dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5aec4936e2b14990b36f20c777c7be91 | O=C(CCCCl)c1ccc(F)cc1>>O=C(c1ccc(F)cc1)C1CC1 | ClCCCC(=O)C1=CC=C(C=C1)F.[OH-].[K+]>>C1(CC1)C(=O)C1=CC=C(C=C1)F | Cl[CH2:11][CH2:12][CH2:10][C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12]1 | O=C(CCCCl)c1ccc(F)cc1 | O=C(c1ccc(F)cc1)C1CC1 | null | null | O | Functional Group Interconversion | OtherReaction | ba8a5853cba106ae1f1dcc05bcdfa09e62558319dc12ba5eccf6e53858edaf29 | d3448bc803db0fe7d73b7f0b0223b52cbc55d6c3e8733418e0ff66fb97fe6c3c | O=C(c1ccccc1)C1CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[O;D1;H0:5]=[C:4](-[c:6])-[CH;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-1 | null | [] | null | null | 40 | MINUTE | Add 20.0 g (0.10 mole) γ-chloro-p-fluorobutyrophenone dropwise to a methanolic KOH solution (prepared from 9.8 g of 86% KOH pellets and 60 ml of methanol). Stir the mixture at room temperature for 40 minutes and pour into 100 ml of water and then extract with 3×30 ml of methylene chloride. Wash the methylene chloride e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | C1CC1 | c1ccccc1.C1CC1 | HCl | O | null | 0.666667 | O=C(CCCCl)c1ccc(F)cc1>O>O=C(c1ccc(F)cc1)C1CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-92b0f2861ac34052b60247cb0c8be69d | O=C(Cc1ccc(F)cc1)C1CC1>>OC(c1ccc(F)cc1)C1CC1 | C1(CC1)C(=O)CC1=CC=C(C=C1)F.[BH4-].[Na+].C(C)(=O)O>>C1(CC1)C(O)C1=CC=C(C=C1)F | C([C:2](=[O:1])[CH:10]1[CH2:11][CH2:12]1)[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12]1 | O=C(Cc1ccc(F)cc1)C1CC1 | OC(c1ccc(F)cc1)C1CC1 | null | null | C(C)O | Miscellaneous | OtherReaction | daa987aec145c5852e562241e17e37111eea3b585b24d8bb5f6c658727c519bc | 65c0f1e474134afe581396038c9eec1081d3cf2c66a067b33a419661521d5253 | c1ccc(CC2CC2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-C-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[C:8]1-[C:9]-[C:10]-1>>[OH;D1;+0:1]-[CH;D3;+0:2](-[C:8]1-[C:9]-[C:10]-1)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | null | [] | null | null | 6 | HOUR | Add 3.2 g (0.085 mole) cyclopropyl-4-fluorobenzylmethanone to 80 ml of 3.2 g (0.085 mole) sodium borohydride partially dissolved in absolute ethanol, following the reaction by thin-layer chromatography. After about 6 hours at room temperature, cool the reaction in an ice bath and add acetic acid. Extract the mixture wi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | Other | C(C)O | null | 6 | O=C(Cc1ccc(F)cc1)C1CC1>C(C)O>OC(c1ccc(F)cc1)C1CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e683030b619748749d3b54d0c6f9699e | Cl.OC(c1ccc(F)cc1)C1CC1>>Fc1ccc(/C=C/CCCl)cc1 | C1(CC1)C(O)C1=CC=C(C=C1)F.Cl>>ClCC/C=C/C1=CC=C(C=C1)F | [ClH:10].O[CH:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:12][cH:11]1)[CH:7]1[CH2:8][CH2:9]1>>[F:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[CH2:8][CH2:9][Cl:10])[cH:11][cH:12]1 | Cl.OC(c1ccc(F)cc1)C1CC1 | Fc1ccc(/C=C/CCCl)cc1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 38776c52da3dcee213ec339130f3a6eb8327d8aaa90f172b6e0d73056aef0190 | 8452b9e7b957d084b8e6296c5c757c325bf3c4bf79ebb0ec829e6b9eb1c76119 | c1ccccc1 | O-[CH;D3;+0:1](-[CH;D3;+0:2]1-[C:3]-[CH2;D2;+0:4]-1)-[c:5](:[c:6]):[c:7].[ClH;D0;+0:8]>>[Cl;H0;D1;+0:8]-[CH2;D2;+0:4]-[C:3]/[CH;D2;+0:2]=[CH;D2;+0:1]/[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Dissolve 12.8 g (0.077 mole) of α-cyclopropyl-4-fluorobenzenemethanol in 60 ml of CHCl3, add 20 ml of concentrated HCl and reflux overnight. Separate the two layers, and extract the aqueous layer with methylene chloride. Combine the methylene chloride extracts with the chloroform layer and wash with saturated aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary halide | C1CC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | Cl.OC(c1ccc(F)cc1)C1CC1>C(Cl)(Cl)Cl>Fc1ccc(/C=C/CCCl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ba9c9b48fdb74de58d6c82f059e70a26 | C=C=COC.Clc1ccc(Br)cc1>>C#CCc1ccc(Cl)cc1 | BrC1=CC=C(C=C1)Cl.[Cl-].[NH4+].BrC1=CC=C(C=C1)Cl.COC=C=C.[Mg]>>ClC1=CC=C(C=C1)CC#C | CO[CH:1]=[C:2]=[CH2:3].Br[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[CH:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | C=C=COC.Clc1ccc(Br)cc1 | C#CCc1ccc(Cl)cc1 | null | null | CCOCC.OC(CN1C=NC=C1)C1=CC=C(C=C1)NS(=O)(=O)C | C-C Coupling | OtherReaction | d463bef59147a48ffa0bdcc2f2f7a5cbe0a47fb61f5677cff6959b17d4edaee0 | 959abc43744b7d49d3e4fd04c436d5ff1da10d013edea2fdc4015d8e383fb9c0 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-O-[CH;D2;+0:6]=[C;H0;D2;+0:7]=[CH2;D1;+0:8]>>[CH;D1;+0:6]#[C;H0;D2;+0:7]-[CH2;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In a flask containing 59 g (2.43 mole) magnesium turnings in 500 ml anhydrous ether under an atmosphere of nitroge add slowly a solution of 465 g (2.43 mole) of 4-bromochlorobenzene in 1 liter 4 anhydrous ether. With caution, once the Grignard has started maintain slow reflux until all 4-bromochlorobenzene has been add... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Allene | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CCOCC.OC(CN1C=NC=C1)C1=CC=C(C=C1)NS(=O)(=O)C | null | null | C=C=COC.Clc1ccc(Br)cc1>CCOCC.OC(CN1C=NC=C1)C1=CC=C(C=C1)NS(=O)(=O)C>C#CCc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b179caa1edde4d7db85b74b59893ce31 | C#CCc1ccc(Cl)cc1.C=O>>CC#CC(O)c1ccc(Cl)cc1 | [Cl-].[Na+].ClC1=CC=C(C=C1)CC#C.C(CCC)[Li].C=O>>ClC1=CC=C(C=C1)C(C#CC)O | [CH:2]#[C:3][CH2:4][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[CH2:1]=[O:5]>>[CH3:1][C:2]#[C:3][CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | C#CCc1ccc(Cl)cc1.C=O | CC#CC(O)c1ccc(Cl)cc1 | null | null | CCCCCC.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | a680c0cf8515532e7e0210252422e861ecf3c6c70d246905f921324730c1f764 | 28d240c35612efe41f2146d35d9bbe8f29ec1a21f7fa08aecaf86256546f8ff7 | c1ccccc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[CH;D1;+0:3]#[C:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[CH3;D1;+0:1]-[C;H0;D2;+0:3]#[C:4]-[CH;D3;+0:5](-[OH;D1;+0:2])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 30 | MINUTE | Under nitrogen and with cooling, to a solution of 150.6 g (1.0 mole) 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether, add dropwise 400 ml of 2.5M n-butyllithium (1.0 mole) in hexane. When addition is complete, stir a further 30 minutes and under N2 add 31 g of para-formaldehyde. Stir the mixture in a dry ic... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Secondary alcohol.Alkyne | null | null | c1ccccc1 | null | CCCCCC.CCOCC | null | 0.5 | C#CCc1ccc(Cl)cc1.C=O>CCCCCC.CCOCC>CC#CC(O)c1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-93abc6b367ac4c85828867dcc8b49366 | CC#CC(O)c1ccc(Cl)cc1>>C/C=C\C(O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)C(C#CC)O>>ClC1=CC=C(C=C1)C(\C=C/C)O | [CH3:1][C:2]#[C:3][CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH3:1]/[CH:2]=[CH:3]\[CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | CC#CC(O)c1ccc(Cl)cc1 | C/C=C\C(O)c1ccc(Cl)cc1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | null | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccccc1 | [C;D1;H3:1]-[C;H0;D2;+0:2]#[C;H0;D2;+0:3]-[C:4](-[O;D1;H1:5])-[c:6]>>[C;D1;H3:1]/[CH;D2;+0:2]=[CH;D2;+0:3]\[C:4](-[O;D1;H1:5])-[c:6] | null | [] | null | null | 2 | DAY | Under nitrogen, hydrogenate a mixture of 10 g (0.055 mole) of 1-(4-chlorophenyl)-2-butyn-1-ol and 0.6 g Lindlar catalyst. Following the reaction via NMR the reaction is complete in about two days. The hydrogenation is stopped and the reaction stirred under N2 at room temperature overnight. Filter off the catalysts, was... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | null | 48 | CC#CC(O)c1ccc(Cl)cc1>[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2]>C/C=C\C(O)c1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0dd86c3f04a44ab8bb79b472f6559150 | C/C=C\C(O)c1ccc(Cl)cc1.Cc1ccc(S(=O)(=O)Cl)cc1.