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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bc960501e1624bcb928fa29cddc47230 | c1ccc(-c2ncc[nH]2)cc1>>c1c[nH]c(C2CCCCC2)n1 | C1(=CC=CC=C1)C=1NC=CN1>>C1(CCCCC1)C=1NC=CN1 | [cH:1]1[cH:2][nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11]1>>[cH:1]1[cH:2][nH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]1 | c1ccc(-c2ncc[nH]2)cc1 | c1c[nH]c(C2CCCCC2)n1 | null | [Rh] | Cl | Reduction | Arene hydrogenation | cfd1f3b98f7cd3ca3735c14f302dc0acdc6f0d4501cd6920cbb5c1a3d892ff3a | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1c[nH]c(C2CCCCC2)n1 | [#7;a:1]1:[c:2]:[c:3]:[#7;a:4]:[c;H0;D3;+0:5]:1-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[#7;a:1]1:[c:2]:[c:3]:[#7;a:4]:[c;H0;D3;+0:5]:1-[CH;D3;+0:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | 24 | HOUR | To a solution of 6.8 g of 2-phenylimidazole in 200 mL 3N hydrochloric acid was added 5% Rhodium on Carbon, Degussa type G10 NB/W. The mixture was hydrogenated at 100 psi for 24 hours then filtered through celite. The solution was neutralized with sodium hydroxide and extracted with 2×100 mL ethyl acemic. The combined e... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | C1CCCCC1 | c1c[nH]cn1.C1CCCCC1 | null | [Rh].Cl | null | 24 | c1ccc(-c2ncc[nH]2)cc1>[Rh].Cl>c1c[nH]c(C2CCCCC2)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b7ba1733d6014d78b0f33cc6ae18abd4 | C[Si](C)(C)[N-][Si](C)(C)C.Cc1ccc(C#N)cc1>>Cc1ccc(C(=N)N)cc1 | Cl.C1(=CC=C(C=C1)C#N)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>Cl.CC1=CC=C(C(=N)N)C=C1 | C[Si](C)(C)[N-:8][Si](C)(C)C.[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[cH:9][cH:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[NH:7])[NH2:8])[cH:9][cH:10]1 | C[Si](C)(C)[N-][Si](C)(C)C.Cc1ccc(C#N)cc1 | Cc1ccc(C(=N)N)cc1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 9cbdc9ae20ed5aba7a68cb6b7c171a3ae63df4a7429ffed664868f4249cdb990 | 04b1bd993fe152cf3b08f7671459ffc927738e9d35fd2be50e01d1884b692a62 | c1ccccc1 | C-[Si](-C)(-C)-[N-;H0;D2:1]-[Si](-C)(-C)-C.[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:1]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 12.4 g p-tolunitrile in 500 mL of diethyl ether was added 23 g of solid lithium bis(trimethylsilyl)amide at ambient temperature. The mixture was stirred for 2 hours then hydrolysed-with 10% HCl at 0° C. The mixture was stirred for an additional 30 minutes and then concentrated to dryness to yield 6 g o... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Silyl protective group.Silyl protective group | Primary amine | null | null | c1ccccc1 | Other | C(C)OCC | null | 2 | C[Si](C)(C)[N-][Si](C)(C)C.Cc1ccc(C#N)cc1>C(C)OCC>Cc1ccc(C(=N)N)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4d92bb7ce9ba467782396d6e4ffdbd38 | CC(=O)C(O)O.Cc1ccc(C(=N)N)cc1>>Cc1ccc(-c2ncc(CO)[nH]2)cc1 | Cl.CC1=CC=C(C(=N)N)C=C1.OC(C(C)=O)O.[Cl-].[NH4+]>>CC1=CC=C(C=C1)C=1NC(=CN1)CO | O=[C:9]([CH3:8])[CH:10](O)[OH:11].[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[NH:7])[NH2:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH2:10][OH:11])[nH:12]2)[cH:13][cH:14]1 | CC(=O)C(O)O.Cc1ccc(C(=N)N)cc1 | Cc1ccc(-c2ncc(CO)[nH]2)cc1 | null | null | [OH-].[NH4+] | Aromatic Heterocycle Formation | OtherReaction | 9afeb59639ae2e2be5ab48b8076c2f4833c8b68f055c287f8fb94fe25d3d85b3 | 7683277447c6e8e8dc2d7b97bbda962a2e4dec4e791f3317e15a279aa7742d94 | c1ccc(-c2ncc[nH]2)cc1 | O-[CH;D3;+0:1](-[O;D1;H1:2])-[C;H0;D3;+0:3](=O)-[CH3;D1;+0:4].[NH2;D1;+0:5]-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[n;H0;D2;+0:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[nH;D2;+0:5]:1 | null | [] | 90 | CELSIUS | null | null | A solution of 4 g 4-methylbenzamidine hydrochloride in 60 mL ammonium hydroxide was treated with 4.0 g with dihydroxyacetone and 4.8 g ammonium chloride. The reaction mixture was heated to 90° C. for 4 hours in a sealed tube. On cooling to room temperature a the solid formed was collected by filtration to yield 3.0 g 2... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Secondary alcohol.Primary amine | Primary alcohol | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HO- | [OH-].[NH4+] | 90 | null | CC(=O)C(O)O.Cc1ccc(C(=N)N)cc1>[OH-].[NH4+]>Cc1ccc(-c2ncc(CO)[nH]2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-241a025a74b74c95954f4b92c7aec5c8 | N=C(N)c1ccccc1.O=C1CCCCC1O>>c1ccc(-c2nc3c([nH]2)CCCC3)cc1 | Cl.C(C1=CC=CC=C1)(=N)N.OC1C(CCCC1)=O>>C1(=CC=CC=C1)C=1NC2=C(N1)CCCC2 | [cH:1]1[cH:2][cH:3][c:4]([C:5](=[NH:6])[NH2:9])[cH:14][cH:15]1.O=[C:7]1[CH:8](O)[CH2:10][CH2:11][CH2:12][CH2:13]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][c:7]3[c:8]([nH:9]2)[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15]1 | N=C(N)c1ccccc1.O=C1CCCCC1O | c1ccc(-c2nc3c([nH]2)CCCC3)cc1 | null | null | [OH-].[NH4+] | Aromatic Heterocycle Formation | OtherReaction | 5b4e904d6d6c8a0f0f9c92c112cc2d2feff33ecd0430f69f446cd8e83459f01c | 38e78b827f0d303fff8f01947195dfa26d7f4e7432ebab4deea8fb630c8f9d03 | c1ccc(-c2nc3c([nH]2)CCCC3)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=O.[NH2;D1;+0:7]-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:6]2:[c;H0;D3;+0:1](:[nH;D2;+0:7]:1)-[C:2]-[C:3]-[C:4]-[C:5]-2):[c:13]:[c:14] | 37.6 | [{"value": 37.6, "product": "C1(=CC=CC=C1)C=1NC2=C(N1)CCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 6.3 g benzamidine hydrochloride in 60 mL ammonium hydroxide was added 4.6 g 2-hydroxycyclohexanone. The reaction mixture was heated to 90° C. for 7 hours in a sealed tube. On cooling to room temperature the crystals formed were collected by filtration and after drying yielded 3.0g 2-phenyl-4,5,6,7,-tet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Primary amine | null | C1CCCCC1 | c1nc2c([nH]1)CCCC2 | c1ccccc1.c1nc2c([nH]1)CCCC2 | HO- | [OH-].[NH4+] | 90 | null | N=C(N)c1ccccc1.O=C1CCCCC1O>[OH-].[NH4+]>c1ccc(-c2nc3c([nH]2)CCCC3)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c2ab04057e384a29b4ea1557514d2d18 | C[C@@H]1CNC[C@H](C)N1.Clc1ncccn1>>C[C@@H]1CNC[C@H](C)N1c1ncccn1 | ClC1=NC=CC=N1.C[C@@H]1N[C@@H](CNC1)C>>C[C@@H]1N([C@@H](CNC1)C)C1=NC=CC=N1 | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]([CH3:7])[NH:8]1.Cl[c:9]1[n:10][cH:11][cH:12][cH:13][n:14]1>>[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]([CH3:7])[N:8]1[c:9]1[n:10][cH:11][cH:12][cH:13][n:14]1 | C[C@@H]1CNC[C@H](C)N1.Clc1ncccn1 | C[C@@H]1CNC[C@H](C)N1c1ncccn1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11](-[C;D1;H3:12])-[N;H0;D3;+0:13]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 820 mg 2-chloropyrimidine and 1.6 g cis-2,6-dimethylpiperazine in 25 mL toluene was heated at reflux temperature for 12 hours. The solvent was evaporated, the residue was basified with 5% sodium hydroxide and extracted with 2×100mL of dichloromethane. The combined organic extracts were dried over anhydrou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | C1C[NH]CCN1.c1cncnc1 | C1C[NH]CCN1.c1cncnc1 | HCl | C1(=CC=CC=C1)C | null | null | C[C@@H]1CNC[C@H](C)N1.Clc1ncccn1>C1(=CC=CC=C1)C>C[C@@H]1CNC[C@H](C)N1c1ncccn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c80d3a6831954721808c18449d23b436 | C1CCC(NC2CCCCC2)CC1.O=C(Cl)CCCCC1CCCCC1>>C1CCC([NH2+]C2CCCCC2)CC1.[Cl-] | N1CCC(CC1)C=1N=CNC1.C1(CCCCC1)NC1CCCCC1.C1(CCCCC1)CCCCC(=O)Cl>>[Cl-].C1(CCCCC1)[NH2+]C1CCCCC1 | [CH2:1]1[CH2:2][CH2:3][CH:4]([NH:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH2:13]1.O=C(CCCCC1CCCCC1)[Cl:14]>>[CH2:1]1[CH2:2][CH2:3][CH:4]([NH2+:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH2:13]1.[Cl-:14] | C1CCC(NC2CCCCC2)CC1.O=C(Cl)CCCCC1CCCCC1 | C1CCC([NH2+]C2CCCCC2)CC1.[Cl-] | null | null | ClCCl.C(C)#N | Miscellaneous | OtherReaction | 859e3bb515bd18081fb45cc9a10812dee4e194dcf8ad9f803e40c066a14f9d77 | b9e33d1fd31dac290741b2a8bb1407015322a636c824a33ea58c5cebbb326224 | C1CCC([NH2+]C2CCCCC2)CC1 | O=C(-[Cl;H0;D1;+0:1])-C-C-C-C-C1-C-C-C-C-C-1.[C:2]-[C:3](-[NH;D2;+0:4]-[C:5](-[C:6])-[C:7])-[C:8]>>[C:2]-[C:3](-[NH2+;D2:4]-[C:5](-[C:6])-[C:7])-[C:8].[Cl-;H0;D0:1] | 68 | [{"value": 68.0, "product": "[Cl-].C1(CCCCC1)[NH2+]C1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of 755 mg (5.00 mmol) 4-(4-piperidyl)-1-H-imidazole and 942 mg (5.20 mmol) of dicyclohexylamine in 10 ml anhydrous acetonitrile at 25° C. was slowly added 1.06 g (5.20 mmol) cyclohexanevaleroyl chloride in 2 ml of dichloromethane over a period of 10 min with stirring; then the reaction mixture was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | null | C1CCCCC1 | null | C1CCCCC1.C1CCCCC1 | HO- | ClCCl.C(C)#N | 60 | null | C1CCC(NC2CCCCC2)CC1.O=C(Cl)CCCCC1CCCCC1>ClCCl.C(C)#N>C1CCC([NH2+]C2CCCCC2)CC1.[Cl-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-66ff7f10eb6a48de846e496529f46089 | CS(=O)c1ccccc1C(N)=O>>O=c1[nH]sc2ccccc12 | I(=O)(=O)(=O)O.CS(=O)C1=C(C(=O)N)C=CC=C1.S(=O)(Cl)Cl>>S1NC(C2=C1C=CC=C2)=O | C[S:4](=O)[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:2](=[O:1])[NH2:3]>>[O:1]=[c:2]1[nH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | CS(=O)c1ccccc1C(N)=O | O=c1[nH]sc2ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ac8008ffaf0746a7c379858d329a50385e03cd81133d76cd303c0506482cefe1 | b08207f6d99f9cbf9fc5e88a29231cec7dc9821b769142656322918453c1b9fc | O=c1[nH]sc2ccccc12 | C-[S;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[s;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | null | [] | null | null | null | null | In this method, 2-(methylthio)benzamide is produced from 2-(methylthio)benzoyl chloride; oxidized with periodic acid to 2-(methylsulfinyl)benzamide; and cyclized in the presence of thionyl chloride to yield a 1,2-benzisothiazol-3-one. ##STR1## (B) Org. Prep. Proced. Int., 15, 315-319(1983)
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Sulfoxide | null | c1ccccc1 | c1nsc2ccccc12 | c1nsc2ccccc12 | HO- | null | null | null | CS(=O)c1ccccc1C(N)=O>>O=c1[nH]sc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8e36c12d6bee48f7b869e675e19ea709 | CSc1ccccc1C=NO.O=S(=O)(Cl)Cl>>O=c1[nH]sc2ccccc12 | S(=O)(=O)(Cl)Cl.CSC1=C(C=NO)C=CC=C1.CSC1=C(C=NO)C=CC=C1.ClCl>>S1NC(C2=C1C=CC=C2)=O | C[S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:2]=[N:3]O.O=S(Cl)(Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | CSc1ccccc1C=NO.O=S(=O)(Cl)Cl | O=c1[nH]sc2ccccc12 | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 20b908e6a61eb73cb90fa20cc56305c2220c1f4dc29fc540907f3405dcc5d195 | 43242875d798d7c58c444d4bc73d375bf28b097946916be399c5389bd7bc8c53 | O=c1[nH]sc2ccccc12 | C-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH;D2;+0:5]=[N;H0;D2;+0:6]-O):[c:7].Cl-S(-Cl)(=O)=[O;H0;D1;+0:8]>>[O;H0;D1;+0:8]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[s;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:7] | 91.1 | [{"value": 91.1, "product": "S1NC(C2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | From the monochlorobenzene layer obtained by the same procedures as in Example 1, 2-(methylthio)benzaldehyde oxime was isolated in the same manner as in Example 2. 39.7 g of the oxime isolated was dissolved in 150 g of monochlorobenzene. Then, the oxime was cyclized in the same manner as in Example 1 except that chlori... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Oxime | null | c1ccccc1 | c1nsc2ccccc12 | c1nsc2ccccc12 | HCl | ClC1=CC=CC=C1 | null | null | CSc1ccccc1C=NO.O=S(=O)(Cl)Cl>ClC1=CC=CC=C1>O=c1[nH]sc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec3883f08a9549f0b176e5b6eb825c8b | CSc1ccccc1C#N.O=S(=O)(Cl)Cl>>O=c1[nH]sc2ccccc12 | S(=O)(=O)(Cl)Cl.CSC1=C(C#N)C=CC=C1.O>>S1NC(C2=C1C=CC=C2)=O | C[S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:2]#[N:3].O=S(Cl)(Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | CSc1ccccc1C#N.O=S(=O)(Cl)Cl | O=c1[nH]sc2ccccc12 | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 956261d5e76c6da2b388498c3fe171bfa3765ab413a81ed43a54fceb1870492b | 8ddbbfecda7508b691f70905b5d5c8f5ddcc193b4d838addc69cac235e5acf9f | O=c1[nH]sc2ccccc12 | C-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7].Cl-S(-Cl)(=O)=[O;H0;D1;+0:8]>>[O;H0;D1;+0:8]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[s;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:7] | 95.9 | [{"value": 95.9, "product": "S1NC(C2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 500 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 29.8 g (0.2 mol) of 2-(methylthio)benzonitrile, 100 g of monochlorobenzene, and 4.32 g (0.24 mol) of water were added. To the flask, 29.7 g (0.22 mol) of sulfuryl chloride was added with stirring at a temperature of from 5° to 15° C.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Monosulfide | null | c1ccccc1 | c1nsc2ccccc12 | c1nsc2ccccc12 | HCl | ClC1=CC=CC=C1 | null | null | CSc1ccccc1C#N.O=S(=O)(Cl)Cl>ClC1=CC=CC=C1>O=c1[nH]sc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a71703d6b6b4447d8aef3942b26b3745 | Clc1ccccc1-n1nnnc1Cl.[OH-]>>O=c1nn[nH]n1-c1ccccc1Cl | [OH-].[Na+].ClC1=C(C=CC=C1)N1N=NN=C1Cl>>C1=CC=C(C(=C1)N2C(=O)N=NN2)Cl | Cl[c:2]1[n:3][n:4][n:5][n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Cl:13].[OH-:1]>>[O:1]=[c:2]1[n:3][n:4][nH:5][n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Cl:13] | Clc1ccccc1-n1nnnc1Cl.[OH-] | O=c1nn[nH]n1-c1ccccc1Cl | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | d09f5b0107ac39cb0a8287d5f2f13de743c0ee63864e899f8299b633d0131f45 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=c1nn[nH]n1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[n;H0;D2;+0:4]:[#7;a:5]:1-[c:6].[OH-;D0:7]>>[O;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[nH;D2;+0:4]:[#7;a:5]:1-[c:6] | 96 | [{"value": 96.0, "product": "C1=CC=C(C(=C1)N2C(=O)N=NN2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C1=CC=C(C(=C1)N2C(=O)N=NN2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A solution of sodium hydroxide (13 g, about 45% by weight) in water, 1-(2-chloro-phenyl)-5-chlorotetrazole (12.9 g) in water (6.5 ml) were mixed and the mixture was heated to 110° C. The reaction was initiated and the temperature increased to 115° C. After 3 minutes from the initiation of the reaction, the temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1nnn[nH]1 | c1nnn[nH]1 | c1nnn[nH]1.c1ccccc1 | Other | O | 110 | null | Clc1ccccc1-n1nnnc1Cl.[OH-]>O>O=c1nn[nH]n1-c1ccccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-836e3f9d0818470090395e9e815e5fd8 | [C-]#[N+]c1ccccc1Cl.[N-]=[N+]=[N-].[OH-]>>O=c1nn[nH]n1-c1ccccc1Cl | [N-]=[N+]=[N-].[Na+].ClC1=C(C=CC=C1)[N+]#[C-].[OH-].[Na+]>>C1=CC=C(C(=C1)N2C(=O)N=NN2)Cl | [C-:2]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Cl:13].[N-:3]=[N+:4]=[N-:5].[OH-:1]>>[O:1]=[c:2]1[n:3][n:4][nH:5][n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Cl:13] | [C-]#[N+]c1ccccc1Cl.[N-]=[N+]=[N-].[OH-] | O=c1nn[nH]n1-c1ccccc1Cl | null | null | O.CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | a9e25b88e3e544b40930c84f8e1c2b6ba2612a468a663c83477359fabb2a779d | dd2f0d2528fe1559d0858d6d01b272efcd2c4c4bdbd367a6de3dc4d3ab737fb7 | O=c1nn[nH]n1-c1ccccc1 | [C-;H0;D1:1]#[N+;H0;D2:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[Cl;D1;H0:7]):[c:8].[N-;H0;D1:9]=[N+;H0;D2:10]=[N-;H0;D1:11].[OH-;D0:12]>>[Cl;D1;H0:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[n;H0;D3;+0:2]1:[nH;D2;+0:11]:[n;H0;D2;+0:10]:[n;H0;D2;+0:9]:[c;H0;D3;+0:1]:1=[O;H0;D1;+0:12]):[c:4]:[c:5] | 94 | [{"value": 94.0, "product": "C1=CC=C(C(=C1)N2C(=O)N=NN2)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To sodium azide (0.65 g) dissolved in water (3.5 ml) a solution of 2-chlorophenylisocyanide, dichloride (2.09 g) in acetone (8 ml) was added with stirring. The mixture was heated to 50° C. and stirred for 15 minutes while maintaining this temperature. Thereafter, the mixture was heated for further 30 minutes with reflu... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanide | null | null | c1nnn[nH]1 | c1nnn[nH]1.c1ccccc1 | null | O.CC(=O)C | 50 | null | [C-]#[N+]c1ccccc1Cl.[N-]=[N+]=[N-].[OH-]>O.CC(=O)C>O=c1nn[nH]n1-c1ccccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-86064e2200354d298149ffa2dbc03c8b | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1>>C=C(Cn1cncn1)c1ccc(F)cc1F | BrCC(C)(C1=C(C=C(C=C1)F)F)Br.N1N=CN=C1.O>>N1(N=CN=C1)CC(=C)C1=C(C=C(C=C1)F)F | Br[C:2]([CH3:1])([CH2:3]Br)[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16].[nH:4]1[cH:5][n:6][cH:7][n:8]1>>[CH2:1]=[C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16] | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1 | C=C(Cn1cncn1)c1ccc(F)cc1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 92db0b3b53885d3223b3f2bf1332a7fd2c0d036f6e16add08a47f1d0b666b611 | d27bae16fd67f5a47665f4687fc7fd3e21fa9734d3d526df3f73a82117ac3097 | C=C(Cn1cncn1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-Br)(-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6].[#7;a:7]1:[c:8]:[nH;D2;+0:9]:[#7;a:10]:[c:11]:1>>[CH2;D1;+0:3]=[C;H0;D3;+0:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[#7;a:7]:[c:8]:1)-[c:4](:[c:5]):[c:6] | 30 | [{"value": 30.0, "product": "N1(N=CN=C1)CC(=C)C1=C(C=C(C=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.9, "product": "N1(N=CN=C1)CC(=C)C1=C(C=C(C=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5 g (15.9 mmol) of 1,2-dibromo-2-(2,4-difluorophenyl) propane VIII and 3.3 g (48 mmol) of 1,2,4-triazole in DMF was refluxed for 15 hours. The reaction mixture was cooled down to room temperature, water (40 mL) was added and product was extracted with EtOAc (2×50 mL). The EtOAc phase was washed with water and dried (Na... