1ccnc1)n1ccnc1 | CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)Cc1ccccc1 | null | null | C(Cl)(Cl)Cl.O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C(NCCNCc1ccccc1)NCCS(=O)(=O)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | null | null | null | null | A solution of 17.90 g (0.045 mole) of N-methyl-N-(phenylmethyl)-1,2-ethanediamine and 1,1'-carbonyldiimidazole (0.05 mole) in 100 ml of tetrahydrofuran was stirred at room temperature for 1 hour. To the mixture was added 10.52 g, (0.04 mole) of 1-methyl-N-[2-(phenysulfonyl)ethyl]ethanamine and the resulting solution he... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)Cl.O1CCCC1 | null | null | CC(C)NCCS(=O)(=O)c1ccccc1.CN(CCN)Cc1ccccc1.O=C(n1ccnc1)n1ccnc1>C(Cl)(Cl)Cl.O1CCCC1>CC(C)N(CCS(=O)(=O)c1ccccc1)C(=O)NCCN(C)Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fefe59a7cdf245f1bf02e5ac9fe770f6 | CCNCCN(CC)CC.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCN(CC)C(=O)NCCS(=O)(=O)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)CCN.C(=O)(N1C=NC=C1)N1C=NC=C1.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)N(CCNCC)CC>>C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)N(CCN(C(=O)NCCS(=O)(=O)C1=CC=CC=C1)CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][CH2:9][CH3:10].[NH2:13][CH2:14][CH2:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.c1cn([C:11](n2ccnc2)=[O:12])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]([CH2:9][CH3:10])[C:11](=[O:12])[NH:13][CH2:14][CH2:15][S:16](=[O:17])... | CCNCCN(CC)CC.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCN(CC)C(=O)NCCS(=O)(=O)c1ccccc1 | null | null | CCOCC.CO.O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C;D1;H3:8].[O;D1;H0:9]=[C;H0;D3;+0:10](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C;D1;H3:8] | 52 | [{"value": 52.0, "product": "C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)N(CCN(C(=O)NCCS(=O)(=O)C1=CC=CC=C1)CC)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5.55 g (0.030 mole) of 2-(phenylsulfonyl)ethanamine and 5.35 g (0.033 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 4.62 g (0.032 mole) of N,N,N'-triethylethylenediamine in 50 ml of tetrahydrofuran was added, and the mixture was refl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | CCOCC.CO.O1CCCC1 | null | null | CCNCCN(CC)CC.NCCS(=O)(=O)c1ccccc1.O=C(n1ccnc1)n1ccnc1>CCOCC.CO.O1CCCC1>CCN(CC)CCN(CC)C(=O)NCCS(=O)(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d4c4a71d951f42169d6ac22f3b988c3e | CCN(CC)CCN.COc1ccc(S(=O)(=O)CCNC(C)C)cc1.O=C(n1ccnc1)n1ccnc1>>CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccc(OC)cc1)C(C)C | COC1=CC=C(C=C1)S(=O)(=O)CCNC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CCN)CC>>C(C)N(CCNC(N(C(C)C)CCS(=O)(=O)C1=CC=C(C=C1)OC)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].[NH:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1)[CH:25]([CH3:26])[CH3:27].c1cn([C:9](n2ccnc2)=[O:10])cn1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][S:14]... | CCN(CC)CCN.COc1ccc(S(=O)(=O)CCNC(C)C)cc1.O=C(n1ccnc1)n1ccnc1 | CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccc(OC)cc1)C(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:3]-[C:2]-[C:1] | 67.3 | [{"value": 67.3, "product": "C(C)N(CCNC(N(C(C)C)CCS(=O)(=O)C1=CC=C(C=C1)OC)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "C(C)N(CCNC(N(C(C)C)CCS(=O)(=O)C1=CC=C(C=C1)OC)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4.54 g (0.28 mole) of 1,1'-carbonyldiimidazole and 2.90 g (0.025 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.89 g (0.0229 mole) of N-[2-[(4-methoxyphenyl)sulfonyl]ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1 | Other | O1CCCC1 | null | null | CCN(CC)CCN.COc1ccc(S(=O)(=O)CCNC(C)C)cc1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCN(CC)CCNC(=O)N(CCS(=O)(=O)c1ccc(OC)cc1)C(C)C |
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