[OH-]>>Cc1ccc(S(=O)(=O)[O-])cc1.OC/C=C\Cc1ccc(Cl)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.ClC1=CC=C(C=C1)C(\C=C/C)O.[OH-].[K+]>>ClC1=CC=C(C=C1)C\C=C/CO.CC1=CC=C(C=C1)S(=O)(=O)[O-] | [OH:12][CH:16](/[CH:15]=[CH:14]\[CH3:13])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:11][cH:10]1)(=[O:7])=[O:8].[OH-:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O-:9])[cH:10][cH:11]1.[OH:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][c:17]1[cH:18][cH:19][c:20]([Cl:... | C/C=C\C(O)c1ccc(Cl)cc1.Cc1ccc(S(=O)(=O)Cl)cc1.[OH-] | Cc1ccc(S(=O)(=O)[O-])cc1.OC/C=C\Cc1ccc(Cl)cc1 | null | null | CCOCC | Acylation | OtherReaction | 8d4c958d57c5893436aa88ba1f5a74f2b58c73a3b83674dc98a2d1b6d9b25311 | 5bc8747d49693f36603549f26fda054bb5784c3dcc17d9b54a3a2bf840b3fcaf | c1ccccc1.c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[CH3;D1;+0:7]/[C:8]=[C:9]\[CH;D3;+0:10](-[OH;D1;+0:11])-[c:12](:[c:13]):[c:14].[OH-;D0:15]>>[O-;H0;D1:15]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[OH;D1;+0:11]-[CH2;D2;+0:7]/[C:8]=[C:9]\[CH2;D2;+0:10]-[c:12](:[c:13]):[c:14] | null | [] | null | null | null | null | Dissolve 6.7 g (0.036 mole) of (Z)-1-(4-chlorophenyl)-2-buten-1-ol in 100 ml of anhydrous ether, add 3.2 g of powdered KOH. Stir the mixture and with cooling add a solution of 7.0 g p-toluenesulfonylchloride in 30 ml of anhydrous ether. Continue to stir with cooling for 30 minutes, then allow to warm to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate.Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | CCOCC | null | null | C/C=C\C(O)c1ccc(Cl)cc1.Cc1ccc(S(=O)(=O)Cl)cc1.[OH-]>CCOCC>Cc1ccc(S(=O)(=O)[O-])cc1.OC/C=C\Cc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ba1cfec2e5b445d2b5b9aeef73074f39 | CS(=O)(=O)Cl.Nc1ccccc1>>CS(=O)(=O)Nc1ccccc1 | NC1=CC=CC=C1.N1=CC=CC=C1.CS(=O)(=O)Cl>>C1(=CC=CC=C1)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | CS(=O)(=O)Cl.Nc1ccccc1 | CS(=O)(=O)Nc1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a 0° C. solution of 250 g (2.68 mole) of aniline and 233.2 g (2.95 mole) of pyridine in 1.25 L of methylene chloride and 319.6 g (2.79 mole) of methanesulfonyl chloride dropwise. Stir the resulting solution at 0° C. for about 30 minutes then warm to ambient temperature for about 16 hours. Extract the mixture with 2N... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | CS(=O)(=O)Cl.Nc1ccccc1>C(Cl)Cl>CS(=O)(=O)Nc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-03a078946e734c8a99d29a0b27efcafc | CS(=O)(=O)Nc1ccccc1.O=C(Cl)CCl>>CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1 | C1(=CC=CC=C1)NS(=O)(=O)C.ClCC(=O)Cl.Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>ClCC(=O)C1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:14][cH:15]1.Cl[C:10](=[O:11])[CH2:12][Cl:13]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][Cl:13])[cH:14][cH:15]1 | CS(=O)(=O)Nc1ccccc1.O=C(Cl)CCl | CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | -10 | CELSIUS | 16 | HOUR | In a flask containing 128.4 g (0.75 mole) of N-phenylmethanesulfonamide, 169.5 g (1.50 mole) of chloroacetyl chloride in 1 L of methylene chloride under an atmosphere of nitrogen and cooled to about -10° C. add 300 g (2.25 mole) of aluminum chloride. Stir the resulting mixture for about 16 hours. Pour the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | -10 | 16 | CS(=O)(=O)Nc1ccccc1.O=C(Cl)CCl>C(Cl)Cl>CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-708517c15fa34a6a9187edfc91752e67 | COc1ccc(CCCBr)cc1.Cn1ccnc1>>COc1ccc(CCC[n+]2ccn(C)c2)cc1.[Br-] | CN1C=NC=C1.BrCCCC1=CC=C(C=C1)OC>>[Br-].COC1=CC=C(C=C1)CCC[N+]1=CN(C=C1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][Br:18])[cH:16][cH:17]1.[n:10]1[cH:11][cH:12][n:13]([CH3:14])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][n+:10]2[cH:11][cH:12][n:13]([CH3:14])[cH:15]2)[cH:16][cH:17]1.[Br-:18] | COc1ccc(CCCBr)cc1.Cn1ccnc1 | COc1ccc(CCC[n+]2ccn(C)c2)cc1.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCC[n+]2cc[nH]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:1>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9]1:[c:8]:[c:7]:[#7;a:6](-[C;D1;H3:5]):[c:10]:1 | null | [] | 140 | CELSIUS | null | null | A mixture of 2.50 g (0.03 mole) of 1-methyl-1H-imidazole and 6.9 g (0.03 mole) of 1-(3-bromopropyl)-4-methoxybenzene is heated at 140° C. for 1.5 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5). At the completion, the cooled reaction product is t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1ccccc1.c1c[n+]cn1 | null | null | 140 | null | COc1ccc(CCCBr)cc1.Cn1ccnc1>>COc1ccc(CCC[n+]2ccn(C)c2)cc1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-713fc3bc0f894dfc920890737d051b18 | CCCCn1ccnc1.COc1ccc(CCCBr)cc1>>CCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] | C(CCC)N1C=NC=C1.BrCCCC1=CC=C(C=C1)OC>>[Br-].C(CCC)[N+]1=CN(C=C1)CCCC1=CC=C(C=C1)OC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][n:8][cH:20]1.[CH2:9]([CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]1)[Br:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][n+:5]1[cH:6][cH:7][n:8]([CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]2)[cH:20]1.[Br-:21] | CCCCn1ccnc1.COc1ccc(CCCBr)cc1 | CCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCn2cc[nH+]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]:1>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:9]1:[c:8]:[n+;H0;D3:7](-[C:6]-[C:5]):[c:11]:[c:10]:1 | null | [] | 140 | CELSIUS | null | null | A mixture of 2.5 g (0.02 mole) of 1-butyl-1H-imidazole and 4.61 g (0.02 mole) of 1-(3-bromopropyl)-4-methoxybenzene is heated at 140° C. for about 1.5 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol: 1M sodium chloride, 95:5). At the completion of the reaction, the cooled... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1.c1ccccc1 | null | null | 140 | null | CCCCn1ccnc1.COc1ccc(CCCBr)cc1>>CCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0975481c31384d8881e268fde82a7716 | CCCCCCCn1ccnc1.COc1ccc(CCCBr)cc1>>CCCCCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] | C(CCCCCC)N1C=NC=C1.BrCCCC1=CC=C(C=C1)OC>>[Br-].C(CCCCCC)[N+]1=CN(C=C1)CCCC1=CC=C(C=C1)OC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][cH:23]1.[CH2:12]([CH2:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[Br:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n+:8]1[cH:9][cH:10][n:11]([CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[... | CCCCCCCn1ccnc1.COc1ccc(CCCBr)cc1 | CCCCCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCn2cc[nH+]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]:1>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:9]1:[c:10]:[c:11]:[n+;H0;D3:7](-[C:6]-[C:5]):[c:8]:1 | null | [] | 140 | CELSIUS | null | null | A mixture of 2.5 g (0.015 mole) of 1-heptyl-1H-imidazole and 3.45 g (0.015 mole) of 1-(3-bromopropyl)-4-methoxybenzene is heated at 140° C. for about 1.5 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol: 1M sodium chloride, 95:5). At the completion of the reaction, the coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1.c1ccccc1 | null | null | 140 | null | CCCCCCCn1ccnc1.COc1ccc(CCCBr)cc1>>CCCCCCC[n+]1ccn(CCCc2ccc(OC)cc2)c1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-511fd087a3a740b095b9c1e3aec28d32 | CCCCCCCn1ccnc1.COc1ccc(CCCCBr)cc1>>CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1.[Br-] | C(CCCCCC)N1C=NC=C1.BrCCCCC1=CC=C(C=C1)OC>>[Br-].C(CCCCCC)[N+]1=CN(C=C1)CCCCC1=CC=C(C=C1)OC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][cH:24]1.