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary halide | Vinyl | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1 | HBr | CN(C)C=O | null | null | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1>CN(C)C=O>C=C(Cn1cncn1)c1ccc(F)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4b7523b1bc6a47c699de0359598fc906 | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1>>OCC(O)CN1C=NCN1c1ccc(F)cc1F | C(=O)([O-])[O-].[K+].[K+].BrC(CBr)(C)C1=C(C=C(C=C1)F)F.C(C)#N.[O-][Mn](=O)(=O)=O.[K+].N1N=CN=C1>>FC1=C(C=CC(=C1)F)N1N(C=NC1)CC(CO)O | Br[C:3]([CH3:2])([CH2:5]Br)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[F:18].[n:6]1[cH:7][n:8][cH:9][nH:10]1>>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][N:6]1[CH:7]=[N:8][CH2:9][N:10]1[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[F:18] | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1 | OCC(O)CN1C=NCN1c1ccc(F)cc1F | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4dd04bb5990166fc8706ee4af7931f8c63cd8c801b5492652472ff7b0c028a45 | a0aa76a953e6cca9cdb5384ddc87a120b25293091bc7d4f18a4ae8feed8119ad | C1=NCN(c2ccccc2)N1 | Br-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-Br)(-[CH3;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[cH;D2;+0:10]1:[n;H0;D2;+0:11]:[nH;D2;+0:12]:[cH;D2;+0:13]:[n;H0;D2;+0:14]:1>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[N;H0;D3;+0:12]1-[CH2;D2;+0:13]-[N;H0;D2;+0:14]=[CH;D2;+0:10]-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1... | 27 | [{"value": 27.0, "product": "FC1=C(C=CC(=C1)F)N1N(C=NC1)CC(CO)O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | 2-Bromo-2-(2,4-difluorophenyl)-1-bromopropane (3) (20.0 g, 63.7 mmol) was dissolved in acetonitrile (300 mL) at 20° C. and K2CO3 (17.6g, 127 mmol) was added in one portion with efficient stirring. The reaction mixture was heated to reflux for 11 hours and then cooled to 20° C. 1,2,4-Triazole (8.80 g, 127 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary halide | Hydrazine.Primary alcohol.Secondary alcohol | c1ccccc1.c1nc[nH]n1 | C1=NC[NH][NH]1.c1ccccc1 | C1=NC[NH][NH]1.c1ccccc1 | null | O | 20 | null | CC(Br)(CBr)c1ccc(F)cc1F.c1nc[nH]n1>O>OCC(O)CN1C=NCN1c1ccc(F)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-553c1de6521b4135bb3b5f05a2676673 | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1>>O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCc1ccccc1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].COC(C=1C(NC(CSCCCC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O>>ClC1=CC=C2C(=C(C(NC2=C1)=O)SCCCC1=CC=CC=C1)O | CO[C:11]([c:10]1[c:4]([NH:3][C:2](=[O:1])[CH2:13][S:14][CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:5][c:6]([Cl:7])[cH:8][cH:9]1)=[O:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]2[c:11]([OH:12])[c:13]1[S:14][CH2:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23... | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1 | O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCc1ccccc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a80509f1be2044db00bda28bf58d1929a6ec6cfc2594830aac457dceae07050f | 45512051a04a30c77fe95d59a24998d79363e30b8624aca147f6fb45668b9ecf | O=c1[nH]c2ccccc2cc1SCCCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10]-[C:11]):[c:12]>>[C:11]-[#16:10]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:12]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | null | [] | null | null | 2 | HOUR | 2 g (5.3 mmol) of 4-chloro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0°. A 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide is added dropwise thereto. The mixture is then stirred for 20 minutes at 0° and for 2 hours at room temperature. The re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Monosulfide | Aromatic alcohol.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 2 | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1>O1CCCC1>O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b65637eaee214615974c0cc5a630c36a | CCOC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CBr.SCCCc1ccccc1>>CC(=O)[O-].COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1 | C1=CC=C(C=C1)CCCS.[H-].[Na+].COC(C=1C(NC(CBr)=O)=CC(=CC1)Cl)=O.C(C)(=O)OCC>>C(C)(=O)[O-].COC(C=1C(NC(CSCCCC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O | CC[O:4][C:2]([CH3:1])=[O:3].Br[CH2:19][C:17]([NH:16][c:15]1[c:9]([C:7]([O:6][CH3:5])=[O:8])[cH:10][cH:11][c:12]([Cl:13])[cH:14]1)=[O:18].[SH:20][CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][C:2](=[O:3])[O-:4].[CH3:5][O:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[NH:16... | CCOC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CBr.SCCCc1ccccc1 | CC(=O)[O-].COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1 | null | null | O1CCCC1 | Protection | OtherReaction | d92f220259a177cb2d3b558f2fbfe4e50edf1e3e434bce398186fce734ebc71b | dec6558c097c4e4e1a57653f54e1c65392b57cfa2ea0f80857d517d1ae5cdc3b | O=C(CSCCCc1ccccc1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].C-C-[O;H0;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[C:10]-[C:11]-[SH;D1;+0:12]>>[C;D1;H3:8]-[C:7](-[O-;H0;D1:6])=[O;D1;H0:9].[C:10]-[C:11]-[S;H0;D2;+0:12]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | null | [] | null | null | 30 | MINUTE | 4.3 g (28.7 mmol) of 3-phenylpropylthiol are added dropwise at 0° to a mixture of 1.4 g (31.6 mmol) of sodium hydride dispersion in oil (55%) and 30 ml of tetrahydrofuran. The mixture is then stirred for 30 minutes at 0°. A solution of 4-chloro-N-(bromoacetyl)-anthranilic acid methyl ester in 30 ml of tetrahydrofuran i... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | 0.5 | CCOC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CBr.SCCCc1ccccc1>O1CCCC1>CC(=O)[O-].COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f0092dd1c9064d60bb8e8f2d74dc4e96 | COC(=O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O>>O=C(O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O | ClC1=CC=C2C(=C(C(NC2=C1)=O)SCC(=O)OC)O.Cl>>ClC1=CC=C2C(=C(C(NC2=C1)=O)SCC(=O)O)O | C[O:3][C:2](=[O:1])[CH2:4][S:5][c:6]1[c:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[nH:16][c:17]1=[O:18]>>[O:1]=[C:2]([OH:3])[CH2:4][S:5][c:6]1[c:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[nH:16][c:17]1=[O:18] | COC(=O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O | O=C(O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | The 7-chloro-4-hydroxy-3-(methoxycarbonylmethylthio)-2(1H)-quinolone obtained in accordance with Example 7 is dissolved in 2N sodium hydroxide solution and left to stand for 2 hours at room temperature. The reaction mixture is adjusted to pH 2 with 4N hydrochloric acid and the resulting suspension is filtered. The colo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2ccccc2c1 | Other | [OH-].[Na+] | null | 2 | COC(=O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O>[OH-].[Na+]>O=C(O)CSc1c(O)c2ccc(Cl)cc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c74e80b8099436f9d73ec980f6d944a | COC(=O)CSCC(=O)Cl.COC(=O)c1ccc(Cl)cc1N>>COC(=O)CSCC(=O)Nc1cc(Cl)ccc1C(=O)OC | COC(C=1C(N)=CC(=CC1)Cl)=O.COC(CSCC(=O)Cl)=O.C(C)N(CC)CC>>COC(C=1C(NC(CSCC(=O)OC)=O)=CC(=CC1)Cl)=O | Cl[C:8]([CH2:7][S:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:9].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[C:18](=[O:19])[O:20][CH3:21]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][S:6][CH2:7][C:8](=[O:9])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[C:18](=[O:19])[O:20][CH3:21] | COC(=O)CSCC(=O)Cl.COC(=O)c1ccc(Cl)cc1N | COC(=O)CSCC(=O)Nc1cc(Cl)ccc1C(=O)OC | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:6](-[#8:5])=[O;D1;H0:7] | null | [] | null | null | 3 | HOUR | 21.24 g (0.114 mol) of 4-chloroanthranilic acid methyl ester and 19.1 ml (0.137 mol) of triethylamine are placed in 180 ml of methylene chloride at 0°. A solution of 20.9 g (0.114 mol) of 2-(chloroformylmethylthio)-acetic acid methyl ester (T. Terasawa and T. Okada, J. Org. Chem., 42, 1163 (1977)) in 20 ml of methylene... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 3 | COC(=O)CSCC(=O)Cl.COC(=O)c1ccc(Cl)cc1N>C(Cl)Cl>COC(=O)CSCC(=O)Nc1cc(Cl)ccc1C(=O)OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1d1ccd59bf5a48d8990196a9d96b64c4 | COC(=O)CCCSCC(=O)Nc1cc(Cl)ccc1C(=O)OC>>COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O | COC(C=1C(NC(CSCCCC(=O)OC)=O)=CC(=CC1)Cl)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=CC=C2C(=C(C(NC2=C1)=O)SCCCC(=O)OC)O | CO[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]1[NH:19][C:20]([CH2:9][S:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][S:8][c:9]1[c:10]([OH:11])[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[nH:19][c:20]1=[O:21] | COC(=O)CCCSCC(=O)Nc1cc(Cl)ccc1C(=O)OC | COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a80509f1be2044db00bda28bf58d1929a6ec6cfc2594830aac457dceae07050f | 45512051a04a30c77fe95d59a24998d79363e30b8624aca147f6fb45668b9ecf | O=c1ccc2ccccc2[nH]1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10]-[C:11]):[c:12]>>[C:11]-[#16:10]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:12]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | null | [] | null | null | 30 | MINUTE | 2.0 g (5.6 mmol) of 4-chloro-N-(3-methoxycarbonylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0° , and 16.8 ml of a 1M solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 30 minutes at 0° and the reaction mixture Is then pou... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Monosulfide | Aromatic alcohol.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1 | HO- | O1CCCC1 | null | 0.5 | COC(=O)CCCSCC(=O)Nc1cc(Cl)ccc1C(=O)OC>O1CCCC1>COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6b159afa024e4b35a38eb10ab811eab4 | COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O>>O=C(O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O | ClC1=CC=C2C(=C(C(NC2=C1)=O)SCCCC(=O)OC)O.Cl>>C(=O)(O)CCCSC=1C(NC2=CC(=CC=C2C1O)Cl)=O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][S:7][c:8]1[c:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[nH:18][c:19]1=[O:20]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][S:7][c:8]1[c:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[nH:18][c:19]1=[O:20] | COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O | O=C(O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | 895 mg (2.73 mmol) of 7-chloro-4-hydroxy-3-(3-methoxycarbonylpropylthio)-2(1H)-quinolone are dissolved in 10 ml of 2N sodium hydroxide solution and the resulting solution is stirred for one hour at room temperature. The reaction mixture is adjusted to pH 2 with concentrated hydrochloric acid and the resulting white sus... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2ccccc2c1 | Other | [OH-].[Na+] | null | 1 | COC(=O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O>[OH-].[Na+]>O=C(O)CCCSc1c(O)c2ccc(Cl)cc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cfcefff489c14c4f9d86aae323fb0601 | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCCc1ccccc1>>O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCCc1ccccc1 | COC(C=1C(NC(CSCCCCC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=CC=C2C(=C(C(NC2=C1)=O)SCCCCC1=CC=CC=C1)O | CO[C:11]([c:10]1[c:4]([NH:3][C:2](=[O:1])[CH2:13][S:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:5][c:6]([Cl:7])[cH:8][cH:9]1)=[O:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]2[c:11]([OH:12])[c:13]1[S:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:... | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCCc1ccccc1 | O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCCc1ccccc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a80509f1be2044db00bda28bf58d1929a6ec6cfc2594830aac457dceae07050f | 45512051a04a30c77fe95d59a24998d79363e30b8624aca147f6fb45668b9ecf | O=c1[nH]c2ccccc2cc1SCCCCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10]-[C:11]):[c:12]>>[C:11]-[#16:10]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:12]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | null | [] | null | null | 30 | MINUTE | 6.3 g (16.12 mmol) of 4-chloro-N-(4-phenylbutylthio)acetyl-anthranilic acid methyl ester are placed in 60 ml of tetrahydrofuran at 0°, and 48.3 ml of a 1-molar solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 30 minutes at room temperature. The reaction mixture is p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Monosulfide | Aromatic alcohol.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | COC(=O)c1ccc(Cl)cc1NC(=O)CSCCCCc1ccccc1>O1CCCC1>O=c1[nH]c2cc(Cl)ccc2c(O)c1SCCCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-54b0cf48149a479facc2b574676e1020 | COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1>>O=c1[nH]c2cc(Cl)ccc2c(O)c1S(=O)Cc1ccccc1 | O.COC(C=1C(NC(CS(=O)CC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O.[H-].[Na+].Cl>>ClC1=CC=C2C(=C(C(NC2=C1)=O)S(=O)CC1=CC=CC=C1)O | CO[C:11]([c:10]1[c:4]([NH:3][C:2](=[O:1])[CH2:13][S:14](=[O:15])[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:5][c:6]([Cl:7])[cH:8][cH:9]1)=[O:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]2[c:11]([OH:12])[c:13]1[S:14](=[O:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1 | O=c1[nH]c2cc(Cl)ccc2c(O)c1S(=O)Cc1ccccc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 78ae63408e600ec3d0a96f7bbee64543b4332521927c79c8fd2564a165576b91 | b166fd4787c3630128d6d94c10252087a6024124cd3c82ee40676dbbf7ecd553 | O=c1[nH]c2ccccc2cc1S(=O)Cc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10](-[C:11])=[O;D1;H0:12]):[c:13]>>[C:11]-[#16:10](=[O;D1;H0:12])-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:13]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | null | [] | null | null | 2 | HOUR | 1.0 g (2.73 mmol) of N-(benzylsulfinyl)acetyl-4-chloro-anthranilic acid methyl ester is placed in 10 ml of tetrahydrofuran at 0°, and 0.13 g (3 mmol) of sodium hydride dispersion in oil (55%) is added thereto. The mixture is then stirred for 15 minutes at 0° and for 2 hours at room temperature. Water is added and the r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Aromatic alcohol | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 2 | COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1>O1CCCC1>O=c1[nH]c2cc(Cl)ccc2c(O)c1S(=O)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-50a5ddf043b5465db6af6da3b8246254 | CC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CSCc1ccccc1>>COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1 | COC(C=1C(NC(CSCC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O.I(=O)(=O)(=O)[O-].[Na+].CC(=O)C>>COC(C=1C(NC(CS(=O)CC2=CC=CC=C2)=O)=CC(=CC1)Cl)=O | CC(C)=[O:17].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[NH:12][C:13](=[O:14])[CH2:15][S:16][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[NH:12][C:13](=[O:14])[CH2:15][S:16](=[O:17])[CH2:18][c:19]1[cH:20][cH:21][cH:... | CC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CSCc1ccccc1 | COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1 | null | null | O | Oxidation | OtherReaction | f0ee576d888dd79d4e216efb91dda7661b2708fce757b8db37aa54905eb1598d | a91229c7aa0fa96207a18852598e8a8b3767ca197262df789b314b09b4adddb0 | O=C(CS(=O)Cc1ccccc1)Nc1ccccc1 | C-C(-C)=[O;H0;D1;+0:1].[O;D1;H0:2]=[C:3](-[#7:4]-[c:5])-[C:6]-[S;H0;D2;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[C:3](-[#7:4]-[c:5])-[C:6]-[S;H0;D3;+0:7](=[O;H0;D1;+0:1])-[C:8]-[c:9] | null | [] | null | null | null | null | 2 g (5.7 mmol) of N-(benzylthio)acetyl-4-chloro-anthranilic acid methyl ester and 3.66 g (17.1 mmol) of sodium metaperiodate are dissolved in 12 ml of water and 48 ml of acetone and the resulting solution is stirred at reflux for 6 hours. The reaction mixture is allowed to cool, filtered and concentrated by evaporation... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1 | Other | O | null | null | CC(C)=O.COC(=O)c1ccc(Cl)cc1NC(=O)CSCc1ccccc1>O>COC(=O)c1ccc(Cl)cc1NC(=O)CS(=O)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f96535ebed4f49b298075deda61158bb | CC(C)(C)OC(=O)CS.COC(=O)C(Br)CCc1ccccc1>>CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C | O1CCCC1.[H-].[Na+].C(C)(C)(C)OC(CS)=O.O1CCCC1.COC(C(CCC1=CC=CC=C1)Br)=O>>C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)OC(C)(C)C)=O | [SH:15][CH2:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].Br[CH:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[S:15][CH2:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22]... | CC(C)(C)OC(=O)CS.COC(=O)C(Br)CCc1ccccc1 | CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 52aca8127bc297752bef4ceb545de321a64aebe4f07cbb983a701f60f54a1e68 | 0e4d19814363a7c0eeb85a0f67452d7f5812edb5106b8c36a823cf3926efc727 | c1ccccc1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[CH3;D1;+0:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[SH;D1;+0:16]>>[C:3]-[C:2]-[CH;D3;+0:1](-[S;H0;D2;+0:16]-[C:15]-[C:13](=[O;D1;H0:14])-[#8:12]-[C:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:4](=[O;D1;H0:5])-[... | 38 | [{"value": 38.0, "product": "C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 2.3 g (53.2 mmol) of sodium hydride in the form of a suspension in mineral oil are placed at 0° in 30 ml of tetrahydrofuran. Then at 0° to 10°, 6.6 g (44.:3 mmol) of thioglycolic acid tert-butyl ester are added dropwise thereto. A viscous suspension is formed which is diluted with 50 ml of tetrahydrofuran. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aliphatic thiol | Ester.Monosulfide | null | null | c1ccccc1 | null | C(C)(=O)OCC | null | 0.333333 | CC(C)(C)OC(=O)CS.COC(=O)C(Br)CCc1ccccc1>C(C)(=O)OCC>CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea5b8ee1ea694bff967d8ba3b4ba4b90 | CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C>>CCOC(=O)C(CCc1ccccc1)SCC(=O)O | C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)OC(C)(C)C)=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F>>C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)O)=O | CC(C)(C)[O:19][C:17]([CH2:16][S:15][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[O:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[S:15][CH2:16][C:17](=[O:18])[OH:19] | CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C | CCOC(=O)C(CCc1ccccc1)SCC(=O)O | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 104.3 | [{"value": 100.0, "product": "C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "C(C)OC(C(CCC1=CC=CC=C1)SCC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 5.6 g (16.5 mmol) of 2-tert-butyloxycarbonylmethylthio-4-phenyl-butyric acid ethyl ester are placed at room temperature in 60 ml of dichloromethane. 3.8 ml (49.6 mmol) of trifluoro-acetic acid are added and the mixture is stirred for 16 hours at room temperature, then a further 3.8 ml of trifluoroacetic acid is added a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1 | Other | ClCCl | null | 16 | CCOC(=O)C(CCc1ccccc1)SCC(=O)OC(C)(C)C>ClCCl>CCOC(=O)C(CCc1ccccc1)SCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d834c0a4d8694053b1b0490983c7829b | CC(=O)Cl.CC(=O)Cl.OC(CBr)Cc1ccccc1>>CC(=O)OC(CBr)Cc1ccccc1.CC(=O)[O-] | OC(CBr)CC1=CC=CC=C1.C(C)(=O)Cl.C(C)(=O)Cl>>C(C)(=O)[O-].C(C)(=O)OC(CBr)CC1=CC=CC=C1 | Cl[C:2]([CH3:1])=[O:3].Cl[C:16]([CH3:15])=[O:18].[OH:4][CH:5]([CH2:6][Br:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][Br:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:15][C:16](=[O:17])[O-:18] | CC(=O)Cl.CC(=O)Cl.OC(CBr)Cc1ccccc1 | CC(=O)OC(CBr)Cc1ccccc1.CC(=O)[O-] | null | null | ClCCl | Acylation | OtherReaction | 65751ec43893c586e84e4881c4e898fa70b0e6966872a803d47f5508d749a372 | c2f25f4550f08946ee4c948d7a14ea5a2bb3db19e2770a00c70d611a468d612d | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].Cl-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;H0;D1;+0:6].[C:7]-[C:8](-[C:9])-[OH;D1;+0:10]>>[C;D1;H3:5]-[C;H0;D3;+0:4](-[O-;H0;D1:6])=[O;D1;H0:11].[C:7]-[C:8](-[C:9])-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 167.9 | [{"value": 83.0, "product": "C(C)(=O)OC(CBr)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 167.9, "product": "C(C)(=O)OC(CBr)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8 g (37.2 mmol) of 2-hydroxy-3-phenyl-propyl bromide are dissolved at room temperature in 80 ml of dichloromethane; with stirring, 2.64 ml (37.2 mmol) of acetyl chloride and after 3 hours a further 2.64 ml (37.2 mmol) of acetyl chloride are added dropwise thereto; the mixture is stirred for 4 hours at 60° and for 16 ho... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1 | HCl | ClCCl | null | null | CC(=O)Cl.CC(=O)Cl.OC(CBr)Cc1ccccc1>ClCCl>CC(=O)OC(CBr)Cc1ccccc1.CC(=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6937ac7543b0415098b30c4f53a96fa5 | COC(=O)c1c(NC(=O)CSCCCc2ccccc2)cc(Cl)cc1[N+](=O)[O-]>>O=c1[nH]c2cc(Cl)cc([N+](=O)[O-])c2c(O)c1SCCCc1ccccc1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].COC(C=1C(NC(CSCCCC2=CC=CC=C2)=O)=CC(=CC1[N+](=O)[O-])Cl)=O>>ClC1=CC(=C2C(=C(C(NC2=C1)=O)SCCCC1=CC=CC=C1)O)[N+](=O)[O-] | CO[C:14]([c:13]1[c:4]([NH:3][C:2](=[O:1])[CH2:16][S:17][CH2:18][CH2:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:5][c:6]([Cl:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12])=[O:15]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]2[c:14]([OH:15])[c:16]1[S:17][CH2:18][CH2:19][CH... | COC(=O)c1c(NC(=O)CSCCCc2ccccc2)cc(Cl)cc1[N+](=O)[O-] | O=c1[nH]c2cc(Cl)cc([N+](=O)[O-])c2c(O)c1SCCCc1ccccc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a80509f1be2044db00bda28bf58d1929a6ec6cfc2594830aac457dceae07050f | 45512051a04a30c77fe95d59a24998d79363e30b8624aca147f6fb45668b9ecf | O=c1[nH]c2ccccc2cc1SCCCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10]-[C:11]):[c:12]>>[C:11]-[#16:10]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:12]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | 73.6 | [{"value": 73.0, "product": "ClC1=CC(=C2C(=C(C(NC2=C1)=O)SCCCC1=CC=CC=C1)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "ClC1=CC(=C2C(=C(C(NC2=C1)=O)SCCCC1=CC=CC=C1)O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 0.55 g (1.3 mmol) of 4-chloro-6-nitro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 6 ml of tetrahydrofuran at 0° under nitrogen. 2.6 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 1 hour at 0°. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Monosulfide | Aromatic alcohol.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 1 | COC(=O)c1c(NC(=O)CSCCCc2ccccc2)cc(Cl)cc1[N+](=O)[O-]>O1CCCC1>O=c1[nH]c2cc(Cl)cc([N+](=O)[O-])c2c(O)c1SCCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3ebbc2fbc5194be2a669f26f3b500cb1 | CCOC(=S)CC.Nc1cc(Cl)cc([N+](=O)[O-])c1>>CSc1c([N+](=O)[O-])c2cc(Cl)ccc2[nH]c1=O | C(C)N(CC)CC.C(C)OC(CC)=S.ClCCl.ClC=1C=C(N)C=C(C1)[N+](=O)[O-].ClCCl.ClOC(C)(C)C.ClCCl>>ClC=1C=C2C(=C(C(NC2=CC1)=O)SC)[N+](=O)[O-] | CC[O:17][C:16](=[S:2])[CH2:3][CH3:4].[N+:5](=[O:6])([O-:7])[c:13]1[cH:8][c:14]([NH2:15])[cH:9][c:10]([Cl:11])[cH:12]1>>[CH3:1][S:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[nH:15][c:16]1=[O:17] | CCOC(=S)CC.Nc1cc(Cl)cc([N+](=O)[O-])c1 | CSc1c([N+](=O)[O-])c2cc(Cl)ccc2[nH]c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2b649a2d39d5bcbc2b10ea98520966dee8b2565c1b33dfdb375f6c2d79e1d6b6 | 9b19abc46821f9b4ca435ff2a0c6feaceb83ffa694c1b853b969d2a9ae1c5748 | O=c1ccc2ccccc2[nH]1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[S;H0;D1;+0:3])-[CH2;D2;+0:4]-[CH3;D1;+0:5].[Cl;D1;H0:6]-[c:7]1:[c:8]:[c;H0;D3;+0:9](-[N+;H0;D3:10](-[O;-;D1;H0:11])=[O;D1;H0:12]):[cH;D2;+0:13]:[c;H0;D3;+0:14](-[NH2;D1;+0:15]):[cH;D2;+0:16]:1>>[C;D1;H3:17]-[S;H0;D2;+0:3]-[c;H0;D3;+0:4]1:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:15]:... | 40 | [{"value": 40.0, "product": "ClC=1C=C2C(=C(C(NC2=CC1)=O)SC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 14.2 g (82.3 mmol) of 3-chloro-5-nitro-aniline am dissolved under nitrogen at -65° in 235 ml of dichloromethane, and a solution of 9.8 ml (82.3 mmol) of tert-butyl hypochlorite in 30 ml of dichloromethane is added dropwise thereto. The mixture is then stirred for 10 minutes at -65° and then a solution of 10.6 ml (82.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Primary amine.Thiocarbonyl | Nitro group.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1 | Other | null | null | 0.166667 | CCOC(=S)CC.Nc1cc(Cl)cc([N+](=O)[O-])c1>>CSc1c([N+](=O)[O-])c2cc(Cl)ccc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-03f44ecdfc44402a90066612773e8a0e | O=C1Nc2cc(Cl)cc([N+](=O)[O-])c2C1=O.OO>>Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O | OO.ClC1=CC(=C2C(C(NC2=C1)=O)=O)[N+](=O)[O-].Cl>>ClC=1C=C(C(C(=O)O)=C(C1)[N+](=O)[O-])N | O=C1[NH:1][c:2]2[cH:3][c:4]([Cl:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]2[C:12]1=[O:13].O[OH:14]>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[C:12](=[O:13])[OH:14] | O=C1Nc2cc(Cl)cc([N+](=O)[O-])c2C1=O.OO | Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O | null | null | [OH-].[Na+] | Acylation | OtherReaction | 3d8e092f42f5af4743fd56124d55f8f8e78d5130caa7542eecba379d77329a3d | 329d39783e8afd331305e50e87fd6bd8b796086004223bf48232f981b7dab9d6 | c1ccccc1 | O-[OH;D1;+0:1].O=C1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;D1;H0:8]>>[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:1]):[c:6] | 87.8 | [{"value": 87.8, "product": "ClC=1C=C(C(C(=O)O)=C(C1)[N+](=O)[O-])N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4 ml of a 30% hydrogen peroxide solution are added dropwise at room temperature to 3.8 g (16.7 mmol) of 6-chloro-4-nitro-indoline-2,3-dione in 60 ml of sodium hydroxide solution. The mixture is stirred for 2 hours at room temperature, acidified to pH 2 to 3 with 4N hydro-chloric acid, filtered and dried. 3.18 g (87.8% ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide.Peroxide | Carboxylic acid.Primary amine | c1ccc2c(c1)CCN2 | null | c1ccccc1 | Other | [OH-].[Na+] | null | 2 | O=C1Nc2cc(Cl)cc([N+](=O)[O-])c2C1=O.OO>[OH-].[Na+]>Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d7c0badf483346398413ee261ac19298 | COS(=O)(=O)OC.Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O>>COC(=O)c1c(N)cc(Cl)cc1[N+](=O)[O-] | S(=O)(=O)(OC)OC.ClC=1C=C(C(C(=O)O)=C(C1)[N+](=O)[O-])N.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>COC(C=1C(N)=CC(=CC1[N+](=O)[O-])Cl)=O | COS(=O)(=O)O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15] | COS(=O)(=O)OC.Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O | COC(=O)c1c(N)cc(Cl)cc1[N+](=O)[O-] | null | null | ClCCl | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | C-O-S(=O)(=O)-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] | 48.3 | [{"value": 48.3, "product": "COC(C=1C(N)=CC(=CC1[N+](=O)[O-])Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3.25 g (15 mmol) of 4-chloro-6-nitro-anthranilic acid and 9.73 ml of a 40% aqueous solution of tetrabutylammonium hydroxide are placed in 65 ml of dichloromethane. Then 1.43 ml (15 mmol) of dimethyl sulfate are added dropwise thereto and the mixture is stirred for 1 hour at room temperature and washed in succession wit... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HO- | ClCCl | null | 1 | COS(=O)(=O)OC.Nc1cc(Cl)cc([N+](=O)[O-])c1C(=O)O>ClCCl>COC(=O)c1c(N)cc(Cl)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9c4f46622cfe4c929ea83878701e7abd | COC(=O)c1c(Cl)cc(Cl)cc1NC(=O)CSCCCc1cncnc1>>O=c1[nH]c2cc(Cl)cc(Cl)c2c(O)c1SCCCc1cncnc1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].COC(C=1C(NC(CSCCCC=2C=NC=NC2)=O)=CC(=CC1Cl)Cl)=O>>ClC1=C2C(=C(C(NC2=CC(=C1)Cl)=O)SCCCC=1C=NC=NC1)O | CO[C:12]([c:11]1[c:4]([NH:3][C:2](=[O:1])[CH2:14][S:15][CH2:16][CH2:17][CH2:18][c:19]2[cH:20][n:21][cH:22][n:23][cH:24]2)[cH:5][c:6]([Cl:7])[cH:8][c:9]1[Cl:10])=[O:13]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[c:11]2[c:12]([OH:13])[c:14]1[S:15][CH2:16][CH2:17][CH2:18][c:19]1[cH:20][n:21][cH:22][n... | COC(=O)c1c(Cl)cc(Cl)cc1NC(=O)CSCCCc1cncnc1 | O=c1[nH]c2cc(Cl)cc(Cl)c2c(O)c1SCCCc1cncnc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a80509f1be2044db00bda28bf58d1929a6ec6cfc2594830aac457dceae07050f | 45512051a04a30c77fe95d59a24998d79363e30b8624aca147f6fb45668b9ecf | O=c1[nH]c2ccccc2cc1SCCCc1cncnc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#16:10]-[C:11]):[c:12]>>[C:11]-[#16:10]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c:3](:[c:4]):[c:5](:[c:12]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;D1;H0:8] | 86.2 | [{"value": 86.2, "product": "ClC1=C2C(=C(C(NC2=CC(=C1)Cl)=O)SCCCC=1C=NC=NC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.2, "product": "ClC1=C2C(=C(C(NC2=CC(=C1)Cl)=O)SCCCC=1C=NC=NC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2.2 g (5.31 mmol) of 4,6-dichloro-N-[3-(pyrimidin-5-yl)-propylthio]acetyl-anthranilic acid methyl ester are placed in 25 ml of tetrahydrofuran at 0° under nitrogen. 10.62 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 2 hours at 0°.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Monosulfide | Aromatic alcohol.Monosulfide | c1ccccc1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1.c1cncnc1 | HO- | O1CCCC1 | null | 2 | COC(=O)c1c(Cl)cc(Cl)cc1NC(=O)CSCCCc1cncnc1>O1CCCC1>O=c1[nH]c2cc(Cl)cc(Cl)c2c(O)c1SCCCc1cncnc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-090ab9c6b546451287c6d7bb1a779f17 | Cc1ccc(S(=O)(=O)Cl)cc1.OCCCc1cncnc1>>Cc1ccc(S(=O)(=O)OCCCc2cncnc2)cc1 | S(=O)(=O)(C1=CC=C(C)C=C1)Cl.N1=CN=CC(=C1)CCCO.C(C)N(CC)CC>>S(=O)(=O)(OCCCC=1C=NC=NC1)C1=CC=C(C)C=C1 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][n:15][cH:16][n:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][n:15][cH:16][n:17][cH:18]2)[cH:19][cH:20]1 | Cc1ccc(S(=O)(=O)Cl)cc1.OCCCc1cncnc1 | Cc1ccc(S(=O)(=O)OCCCc2cncnc2)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCCc1cncnc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 104.9 | [{"value": 104.9, "product": "S(=O)(=O)(OCCCC=1C=NC=NC1)C1=CC=C(C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 9.87 g (51.7 mmol) of tosyl chloride in 50 ml of dichloromethane are added dropwise at room temperature to a solution of 6.5 g (47 mmol) of 3-(pyrimidin-5-yl)propanol and 9 ml (64.6 mmol) of triethylamine in 100 ml dichloromethane that is being stirred under nitrogen. The mixture is stirred for 16 hours at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1cncnc1 | HCl | ClCCl | null | null | Cc1ccc(S(=O)(=O)Cl)cc1.OCCCc1cncnc1>ClCCl>Cc1ccc(S(=O)(=O)OCCCc2cncnc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4b799df316274d97aff941b29aa982ef | CCOC(=S)CCCCc1cncnc1>>OC(=S)CCCCc1cncnc1 | [OH-].[Na+].C(C)OC(CCCCC=1C=NC=NC1)=S.O>>N1=CN=CC(=C1)CCCCC(=S)O | CC[O:1][C:2](=[S:3])[CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][n:10][cH:11][n:12][cH:13]1>>[OH:1][C:2](=[S:3])[CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][n:10][cH:11][n:12][cH:13]1 | CCOC(=S)CCCCc1cncnc1 | OC(=S)CCCCc1cncnc1 | null | null | CO | Deprotection | OtherReaction | 65c01082ec6254926609c8ce3d388338e51acb862ab958fb28659738e366fdad | 6a00535cbd1c6b0a3a91788e21576cc4d0faa02f2346e8f35105ed8723abcf83 | c1cncnc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[S;D1;H0:4]>>[C:3]-[C:2](-[OH;D1;+0:1])=[S;D1;H0:4] | 49.1 | [{"value": 46.0, "product": "N1=CN=CC(=C1)CCCCC(=S)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "N1=CN=CC(=C1)CCCCC(=S)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 20 ml (40 mmol) of 2N sodium hydroxide solution are added dropwise to 7.8 g (32.5 mmol) of 3-(pyrimidin-5-yl)propylthioacetic acid ethyl ester in 20 ml of methanol. The mixture is then stirred for 16 hours at room temperature; a small amount of water is added and the mixture is extracted with dichloromethane, dried ove... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Thiocarbonyl | Thiocarbonyl | null | null | c1cncnc1 | Other | CO | null | 16 | CCOC(=S)CCCCc1cncnc1>CO>OC(=S)CCCCc1cncnc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e31fb2b4a46b4c03b843f7cade657f1a | BrCCCc1cccs1.CCOC(=O)CS>>CCOC(=S)CCCCc1cccs1 | C(C)(=O)OCC.[H-].[Na+].C(C)OC(CS)=O.S1C(=CC=C1)CCCBr>>C(C)OC(CCCCC=1SC=CC1)=S | Br[CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][s:14]1.O=[C:4]([O:3][CH2:2][CH3:1])[CH2:6][SH:5]>>[CH3:1][CH2:2][O:3][C:4](=[S:5])[CH2:6][CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][s:14]1 | BrCCCc1cccs1.CCOC(=O)CS | CCOC(=S)CCCCc1cccs1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 39f85f22bf588facb53578391e351eba20bf7b6781574f26ca816ff4aa46642f | d47b93f0b5900ca53424e3cfc375edfb3844d861af9daf89b9e35566198e7360 | c1ccsc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].O=[C;H0;D3;+0:4](-[#8:5]-[C:6])-[CH2;D2;+0:7]-[SH;D1;+0:8]>>[C:6]-[#8:5]-[C;H0;D3;+0:4](=[S;H0;D1;+0:8])-[CH2;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 80.2 | [{"value": 80.2, "product": "C(C)OC(CCCCC=1SC=CC1)=S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 995 mg (22.8 mmol) of sodium hydride in the form of a 55% suspension in mineral oil are placed at from 0° to 5° in 30 ml of tetrahydrofuran, and 2.1 25 ml (19 mmol) of thioglycolic acid ethyl ester are added dropwise thereto. The mixture is stirred for 30 minutes at from 0° to 5°; 3.9 g (19 mmol) of 3-(2-thienyl)propyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aliphatic thiol | Ether.Thiocarbonyl | null | null | c1ccsc1 | HBr | O1CCCC1 | null | 0.5 | BrCCCc1cccs1.CCOC(=O)CS>O1CCCC1>CCOC(=S)CCCCc1cccs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-746b64fc659346af9a237e1ab8e9af1a | Nc1ccc(C(=O)O)cc1.[2H]c1c([2H])c([2H])c(N)c(N)c1[2H]>>Nc1ccc(-c2nc3ccccc3[nH]2)cc1 | [2H]C1=C(C(=C(C(=C1[2H])N)N)[2H])[2H].NC1=CC=C(C(=O)O)C=C1>>NC1=CC=C(C=C1)C=1NC2=C(N1)C=CC=C2 | O=[C:6](O)[c:5]1[cH:4][cH:3][c:2]([NH2:1])[cH:16][cH:15]1.[2H][c:9]1[c:8]([NH2:7])[c:13]([NH2:14])[c:12]([2H])[c:11]([2H])[c:10]1[2H]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[nH:14]2)[cH:15][cH:16]1 | Nc1ccc(C(=O)O)cc1.[2H]c1c([2H])c([2H])c(N)c(N)c1[2H] | Nc1ccc(-c2nc3ccccc3[nH]2)cc1 | null | null | O.C([O-])([O-])=O.[K+].[K+] | Aromatic Heterocycle Formation | OtherReaction | 8409c8c0d4e4ea3a5ac4d357a90931cd25bdeaf070f3095e8e16fa38a40808ca | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[nH;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:11]:[c:10]:1:[c:12] | 88.2 | [{"value": 88.2, "product": "NC1=CC=C(C=C1)C=1NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 195 | CELSIUS | null | null | This intermediate was prepared according to the procedure given in E. Acalade et al., J. Org. Chem. 52:5009-15 (1987). A mixture of 3.21 g (0.0247 moles) of O-phenylenediamine, 3.93 g (0.0287 moles) of 4-aminobenzoic acid and 42 g of polyphosphoric acid was heated to 195° C. for 5 hours. After cooling to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | O.C([O-])([O-])=O.