[CH2:12]([CH2:13][CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]1)[Br:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n+:8]1[cH:9][cH:10][n:11]([CH2:12][CH2:13][CH2:14][CH2:15][c:16]2[cH:17][cH:18][c:19](... | CCCCCCCn1ccnc1.COc1ccc(CCCCBr)cc1 | CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCCn2cc[nH+]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]:1>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:9]1:[c:10]:[c:11]:[n+;H0;D3:7](-[C:6]-[C:5]):[c:8]:1 | null | [] | 140 | CELSIUS | null | null | A mixture of 2.5 g (0.015 mole) of 1-heptyl-1H-imidazole and 3.66 g (0.015 mole) of 1-(4-bromobutyl)-4-methoxybenzene is heated at 140° C. for about 2 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol: 1M sodium chloride, 95:5). At the completion of the reaction, the cooled... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1.c1ccccc1 | null | null | 140 | null | CCCCCCCn1ccnc1.COc1ccc(CCCCBr)cc1>>CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-31255a6f17e14a98850eb525acf68772 | CCCCCCCn1ccnc1C.COc1ccc(CCCCBr)cc1>>CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1C.[Br-] | C(CCCCCC)N1C(=NC=C1)C.BrCCCCC1=CC=C(C=C1)OC>>[Br-].C(CCCCCC)[N+]1=C(N(C=C1)CCCCC1=CC=C(C=C1)OC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][c:24]1[CH3:25].[CH2:12]([CH2:13][CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]1)[Br:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n+:8]1[cH:9][cH:10][n:11]([CH2:12][CH2:13][CH2:14][CH2:15][c:16]2[cH:17][cH:18]... | CCCCCCCn1ccnc1C.COc1ccc(CCCCBr)cc1 | CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1C.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | f4daa7bb824cdaa37f41c90ce9b52b8d64e0bc7c78bf6b7cb7ce4ccad42f806e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCCn2cc[nH+]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11]:1-[C;D1;H3:12]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[n+;H0;D3:7](-[C:6]-[C:5]):[c:11]:1-[C;D1;H3:12] | null | [] | 140 | CELSIUS | null | null | A mixture of 2.50 g (0.0139 mole) of 1-heptyl-2-methyl-1H-imidazole and 3.37 g (0.0139 mole) of 1-(4-bromobutyl)-4-methoxybenzene is heated at 140° C. for about 2 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5). At the completion of the reaction,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc[nH]1 | c1ncc[n+]1 | c1ncc[n+]1.c1ccccc1 | null | null | 140 | null | CCCCCCCn1ccnc1C.COc1ccc(CCCCBr)cc1>>CCCCCCC[n+]1ccn(CCCCc2ccc(OC)cc2)c1C.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4ca4ceb16eef4cdaa4b6731e37e52fb8 | CCCCCCCn1ccnc1.Cc1cccc(C)c1NS(=O)(=O)CCCCl>>CCCCCCCn1cc[n+](CCCS(=O)(=O)Nc2c(C)cccc2C)c1.[Cl-] | C(CCCCCC)N1C=NC=C1.ClCCCS(=O)(=O)NC1=C(C=CC=C1C)C>>[Cl-].CC1=C(C(=CC=C1)C)NS(=O)(=O)CCC[N+]1=CN(C=C1)CCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][cH:27]1.[CH2:12]([CH2:13][CH2:14][S:15](=[O:16])(=[O:17])[NH:18][c:19]1[c:20]([CH3:21])[cH:22][cH:23][cH:24][c:25]1[CH3:26])[Cl:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n+:11]([CH2:12][CH2:13][CH2:14][S:15](=[O:1... | CCCCCCCn1ccnc1.Cc1cccc(C)c1NS(=O)(=O)CCCCl | CCCCCCCn1cc[n+](CCCS(=O)(=O)Nc2c(C)cccc2C)c1.[Cl-] | null | null | O | Functional Group Interconversion | OtherReaction | af9372efd0d4cbb040a1d2fa469660cc7709681c6c0eb3b6dabfb715f74188ec | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=S(=O)(CCC[n+]1cc[nH]c1)Nc1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[CH2;D2;+0:9]-[Cl;H0;D1;+0:10]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[n+;H0;D3:4]1:[c:5]:[c:6]:[#7;a:2](-[C:1]):[c:3]:1.[Cl-;H0;D0:10] | null | [] | null | null | null | null | Combine 15.0 g (0.0919 mole) 1-heptyl-1H-imidazole and 25.5 g (0.0974 mole) 3-chloro-N-(2,6-dimethylphenyl)propanesulfonamide and heat for about 24 hours at 130° C. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 9:1). At the completion of the reaction, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1 | null | O | null | null | CCCCCCCn1ccnc1.Cc1cccc(C)c1NS(=O)(=O)CCCCl>O>CCCCCCCn1cc[n+](CCCS(=O)(=O)Nc2c(C)cccc2C)c1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-755407445f384b12b9268816db7e0b34 | CCCCCCCn1ccnc1.ClCCCCc1ccccc1>>CCCCCCC[n+]1ccn(CCCCc2ccccc2)c1.[Cl-] | ClCCCCC1=CC=CC=C1.C(CCCCCC)N1C=NC=C1>>[Cl-].C(CCCCCC)[N+]1=CN(C=C1)CCCCC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][cH:22]1.[CH2:12]([CH2:13][CH2:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[Cl:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n+:8]1[cH:9][cH:10][n:11]([CH2:12][CH2:13][CH2:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2... | CCCCCCCn1ccnc1.ClCCCCc1ccccc1 | CCCCCCC[n+]1ccn(CCCCc2ccccc2)c1.[Cl-] | null | null | CO | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCCn2cc[nH+]c2)cc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]:1>>[C:1]-[C:2]-[CH2;D2;+0:3]-[n;H0;D3;+0:9]1:[c:10]:[c:11]:[n+;H0;D3:7](-[C:6]-[C:5]):[c:8]:1.[Cl-;H0;D0:4] | null | [] | null | null | null | null | Combine 5.35 g (0.32 mole) of (4-chlorobutyl)benzene and 5.27 g (0.32 mole) 1-heptyl-1H-imidazole, stir the mixture at approximately 145° C. for about 30 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide 9:1). At the completion of the reaction, dissol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1.c1ccccc1 | null | CO | null | null | CCCCCCCn1ccnc1.ClCCCCc1ccccc1>CO>CCCCCCC[n+]1ccn(CCCCc2ccccc2)c1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-65a238fbcc58467ca44415ceb2512a3b | CC(=O)Nc1ccc(CCCCOS(=O)(=O)c2ccc(C)cc2)cc1.CCCCCCCn1ccnc1>>CCCCCCCn1cc[n+](CCCCc2ccc(NC(C)=O)cc2)c1.Cc1ccc(S(=O)(=O)[O-])cc1 | C(C)(=O)NC1=CC=C(C=C1)CCCCOS(=O)(=O)C1=CC=C(C=C1)C.C(CCCCCC)N1C=NC=C1>>CC1=CC=C(C=C1)S(=O)(=O)[O-].C(C)(=O)NC1=CC=C(C=C1)CCCC[N+]1=CN(C=C1)CCCCCCC | [CH2:12]([CH2:13][CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24][cH:25]1)[O:35][S:32]([c:31]1[cH:30][cH:29][c:28]([CH3:27])[cH:37][cH:36]1)(=[O:33])=[O:34].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n:11][cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH... | CC(=O)Nc1ccc(CCCCOS(=O)(=O)c2ccc(C)cc2)cc1.CCCCCCCn1ccnc1 | CCCCCCCn1cc[n+](CCCCc2ccc(NC(C)=O)cc2)c1.Cc1ccc(S(=O)(=O)[O-])cc1 | null | null | null | Functional Group Interconversion | OtherReaction | f6336a3ca2c058a82dc422254532a6256a33456d0cf2f851f353d7a1b3fa3922 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(CCCC[n+]2cc[nH]c2)cc1.c1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]1:[c:15]:[c:16]:[c:17](-[C;D1;H3:18]):[c:19]:[c:20]:1>>[C;D1;H3:18]-[c:17]1:[c:16]:[c:15]:[c:14](-[#16:11](-[O-;H0;D1:10])(=[O;D1;H0:12])=[O;D1;H0:13]):[c:20]:[c:19]:1.[C:7]-[C:8]-[C... | null | [] | null | null | 5 | HOUR | Heat a mixture of 6.23 g (0.017 mole) 4-methylbenzenesulfonic acid 4-(4-acetylaminophenyl)butyl ester and 2.9 g (0.017 mole) 1-heptyl-1H-imidazole to 80° C., for 5 hours, following the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 90:10). At the completion of the reaction, tritu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1.c1ccccc1 | null | null | null | 5 | CC(=O)Nc1ccc(CCCCOS(=O)(=O)c2ccc(C)cc2)cc1.CCCCCCCn1ccnc1>>CCCCCCCn1cc[n+](CCCCc2ccc(NC(C)=O)cc2)c1.Cc1ccc(S(=O)(=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-179c26676e05430697577cc67e854849 | Cc1nccn1C.ClCCCCc1ccc(Cl)cc1>>Cc1n(C)cc[n+]1CCCCc1ccc(Cl)cc1.[Cl-] | ClC1=CC=C(C=C1)CCCCCl.CN1C(=NC=C1)C>>[Cl-].ClC1=CC=C(C=C1)CCCC[N+]1=C(N(C=C1)C)C | [CH3:1][c:2]1[n:3]([CH3:4])[cH:5][cH:6][n:7]1.[CH2:8]([CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[Cl:19]>>[CH3:1][c:2]1[n:3]([CH3:4])[cH:5][cH:6][n+:7]1[CH2:8][CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.[Cl-:19] | Cc1nccn1C.ClCCCCc1ccc(Cl)cc1 | Cc1n(C)cc[n+]1CCCCc1ccc(Cl)cc1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | 3d5d015c2046556debcf6aeafac05350e91208eeb74adef0cc21fd56e7fc95e0 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCC[n+]2cc[nH]c2)cc1 | [C;D1;H3:1]-[c:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7].