[K+].[K+] | 195 | null | Nc1ccc(C(=O)O)cc1.[2H]c1c([2H])c([2H])c(N)c(N)c1[2H]>O.C([O-])([O-])=O.[K+].[K+]>Nc1ccc(-c2nc3ccccc3[nH]2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-70ce5b12522c4ce1aa2b696b77b4c4ca | NNC(=O)c1ccccc1Br.O=S(=O)(Cl)c1ccccc1>>O=C(NNS(=O)(=O)c1ccccc1)c1ccccc1Br | BrC1=C(C(=O)NN)C=CC=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>C1(=CC=CC=C1)S(=O)(=O)NNC(C1=C(C=CC=C1)Br)=O | [O:1]=[C:2]([NH:3][NH2:4])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Br:20].Cl[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([NH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Br:20] | NNC(=O)c1ccccc1Br.O=S(=O)(Cl)c1ccccc1 | O=C(NNS(=O)(=O)c1ccccc1)c1ccccc1Br | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 1d7782d13faad590a954d6d254ec5fc1e568084640ff236ac5cf433eecd9384e | 53d94e045a6cc897b7aa22bd88fc0cbf2a5e03cfb9e60b6d258d000dc8961a94 | O=C(NNS(=O)(=O)c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[O;D1;H0:10]=[C:9](-[c:11])-[#7:8]-[NH;D2;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 4 | HOUR | To a solution of 2-bromobenzoic acid hydrazide (132 g) in pyridine (1.2 L) cooled to about 10 C with an ice bath, was added benzensulfonyl chloride (78.3 ml). After complete addition, the reaction was stirred at ambient temperature for four hours, and then poured into ice-hydrochloric acid to precipitate a yellow solid... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 4 | NNC(=O)c1ccccc1Br.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>O=C(NNS(=O)(=O)c1ccccc1)c1ccccc1Br |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-94584e0d79da414891e1c45cffb921e5 | CN1CCNCC1.O=S(=O)(NN=C(Cl)c1ccccc1Br)c1ccccc1>>CN1CCN(C(=NNS(=O)(=O)c2ccccc2)c2ccccc2Br)CC1 | C1(=CC=CC=C1)S(=O)(=O)NN=C(C1=C(C=CC=C1)Br)Cl.CN1CCNCC1>>C1(=CC=CC=C1)S(=O)(=O)NN=C(N1CCN(CC1)C)C1=C(C=CC=C1)Br | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.Cl[C:6](=[N:7][NH:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Br:24]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[N:7][NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19... | CN1CCNCC1.O=S(=O)(NN=C(Cl)c1ccccc1Br)c1ccccc1 | CN1CCN(C(=NNS(=O)(=O)c2ccccc2)c2ccccc2Br)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 531a351b3c36fc2024ad4ea9c75c48da9e3f20ebbfd1ec068e2e71b153cc8eb4 | f467b2f5549c62a7ced962cf023662eb609a8559cb251f46db33d9d1c2d3a67a | O=S(=O)(NN=C(c1ccccc1)N1CCNCC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[#7:2]-[#7:3]-[#16:4])-[c:5](:[c:6]):[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#16:4]-[#7:3]-[#7:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1)-[c:5](:[c:6]):[c:7] | 124.8 | [{"value": 124.8, "product": "C1(=CC=CC=C1)S(=O)(=O)NN=C(N1CCN(CC1)C)C1=C(C=CC=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution, under nitrogen, of α-chloro-2-bromobenzaldehyde phenylsulfonylhydrazone (271.1 g; 720 mmol) in tetrahydrofuran (THF; 2 L), was added dropwise N-methylpiperazine (159.7 g; 1600 mmol). The reaction was stirred at ambient temperature for three hours, and then permitted to stand at ambient temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Alkenyl halide.Secondary amine | Hydrazone.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | 3 | CN1CCNCC1.O=S(=O)(NN=C(Cl)c1ccccc1Br)c1ccccc1>O1CCCC1>CN1CCN(C(=NNS(=O)(=O)c2ccccc2)c2ccccc2Br)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6035ffd6afb6489ca4eec289dc56700e | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.N#CBr>>N#CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | O.CN1CCN(CC1)C1=NN(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].N#CBr>>C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C#N | C[N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][n:9]([S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[CH2:25][CH2:26]1.Br[C:2]#[N:1]>>[N:1]#[C:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][n:9]([S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[c... | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.N#CBr | N#CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | e2177b420c88bb09a422917d53ad2376f53f76cfbde917cd2687c997e8578ffb | e5eafa37465591fc2fb10ac764a8f9c12513e10ca4009976ba714e6a1612f9ec | O=S(=O)(c1ccccc1)n1nc(N2CCNCC2)c2ccccc21 | Br-[C;H0;D2;+0:1]#[N;D1;H0:2].C-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[#7:6]-[C:7]-[C:8]-1>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[#7:6]-[C:7]-[C:8]-1 | null | [] | null | null | 5.5 | HOUR | To a stirred mixture of 3-(4-methyl-1-piperazinyl)-1-phenylsulfonyl-1H-indazole (237 g, 0.67 mole), K2CO3 (102 g, 0.74 mole) and dimethylsulfoxide (DMSO, 2000 ml), under nitrogen, was added cyanogen bromide (72 g, 0.68 mmol) dissolved in DMSO (525 ml). The reaction was stirred at ambient temperature for 5.5 hours and w... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Tertiary amine | Cyanamide | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1[nH]nc2ccccc12 | HBr | CS(=O)C | null | 5.5 | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.N#CBr>CS(=O)C>N#CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-90240f3c544f484abdfaef8b15e7133b | N#CN1CCN(c2n[nH]c3ccccc23)CC1>>c1ccc2c(N3CCNCC3)n[nH]c2c1 | N1N=C(C2=CC=CC=C12)N1CCN(CC1)C#N.[OH-].[Na+]>>N1(CCNCC1)C1=NNC2=CC=CC=C12 | N#C[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[c:4]3[cH:3][cH:2][cH:1][cH:15][c:14]3[nH:13][n:12]2)[CH2:11][CH2:10]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([N:6]3[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[n:12][nH:13][c:14]2[cH:15]1 | N#CN1CCN(c2n[nH]c3ccccc23)CC1 | c1ccc2c(N3CCNCC3)n[nH]c2c1 | null | null | OS(=O)(=O)O | Deprotection | Hydrogenolysis of tertiary amines | bd6471e541530886adfb2fb080deec41adfcb0988d9cfc00a46fef6615f95dc3 | c68eaa894cb0095de96c90a0f5302eae2f19124db629c97767c4d7e80723434b | c1ccc2c(N3CCNCC3)n[nH]c2c1 | N#C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 73 | [{"value": 73.0, "product": "N1(CCNCC1)C1=NNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(1H-indazol-3-yl)-1-piperazinecarbonitrile (8.0 g, 40 mmol) and 25% H2SO4 (100 ml) was stirred at reflux for 4.5 hours. The reaction was cooled in an ice bath and made basic by the dropwise addition of 50% NaOH. The basic solution was extracted with ethyl acetate. The ethyl acetate was washed with H2O, d... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccc2n[nH]cc2c1 | Other | OS(=O)(=O)O | null | null | N#CN1CCN(c2n[nH]c3ccccc23)CC1>OS(=O)(=O)O>c1ccc2c(N3CCNCC3)n[nH]c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-06ab1d2ae2b84da2af040ee4755e0bd6 | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=C(C=C(C=C1)C(C)=O)OC.CN(C=O)C>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1 | Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14]... | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 58.6 | [{"value": 58.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole hydrochloride (5.1 g, 20 mmol), K2CO3 (5.2 g, 40 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.3 g, 22 mmol), and dimethylformamide (60 ml) was heated at 90° C. for 16 hours. The reaction was poured into water, and the aqueous mixture was ext... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | O | 90 | null | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>O>COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e9e4931af9624c3ea2f7176c6fbf9d62 | COc1cc(C(C)=O)ccc1OCCCCl>>CC(=O)c1ccc(OCCCCl)c(O)c1 | B(Br)(Br)Br.C(=O)(O)[O-].[Na+].ClCCCOC1=C(C=C(C=C1)C(C)=O)OC.C(=O)=O.CO.C(=O)(O)[O-].[Na+].B(Br)(Br)Br>>ClCCCOC1=C(C=C(C=C1)C(C)=O)O | C[O:14][c:13]1[c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:15]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13]([OH:14])[cH:15]1 | COc1cc(C(C)=O)ccc1OCCCCl | CC(=O)c1ccc(OCCCCl)c(O)c1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 86.4 | [{"value": 86.4, "product": "ClCCCOC1=C(C=C(C=C1)C(C)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (10.0 g, 41 mmol) in methylene chloride (120 ml) cooled to -50° C. (dry ice-methanol) was added, dropwise, 1M boron tribromide in methylene chloride (123 ml, 120 mmol). The temperature was kept between -40° C. and -50° C. After complete addition, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | null | COc1cc(C(C)=O)ccc1OCCCCl>C(Cl)Cl>CC(=O)c1ccc(OCCCCl)c(O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d04301b06ccb4a089dfd3a7bd9dafd39 | COc1ccccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1ccccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].COC1=C(OCCCCl)C=CC=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=CC=C2)OC)C=C1 | Cl[CH2:12][CH2:11][CH2:10][O:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.[NH:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n:18][o:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n... | COc1ccccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1ccccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | 90 | CELSIUS | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.45 g; 11.1 mmol), K2CO3 (2.0 g), and 3-(2-methoxyphenoxy)propyl chloride (3.5 g, 17.4 mmol) in acetonitrile (40 ml) was heated at 90° C. for 4 hours. At the end of the reaction, the solvent was removed, and the solids were dissolved into dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(C)#N.C(C)O | 90 | null | COc1ccccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>COc1ccccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac3f393cf65e428dbd9554c8bd93aaaa | COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC=1C=C(C=CC1OC)C1(CC=CC=C1)C=O>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2OC)C2(CC=CC=C2)C=O)C=C1 | Cl[CH2:20][CH2:19][CH2:18][O:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([C:7]2([CH:8]=[O:9])[CH:10]=[CH:11][CH:12]=[CH:13][CH2:14]2)[cH:15]1.[NH:21]1[CH2:22][CH2:23][CH:24]([c:25]2[n:26][o:27][c:28]3[cH:29][c:30]([F:31])[cH:32][cH:33][c:34]23)[CH2:35][CH2:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH:8]=[O:9... | COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1=CCC(c2cccc(OCCCN3CCC(c4noc5ccccc45)CC3)c2)C=C1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole (2.01 g; 9.13 mmol), K2CO3 (2.0 g), and 1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenyl-methanone (3.93 g; 11.3 mmol) and acetonitrile (50 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was evaporated and the residue was par... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1=CCCC=C1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(C)#N | null | null | COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>COc1ccc(C2(C=O)C=CC=CC2)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-08a96330b3644f5aa7402613aba29867 | BrCCCBr.CN(C)C=O.COc1ccc(C(=O)c2ccccc2)cc1O>>COc1ccc(-c2cccc(C=O)c2)c(OCCCBr)c1 | O.BrCCCBr.OC=1C=C(C(=O)C2=CC=CC=C2)C=CC1OC.[H-].[Na+].CN(C=O)C>>BrCCCOC1=C(C=CC(=C1)OC)C=1C=C(C=CC1)C=O | Br[CH2:17][CH2:18][CH2:19][Br:20].CN(C)[CH:12]=[O:13].O=[C:7](c1[cH:8][cH:9][cH:10][cH:11][cH:14]1)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:15]([OH:16])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH:12]=[O:13])[cH:14]2)[c:15]([O:16][CH2:17][CH2:18][CH2:19][Br:20])[cH:21]1 | BrCCCBr.CN(C)C=O.COc1ccc(C(=O)c2ccccc2)cc1O | COc1ccc(-c2cccc(C=O)c2)c(OCCCBr)c1 | null | null | null | C-C Coupling | OtherReaction | 3ae4e094093ec410d16c18e09843eaa6758e4a476f33742131603281aea2f4b8 | 44b3d0142b494b6beccdb73977eb85c64d3ffeda5de55a1fdaa281ee3f70830a | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-N(-C)-[CH;D2;+0:4]=[O;D1;H0:5].O=[C;H0;D3;+0:6](-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c;H0;D3;+0:10](-[#8:11]-[C;D1;H3:12]):[c;H0;D3;+0:13](-[OH;D1;+0:14]):[cH;D2;+0:15]:1)-c1:[cH;D2;+0:16]:[cH;D2;+0:17]:[c:18]:[c:19]:[cH;D2;+0:20]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:14]-[c;H0;D3;+0:13]1:[cH... | null | [] | 90 | CELSIUS | 2 | HOUR | A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide (35 ml) was treated with sodium hydride (600 mg, 25 mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Tertiary amide.Aromatic alcohol | Aldehyde.Ether.Ether | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | 90 | 2 | BrCCCBr.CN(C)C=O.COc1ccc(C(=O)c2ccccc2)cc1O>>COc1ccc(-c2cccc(C=O)c2)c(OCCCBr)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-afc3ec5dc4014c3b88b1e3e79f01f29d | CC(=O)c1cccc(OCCCCl)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>CC(=O)c1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O | Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC=1C=C(C=CC1)C(C)=O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)C(C)=O)C=C1 | Cl[CH2:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:29]1.[NH:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n:18][o:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1.[O-:30][C:35]([O-:32])=[O:36]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12... | CC(=O)c1cccc(OCCCCl)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | CC(=O)c1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O | null | null | C(C)#N | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8].[O;D1;H0:12]=[C;H0;D3;+0:10](-[O;D1;H1:13])/[C:14]=[C:15]/[C:16](=[O;H0;D1;+0:9])-[OH;D1;+0:11] | 48.2 | [{"value": 48.2, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)C(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (4.53 g, 20.5 mmol), K2CO3 (4.5 g), 1-[3-(3-chloropropoxy)phenyl]ethanone (6.4 g, 29 mmol) in acetonitrile (60 ml) was heated at reflux for 5 hours. At the end of the reaction, the solvent was removed and the residue was extracted into dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(C)#N | null | null | CC(=O)c1cccc(OCCCCl)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>C(C)#N>CC(=O)c1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a7ccb7317b164ee4b3af29b418008271 | CC(=O)c1cc(C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)c1cc(C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1)C)C(C)=O>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C)C(C)=O)C=C1 | Br[CH2:14][CH2:13][CH2:12][O:11][c:10]1[c:4]([C:2]([CH3:1])=[O:3])[cH:5][c:6]([CH3:7])[cH:8][cH:9]1.[NH:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH3:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][N:1... | CC(=O)c1cc(C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)c1cc(C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 46.2 | [{"value": 46.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C)C(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C)C(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (2.87 g, 11.23 mmol), K2CO3 (2.5 g), 1-[2-(3-bromopropoxy)-5-methylphenyl]ethanone (3.74 g, 13.8 mmol) in dimethylformamide (10 ml) and acetonitrile (50 ml) was heated at 95° C. for 6 hours. At the end of the reaction, the solvent was concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.CN(C=O)C | 95 | null | CC(=O)c1cc(C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.CN(C=O)C>CC(=O)c1cc(C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b1c7dd0d984b411492617cb66d9d11f6 | COc1ccc(NC(C)=O)cc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>>COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC=1C=C(C=CC1OC)NC(C)=O.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2OC)NC(C)=O)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2OC)NC(C)=O)C=C1 | Br[CH2:16][CH2:15][CH2:14][O:13][c:12]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[cH:11]1.[n:17]1[c:21]([CH:20]2[CH2:19][CH2:64][NH:49][CH2:48][CH2:47]2)[c:30]2[cH:29][cH:28][c:26]([F:27])[cH:57][c:56]2[o:55]1.[C:24](/[CH:31]=[CH:68]/[C:66](=[O:65])[OH:67])(=[O:71])[OH:72].[C:18]([O-:23])(=[O:42]... | COc1ccc(NC(C)=O)cc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-] | COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | C(C)#N.CN(C=O)C.C(C)O | Aromatic Heterocycle Formation | OtherReaction | ec408c17d807906ded70f207df6495a688b75f12dc20593dcb8485e99e46800a | b1db23f13368ed5c45af33d355b6ede6c53683557ddda49436cc49ba33b244db | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1.c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[F;D1;H0:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c;H0;D3;+0:8]2:[c;H0;D3;+0:9](-[CH;D3;+0:10]3-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[NH;D2;+0:13]-[C:14]-[CH2;D2;+0:15]-3):[n;H0;D2;+0:16]:[o;H0;D2;+0:17]:[c;H0;D3;+0:18]:2:[cH;D2;+0:19]:1.[O-;H0;D1:20]-[C;H0;D3;+0:21](-[O-;H0;D1:22])=[O;H0;D1;+0:23].