[C:8]-[C:9]-[CH2;D2;+0:10]-[Cl;H0;D1;+0:11]>>[C:8]-[C:9]-[CH2;D2;+0:10]-[n+;H0;D3:3]1:[c:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:2]:1-[C;D1;H3:1].[Cl-;H0;D0:11] | null | [] | 115 | CELSIUS | 3 | HOUR | To 4.77 g (0.023 mole) 1-chloro-4-(4-chlorobutyl)benzene add 2.23 g (0.023 mole) 1,2-dimethyl-1H-imidazole. Stir the solution for three hours at about 115° C. Follow the progress of the reaction by thin-layer chromatography on silica gel (MeOH:NaCl(1M), 92:8). At the completion of the reaction, cool to obtain an oil. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc[nH]1 | c1[n+]cc[nH]1 | c1[n+]cc[nH]1.c1ccccc1 | null | null | 115 | 3 | Cc1nccn1C.ClCCCCc1ccc(Cl)cc1>>Cc1n(C)cc[n+]1CCCCc1ccc(Cl)cc1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c554592c9b37465fa73f99fc04d02e8d | CCCCCCCBr.Cc1cccc(C)c1NS(=O)(=O)CCn1ccnc1>>CCCCCCCn1cc[n+](CCS(=O)(=O)Nc2c(C)cccc2C)c1.[Br-] | BrCCCCCCC.CC1=C(C(=CC=C1)C)NS(=O)(=O)CCN1C=NC=C1.O>>[Br-].CC1=C(C(=CC=C1)C)NS(=O)(=O)CC[N+]1=CN(C=C1)CCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:27].[n:8]1[cH:9][cH:10][n:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[NH:17][c:18]2[c:19]([CH3:20])[cH:21][cH:22][cH:23][c:24]2[CH3:25])[cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][n+:11]([CH2:12][CH2:13][S:14](=[O:15])(=[O:16])[NH:... | CCCCCCCBr.Cc1cccc(C)c1NS(=O)(=O)CCn1ccnc1 | CCCCCCCn1cc[n+](CCS(=O)(=O)Nc2c(C)cccc2C)c1.[Br-] | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | af9372efd0d4cbb040a1d2fa469660cc7709681c6c0eb3b6dabfb715f74188ec | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=S(=O)(CC[n+]1cc[nH]c1)Nc1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11]:1>>[Br-;H0;D0:1].[C:5]-[C:6]-[n+;H0;D3:7]1:[c:8]:[c:9]:[n;H0;D3;+0:10](-[CH2;D2;+0:2]-[C:3]-[C:4]):[c:11]:1 | null | [] | null | null | 10 | HOUR | Combine 3.46 g (0.019 mole) 1-bromoheptane and 5.16 g (0.018 mole) N-(2,6-dimethylphenyl)-2-[1H-imidazol-1-yl]ethane sulfonamide in 10 ml DMF and heat to 100° C. Follow progress of reaction by TLC on silica gel (acetonitrile:ammonium hydroxide, 9:1). After about 10 hours, allow reaction mixture to cool to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1 | null | CN(C)C=O | null | 10 | CCCCCCCBr.Cc1cccc(C)c1NS(=O)(=O)CCn1ccnc1>CN(C)C=O>CCCCCCCn1cc[n+](CCS(=O)(=O)Nc2c(C)cccc2C)c1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-560edb78e0de42889fc1ab50fda17b06 | CCCn1ccnc1.ClCCCCc1ccc(Cl)cc1>>CCCn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] | ClC1=CC=C(C=C1)CCCCCl.C(CC)N1C=NC=C1>>[Cl-].ClC1=CC=C(C=C1)CCCC[N+]1=CN(C=C1)CCC | [CH3:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][n:7][cH:19]1.[CH2:8]([CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[Cl:20]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][n+:7]([CH2:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[cH:19]1.[Cl-:20] | CCCn1ccnc1.ClCCCCc1ccc(Cl)cc1 | CCCn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | af9372efd0d4cbb040a1d2fa469660cc7709681c6c0eb3b6dabfb715f74188ec | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCC[n+]2cc[nH]c2)cc1 | [C:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[CH2;D2;+0:9]-[Cl;H0;D1;+0:10]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[n+;H0;D3:4]1:[c:3]:[#7;a:2](-[C:1]):[c:6]:[c:5]:1.[Cl-;H0;D0:10] | null | [] | 130 | CELSIUS | null | null | Add 7.13 g (0.035 mole) of 1-chloro-4-(4-chlorobutyl)benzene to 3.52 g (0.032 mole) of 1-propyl-1H-imidazole and heat to 130° C. for 18 hours. Follow the progress of reaction by NMR (CDCl3). At the completion of the reaction, cool to room temperature to obtain the title compound.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1 | null | null | 130 | null | CCCn1ccnc1.ClCCCCc1ccc(Cl)cc1>>CCCn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ca23741c01464b8fb8b22ddafe07b27d | ClCCCCc1ccc(Cl)cc1.c1cn(CC2CCCCC2)cn1>>Clc1ccc(CCCCn2cc[n+](CC3CCCCC3)c2)cc1.[Cl-] | ClC1=CC=C(C=C1)CCCCCl.C1(CCCCC1)CN1C=NC=C1>>[Cl-].C1(CCCCC1)C[N+]1=CN(C=C1)CCCCC1=CC=C(C=C1)Cl | [Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][CH2:8][CH2:9][Cl:24])[cH:22][cH:23]1.[n:10]1[cH:11][cH:12][n:13]([CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][CH2:8][CH2:9][n:10]2[cH:11][cH:12][n+:13]([CH2:14][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20... | ClCCCCc1ccc(Cl)cc1.c1cn(CC2CCCCC2)cn1 | Clc1ccc(CCCCn2cc[n+](CC3CCCCC3)c2)cc1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | af9372efd0d4cbb040a1d2fa469660cc7709681c6c0eb3b6dabfb715f74188ec | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCCn2cc[n+](CC3CCCCC3)c2)cc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11]:1>>[C:5]-[C:6]-[n+;H0;D3:7]1:[c:8]:[c:9]:[n;H0;D3;+0:10](-[CH2;D2;+0:3]-[C:2]-[C:1]):[c:11]:1.[Cl-;H0;D0:4] | null | [] | 130 | CELSIUS | null | null | Add 6.55 g (0.03 mole) of 1-chloro-4-(4-chlorobutyl)benzene to 4.81 g (0.293 mole) of 1-cyclohexylmethyl-1H-imidazole and heat at 130° C. for 18 hours.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1ccccc1.c1c[nH]c[n+]1.C1CCCCC1 | null | null | 130 | null | ClCCCCc1ccc(Cl)cc1.c1cn(CC2CCCCC2)cn1>>Clc1ccc(CCCCn2cc[n+](CC3CCCCC3)c2)cc1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d30bd7fa8b074e34af76c288efa5a890 | CCCCCCCn1c(C)nc(C)c1C.COc1ccc(CCCCBr)cc1>>CCCCCCC[n+]1c(C)c(C)n(CCCCc2ccc(OC)cc2)c1C.[Br-] | BrCCCCC1=CC=C(C=C1)OC.C(CCCCCC)N1C(=NC(=C1C)C)C>>[Br-].C(CCCCCC)[N+]1=C(N(C(=C1C)C)CCCCC1=CC=C(C=C1)OC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9]([CH3:10])[c:11]([CH3:12])[n:13][c:26]1[CH3:27].[CH2:14]([CH2:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[cH:24][cH:25]1)[Br:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][n+:8]1[c:9]([CH3:10])[c:11]([CH3:12])[n:13]([CH2:14][CH2:15][... | CCCCCCCn1c(C)nc(C)c1C.COc1ccc(CCCCBr)cc1 | CCCCCCC[n+]1c(C)c(C)n(CCCCc2ccc(OC)cc2)c1C.[Br-] | null | null | O | Functional Group Interconversion | OtherReaction | 5e72d8623d1d11df3a484f13beed495bb29975189dd55fb2f640a2dac5643123 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCCn2cc[nH+]c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[n;H0;D3;+0:7]1:[c:8](-[C;D1;H3:9]):[n;H0;D2;+0:10]:[c:11](-[C;D1;H3:12]):[c:13]:1-[C;D1;H3:14]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:10]1:[c:11](-[C;D1;H3:12]):[c:13](-[C;D1;H3:14]):[n+;H0;D3:7](-[C:6]-[C:5]):[c:8]:1-[C;D1;H3:9] | null | [] | 125 | CELSIUS | null | null | Add 3.23 g (0.0133 mole) of 1-(4-bromobutyl)-4-methoxybenzene to 2.77 g (0.0133 mole) of 1-heptyl-2,4,5-trimethyl-1H-imidazole and heat at 125° C. for two hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (methanol: 1M sodium chloride, 95:5). At the completion of the reaction, dissol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[n+]cn1 | c1c[n+]cn1.c1ccccc1 | null | O | 125 | null | CCCCCCCn1c(C)nc(C)c1C.COc1ccc(CCCCBr)cc1>O>CCCCCCC[n+]1c(C)c(C)n(CCCCc2ccc(OC)cc2)c1C.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-902acbb33e034967a63b13b5cc75a2c2 | ClCCCCc1ccc(Cl)cc1.Cn1ccnc1>>Cn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] | ClC1=CC=C(C=C1)CCCCCl.CN1C=NC=C1>>[Cl-].ClC1=CC=C(C=C1)CCCC[N+]1=CN(C=C1)C | [CH2:6]([CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1)[Cl:18].[CH3:1][n:2]1[cH:3][cH:4][n:5][cH:17]1>>[CH3:1][n:2]1[cH:3][cH:4][n+:5]([CH2:6][CH2:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[cH:17]1.[Cl-:18] | ClCCCCc1ccc(Cl)cc1.Cn1ccnc1 | Cn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] | null | null | null | Functional Group Interconversion | OtherReaction | af9372efd0d4cbb040a1d2fa469660cc7709681c6c0eb3b6dabfb715f74188ec | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CCCC[n+]2cc[nH]c2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[CH2;D2;+0:9]-[Cl;H0;D1;+0:10]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[n+;H0;D3:4]1:[c:3]:[#7;a:2](-[C;D1;H3:1]):[c:6]:[c:5]:1.[Cl-;H0;D0:10] | null | [] | null | null | null | null | Combine 6.1 g (0.03 mole) 1-chloro-4-(4-chlorobutyl)benzene with 2.5 g (0.03 mole) 1-methyl-1H-imidazole and heat at 120° C., following the course of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5). At the completion of the reaction, cool and triturate with ether, collect the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1 | null | null | null | null | ClCCCCc1ccc(Cl)cc1.Cn1ccnc1>>Cn1cc[n+](CCCCc2ccc(Cl)cc2)c1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-057cda30ba974403950321e96ed564fa | CI.CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1>>Cn1cc[n+](CC(O)c2ccc(NS(C)(=O)=O)cc2)c1.[I-] | OC(CN1C=NC=C1)C1=CC=C(C=C1)NS(=O)(=O)C.IC>>[I-].OC(C[N+]1=CN(C=C1)C)C1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][I:21].[n:2]1[cH:3][cH:4][n:5]([CH2:6][CH:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[cH:20]1>>[CH3:1][n:2]1[cH:3][cH:4][n+:5]([CH2:6][CH:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[cH:20]1.[I-:21] | CI.CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1 | Cn1cc[n+](CC(O)c2ccc(NS(C)(=O)=O)cc2)c1.[I-] | null | null | CO | Functional Group Interconversion | OtherReaction | f6336a3ca2c058a82dc422254532a6256a33456d0cf2f851f353d7a1b3fa3922 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(CC[n+]2cc[nH]c2)cc1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]-[C:4]-[n;H0;D3;+0:5]1:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]:1>>[C:3]-[C:4]-[n+;H0;D3:5]1:[c:6]:[n;H0;D3;+0:7](-[CH3;D1;+0:1]):[c:8]:[c:9]:1.[I-;H0;D0:2] | null | [] | null | null | null | null | Heat a solution of 4.0 g (14.2 mmole) of (±)-N-[4-[1-hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide, 2 ml (32.1 mmole) of iodomethane and 50 ml methanol in a glass pressure tube to 80° C. for 24 hours. Remove the solvent in vacuo. Crystallize the residue from acetone. Recrystallize from acetone to provide ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]c[n+]1 | c1c[nH]c[n+]1.c1ccccc1 | null | CO | null | null | CI.CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1>CO>Cn1cc[n+](CC(O)c2ccc(NS(C)(=O)=O)cc2)c1.[I-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d7be8a0b10e1453c9251730ccc298a72 | CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1.Cn1ccnc1>>CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1.[Cl-] | ClCC(=O)C1=CC=C(C=C1)NS(=O)(=O)C.CN1C=NC=C1>>[Cl-].CN1C[NH+](C=C1)CC(=O)C1=CC=C(C=C1)NS(=O)(=O)C | [CH2:6]([C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]1)[Cl:21].[CH3:1][n:2]1[cH:3][cH:4][n:5][cH:20]1>>[CH3:1][N:2]1[CH:3]=[CH:4][NH+:5]([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[CH2:20]1.[Cl-:21] | CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1.Cn1ccnc1 | CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1.[Cl-] | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b8a36c115de439e42d925db9132e5b213bced5e9293ac4627b21408663bd0ea9 | 26d4750eaad79ede0d7168e363193f9b045f95289d4a8e5e240badd96495d35b | O=C(C[NH+]1C=CNC1)c1ccccc1 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[Cl;H0;D1;+0:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[NH+;D3:4](-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11])-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[Cl-;H0;D0:7] | null | [] | null | null | null | null | Heat a mixture of 160 g (0.646 mole) of N-[4-(2-chloro-1-oxoethyl)phenyl]methanesulfonamide, 55.7 g (0.678 mole) of 1-methyl-1H-imidazole and 2.1 L of acetonitrile at reflux for about 16 hours. Cool the mixture to room temperature and collect the solid and wash with 2 L of acetonitrile. Drying provides the title compou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Enamine.Ketone | c1c[nH]cn1 | C1=C[NH+]C[NH]1 | C1=C[NH+]C[NH]1.c1ccccc1 | null | C(C)#N | null | null | CS(=O)(=O)Nc1ccc(C(=O)CCl)cc1.Cn1ccnc1>C(C)#N>CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1.[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-04d3b9ce6ec74a958e6dc71bb1716b03 | CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1>>CN1C=C[NH+](CC(O)c2ccc(NS(C)(=O)=O)cc2)C1 | [Cl-].CN1C[NH+](C=C1)CC(=O)C1=CC=C(C=C1)NS(=O)(=O)C>>[Cl-].OC(C[NH+]1CN(C=C1)C)C1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][N:2]1[CH:3]=[CH:4][NH+:5]([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[CH2:20]1>>[CH3:1][N:2]1[CH:3]=[CH:4][NH+:5]([CH2:6][CH:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[CH2:20]1 | CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1 | CN1C=C[NH+](CC(O)c2ccc(NS(C)(=O)=O)cc2)C1 | null | [Pd] | O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=C[NH+](CCc2ccccc2)CN1 | [C:1]=[C:2]-[#7;+:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7](:[c:8]):[c:9]>>[C:1]=[C:2]-[#7;+:3]-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | A solution of 152.3 g (0.463 mole) of 3-methyl-1[2-[4-((methylsulfonyl)amino)phenyl]-2-oxoethyl]-1H-imidazolium chloride in 1 L of distilled water and 7.62 g 10% Pd/C catalyst are placed in a 2 L Parr bottle and hydrogenated at 50 psi pressure for ca. 5 hours.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1=C[NH+]C[NH]1.c1ccccc1 | null | [Pd].O | null | null | CN1C=C[NH+](CC(=O)c2ccc(NS(C)(=O)=O)cc2)C1>[Pd].O>CN1C=C[NH+](CC(O)c2ccc(NS(C)(=O)=O)cc2)C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8942f05ad9b44f1aa6ee60dbe5607694 | O=[N+]([O-])c1ccc(CCn2ccnc2)cc1>>Nc1ccc(CCn2ccnc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)CCN1C=NC=C1>>NC1=CC=C(C=C1)CCN1C=NC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][n:8]2[cH:9][cH:10][n:11][cH:12]2)[cH:13][cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][n:8]2[cH:9][cH:10][n:11][cH:12]2)[cH:13][cH:14]1 | O=[N+]([O-])c1ccc(CCn2ccnc2)cc1 | Nc1ccc(CCn2ccnc2)cc1 | null | [Pd] | Cl.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCn2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 10 g (0.046 mole) of 1-[2-(4-nitrophenyl)ethyl]-1H-imidazole in 100 mL of ethanol, 50 mL of 10% aqueous hydrochloric acid and 1.0 g of 5% Pd/C catalyst are placed in a small Parr bottle and hydrogenated at 50 psi pressure for about 24 hours. Additional H2 is added as needed to maintain 50 psi pressure. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1c[nH]cn1 | Other | [Pd].Cl.C(C)O | null | null | O=[N+]([O-])c1ccc(CCn2ccnc2)cc1>[Pd].Cl.C(C)O>Nc1ccc(CCn2ccnc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cd66aca946ca4ec298c6a1d5a5a8d280 | CS(=O)(=O)Cl.Nc1ccc(CCn2ccnc2)cc1>>CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1 | NC1=CC=C(C=C1)CCN1C=NC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)NC1=CC=C(C=C1)CCN1C=NC=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][n:12]2[cH:13][cH:14][n:15][cH:16]2)[cH:17][cH:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][n:12]2[cH:13][cH:14][n:15][cH:16]2)[cH:17][cH:18]1 | CS(=O)(=O)Cl.Nc1ccc(CCn2ccnc2)cc1 | CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(CCn2ccnc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | -10 | CELSIUS | 30 | MINUTE | To a -10° C. solution of 8 g (0.064 mole) of 1-[2-(4-aminophenyl)ethyl]-1H-imidazole and 10 mL triethylamine in 200 mL of methylene chloride add 5 mL of methanesulfonyl chloride dropwise. Stir the resulting solution at -10° C. for about 30 minutes then warm to ambient temperature for about 30 minutes. Wash the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1c[nH]cn1 | HCl | C(Cl)Cl | -10 | 0.5 | CS(=O)(=O)Cl.Nc1ccc(CCn2ccnc2)cc1>C(Cl)Cl>CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fe6bc469579849c190d98ec39f6d6c77 | CI.CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1>>CN1C=C[NH+](CCc2ccc(NS(C)(=O)=O)cc2)C1.[I-] | N1(C=NC=C1)CCC1=CC=C(C=C1)NS(=O)(=O)C.IC>>[I-].CN1C[NH+](C=C1)CCC1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][I:20].