[O;D1;H... | null | [] | 100 | CELSIUS | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (3.94 g, 15.4 mmol), K2CO3 (3.67 g, 26.6 mmole), N-[3-(3-bromopropoxy)-4-methoxyphenyl]acetamide (5.56 g, 18.6 mmol) in dimethylformamide (75 ml) and acetonitrile (100 mI) was heated at 100° C. for 3 hours. At the end of the reaction, the solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Carboxylic acid.Secondary amine | Aromatic halide.Aromatic halide.Carboxylic acid.Ether.Ether.Secondary amide.Tertiary amine.Tertiary amine | C1CCNCC1.c1ccc2oncc2c1 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | C(C)#N.CN(C=O)C.C(C)O | 100 | null | COc1ccc(NC(C)=O)cc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>C(C)#N.CN(C=O)C.C(C)O>COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.COc1ccc(NC(C)=O)cc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-335e9ad5bb0d472bbce8225ee86a8668 | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)n[nH]c2c1>>COc1cc(C(C)=O)ccc1OCCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | FC1=CC=C2C(=NNC2=C1)C1CCNCC1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=C(C=C(C=C1)C(C)=O)OC.C(C)#N>>FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCCOC1=C(C=C(C=C1)C(C)=O)OC | Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][nH:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14... | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)n[nH]c2c1 | COc1cc(C(C)=O)ccc1OCCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3n[nH]c4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1H- indazole (3.5 g, 16 mmol), K2CO3 (2.2 g), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (3.8 g, 16 mm acetonitrile (90 ml) was refluxed for 16 hours. The reaction was poured into water and the resulting white solid, which precipitated from solution, was collected to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2n[nH]cc2c1 | HCl | O | null | null | COc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)n[nH]c2c1>O>COc1cc(C(C)=O)ccc1OCCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-34a032958888432ead3a3564a265a9ed | CC(=O)c1ccc(OCCCBr)c(C)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>>CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.O=C(O)/C=C/C(=O)O | Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1)C(C)=O)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)C)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)C)C=C1 | Br[CH2:11][CH2:10][CH2:9][O:8][c:7]1[cH:6][cH:35][c:34]([C:32]([CH3:31])=[O:33])[cH:30][c:28]1[CH3:29].[n:12]1[c:16]([CH:15]2[CH2:14][CH2:57][NH:42][CH2:41][CH2:40]2)[c:25]2[cH:24][cH:23][c:21]([F:22])[cH:50][c:49]2[o:48]1.[C:1](/[CH:56]=[CH:64]/[C:62](=[O:61])[OH:63])(=[O:67])[OH:68].[O:3]=[C:13]([O-:18])[O-:38]>>[CH3... | CC(=O)c1ccc(OCCCBr)c(C)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-] | CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.O=C(O)/C=C/C(=O)O | null | null | C(C)#N.CN(C=O)C.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 3dd76288496143ba0dddb4aae0fa0d5cb62a49da99b15d49897b5c459d270a57 | 6abe547074ac919922a66828210b643b081d31def350bd8bdb7ea1d1d407ac80 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1.c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[c:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9](-[C;D1;H3:10])=[O;D1;H0:11]):[cH;D2;+0:12]:[c:13]:1-[C;D1;H3:14].[F;D1;H0:15]-[c;H0;D3;+0:16]1:[c:17]:[c:18]:[c;H0;D3;+0:19]2:[c;H0;D3;+0:20](-[CH;D3;+0:21]3-[CH2;D2;+0:22]-[CH2;D2;+0:23]-[NH;D2;+0:24]-[C:25]-[CH2;D2;+0:26]-3):[n... | null | [] | 95 | CELSIUS | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (3.0 g; 11.7 mmol), K2CO3 (3.0 g), and 1-[4-(3-bromopropoxy)-3-methylphenyl]-ethanone (3.19 g) in dimethylformamide (20 ml) and acetonitrile (50 mi) was heated at 95° C. for 4 hours. At the end of the reaction, the solvent was concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Carboxylic acid.Ketone.Secondary amine | Aromatic halide.Aromatic halide.Carboxylic acid.Ketone.Ketone.Ether.Tertiary amine.Tertiary amine | c1ccccc1.C1CCNCC1.c1ccc2oncc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | C(C)#N.CN(C=O)C.C(C)O | 95 | null | CC(=O)c1ccc(OCCCBr)c(C)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>C(C)#N.CN(C=O)C.C(C)O>CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.CC(=O)c1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(C)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-401aeafbbd5b47e49a77d257771f7840 | COc1cc(C(C)=O)ccc1OCCCCBr.c1ccc2c(N3CCNCC3)nsc2c1>>COc1cc(C(C)=O)ccc1OCCCCN1CCN(c2nsc3ccccc23)CC1 | N1(CCNCC1)C1=NSC2=C1C=CC=C2.BrCCCCOC1=C(C=C(C=C1)C(C)=O)OC.C(=O)([O-])[O-].[K+].[K+]>>S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCCCOC2=C(C=C(C=C2)C(C)=O)OC | Br[CH2:16][CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:17]1[CH2:18][CH2:19][N:20]([c:21]2[n:22][s:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14]... | COc1cc(C(C)=O)ccc1OCCCCBr.c1ccc2c(N3CCNCC3)nsc2c1 | COc1cc(C(C)=O)ccc1OCCCCN1CCN(c2nsc3ccccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCCN2CCN(c3nsc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 86 | [{"value": 39.0, "product": "S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCCCOC2=C(C=C(C=C2)C(C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCCCOC2=C(C=C(C=C2)C(C)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (4.01 g, 8.2 mmol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone (6.0 g, 20.0 mmol), K2CO3 (3.0 g, 21.8 mmol), KI (200 mg), and acetonitrile (125 ml) was stirred at reflux under N2 for 5 hours. Most of the solvent was removed in vacuo and the resultant gummy residue w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2sncc2c1 | HBr | C(C)#N | null | null | COc1cc(C(C)=O)ccc1OCCCCBr.c1ccc2c(N3CCNCC3)nsc2c1>C(C)#N>COc1cc(C(C)=O)ccc1OCCCCN1CCN(c2nsc3ccccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f7a5740c905447f28f6e5f06cb133116 | COc1cc(C#N)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C#N)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C#N)C=C1)OC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C#N)C=C2)OC)C=C1 | Br[CH2:14][CH2:13][CH2:12][O:11][c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9]1.[NH:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:... | COc1cc(C#N)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C#N)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 68.2 | [{"value": 68.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C#N)C=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C#N)C=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (2.8 g), 4-(3-bromopropoxy)-3-methoxybenzonitrile (4.0 g, 14.8 mmol) in acetonitrile (70 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was removed on a rotary evaporator. The organic material was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | COc1cc(C#N)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>COc1cc(C#N)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8a737cfe730f4dabb02e6bc472b52f38 | CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)c1cc(Br)c(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(Br)c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1Br)C(C)=O)Br>>BrC=1C=C(C=C(C1OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)Br)C(C)=O | Br[CH2:12][CH2:11][CH2:10][O:9][c:8]1[c:6]([Br:7])[cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:31][c:29]1[Br:30].[NH:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n:18][o:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[c:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14... | CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)c1cc(Br)c(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(Br)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 58.7 | [{"value": 57.0, "product": "BrC=1C=C(C=C(C1OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)Br)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.7, "product": "BrC=1C=C(C=C(C1OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)Br)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2- benzisoxazole (2.0 g, 9.0 mmol), K2CO3 (1.3 g), and 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone (2.65 g, 9.0 mmol) and acetonitrile (50 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was evaporated and the residue was extracted int... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>CC(=O)c1cc(Br)c(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(Br)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6c8425325edc4f949051071a0292f0b2 | ClCCCOc1ccccc1.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCOc4ccccc4)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=CC=CC=C1.C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=CC=CC=C2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:21][CH2:22]3)[n:23][o:24][c:25]2[cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20... | ClCCCOc1ccccc1.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCOc4ccccc4)CC3)noc2c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 47 | [{"value": 47.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.0 g, 18.2 mmol), K2CO3 (3.0 g, 21.8 mmol), KI (100 mg), 3-chloropropoxybenzene (3.4 g, 20.0 mmol), and acetonitrile was stirred at reflux under nitrogen for 30 hours. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2oncc2c1 | HCl | O | null | null | ClCCCOc1ccccc1.Fc1ccc2c(C3CCNCC3)noc2c1>O>Fc1ccc2c(C3CCN(CCCOc4ccccc4)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1c480c43fa1442d6a80edafd4b0481ec | COc1cc(C(=O)C(F)(F)F)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C(=O)C(F)(F)F)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.ClCCCOC1=C(C=C(C=C1)C(C(F)(F)F)=O)OC.C(=O)([O-])[O-].[K+].[K+].C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C(F)(F)F)=O)OC)C=C1 | Cl[CH2:18][CH2:17][CH2:16][O:15][c:14]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1.[NH:19]1[CH2:20][CH2:21][CH:22]([c:23]2[n:24][o:25][c:26]3[cH:27][c:28]([F:29])[cH:30][cH:31][c:32]23)[CH2:33][CH2:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH... | COc1cc(C(=O)C(F)(F)F)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C(=O)C(F)(F)F)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 56 | [{"value": 56.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C(F)(F)F)=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C(F)(F)F)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.5 g, 6.7 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2,2,2-trifluoroethanone (2.0 g, 6.7 mmol), K2CO3 (0.88 g), KI (0.1 g) and acetonitrile (50 ml) was stirred and refluxed for 16 hours. After cooling, the reaction was poured into water and the aqueous mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | O | null | null | COc1cc(C(=O)C(F)(F)F)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>O>COc1cc(C(=O)C(F)(F)F)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-71d76378c3464ddabc28cf02e3eee9ba | CSc1cc(C(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CSc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1)C(C)=O)SC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)SC)C=C1 | Br[CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([S:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][S:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14]... | CSc1cc(C(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CSc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.88 g, 8.5 mmol), K2CO3 (1.8 g) and 1-[4-(3-bromopropoxy)-3-methylmercaptophenyl]ethanone (2.3 g, 7.6 mmol) in acetonitrile (100 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was concentrated, then diluted with dichlorom... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | CSc1cc(C(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>CSc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-decf42e7f1b6457c8310d9d63c9b2cc5 | BrCCCBr.CC(=O)c1cc(Br)c(O)c(Br)c1>>CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1 | CC(=O)C1=CC(=C(C(=C1)Br)O)Br.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C(C=C1Br)C(C)=O)Br | Br[CH2:10][CH2:11][CH2:12][Br:13].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[c:8]([OH:9])[c:14]([Br:15])[cH:16]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[c:8]([O:9][CH2:10][CH2:11][CH2:12][Br:13])[c:14]([Br:15])[cH:16]1 | BrCCCBr.CC(=O)c1cc(Br)c(O)c(Br)c1 | CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A stirred mixture of 3,5-dibromo-4-hydroxyacetophenone (3.0 g, 10.1 mmol), K2CO3 (2.8 g, 20.3 mmol), 1,3-dibromo- propane (4.0 g, 19.8 mmol) in acetonitrile (100 ml) was heated at reflux for 5 hours. The solvent was removed. The crude product was extracted into dichloromethane (150 ml) and the insoluble inorganics were... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | null | BrCCCBr.CC(=O)c1cc(Br)c(O)c(Br)c1>C(C)#N>CC(=O)c1cc(Br)c(OCCCBr)c(Br)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ddb4b8fc3356481ba514f141e9cf4670 | CCCC(=O)Cc1ccc(OCCCBr)c(OC)c1.Fc1ccc2c(C3CCNCC3)noc2c1>>CCCC(=O)Cc1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(OC)c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1)CC(CCC)=O)OC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)CC(CCC)=O)OC)C=C1 | Br[CH2:14][CH2:13][CH2:12][O:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][C:4]([CH2:3][CH2:2][CH3:1])=[O:5])[cH:34][c:31]1[O:32][CH3:33].[NH:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11... | CCCC(=O)Cc1ccc(OCCCBr)c(OC)c1.Fc1ccc2c(C3CCNCC3)noc2c1 | CCCC(=O)Cc1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(OC)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 68.7 | [{"value": 68.7, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)CC(CCC)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10 mmol), K2CO3 (3 g), 1-[4-(3-bromopropoxy)-3-methoxyphenyl]pentanone (3.7 g, 11.3 mmol) in acetonitrile (140 ml) was heated at reflux for 4 hours. At the end of the reaction, the mixture was cooled and filtered. The filtrate was concentrated to an oil.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | CCCC(=O)Cc1ccc(OCCCBr)c(OC)c1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>CCCC(=O)Cc1ccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c(OC)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6becf365cb5e47da94b5fe7a55ac370a | COc1cc(CC(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(CC(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C=C1)CC(C)=O)OC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)CC(C)=O)OC)C=C1 | Br[CH2:16][CH2:15][CH2:14][O:13][c:12]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH2:6][C:7]([CH3:8])=[O:9])[cH:10][cH:11]1.[NH:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7]([CH3:8])=[O:9])[cH:10][cH:11][c:12]1[O:13]... | COc1cc(CC(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(CC(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 31.8 | [{"value": 31.8, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)CC(C)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.8 g, 15.2 mmol), K2CO3 (3 g), 1-[4-(3-bromopropoxy)-3-methoxyphenyl]propanone (4.6 g, 18.2 mmol) in acetonitrile (100 ml) was heated at reflux for 2 hours. At the end of the reaction, the mixture was filtered and the solvent was concentrated and the residue w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | COc1cc(CC(C)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>COc1cc(CC(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ce06431317004ca896fe72d66da84e93 | COc1cc(C(N)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C(N)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCOC1=C(C=C(C(=O)N)C=C1)OC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C(=O)N)C=C2)OC)C=C1 | Br[CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14]... | COc1cc(C(N)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C(N)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 64.3 | [{"value": 64.3, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C(=O)N)C=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10.0 mmol), K2CO3 (2.0 g) and 4-(3-bromopropoxy)-3-methoxybenzamide (2.32 g, 8.0 mmol) in acetonitrile (80 ml) was heated at reflux for 5 hours. At the end of the reaction the solvent was evaporated. The residue was extracted into dichloromethane. The in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | COc1cc(C(N)=O)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>COc1cc(C(N)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9d242755e71a451b9b2716068ac74197 | CNc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>CNc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=C(C=C(C=C1)C(C)=O)NC.C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)NC)C=C1 | Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[c:3]([NH:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:1... | CNc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | CNc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O.CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 47.9 | [{"value": 47.9, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)NC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.3 g, 10.3 mmol), K2CO3 (1.4 g, 10.3 mmol), 1-[4-(3-chloropropoxy)-3-(methylamino)phenyl]ethanone (2.5 g, 10.3 mmol), KI (0.10 g), and acetonitrile (100 ml) was stirred at reflux under nitrogen for 23 hours. The reaction was cooled to ambient temperature, pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | O.CO.C(Cl)Cl | null | null | CNc1cc(C(C)=O)ccc1OCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>O.CO.C(Cl)Cl>CNc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0451f4d2b6a549b0b6751a0a32f63e51 | BrCCCBr.CSc1cc(C(C)=O)ccc1O>>CSc1cc(C(C)=O)ccc1OCCCBr | OC1=C(C=C(C=C1)C(C)=O)SC.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C(C=C1)C(C)=O)SC | Br[CH2:13][CH2:14][CH2:15][Br:16].[CH3:1][S:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][S:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][Br:16] | BrCCCBr.CSc1cc(C(C)=O)ccc1O | CSc1cc(C(C)=O)ccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | A mixture of 1-[4-hydroxy-3-(methylmercapto)phenyl]-ethanone (5.4 g; 30 mmol), K2CO3 (4.2 g), 1,3-dibromopropane (8 g, 39 mmol) in acetonitrile (150 ml) was heated at reflux for 3 hours and stirred at room temperature overnight. Acetonitrile was removed at reduced pressure and the residue was extracted into dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 8 | BrCCCBr.CSc1cc(C(C)=O)ccc1O>C(C)#N>CSc1cc(C(C)=O)ccc1OCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b19233991fb74194ad04748e0e20bb98 | BrCCCBr.COc1cc(C#N)ccc1O>>COc1cc(C#N)ccc1OCCCBr | OC1=C(C=C(C#N)C=C1)OC.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C(C#N)C=C1)OC | Br[CH2:12][CH2:13][CH2:14][Br:15].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][Br:15] | BrCCCBr.COc1cc(C#N)ccc1O | COc1cc(C#N)ccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmol), K2CO3 (12.5 g), and 1,3-dibromopropane (15 g, 75 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours and left standing at room temperature overnight. The solvent of the reaction was removed on a rotary evaporator, and the crude solid was extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 8 | BrCCCBr.COc1cc(C#N)ccc1O>C(C)#N>COc1cc(C#N)ccc1OCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-58898b95553b47d1819820c71d270579 | BrCCCBr.CC(=O)c1ccc(O)c(C)c1>>CC(=O)c1ccc(OCCCBr)c(C)c1 | CC1=C(C=CC(=C1)C(=O)C)O.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C(C=C1)C(C)=O)C | Br[CH2:9][CH2:10][CH2:11][Br:12].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:13]([CH3:14])[cH:15]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Br:12])[c:13]([CH3:14])[cH:15]1 | BrCCCBr.CC(=O)c1ccc(O)c(C)c1 | CC(=O)c1ccc(OCCCBr)c(C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 4-hydroxy-3-methylacetophenone (14.5 g, 96 mmol), K2CO3 (17.5 g, 144 mmol), and 1,3-dibromopropane (30 g, 144 mmol) in acetonitrile (400 ml) was heated at reflux for 6 hours. At the end of the reaction, the solvent was removed on a rotary evaporator, and the crude solid was extracted into dichloromethane (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | null | BrCCCBr.CC(=O)c1ccc(O)c(C)c1>C(C)#N>CC(=O)c1ccc(OCCCBr)c(C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e251ce829b26467cb8c5347f739bd629 | BrCCCBr.COc1cc(C2(C=O)C=CC=CC2)ccc1O>>COc1cc(C2(C=O)C=CC=CC2)ccc1OCCCBr | OC1=C(C=C(C=C1)C1(CC=CC=C1)C=O)OC.C(=O)([O-])[O-].[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C(C=C1)C1(CC=CC=C1)C=O)OC | Br[CH2:18][CH2:19][CH2:20][Br:21].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]2([CH:7]=[O:8])[CH:9]=[CH:10][CH:11]=[CH:12][CH2:13]2)[cH:14][cH:15][c:16]1[OH:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]2([CH:7]=[O:8])[CH:9]=[CH:10][CH:11]=[CH:12][CH2:13]2)[cH:14][cH:15][c:16]1[O:17][CH2:18][CH2:19][CH2:20][Br:21] | BrCCCBr.COc1cc(C2(C=O)C=CC=CC2)ccc1O | COc1cc(C2(C=O)C=CC=CC2)ccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | C1=CCC(c2ccccc2)C=C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 13.2 | [{"value": 13.2, "product": "BrCCCOC1=C(C=C(C=C1)C1(CC=CC=C1)C=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(4-hydroxy-3-methoxyphenyl)phenyl-methanone (14 g, 61.4 mmol), K2CO3 (13 g, 92.1 mmol), and 1,3-dibromopropane (28 g, 86 mmol) in acetonitrile (400 ml) was heated at reflux for 4 hours. The reaction was followed by thin layer chromatography. At the end of the reaction, the inorganics were filtered off an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1=CCCC=C1 | HBr | C(C)#N | null | null | BrCCCBr.COc1cc(C2(C=O)C=CC=CC2)ccc1O>C(C)#N>COc1cc(C2(C=O)C=CC=CC2)ccc1OCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-936d8d151e1e40e2b4aa3cda87e88ffd | CC(=O)Nc1ccccc1OCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>>CC(=O)Nc1ccccc1OCCCOS(=O)(=O)c1ccccc1 | OCCCOC1=C(C=CC=C1)NC(C)=O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.S(=O)(=O)(C1=CC=C(C)C=C1)Cl>>C1(=CC=CC=C1)S(=O)(=O)OCCCOC1=C(C=CC=C1)NC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][OH:15].C[c:22]1[cH:21][cH:20][c:19]([S:16](Cl)(=[O:17])=[O:18])[cH:24][cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][c... | CC(=O)Nc1ccccc1OCCCO.Cc1ccc(S(=O)(=O)Cl)cc1 | CC(=O)Nc1ccccc1OCCCOS(=O)(=O)c1ccccc1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 05fa5c39bec607db4d2ecbdc0d03c290b9a310bbf0fb1c4f6cab56ff403f2979 | cac1a51abad701d3f26583520679a70ff72a7c9f3ad49ba72aafddf242cb8589 | O=S(=O)(OCCCOc1ccccc1)c1ccccc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[S;H0;D4;+0:5](-Cl)(=[O;D1;H0:6])=[O;D1;H0:7]):[c:8]:[c:9]:1.[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:9]:[c:8]:1 | null | [] | null | null | 16 | HOUR | To a solution of N-[2-(3-hydroxypropoxy)phenyl]-acetamide (Example 113) (7.5 g, 36 mmol) in pyridine (90 ml), cooled to 0° C., was added p-toluenesulfonyl chloride (13.6 g, 56 mmol). After the tosyl chloride went into solution, the reaction was then allowed to stand at 5° C. for 16 hours. The reaction was poured onto i... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Sulfonate | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 16 | CC(=O)Nc1ccccc1OCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>CC(=O)Nc1ccccc1OCCCOS(=O)(=O)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fa4dc98c941f497798bd6103f2e861ce | CC(=O)c1ccc(O)c(N(C)C)c1.ClCCCBr>>CC(=O)c1ccc(OCCCCl)c(N(C)C)c1 | O.BrCCCCl.OC1=C(C=C(C=C1)C(C)=O)N(C)C.[H-].[Na+]>>ClCCCOC1=C(C=C(C=C1)C(C)=O)N(C)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:13]([N:14]([CH3:15])[CH3:16])[cH:17]1.Br[CH2:9][CH2:10][CH2:11][Cl:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13]([N:14]([CH3:15])[CH3:16])[cH:17]1 | CC(=O)c1ccc(O)c(N(C)C)c1.ClCCCBr | CC(=O)c1ccc(OCCCCl)c(N(C)C)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 179 | [{"value": 179.0, "product": "ClCCCOC1=C(C=C(C=C1)C(C)=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 3 | CELSIUS | 45 | MINUTE | To a suspension of sodium hydride (2.3 g, 48.5 mmol of 50% oil dispersion) with dimethylformamide (75 ml), and cooled to 3° C. in an ice-salt bath and under a stream of nitrogen was added, dropwise, 1-(4-hydroxy-3-dimethylamino-phenyl)ethanone (8.7 g, 48.5 mmol) dissolved in dimethylformamide (150 ml) so that the tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | 3 | 0.75 | CC(=O)c1ccc(O)c(N(C)C)c1.ClCCCBr>CN(C=O)C>CC(=O)c1ccc(OCCCCl)c(N(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f256b355642041e6a40f3b85b25d1552 | COc1cc(C(=O)O)ccc1OCCCCl.O=S(Cl)Cl>>COc1cc(C(=O)Cl)ccc1OCCCCl | ClCCCOC1=C(C=C(C(=O)O)C=C1)OC.S(=O)(Cl)Cl>>ClCCCOC1=C(C=C(C(=O)Cl)C=C1)OC | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[cH:10][cH:9]1)=[O:7].O=S(Cl)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[Cl:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][Cl:16] | COc1cc(C(=O)O)ccc1OCCCCl.O=S(Cl)Cl | COc1cc(C(=O)Cl)ccc1OCCCCl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 60.8 | [{"value": 60.8, "product": "ClCCCOC1=C(C=C(C(=O)Cl)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 4-(3-chloropropoxy)-3-methoxybenzoic acid (2.4 g, 10 mmol) in dichloromethane (5 ml) was added thionyl chloride (0.9 ml, 12 mmol) dissolved in dichloromethane (5 ml). The reaction was stirred and refluxed for 1 hour, and then the dichloromethane was removed in vacuo to leave a dark oil. The oil was trit... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | ClCCl | null | null | COc1cc(C(=O)O)ccc1OCCCCl.O=S(Cl)Cl>ClCCl>COc1cc(C(=O)Cl)ccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-42326099ba174817bcc10c28a26190c8 | CC(=O)c1ccc(OCCCCl)c(O)c1>>CC(O)c1ccc(OCCCCl)c(O)c1 | [BH4-].[Na+].ClCCCOC1=C(C=C(C=C1)C(C)=O)O.[BH4-].[Na+]>>ClCCCOC1=C(C=C(C=C1)C(O)C)O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13]([OH:14])[cH:15]1>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13]([OH:14])[cH:15]1 | CC(=O)c1ccc(OCCCCl)c(O)c1 | CC(O)c1ccc(OCCCCl)c(O)c1 | null | null | C(C)O.O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 55 | [{"value": 55.0, "product": "ClCCCOC1=C(C=C(C=C1)C(O)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "ClCCCOC1=C(C=C(C=C1)C(O)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 3 | HOUR | To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was s... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | C(C)O.O1CCCC1 | 10 | 3 | CC(=O)c1ccc(OCCCCl)c(O)c1>C(C)O.O1CCCC1>CC(O)c1ccc(OCCCCl)c(O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-396fef07428141d4887274b35c7dd949 | ClCCCBr.Nc1ccccc1O>>Nc1ccccc1OCCCCl | ClCCCBr.[H-].[Na+].NC1=C(C=CC=C1)O.O>>ClCCCOC1=C(N)C=CC=C1 | Br[CH2:9][CH2:10][CH2:11][Cl:12].[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11][Cl:12] | ClCCCBr.Nc1ccccc1O | Nc1ccccc1OCCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 12.6 | [{"value": 12.6, "product": "ClCCCOC1=C(N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred suspension of sodium hydride (11.0 g, 230 mmol of a 50% oil dispersion) in dimethylformamide (250 ml), under nitrogen, was added, dropwise, 2-aminophenol (25.0 g, 230 mmol) dissolved in dimethylformamide (125 ml). After complete addition, the reaction was stirred at ambient temperature for 1 hour, and then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 1 | ClCCCBr.Nc1ccccc1O>CN(C=O)C>Nc1ccccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9d43a8dc68434d2e8d87e7a3a2c6a2e6 | CC(=O)Nc1cc(C(C)=O)ccc1O.ClCCCBr>>CC(=O)Nc1cc(C(C)=O)ccc1OCCCCl | C(C)(=O)NC=1C=C(C=CC1O)C(C)=O.C(=O)([O-])[O-].[K+].[K+].ClCCCBr>>C(C)(=O)NC=1C=C(C=CC1OCCCCl)C(C)=O | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([C:8]([CH3:9])=[O:10])[cH:11][cH:12][c:13]1[OH:14].Br[CH2:15][CH2:16][CH2:17][Cl:18]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([C:8]([CH3:9])=[O:10])[cH:11][cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][Cl:18] | CC(=O)Nc1cc(C(C)=O)ccc1O.ClCCCBr | CC(=O)Nc1cc(C(C)=O)ccc1OCCCCl | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 78.8 | [{"value": 78.8, "product": "C(C)(=O)NC=1C=C(C=CC1OCCCCl)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl]ethanone (7.7 g, 40 mmol), K2CO3 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the filtrate yielded 8.5 g of a white solid. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CC(=O)Nc1cc(C(C)=O)ccc1O.ClCCCBr>CC(=O)C>CC(=O)Nc1cc(C(C)=O)ccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f383543742fd4f8a8b2cabc91f8739c9 | COc1cc(C(C)=O)ccc1O>>CCc1ccc(O)c(OC)c1 | CC(=O)C1=CC(OC)=C(O)C=C1>>C(C)C1=CC(=C(C=C1)O)OC | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([O:9][CH3:10])[cH:11]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([O:9][CH3:10])[cH:11]1 | COc1cc(C(C)=O)ccc1O | CCc1ccc(O)c(OC)c1 | null | Cl.[Pd] | C(C)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 102.5 | [{"value": 102.5, "product": "C(C)C1=CC(=C(C=C1)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Acetovanillone (Aldrich, 11.0 g, 66 mmol) was dissolved in absolute ethanol (200 ml) and added to 1.5 g of 5% palladium on carbon. A few drops of concentrated hydrochloric acid were added and the mixture hydrogenated on a shaker at 42 psi. The reaction mixture was filtered through Celite, and the filtrate was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | Cl.[Pd].C(C)O | null | null | COc1cc(C(C)=O)ccc1O>Cl.[Pd].C(C)O>CCc1ccc(O)c(OC)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e1abad1c45bc48bdbfa90740a25862b5 | BrCCCBr.CC(=O)Nc1cccc(O)c1>>CC(=O)Nc1cccc(OCCCBr)c1 | BrCCCBr.C(C)(=O)NC=1C=C(C=CC1)O.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)NC=1C=C(OCCCBr)C=CC1 | Br[CH2:11][CH2:12][CH2:13][Br:14].[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:15]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][Br:14])[cH:15]1 | BrCCCBr.CC(=O)Nc1cccc(O)c1 | CC(=O)Nc1cccc(OCCCBr)c1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 24 | HOUR | To 3-acetamidophenol (15.1 g) in dichloromethane (500 ml, dry) was added potassium carbonate (20 g) and then 1,3-dibromopropane (30 g). The resulting mixture was heated at reflux for 6 hours and then overnight at room temperature. After an additional 24 hours, the reaction was complete. Solids were filtered from the re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | ClCCl | null | 24 | BrCCCBr.CC(=O)Nc1cccc(O)c1>ClCCl>CC(=O)Nc1cccc(OCCCBr)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ce71bb537847456a96c15754373c0bb2 | CC(=O)Nc1cccc(OCCCBr)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>>CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)NC=1C=C(OCCCBr)C=CC1>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)NC(C)=O)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)NC(C)=O)C=C1 | Br[CH2:13][CH2:12][CH2:11][O:10][c:9]1[cH:8][cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:30]1.[CH2:16]1[CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:42][CH2:43][NH:44][CH2:59]1.[CH:28](\[C:29](=[O:67])[OH:68])=[CH:64]/[C:65](=[O:61])[OH:63].[C:15]([O-:33])([O-:40])=[O:50]>>[CH3:... | CC(=O)Nc1cccc(OCCCBr)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-] | CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O | null | null | C(C)#N.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 59cb88ec2c57ca8bc2e5e012456f2b6d74a541c81f5ed138cb1a5a4b0a019de7 | 630b7ef6620d4d86970cb03f1f5d9e73de099e25b70c236d475b2a1b59fd1eee | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1.c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[#8;a:5]:[c:6]:[c:7]:[c:8]:1-[CH;D3;+0:9]1-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[NH;D2;+0:12]-[C:13]-[CH2;D2;+0:14]-1.[O-;H0;D1:15]-[C;H0;D3;+0:16](-[O-;H0;D1:17])=[O;H0;D1;+0:18].[O;H0;D1;+0:19]=[C;H0;D3;+0:20](-[OH;D1;+0:21])/[CH;D2;+0:22]=[CH;D2;+0:23]/[C;H0;D3;+0:24](=[O;H0;D1;+0:25]... | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (9.25 g, 42 mmol), K2CO3 (8 g, 58 mmol) and 3-(3-acetamidophenoxy)propyl bromide (11.4 g, 42 mmol) in acetonitrile (350 ml) was heated at reflux for 3 hours. At the end of the i reaction, the reaction was cooled, filtered and the solids washed with dichl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Carboxylic acid.Secondary amine | Aromatic halide.Carboxylic acid.Carboxylic acid.Ether.Secondary amide.Tertiary amine.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | C(C)#N.C(C)O | null | null | CC(=O)Nc1cccc(OCCCBr)c1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C([O-])[O-]>C(C)#N.C(C)O>CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-22cec5ab049b4a498b3b3f0c463b7cab | CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1>>Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(C=CC2)NC(C)=O)C=C1.[OH-].[Na+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C(N)C=CC2)C=C1 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([c:15]3[n:16][o:17][c:18]4[cH:19][c:20]([F:21])[cH:22][cH:23][c:24]34)[CH2:25][CH2:26]2)[cH:27]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([c:15]3[n:16][o:17][c:18]4[... | CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1 | Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 100 | CELSIUS | null | null | A stirred mixture of N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxyl]phenyl]acetamide (9.2 g, 22 mmol), prepared as described in the previous example, in 15% hydrochloric acid (110 ml) was heated at 100° C. for 2.5 hours until a homogeneous solution resulted. The reaction was cooled to 0° C. in an ic... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | Cl | 100 | null | CC(=O)Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1>Cl>Nc1cccc(OCCCN2CCC(c3noc4cc(F)ccc34)CC2)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-001f956185eb430189ca61e55b6e4562 | CNc1cc(C(C)=O)ccc1O.ClCCCBr>>CNc1cc(C(C)=O)ccc1OCCCCl | [H-].[Na+].BrCCCCl.OC1=C(C=C(C=C1)C(C)=O)NC>>ClCCCOC1=C(C=C(C=C1)C(C)=O)NC | [CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[OH:12].Br[CH2:13][CH2:14][CH2:15][Cl:16]>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][Cl:16] | CNc1cc(C(C)=O)ccc1O.ClCCCBr | CNc1cc(C(C)=O)ccc1OCCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 134.5 | [{"value": 134.5, "product": "ClCCCOC1=C(C=C(C=C1)C(C)=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 80 | MINUTE | To a stirred suspension of sodium hydride (0.87 g, 18.2 mmol of a 50% oil dispersion) in dimethylformamide (25 ml) under nitrogen and cooled to 0° in an ice-salt bath was added, dropwise, a solution of 1-(4-hydroxy-3-methylamino-phenyl)-ethanone (3.0 g, 18.2 mmol) dissolved in dimethylformamide (55 ml) so that the temp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 1.333333 | CNc1cc(C(C)=O)ccc1O.ClCCCBr>CN(C=O)C>CNc1cc(C(C)=O)ccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b0c1ee7e1be1484bb6fdedcf7a753ff9 | BrCCCBr.COc1cc(C(=O)N(C)C)ccc1O>>COc1cc(C(=O)N(C)C)ccc1OCCCBr | BrCCCBr.CN(C(C1=CC(=C(C=C1)O)OC)=O)C.C([O-])([O-])=O.[K+].[K+]>>CN(C(C1=CC(=C(C=C1)OCCCBr)OC)=O)C | Br[CH2:15][CH2:16][CH2:17][Br:18].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[cH:11][cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][Br:18] | BrCCCBr.COc1cc(C(=O)N(C)C)ccc1O | COc1cc(C(=O)N(C)C)ccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 83.7 | [{"value": 83.7, "product": "CN(C(C1=CC(=C(C=C1)OCCCBr)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To N,N-dimethyl-4-hydroxy-3-methoxybenzamide (5.64 g, 28.7 mmol) in acetonitrile (450 ml) was added potassium carbonate (7.9 g) followed by 1,3-dibromopropane (11.6 g). The resulting reaction mixture was refluxed for 3 hours and stirred at room temperature for 12 hours. The mixture was filtered and concentrated to an o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 12 | BrCCCBr.COc1cc(C(=O)N(C)C)ccc1O>C(C)#N>COc1cc(C(=O)N(C)C)ccc1OCCCBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4d44acc874ec44b2b6cecd80c22e15c3 | COc1cc(C(=O)N(C)C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C(=O)N(C)C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.CN(C(C1=CC(=C(C=C1)OCCCBr)OC)=O)C.C(=O)([O-])[O-].