[n:2]1[cH:3][cH:4][n:5]([CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][S:13]([CH3:14])(=[O:15])=[O:16])[cH:17][cH:18]2)[cH:19]1>>[CH3:1][N:2]1[CH:3]=[CH:4][NH+:5]([CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][S:13]([CH3:14])(=[O:15])=[O:16])[cH:17][cH:18]2)[CH2:19]1.[I-:20] | CI.CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1 | CN1C=C[NH+](CCc2ccc(NS(C)(=O)=O)cc2)C1.[I-] | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 32965ddc6bb6823ee266c09a6be2c69531f43f0c3e42e160da364d8852910592 | 0e973515f9f7e54073d059763104290284f0f6fd900e82ab9e6c66160ee2e711 | C1=C[NH+](CCc2ccccc2)CN1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]-[C:4]-[n;H0;D3;+0:5]1:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1>>[C:3]-[C:4]-[NH+;D3:5]1-[CH2;D2;+0:6]-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[CH;D2;+0:8]=[CH;D2;+0:9]-1.[I-;H0;D0:2] | null | [] | null | null | null | null | Heat a mixture of 5 g (0.019 mole) of N-[4-[2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide, 5 mL of iodomethane and 25 mL of methanol in a pressure tube at 75° C. for about 24 hours. Cool the mixture to room temperature and remove the solvents in vacuo. Slurry the residue in acetone (50 mL) and filter and wash wit... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine | c1c[nH]cn1 | C1=C[NH+]C[NH]1 | C1=C[NH+]C[NH]1.c1ccccc1 | null | CO | null | null | CI.CS(=O)(=O)Nc1ccc(CCn2ccnc2)cc1>CO>CN1C=C[NH+](CCc2ccc(NS(C)(=O)=O)cc2)C1.[I-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9c952c876e5e4332a35b6f1b55bcb233 | CS(=O)(=O)Nc1ccc(CCn2ccnc2O)cc1>>CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1 | Cl.OC=1N(C=CN1)CCC1=CC=C(C=C1)NS(=O)(=O)C.C[O-].[Na+]>>OC(CN1C=NC=C1)C1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:12][n:13]2[cH:14][cH:15][n:16][c:17]2[OH:11])[cH:18][cH:19]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH:10]([OH:11])[CH2:12][n:13]2[cH:14][cH:15][n:16][cH:17]2)[cH:18][cH:19]1 | CS(=O)(=O)Nc1ccc(CCn2ccnc2O)cc1 | CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1 | null | null | CO | Miscellaneous | OtherReaction | 1763e158f5b6b8a342399a42bad5f4eb7bc3f82e5bebcc25b957a7ea5a15f932 | 061968087242247210331763a175366f5365580fa41e03eed87c9ba3d167230a | c1ccc(CCn2ccnc2)cc1 | [OH;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[OH;D1;+0:1]-[CH;D3;+0:8](-[C:7]-[#7;a:6]1:[c:5]:[c:4]:[#7;a:3]:[cH;D2;+0:2]:1)-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | Heat a mixture of 30.83 g (0.097 mole) of (±)-1-[2-hydroxy-2-[4-((methylsulfonyl)amino)phenyl]ethyl-1H-imidazole hydrochloride and 5.24 g (0.097 mole) of sodium methylate in 100 mL of methanol and filter hot through 300 g of alumina (Fisher, neutral, activity III). Wash the alumina with 20% methanol in methylene chlori... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Secondary alcohol | c1ncc[nH]1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | null | CO | null | null | CS(=O)(=O)Nc1ccc(CCn2ccnc2O)cc1>CO>CS(=O)(=O)Nc1ccc(C(O)Cn2ccnc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0ca5c9efb5e24a3793181b1d509ee238 | CCOC(=O)C(C(=O)OCC)C(C)(C)CCCCCCCCCCC(C)(C)C(C(=O)OCC)C(=O)OCC>>CC(C)(CCCCCCCCCCC(C)(C)CC(=O)O)CC(=O)O | C(C)OC(=O)C(C(CCCCCCCCCCC(C(C(=O)OCC)C(=O)OCC)(C)C)(C)C)C(=O)OCC.[OH-].[K+]>>CC(CC(=O)O)(CCCCCCCCCCC(CC(=O)O)(C)C)C | CCOC(=O)[CH:17]([C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[CH:21](C(=O)OCC)[C:22](=[O:23])[O:24]CC)([CH3:15])[CH3:16])[C:18](=[O:19])[O:20]CC>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:15])([C... | CCOC(=O)C(C(=O)OCC)C(C)(C)CCCCCCCCCCC(C)(C)C(C(=O)OCC)C(=O)OCC | CC(C)(CCCCCCCCCCC(C)(C)CC(=O)O)CC(=O)O | null | null | C(C)OCC | Reduction | OtherReaction | c66b299b40f3bbe41ba1575d603bfa618c1cfd61a8332cce6a45cf083197b05c | 710ca63f65f20afd2d083b70f6465deae8116e1dce84a7e30ca74e667dfb146a | null | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C)-[C:5](-[C:6])(-[C;D1;H3:7])-[C;D1;H3:8].C-C-O-C(=O)-[CH;D3;+0:9](-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-C-C)-[C:13](-[C:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[C:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:14]-[C:13]... | null | [] | null | null | null | null | A mixture of 17.0 g of the tetra-ester of Example 1 and 300 ml of a 25% aqueous KOH solution was heated in an oil bath to reflux temperature and the mixture was refluxed until the organic phase has completely disappeared (about 48 hours). The aqueous solution was then cooled to room temperature, extracted with ether, f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | null | HO- | C(C)OCC | null | null | CCOC(=O)C(C(=O)OCC)C(C)(C)CCCCCCCCCCC(C)(C)C(C(=O)OCC)C(=O)OCC>C(C)OCC>CC(C)(CCCCCCCCCCC(C)(C)CC(=O)O)CC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-145fe5702635444bbf4bf1aa20451280 | O=C(O)CC(CCC(=O)CCCCC(=O)CCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1>>O=C(O)CC(CCCCCCCCCCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(CC(=O)O)(CCC(CCCCC(CCC(CC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O)C1=CC=CC=C1.O.NN.[OH-].[K+]>>C1(=CC=CC=C1)C(CC(=O)O)(CCCCCCCCCCC(CC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | O=[C:8]([CH2:7][CH2:6][C:5]([CH2:4][C:2](=[O:1])[OH:3])([c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13](=O)[CH2:14][CH2:15][C:16]([CH2:17][C:18](=[O:19])[OH:20])([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][... | O=C(O)CC(CCC(=O)CCCCC(=O)CCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 | O=C(O)CC(CCCCCCCCCCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | O.C(COCCOCCO)O | Reduction | OtherReaction | 3437f16d0dd3b11b660197591cbb75aa04be8c11f375001f94aed07467d803aa | 6649363095331d33ffc4a587081bd0362ca141cb8f6a811c996a9356e6f05344 | c1ccc(C(CCCCCCCCCCC(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6](=O)-[C:7]-[C:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-[CH2;D2;+0:6]-[C:7]-[C:8] | 58 | [{"value": 58.0, "product": "C1(=CC=CC=C1)C(CC(=O)O)(CCCCCCCCCCC(CC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 0.27 g of 3,3,14,14-tetraphenyl-6,11-diketohexadecane-1,16-dioic acid prepared as described in Example 23 and 0.23 ml of 85% hydrazine hydrate were added to a solution of 0.4 g KOH in 10 ml of triethyleneglycol. The mixture was heated at 120° C. for 24 h, then heated to 195° C. with the evaporation of water followed by... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | O.C(COCCOCCO)O | 120 | null | O=C(O)CC(CCC(=O)CCCCC(=O)CCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1>O.C(COCCOCCO)O>O=C(O)CC(CCCCCCCCCCC(CC(=O)O)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-78276eeaba744eaabcd654099a62e06f | COC(=O)N1CCC(=O)C(C)C1.C[N+](=O)[O-]>>COC(=O)N1CC=C(C[N+](=O)[O-])C(C)C1 | CC1CN(CCC1=O)C(=O)OC.C(CN)N.[N+](=O)([O-])C>>CC1CN(CC=C1C[N+](=O)[O-])C(=O)OC | O=[C:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH:13]1[CH3:14].[CH3:9][N+:10](=[O:11])[O-:12]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH:7]=[C:8]([CH2:9][N+:10](=[O:11])[O-:12])[CH:13]([CH3:14])[CH2:15]1 | COC(=O)N1CCC(=O)C(C)C1.C[N+](=O)[O-] | COC(=O)N1CC=C(C[N+](=O)[O-])C(C)C1 | null | null | null | C-C Coupling | OtherReaction | 2d30abe5d929ae968f04050cad94efe1d8c00104f747873587301c7d85c7b868 | 04707d47c6d6b8f2f7722c07a7f221fd5b5734d3345e34e53c95ebad5e4e59e3 | C1=CCNCC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[#7:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]-1-[C;D1;H3:10].