[K+].[K+]>>CN(C(C1=CC(=C(C=C1)OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)OC)=O)C | Br[CH2:17][CH2:16][CH2:15][O:14][c:13]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1.[NH:18]1[CH2:19][CH2:20][CH:21]([c:22]2[n:23][o:24][c:25]3[cH:26][c:27]([F:28])[cH:29][cH:30][c:31]23)[CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[cH:11][cH:... | COc1cc(C(=O)N(C)C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C(=O)N(C)C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.9 g, 17.7 mmol), N,N-dimethyl-4-bromopropoxy-3-methoxybenzamide (5.54 g, 17.5 mmol) and K2CO3 (3 g) in acetonitrile (250 ml) was heated at reflux for one hour. At the end of the reaction, the insolubles were filtered and washed with dichloromethane. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | COc1cc(C(=O)N(C)C)ccc1OCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>COc1cc(C(=O)N(C)C)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d035a777fbd54ee4acc5ab3dc8fbbf4f | COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.NN>>COc1cc(C(C)=NN)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1.NN>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=NN)OC)C=C1 | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([c:21]3[n:22][o:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]34)[CH2:31][CH2:32]2)[cH:11][cH:10]1)[CH3:7].[NH2:8][NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[N:8][NH2:9])[cH:10][cH:11][c:12]1[O:13]... | COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.NN | COc1cc(C(C)=NN)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[N;D1;H2:6])-[c:3](:[c:4]):[c:5] | 381.4 | [{"value": 381.4, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=NN)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone (4.3 g, 10 mmol), prepared as in Example 3 above, hydrazine (0.8 g, 2.5 mmol), and ethanol (40 ml) was refluxed for 16 hours. The cooled solution was concentrated to yield an oily residue. The residue was tr... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | C(C)O | null | null | COc1cc(C(C)=O)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1.NN>C(C)O>COc1cc(C(C)=NN)ccc1OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-258e311bdf404dafbeaf97882dcff230 | CC(=O)c1ccc(OCc2ccccc2)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1>>CC(=O)c1ccc(O)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)C/C=C/COC=2C=C(C=CC2OCC2=CC=CC=C2)C(C)=O)C=C1.Cl>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)C/C=C/COC=2C=C(C=CC2O)C(C)=O)C=C1 | c1ccc(C[O:8][c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:31][c:9]2[O:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([c:19]3[n:20][o:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]34)[CH2:29][CH2:30]2)cc1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([O:10][CH2:11]/[CH:12]=[CH:13]... | CC(=O)c1ccc(OCc2ccccc2)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1 | CC(=O)c1ccc(O)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1 | null | null | C(C)(=O)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | C(=C/CN1CCC(c2noc3ccccc23)CC1)\COc1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | 75 | CELSIUS | null | null | The mixture of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-benzyloxyphenyl]ethanone (5.5 g, 10.7 mmol), acetic acid (50 ml), and hydrochloric acid (6 ml) was heated at 75° C. for 2 hours. At the end of reaction, the solvent was reduced to about 20 ml on a rotary evaporator. The solu... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | Other | C(C)(=O)O | 75 | null | CC(=O)c1ccc(OCc2ccccc2)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1>C(C)(=O)O>CC(=O)c1ccc(O)c(OC/C=C/CN2CCC(c3noc4cc(F)ccc34)CC2)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dc56d68f8e024645830d6abe9c3358fe | ClCCCBr.Oc1cccc2cc[nH]c12>>ClCCCOc1cccc2cc[nH]c12 | BrCCCCl.[H-].[Na+].OC=1C=CC=C2C=CNC12.O>>ClCCCOC=1C=CC=C2C=CNC12 | Br[CH2:4][CH2:3][CH2:2][Cl:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][cH:12][nH:13][c:14]12>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][cH:12][nH:13][c:14]12 | ClCCCBr.Oc1cccc2cc[nH]c12 | ClCCCOc1cccc2cc[nH]c12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | 0.5 | HOUR | To a stirred suspension of sodium hydride (0.8 g, 17 mmol of a 50% oil dispersion) in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 15.7 mmol) in dimethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hour and then cooled to 15... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C | null | 0.5 | ClCCCBr.Oc1cccc2cc[nH]c12>CN(C=O)C>ClCCCOc1cccc2cc[nH]c12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7970b8ae4bf74445a0f46c8c1fe5af25 | Fc1ccc2c(C3CCNCC3)noc2c1.OCCCBr>>OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCO.C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCO)C=C1 | [NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1.Br[CH2:4][CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | Fc1ccc2c(C3CCNCC3)noc2c1.OCCCBr | OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 63.9 | [{"value": 63.9, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (10.0 g, 45 mmol), K2CO3 (10.0 g), 3-bromo-1-propanol (7.3 g, 46 mmol) and acetonitrile (200 ml) was refluxed for 3 hours. The reaction was poured into H2O and 7.1 g of a beige solid was collected. The filtrate was extracted with dichloromethane, and aft... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | O | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.OCCCBr>O>OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fb6eca1450fd4a87bc762c4437296cf6 | CS(=O)(=O)OCC1COc2ccccc2O1>>CC1COc2ccccc2O1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].CS(=O)(=O)OCC1COC2=C(O1)C=CC=C2>>CC1COC2=C(O1)C=CC=C2 | CS(=O)(=O)O[CH2:1][CH:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[O:11]1>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[O:11]1 | CS(=O)(=O)OCC1COc2ccccc2O1 | CC1COc2ccccc2O1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | b912c78cb197e36ec1377256b010930a62c194e425d624f79bd79646c51988b4 | 28e81ae8a7ce8bef7c0a5c5aadad67636bd3c9bf494add5caa6f4f660788ae85 | c1ccc2c(c1)OCCO2 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6]>>[#8:6]-[C:5]-[C:2](-[CH3;D1;+0:1])-[#8:3]-[c:4] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (2.45 g, 17.7 mmol), 2-methanesulfonyloxymethyl-1,4-benzodioxan (3.35 g, 13.7 mmole) in acetonitrile (100 ml) was heated at reflux for 12 hours. At the end of the reaction, the insolubles were filtered and rinsed with dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | null | null | c1ccc2c(c1)OCCO2 | MsOH.HO- | C(C)#N | null | null | CS(=O)(=O)OCC1COc2ccccc2O1>C(C)#N>CC1COc2ccccc2O1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-60135d7d08d440a1b33e063e3d2699be | CS(=O)(=O)Cl.OCCC1COc2ccccc2O1>>CS(=O)(=O)OCCC1COc2ccccc2O1 | S(=O)(=O)(C)Cl.OCCC1COC2=C(O1)C=CC=C2.C(C)N(CC)CC>>S(=O)(=O)(C)OCCC1COC2=C(O1)C=CC=C2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][CH:8]1[CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][CH:8]1[CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17]1 | CS(=O)(=O)Cl.OCCC1COc2ccccc2O1 | CS(=O)(=O)OCCC1COc2ccccc2O1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(c1)OCCO2 | 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 | 1 | HOUR | To the compound 2-hydroxyethyl-1,4-benzodioxan (11.96 g) in dichloromethane (450 ml) was added triethylamine (0.12 mol, 10 ml). Mesylchloride (9.2 g) was then added dropwise and the reaction mixture was stirred for one hour at room temperature. After completion of the reaction, the solution was washed with water, brine... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2c(c1)OCCO2 | HCl | ClCCl | null | 1 | CS(=O)(=O)Cl.OCCC1COc2ccccc2O1>ClCCl>CS(=O)(=O)OCCC1COc2ccccc2O1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e35fbcdcb13241568a28c7d7e5bccbf5 | COc1cc2c(cc1O)CCCC2=O.ClCCCBr>>COc1cc2c(cc1OCCCCl)CCCC2=O | OC=1C=C2CCCC(C2=CC1OC)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClCCCOC=1C=C2CCCC(C2=CC1OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[CH2:14][CH2:15][CH2:16][C:17]2=[O:18].Br[CH2:10][CH2:11][CH2:12][Cl:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][Cl:13])[CH2:14][CH2:15][CH2:16][C:17]2=[O:18] | COc1cc2c(cc1O)CCCC2=O.ClCCCBr | COc1cc2c(cc1OCCCCl)CCCC2=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1CCCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 95.4 | [{"value": 95.4, "product": "ClCCCOC=1C=C2CCCC(C2=CC1OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-hydroxy-7-methoxy-1-tetralone (J. Org. Chem., 1985, 50, 4937) (1.5 g, 7.8 mmol), K2CO3 (1.7 g, 12.3 mmol), and acetone (30 ml) was stirred at reflux under nitrogen for 45 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (1.9 g, 12.1 mmol) dissolved in 8 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCC2 | HBr | CC(=O)C | null | null | COc1cc2c(cc1O)CCCC2=O.ClCCCBr>CC(=O)C>COc1cc2c(cc1OCCCCl)CCCC2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0dc191c76def4dfb8ef96722edca6def | CC(=O)O.O=c1oc2ccccc2n1CCCCl>>CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl | ClCCCN1C(OC2=C1C=CC=C2)=O.C(C)(=O)O>>ClCCCN1C(OC2=C1C=CC(=C2)C(C)=O)=O | O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[o:10][c:11](=[O:12])[n:13]2[CH2:14][CH2:15][CH2:16][Cl:17]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[o:10][c:11](=[O:12])[n:13]2[CH2:14][CH2:15][CH2:16][Cl:17] | CC(=O)O.O=c1oc2ccccc2n1CCCCl | CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl | null | null | null | C-C Coupling | Friedel-Crafts acylation | c242d3073453ac339ae245b9c535d68c6c0031c8a5f169d0115c28b1ae1f4aad | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=c1[nH]c2ccccc2o1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]1:[c:5]:[#8;a:6]:[c:7]2:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:1:2>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]2:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:2:[c:8]:1 | null | [] | 100 | CELSIUS | null | null | A mixture of N-(3-chloropropyl)-2-benzoxazolinone (8.5 g, 40 mmol), polyphosphoric acid (100 g), and acetic acid (2.4 g, 2.3 ml, 40 mmol), was stirred and heated at 100° C. for 2 hours. The hot solution was poured into ice-water to deposit a yellow gum. The mixture was extracted with dichloromethane, and insolubles wer... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | null | 100 | null | CC(=O)O.O=c1oc2ccccc2n1CCCCl>>CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-68c9ef095ec04b27aee26937c9314b24 | CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)c1ccc2c(c1)oc(=O)n2CCCN1CCC(c2noc3cc(F)ccc23)CC1 | C(C)#N.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.ClCCCN1C(OC2=C1C=CC(=C2)C(C)=O)=O.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(OC3=C2C=CC(=C3)C(C)=O)=O)C=C1 | Cl[CH2:16][CH2:15][CH2:14][n:13]1[c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:9][c:8]2[o:10][c:11]1=[O:12].[NH:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[o:10][c:11](=[O:12])[n:13]2[C... | CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)c1ccc2c(c1)oc(=O)n2CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1oc2ccccc2n1CCCN1CCC(c2noc3ccccc23)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 31 | [{"value": 31.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(OC3=C2C=CC(=C3)C(C)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.5, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(OC3=C2C=CC(=C3)C(C)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.0 g, 9 mmol), N-(3-chloropropyl)-6-acetyl-2-benzoxazolinone (2.4 g, 9 mmol), K2CO3 (3.6 g), a few crystals of KI, and acetonitrile (50 ml) was stirred and refluxed for 13 hours. The reaction was poured into water, and a dark, brown solid that separated was co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ocnc2c1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | O | null | null | CC(=O)c1ccc2c(c1)oc(=O)n2CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>O>CC(=O)c1ccc2c(c1)oc(=O)n2CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2a34613624fa460bbb5b88ce64280d91 | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1c2ccccc2C(=O)N1CCCBr>>O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCN1C(C=2C(C1=O)=CC=CC2)=O>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1 | [NH:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[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][N:15]1[CH... | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1c2ccccc2C(=O)N1CCCBr | O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3ccccc23)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (6.44 g, 29.1 mmole), K2CO3 (6.4 g, 46 mmol), N-(3-bromopropyl)phthalimide (8.4 g, 31 mmol) in acetonitrile (150 ml) was heated at reflux for 3.5 hours. The insolubles were filtered. The solvent was removed at reduced pressure and the residue was purified by sil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1c2ccccc2C(=O)N1CCCBr>C(C)#N>O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0ae25fd0b49f45808911c63eda16d258 | Cl.O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1>>Cl.NCCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1.O.NN.Cl.O>>Cl.Cl.NCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | [ClH:2].O=C1c2ccccc2C(=O)[N:3]1[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[ClH:2].[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | Cl.O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.NCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | CO.C(C)O | Miscellaneous | OtherReaction | cd703f280330e7612c3c3b2e3cc2f8f9332381f29a1fd88b2de2a38281774976 | febc1d4b7b44ea3f7762312e158d5ab0fc0ca67ce6d66e23a51e3baafdb353e3 | c1ccc2c(C3CCNCC3)noc2c1 | 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 | null | null | A mixture of N-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propyl]phthalimide (8.5 g, 21 mmol), hydrazine monohydrate (1.5 g, 30 mmol) in methanol (60 ml) was heated at reflux for 2 hours. At the end of the reaction, methanol was removed to leave a crude solid. To this was added water (60 ml), then the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | CO.C(C)O | null | null | Cl.O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1>CO.C(C)O>Cl.NCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-02faebe0b9634c2faa2a68acb5916280 | NCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>>O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.NCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F.[C@@H]12[C@@H](CCCC1)C(=O)OC2=O>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2C([C@H]3CCCC[C@H]3C2=O)=O)C=C1 | [NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.O1[C:3](=[O:2])[C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]2[C:10]1=[O:11]>>[O:2]=[C:3]1[C@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:1... | NCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12 | O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | N1=CC=CC=C1.C(C)O | Acylation | OtherReaction | e31ab6bc2910da58d432cb5913ab0c5fdac34539ca9cc021c162ad6628b3e161 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[C:6](-[C:7])-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-[C;H0;D3;+0:10]-1=[O;D1;H0:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:6](-[C:7])-[C:5](-[C:4])-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | null | [] | null | null | null | null | A mixture of 1-(3-aminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.01 g, 10.8 mmol) and cis-1,2-cyclohexane-dicarboxylic anhydride (1.9 g, 12.3 mmol) in dry pyridine (30 ml) was heated at reflux for 16 hours. The dark brown solution was concentrated to dryness on a rotary evaporator. The crude residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC[C@H]2COC[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | N1=CC=CC=C1.C(C)O | null | null | NCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>N1=CC=CC=C1.C(C)O>O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bccd423ebdd84910b6ddb91c613e5d26 | Cl.O=C1c2ccccc2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1>>Cl.NCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1.O.NN.Cl.Cl>>Cl.Cl.NCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | [ClH:2].O=C1c2ccccc2C(=O)[N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][o:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[CH2:22][CH2:23]1>>[ClH:2].[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][o:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[... | Cl.O=C1c2ccccc2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cl.NCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O.CO.C(C)O | Miscellaneous | OtherReaction | cd703f280330e7612c3c3b2e3cc2f8f9332381f29a1fd88b2de2a38281774976 | febc1d4b7b44ea3f7762312e158d5ab0fc0ca67ce6d66e23a51e3baafdb353e3 | c1ccc2c(C3CCNCC3)noc2c1 | 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 | null | null | A mixture of N-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl) piperidinyl]-butyl]phthalimide (6.9 g, 16.4 mmol) and hydrazine monohydrate (1.64 g, 32.8 mmol) in methanol (70 ml) was heated at reflux for 3 hours. At the end of the reaction, methanol was removed to leave a crude solid. This was dissolved in water and acidified w... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | O.CO.C(C)O | null | null | Cl.O=C1c2ccccc2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1>O.CO.C(C)O>Cl.NCCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b50c7c6d9e574669b395321792a400d9 | NCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>>O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1 | NCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F.[C@@H]12[C@@H](CCCC1)C(=O)OC2=O.Cl>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCN2C([C@H]3CCCC[C@H]3C2=O)=O)C=C1 | [NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1.O1[C:3](=[O:2])[C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]2[C:10]1=[O:11]>>[O:2]=[C:3]1[C@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]2[C:10](=[O:11])[N:12]1[CH2:1... | NCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12 | O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | N1=CC=CC=C1.C(C)O | Acylation | OtherReaction | e31ab6bc2910da58d432cb5913ab0c5fdac34539ca9cc021c162ad6628b3e161 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[C:6](-[C:7])-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-[C;H0;D3;+0:10]-1=[O;D1;H0:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:6](-[C:7])-[C:5](-[C:4])-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | null | [] | null | null | null | null | A mixture of 1-(4-aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.7 g, 16.1 mmol) and cis-1,2-cyclohexanedicarboxylic anhydride (3.23 g, 21 mmol) in pyridine (45 ml) was heated at reflux for 8 hours. At the end of the reaction, pyridine was removed to dryness. The crude product was purified on a silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC[C@H]2COC[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | N1=CC=CC=C1.C(C)O | null | null | NCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>N1=CC=CC=C1.C(C)O>O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bff860049e7946ec877ebcf568a58b72 | COC1=CC(C(C)=O)=CCC1=S.ClCCCBr>>COc1cc(C(C)=O)ccc1SCCCCl | C1CCCCC1.BrCCCCl.CC(=O)C1=CCC(=S)C(=C1)OC.C([O-])([O-])=O.[K+].[K+]>>ClCCCSC1=C(C=C(C=C1)C(C)=O)OC | [CH3:1][O:2][C:3]1=[CH:4][C:5]([C:6]([CH3:7])=[O:8])=[CH:9][CH2:10][C:11]1=[S:12].Br[CH2:13][CH2:14][CH2:15][Cl:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[S:12][CH2:13][CH2:14][CH2:15][Cl:16] | COC1=CC(C(C)=O)=CCC1=S.ClCCCBr | COc1cc(C(C)=O)ccc1SCCCCl | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 132ede8accb79a3dfe164563ac4e05553652537beaca2e2af08bff739a4134cc | c16c2d996ab4f68a3470e2dc90106295e6ea23177c1afac41a82fad78fa6fdec | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#8:5]-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[C;H0;D3;+0:8](-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])=[CH;D2;+0:12]-[CH2;D2;+0:13]-[C;H0;D3;+0:14]-1=[S;H0;D1;+0:15]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:15]-[c;H0;D3;+0:14]1:[cH;D2;+0:13]:[cH;D2;+0:12]:[c;H0;D3;+0:8](-[C:9](-[C;D1;H3:10])=[O;D... | null | [] | null | null | null | null | A mixture of 1-(4-thio-3-methoxyphenyl)ethanone (10.0 g, 54.9 mmol), potassium carbonate (9.0 g, 65.1 mmol), and acetone (100 ml) was stirred at reflux under nitrogen for 30 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (6.5 ml, 9.5 g, 60.4 mmol) dissolved in acetone ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Thiocarbonyl | Ketone.Ether.Monosulfide | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)C | null | null | COC1=CC(C(C)=O)=CCC1=S.ClCCCBr>CC(=O)C>COc1cc(C(C)=O)ccc1SCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-39373f333d0d42a6986d820db905709a | COc1cc(C(C)=O)ccc1SCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C(C)=O)ccc1SCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.ClCCCSC1=C(C=C(C=C1)C(C)=O)OC.C(=O)([O-])[O-].[K+].[K+].CC#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCSC2=C(C=C(C=C2)C(C)=O)OC)C=C1 | Cl[CH2:15][CH2:14][CH2:13][S:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[S:12][CH2:13][CH2:14]... | COc1cc(C(C)=O)ccc1SCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C(C)=O)ccc1SCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(SCCCN2CCC(c3noc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 113 | [{"value": 113.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCSC2=C(C=C(C=C2)C(C)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 65 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), 1-[4-[(3-chloropropyl)-thio]-3-methoxyphenyl]ethanone (3.5 g, 13.6 mmol), K2CO3 (2.3 g, 16.6 mmol), KI (200 mg) and CH3CN (100 ml) was stirred at reflux under nitrogen for 7.5 hours and then was left at ambient temperature for 65 hours. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | O | null | 65 | COc1cc(C(C)=O)ccc1SCCCCl.Fc1ccc2c(C3CCNCC3)noc2c1>O>COc1cc(C(C)=O)ccc1SCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e4e43db029b34b738148853283537513 | COc1ccccc1CCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1ccccc1C(CCCc1noc2cc(F)ccc12)N1CCCCC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCC1=C(C=CC=C1)OC.C(C)#N.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)CCCC(C2=C(C=CC=C2)OC)N2CCCCC2)C=C1 | Br[CH2:12][CH2:11][CH2:10][CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.[c:13]1([CH:26]2[CH2:25][CH2:24][NH:23][CH2:28][CH2:27]2)[n:14][o:15][c:16]2[cH:17][c:18]([F:19])[cH:20][cH:21][c:22]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([CH2:10][CH2:11][CH2:12][c:13]1[n:14][o:15][c:16]2[cH:17][c:... | COc1ccccc1CCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1ccccc1C(CCCc1noc2cc(F)ccc12)N1CCCCC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 02264b3a4a623804c30c2b64e17c9ec3bb45136b9b4a28b6b973d8d05ea1bc46 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C(CCCc2noc3ccccc23)N2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#8;a:10]:[#7;a:11]:[c;H0;D3;+0:12](-[CH;D3;+0:13]2-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-2):[c:19]:1:[c:20]>>[c:8]:[c:9]1:[#8;a:10]:[#7;a:11]:[c;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-[N;H0;D3;+0:16]2-[C:15]-[C:14]-[CH2;D2;+... | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.36 g, 10.7 mmol), K2CO3 (2 g, 14.5 mmol) and 2-(4-bromobutyl)anisole (2.4 g, 10 mmol) in acetonitrile (100 ml) was heated at reflux for 2.5 hours. At the end of reaction, the solvent was removed. The residue was extracted into dichloromethane (200 ml) and fil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2oncc2c1 | c1ccc2oncc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccc2oncc2c1.C1CC[NH]CC1 | HBr | C(C)O | null | null | COc1ccccc1CCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)O>COc1ccccc1C(CCCc1noc2cc(F)ccc12)N1CCCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5060da791a9b4aa590647184e4d80a2c | CC(=O)c1ccc(Br)cc1.SCCCS>>CC(c1ccc(Br)cc1)C1SCCCS1 | BrC1=CC=C(C=C1)C(C)=O.C(CCS)S.B(F)(F)F.CCOCC>>BrC1=CC=C(C=C1)C(C)C1SCCCS1 | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[SH:11][CH2:12][CH2:13][CH2:14][SH:15]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[CH:10]1[S:11][CH2:12][CH2:13][CH2:14][S:15]1 | CC(=O)c1ccc(Br)cc1.SCCCS | CC(c1ccc(Br)cc1)C1SCCCS1 | null | null | ClCCl.ClC(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 4758dc84fa113e6f0c3b6850de21934960e643c3350412341d86e1faa5438e76 | cca0c476bcede45e7917ec20f9c51c08f1c759c1b0a2d2c92077062e73c24406 | c1ccc(CC2SCCCS2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[SH;D1;+0:6]-[C:7]-[C:8]-[C:9]-[SH;D1;+0:10]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C:11]1-[S;H0;D2;+0:6]-[C:7]-[C:8]-[C:9]-[S;H0;D2;+0:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 48 | HOUR | To the compound p-bromoacetophenone (36.85 g, 185 mmol) in trichloro-methane (300 ml) was added 1,3-propanedithiol (25 g, 230 mmol) and boron trifluoride etherate (3 ml). The resulting mixture was stirred at room temperature for 48 hours. The mixture was diluted with dichloromethane (500 ml), washed twice with 10% sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aliphatic thiol.Aliphatic thiol | Monosulfide.Monosulfide | null | C1CSCSC1 | c1ccccc1.C1CSCSC1 | null | ClCCl.ClC(Cl)Cl | null | 48 | CC(=O)c1ccc(Br)cc1.SCCCS>ClCCl.ClC(Cl)Cl>CC(c1ccc(Br)cc1)C1SCCCS1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b0750c9f2a1e4637afa6441b93b01099 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1>>CC(c1ccc(CCCCBr)cc1)C1SCCCS1 | C(C)(=O)OCC.BrCCCCBr.BrC1=CC=C(C=C1)C(C)C1SCCCS1.C(C)(CC)[Li]>>BrCCCCC1=CC=C(C=C1)C(C)C1SCCCS1 | Br[CH2:7][CH2:8][CH2:9][CH2:10][Br:11].Br[c:6]1[cH:5][cH:4][c:3]([CH:2]([CH3:1])[CH:14]2[S:15][CH2:16][CH2:17][CH2:18][S:19]2)[cH:13][cH:12]1>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13]1)[CH:14]1[S:15][CH2:16][CH2:17][CH2:18][S:19]1 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1 | CC(c1ccc(CCCCBr)cc1)C1SCCCS1 | null | null | O1CCCC1 | C-C Coupling | Negishi | 530a9bd1eaaebd54d09786b6168a1d1d89df12b3fda60e0c00afadb98df85946 | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | c1ccc(CC2SCCCS2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].Br-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | null | null | 1.5 | HOUR | A solution of 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene (27.2 g, 94 mmol) in tetrahydrofuran (200 ml) was charged with sec-butyllithium (99 ml, 1.3M in cyclohexane, 0.13 mole) dropwise at -78° C. under nitrogen. The mixture was stirred at ambient temperature for 1.5 hours, and then quenched with 1,4-dibromobutane (42 g,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CSCSC1 | Br- | O1CCCC1 | null | 1.5 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1>O1CCCC1>CC(c1ccc(CCCCBr)cc1)C1SCCCS1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9b2ca3b6bf9b424c85e44625e423693d | CCOC(=O)C1CCN(Cc2ccccc2)C1.Fc1cccc(F)c1>>O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | FC1=CC(=CC=C1)F.[Cl-].[Al+3].[Cl-].[Cl-].C(C(=O)O)(=O)O.S(=O)(Cl)Cl.C(C)OC(=O)C1CN(CC1)CC1=CC=CC=C1>>C(C(=O)O)(=O)O.FC1=C(C=CC(=C1)F)C(=O)C1CN(CC1)CC1=CC=CC=C1 | CCO[C:8](=[O:7])[CH:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28]1.[cH:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16]>>[O:7]=[C:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16])[CH:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2... | CCOC(=O)C1CCN(Cc2ccccc2)C1.Fc1cccc(F)c1 | O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | null | null | Cl.CCOCC.C(C)O | C-C Coupling | Friedel-Crafts acylation | f71c5083a5ac794cf8cea99a1f880de7dc082a90bfbd324fa7eea301f55849c8 | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(c1ccccc1)C1CCN(Cc2ccccc2)C1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[#7:6].[F;D1;H0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[#7:6]-[C:5]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8](-[F;D1;H0:7]):[c:9])-[C:4] | 57.4 | [{"value": 57.4, "product": "C(C(=O)O)(=O)O.FC1=C(C=CC(=C1)F)C(=O)C1CN(CC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | In a 1 liter round bottom flask, a solution of ethyl-N-benzyl-3-pyrrolidine carboxylate (21.8 g, 11.7 mmol) in 140 ml of 6N HCl was heated at reflux for 2.5 hours. The solution was cooled and the solvent was removed to dryness with a vacuum pump. The residue was then treated with thionyl chloride (100 ml) for 16 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | Cl.CCOCC.C(C)O | 55 | null | CCOC(=O)C1CCN(Cc2ccccc2)C1.Fc1cccc(F)c1>Cl.CCOCC.C(C)O>O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a17243f558eb4ae59dae915a3a6405cc | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>>ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | FC1=C(C=CC(=C1)F)C(=O)C1CN(CC1)CC1=CC=CC=C1.NO.Cl.C(C)(=O)[O-].[NH4+]>>FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1 | [OH:1][NH2:2].O=[C:3]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11])[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>>[OH:1][N:2]=[C:3]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11])[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH... | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1ccccc1)C1CCN(Cc2ccccc2)C1 | O=[C;H0;D3;+0:1](-[C:2](-[C:3])-[C:4]-[#7:5])-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[O;D1;H1:10]>>[#7:5]-[C:4]-[C:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[O;D1;H1:10])-[c:6](:[c:7]):[c:8])-[C:3] | 52 | [{"value": 52.0, "product": "FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To the compound (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone (22 g) in 95% ethanol (350 ml) and water (100 ml) was added NH2OH.HCl (10.1 g) and ammonium acetate (12.7 g, 2.1 eq). The resulting mixture was refluxed for 3.5 hours. The mixture was then allowed to stir at room temperature for 24 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | O.C(C)O | null | 24 | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>O.C(C)O>ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-20884847f6734dc59411b86379272b34 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>>Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 | FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1.[OH-].[K+].O.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CN(CC2)CC2=CC=CC=C2)C=C1 | F[c:21]1[c:5]([C:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18]2)=[N:19][OH:20])[cH:4][cH:3][c:2]([F:1])[cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[CH2:18]3)[n:19][o:20][c:21]2[cH:22]1 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | cfebb679a94a29342a57758c91b6c629149cdccb6d62df316a2e291ec25d681b | c3af886e80a4d8a4db0b9015a14ae7edf5d5d18deb2717f7ce3620ceac08ea61 | c1ccc(CN2CCC(c3noc4ccccc34)C2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[N;H0;D2;+0:6]-[OH;D1;+0:7])-[C:8](-[C:9])-[C:10]-[#7:11]):[c:12]>>[#7:11]-[C:10]-[C:8](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[o;H0;D2;+0:7]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:1:[c:12])-[C:9] | 74.8 | [{"value": 74.8, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CN(CC2)CC2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime (10.8 g, 34.2 mmol), potassium hydroxide (10 g), water (100 ml), and ethanol (100 ml) was heated at reflux for 2 hours. At the end of the reaction, the solution was cooled and ethanol was removed on a rotary evaporator. The aqueous mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Oxime | null | c1ccccc1 | c1ccc2oncc2c1 | C1CC[NH]C1.c1ccccc1.c1ccc2oncc2c1 | HF | C(C)O | null | null | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>C(C)O>Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9ce5e4dcf1604259b32f026b983341f2 | COc1cc(C=O)ccc1O.ClCCCBr>>COc1cc(C=O)ccc1OCCCCl | O.O=CC1=CC(OC)=C(O)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClCCCOC1=C(C=C(C=O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[OH:11].Br[CH2:12][CH2:13][CH2:14][Cl:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][Cl:15] | COc1cc(C=O)ccc1O.ClCCCBr | COc1cc(C=O)ccc1OCCCCl | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 37 | [{"value": 37.0, "product": "ClCCCOC1=C(C=C(C=O)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.9, "product": "ClCCCOC1=C(C=C(C=O)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of vanillin (30.4 g, 200 mmol), K2CO3 (27.6 g) and acetone (150 ml) was stirred and refluxed for 0.5 hours. Heating was removed and 1-bromo-3-chloropropane (40.8 g, 260 mmol) in acetone was added dropwise. The reaction was stirred and refluxed for 16 hours, and then it was poured into water. The aqueous mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | COc1cc(C=O)ccc1O.ClCCCBr>CC(=O)C>COc1cc(C=O)ccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a941e0f735bb499b843a469159a29395 | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1>>Fc1ccc2c(C3CCNC3)noc2c1 | C(=C)OC(=O)N1CC(CC1)C1=NOC2=C1C=CC(=C2)F.Cl>>Cl.FC1=CC2=C(C(=NO2)C2CNCC2)C=C1 | C=COC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[c:6]3[cH:5][cH:4][c:3]([F:2])[cH:16][c:15]3[o:14][n:13]2)[CH2:12]1>>[F:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH:8]3[CH2:9][CH2:10][NH:11][CH2:12]3)[n:13][o:14][c:15]2[cH:16]1 | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1 | Fc1ccc2c(C3CCNC3)noc2c1 | null | null | C(C)(C)O | Reduction | Hydrogenolysis of tertiary amines | b8f95e8847b8644bde7f55684fbdd5ce4dd641748931e44ce5a651614b5011ea | 4693d071c7195c4d1d1e30a5794ffc365d4c1fab9edd2d709ddf2a18cef75754 | c1ccc2c(C3CCNC3)noc2c1 | C=C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1>>[C:2]1-[C:3]-[C:4]-[C:5]-[NH;D2;+0:1]-1 | null | [] | 0 | CELSIUS | null | null | A mixture of 3-(6-fluoro-1,2-benzisoxazol-3-yl)-1-pyrrolidinylcarboxylic acid ethenyl ester (5.1 g, 18.4 mmol, hydrochloric acid (5 ml), and isopropyl alcohol (50 ml) was heated at reflux for 3.5 hours. At the end of the reaction, the solvent was reduced to about 30 ml on a rotary evaporator and the mixture was cooled ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Vinyl | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccc2oncc2c1 | HO- | C(C)(C)O | 0 | null | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1>C(C)(C)O>Fc1ccc2c(C3CCNC3)noc2c1 |
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