[CH3;D1;+0:11]-[#7;+:12](-[O;-;D1;H0:13])=[O;D1;H0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[#7:4]1-[C:8]-[C:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](-[CH2;D2;+0:11]-[#7;+:12](-[O;-;D1;H0:13])=[O;D1;H0:14])=[CH;D2;+0:2]-[C:3]-1 | 87.2 | [{"value": 87.2, "product": "CC1CN(CC=C1C[N+](=O)[O-])C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 64 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate, 305 parts of nitromethane and 3.02 parts of 1,2-ethanediamine was stirred and refluxed for 4 hours. The reaction mixture was evaporated. The residue was taken up in trichloromethane. The solution was washed twice with a dilute hydrochloric acid sol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Nitro group | C1CC[NH]CC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1 | HO- | null | null | null | COC(=O)N1CCC(=O)C(C)C1.C[N+](=O)[O-]>>COC(=O)N1CC=C(C[N+](=O)[O-])C(C)C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-72abaa3c2d9c442991cf635fc70be709 | CCOC(=O)N1CCC(=O)CC1.C[N+](=O)[O-]>>CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1 | O=C1CCN(CC1)C(=O)OCC.[N+](=O)([O-])C.C[O-].[Na+]>>OC1(CCN(CC1)C(=O)OCC)C[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH2:15][CH2:16]1.[CH3:11][N+:12](=[O:13])[O-:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C:9]([OH:10])([CH2:11][N+:12](=[O:13])[O-:14])[CH2:15][CH2:16]1 | CCOC(=O)N1CCC(=O)CC1.C[N+](=O)[O-] | CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1 | null | null | CO | C-C Coupling | Henry Reaction | b4bc771a3c4b2ab61f0ff05eb4e9a10f23529852e8464d6fe5f008137056d647 | b784cb10b22de077efeecdc9f77dadffa83c0aad754bce89e06fd63e3bb6c28a | C1CCNCC1 | [CH3;D1;+0:1]-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1>>[O;-;D1;H0:3]-[#7;+:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[C;H0;D4;+0:6]1(-[OH;D1;+0:5])-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1 | null | [] | null | null | 8 | HOUR | To a stirred and cooled mixture of 85.5 parts of ethyl 4-oxo-1-piperidinecarboxylate, 33.6 parts of nitromethane and 240 parts of methanol were added dropwise 10 parts of a sodium methoxide solution 30% at 10°~15° C. Upon completion, stirring was continued first for 2 hours at about 10° C. and further overnight at room... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Nitro group.Tertiary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | null | CO | null | 8 | CCOC(=O)N1CCC(=O)CC1.C[N+](=O)[O-]>CO>CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5ff753d9df04493ba4054e7e71de4b30 | CCOC(=O)N1CC=C(C[N+](=O)[O-])CC1>>CCOC(=O)N1CCC(CN)CC1 | N.[N+](=O)([O-])CC=1CCN(CC1)C(=O)OCC.[H][H]>>NCC1CCN(CC1)C(=O)OCC | O=[N+:11]([O-])[CH2:10][C:9]1=[CH:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:13][CH2:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][NH2:11])[CH2:12][CH2:13]1 | CCOC(=O)N1CC=C(C[N+](=O)[O-])CC1 | CCOC(=O)N1CCC(CN)CC1 | null | [Ni] | CO | Reduction | OtherReaction | 5889e730401aed00e40fafd9b46e5746f82f14df365183900a6f8d37eff473dc | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C1CCNCC1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C:5]-[#7:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-[C:11]-1>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7:6]1-[C:10]-[C:11]-[CH;D3;+0:3](-[C:2]-[NH2;D1;+0:1])-[CH2;D2;+0:4]-[C:5]-1 | 98.9 | [{"value": 98.9, "product": "NCC1CCN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 41 parts of ethyl 3,6-dihydro-4-(nitromethyl)-1(2H)-pyridinecarboxylate and 400 parts of methanol, saturated with ammonia, was hydrogenated at normal pressure and at room temperature with 6 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | C1=CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | [Ni].CO | null | null | CCOC(=O)N1CC=C(C[N+](=O)[O-])CC1>[Ni].CO>CCOC(=O)N1CCC(CN)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-446a94c66a0c4158844c2afd4599238d | CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1>>CCOC(=O)N1CCC(O)(CN)CC1 | OC1(CCN(CC1)C(=O)OCC)C[N+](=O)[O-].CO.[H][H]>>NCC1(CCN(CC1)C(=O)OCC)O | O=[N+:12]([O-])[CH2:11][C:9]1([OH:10])[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:14][CH2:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C:9]([OH:10])([CH2:11][NH2:12])[CH2:13][CH2:14]1 | CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1 | CCOC(=O)N1CCC(O)(CN)CC1 | null | [Pd] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C1CCNCC1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A mixture of 73 parts of ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate, 400 parts of methanol and 150 parts of acetic acid was hydrogenated in the Parr-apparatus with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filt... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1 | Other | [Pd].C(C)(=O)O | null | null | CCOC(=O)N1CCC(O)(C[N+](=O)[O-])CC1>[Pd].C(C)(=O)O>CCOC(=O)N1CCC(O)(CN)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e93f204559cf4920afe9669d4b4737e9 | CC(=O)N1CCC(CN)CC1.S=C=S>>CC(=O)N1CCC(CN=C=S)CC1 | C(=S)=S.C(C)(=O)N1CCC(CC1)CN>>C(C)(=O)N1CCC(CC1)CN=C=S | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH2:9])[CH2:12][CH2:13]1.S=[C:10]=[S:11]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][N:9]=[C:10]=[S:11])[CH2:12][CH2:13]1 | CC(=O)N1CCC(CN)CC1.S=C=S | CC(=O)N1CCC(CN=C=S)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 99faaca01b29bb4aacdf8b5dd838744c8a4a0ba5e793c41d71f6ab61fd987eaa | b4d1d5962cf9cde357eea1a492f332beb32c18a22c0b29a341204737bdcfdaa7 | C1CCNCC1 | S=[C;H0;D2;+0:1]=[S;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D2;+0:1]=[S;D1;H0:2] | 100 | [{"value": 100.0, "product": "C(C)(=O)N1CCC(CC1)CN=C=S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred and cooled (-10° C.) mixture of 41.6 parts of N,N'-methanetetraylbis[cyclohexanamine], 101 parts of carbon disulfide and 450 parts of tetrahydrofuran was added dropwise a solution of 31.2 parts of 1-acetyl-4-piperidinmethanamine in 90 parts of tetrahydrofuran. Upon completion, stirring was continued overni... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Isothiocyanate | null | null | C1CC[NH]CC1 | Other | O1CCCC1 | null | 8 | CC(=O)N1CCC(CN)CC1.S=C=S>O1CCCC1>CC(=O)N1CCC(CN=C=S)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1ab8dde909e448d38b66977ecfbc2c78 | CC(=O)N1CCC(CN=C=S)CC1.Nc1ccc(F)cc1>>CC(=O)N1CCC(CNC(=S)Nc2ccc(F)cc2)CC1 | C(C)(=O)N1CCC(CC1)CN=C=S.FC1=CC=C(C=C1)N>>C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC=C(C=C1)F | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][N:9]=[C:10]=[S:11])[CH2:20][CH2:21]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[S:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1 | CC(=O)N1CCC(CN=C=S)CC1.Nc1ccc(F)cc1 | CC(=O)N1CCC(CNC(=S)Nc2ccc(F)cc2)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | S=C(NCC1CCNCC1)Nc1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 100 | [{"value": 100.0, "product": "C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4 parts of 1-acetyl-4-(isothiocyanatomethyl)piperidine, 2.2 parts of 4-fluorobenzenamine and 90 parts of tetrahydrofuran was stirred overnight at reflux temperature. The reaction mixture was evaporated, yielding 6.2 parts (100%) of N-[(1-acetyl-4-piperidinyl)methyl]-N'-(4-fluorophenyl)thiourea as a residue... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | C1CC[NH]CC1.c1ccccc1 | null | O1CCCC1 | null | 8 | CC(=O)N1CCC(CN=C=S)CC1.Nc1ccc(F)cc1>O1CCCC1>CC(=O)N1CCC(CNC(=S)Nc2ccc(F)cc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b8d469ec02df442d9a9d4e4733d2e923 | CC(=O)N1CCC(CN)CC1.S=C=Nc1ccc(Cl)cc1>>CC(=O)N1CCC(CNC(=S)Nc2ccc(Cl)cc2)CC1 | C(C)(=O)N1CCC(CC1)CN.ClC1=CC=C(C=C1)N=C=S>>C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH2:9])[CH2:20][CH2:21]1.[C:10](=[S:11])=[N:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[S:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1 | CC(=O)N1CCC(CN)CC1.S=C=Nc1ccc(Cl)cc1 | CC(=O)N1CCC(CNC(=S)Nc2ccc(Cl)cc2)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | S=C(NCC1CCNCC1)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[S;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[S;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99.7 | [{"value": 99.7, "product": "C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 3.1 parts of 1-acetyl-4-piperidinemethanamine, 3.4 parts of 1-chloro-4-isothiocyanatobenzene and 90 parts of tetrahydrofuran was stirred for 3 hours at room temperature. The reaction mixture was evaporated, yielding 6.5 parts (99.7%) of N-[(1-acetyl-4-piperidinyl)methyl]-N'-(4-chlorophenyl)thiourea as a re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | C1CC[NH]CC1.c1ccccc1 | null | O1CCCC1 | null | 3 | CC(=O)N1CCC(CN)CC1.S=C=Nc1ccc(Cl)cc1>O1CCCC1>CC(=O)N1CCC(CNC(=S)Nc2ccc(Cl)cc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ee56261ae4364f3eb952ade8c36ca8dd | CC(=O)N1CCC(CNC(=S)Nc2ccccc2)CC1>>CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1 | C(C)O.C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC=CC=C1.ClC(Cl)(Cl)Cl.BrBr>>C(C)(=O)N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2 | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)=[S:18])[CH2:19][CH2:20]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[s:18]2)[CH2:19][CH2:20]1 | CC(=O)N1CCC(CNC(=S)Nc2ccccc2)CC1 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc2sc(NCC3CCNCC3)nc2c1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[S;H0;D1;+0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C:1]-[#7:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[s;H0;D2;+0:4]:1 | null | [] | null | null | null | null | To a stirred mixture of 5.8 parts of N-[(1-acetyl-4-piperidinyl)methyl]-N'-phenylthiourea and 160 parts of tetrachloromethane were added 3.7 parts of bromine. The whole was stirred and refluxed for 15 minutes. After the additions of 16 parts of ethanol and 16 parts of acetonitrile, the reaction mixture was cooled. The ... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | C1CC[NH]CC1.c1ccc2scnc2c1 | null | C(C)#N | null | null | CC(=O)N1CCC(CNC(=S)Nc2ccccc2)CC1>C(C)#N>CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d5e504cf6ef4230b04acc78d845b3d1 | BrBr.CC(=O)N1CCC(CNC(=S)Nc2ccc3c(c2)OCO3)CC1>>Br.c1c2c(cc3sc(NCC4CCNCC4)nc13)OCO2 | C(C)(=O)N1CCC(CC1)CNC(=S)NC1=CC2=C(OCO2)C=C1.Br.BrBr>>Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=C1C(=C2)OCO1 | Br[Br:2].CC(=O)[N:15]1[CH2:14][CH2:13][CH:12]([CH2:11][NH:10][C:9](=[S:8])[NH:18][c:19]2[cH:3][c:4]3[c:5]([cH:6][cH:7]2)[O:20][CH2:21][O:22]3)[CH2:17][CH2:16]1>>[BrH:2].[cH:3]1[c:4]2[c:5]([cH:6][c:7]3[s:8][c:9]([NH:10][CH2:11][CH:12]4[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]4)[n:18][c:19]13)[O:20][CH2:21][O:22]2 | BrBr.CC(=O)N1CCC(CNC(=S)Nc2ccc3c(c2)OCO3)CC1 | Br.c1c2c(cc3sc(NCC4CCNCC4)nc13)OCO2 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | b21aac40b9fa5db102a5f0ced2b27c262361293cdbbfa875470bd435c685e345 | 91b316de46b0059d06bca8c45d016b409246fcf8be4d5e8a003be4245d82d8e4 | c1c2c(cc3sc(NCC4CCNCC4)nc13)OCO2 | Br-[Br;H0;D1;+0:1].C-C(=O)-[N;H0;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6].[#8:7]-[c:8]:[c:9]:[cH;D2;+0:10]:[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[S;H0;D1;+0:14])-[#7:15]-[C:16]):[c:17]>>[#8:7]-[c:8]:[c:9]:[c;H0;D3;+0:10]1:[s;H0;D2;+0:14]:[c;H0;D3;+0:13](-[#7:15]-[C:16]):[n;H0;D2;+0:12]:[c:11]:1:[c:17].[C:4]-[C:3]-[NH;D2;+0:... | 58.4 | [{"value": 58.4, "product": "Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=C1C(=C2)OCO1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 33.3 parts of N-[(1-acetyl-4-piperidinyl)methyl]-N'-(1,3-benzodioxol-5-yl)thiourea, 112.5 parts of a hydrobromic acid solution 48% in water and 75 parts of water was stirred till all solid entered the solution. Then there were added 16 parts of bromine and stirring was continued overnight at reflux. After ... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Tertiary amide | Secondary amine | C1CC[NH]CC1.c1ccc2c(c1)OCO2 | C1CCNCC1.c1nc2cc3c(cc2s1)OCO3 | C1CCNCC1.c1nc2cc3c(cc2s1)OCO3 | HBr | O | null | 8 | BrBr.CC(=O)N1CCC(CNC(=S)Nc2ccc3c(c2)OCO3)CC1>O>Br.c1c2c(cc3sc(NCC4CCNCC4)nc13)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e394f3d7b4114983b64b840292c23c89 | CI.Nc1ncnc2sc(S)nc12>>CSc1nc2c(N)ncnc2s1 | [H-].[Na+].NC=1C2=C(N=CN1)SC(=N2)S.CN(C=O)C.IC>>CSC=1SC=2N=CN=C(C2N1)N | I[CH3:1].[SH:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][cH:9][n:10][c:11]2[s:12]1>>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][cH:9][n:10][c:11]2[s:12]1 | CI.Nc1ncnc2sc(S)nc12 | CSc1nc2c(N)ncnc2s1 | null | null | O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | cbeef1e4b9250d05ec80fbfc2f139c184e610b2c8de8aec4214044a1d69bd441 | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | c1ncc2ncsc2n1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]1:[#16;a:4]:[c:5](-[SH;D1;+0:6]):[#7;a:7]:[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:2]:[c:3]1:[#16;a:4]:[c:5](-[S;H0;D2;+0:6]-[CH3;D1;+0:1]):[#7;a:7]:[c:8]:1:[c:9]:[#7;a:10] | null | [] | null | null | 4 | HOUR | To a stirred and cooled (below 25° C.) mixture of 13.9 parts of 7-aminothiazolo[5,4-d]pyrimidin-2-thiol and 180 parts of N,N-dimethylformamide were added portionwise 4.3 parts of a sodium hydride dispersion 50% while cooling. After stirring for 1 hour, 11.5 parts of iodomethane were added dropwise at a temperature belo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | null | null | c1ncc2ncsc2n1 | HI | O | null | 4 | CI.Nc1ncnc2sc(S)nc12>O>CSc1nc2c(N)ncnc2s1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9e71969e97bc4104b9560ff69314f6e6 | CC(=O)N1CCC(CN)CC1.CSc1nc2cccnc2s1>>CC(=O)N1CCC(CNc2nc3cccnc3s2)CC1 | C(C)(=O)N1CCC(CC1)CN.CSC=1SC2=NC=CC=C2N1>>C(C)(=O)N1CCC(CC1)CNC=1SC2=NC=CC=C2N1 | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH2:9])[CH2:19][CH2:20]1.CS[c:10]1[n:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[s:18]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][n:16][c:17]3[s:18]2)[CH2:19][CH2:20]1 | CC(=O)N1CCC(CN)CC1.CSc1nc2cccnc2s1 | CC(=O)N1CCC(CNc2nc3cccnc3s2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 23be8ab067f9bcd8ca31730b1ce864559d67359a071482ff9cb09b381b50c384 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1cnc2sc(NCC3CCNCC3)nc2c1 | C-S-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:1 | 93 | [{"value": 93.0, "product": "C(C)(=O)N1CCC(CC1)CNC=1SC2=NC=CC=C2N1", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 11 parts of 1-acetyl-4-piperidinemethanamine and 9 parts of 2-(methylthio)thiazolo[5,4-b]pyridine was stirred and heated for 20 hours at 140° C. The whole was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions we... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2scnc2c1 | c1cnc2scnc2c1 | C1CC[NH]CC1.c1cnc2scnc2c1 | Other | null | 140 | null | CC(=O)N1CCC(CN)CC1.CSc1nc2cccnc2s1>>CC(=O)N1CCC(CNc2nc3cccnc3s2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8ac978557b4942dd8db7d2fbfc8ff579 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1.CI>>CC(=O)N1CCC(CN(C)c2nc3ccccc3s2)CC1 | IC.C(C)(=O)N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2.[H-].[Na+].CN(C=O)C>>C(C)(=O)N1CCC(CC1)CN(C)C=1SC2=C(N1)C=CC=C2 | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[s:19]2)[CH2:20][CH2:21]1.I[CH3:10]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][N:9]([CH3:10])[c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[s:19]2)[CH2:20][CH2:21]1 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1.CI | CC(=O)N1CCC(CN(C)c2nc3ccccc3s2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc2sc(NCC3CCNCC3)nc2c1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1 | 84 | [{"value": 84.0, "product": "C(C)(=O)N1CCC(CC1)CN(C)C=1SC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 8.7 parts of 1-acetyl-N-(2-benzothiazolyl)-4-piperidinemethanamine, 1.44 parts of a sodium hydride dispersion 60% and 270 parts of N,N-dimethylformamide was stirred for 1 hour at room temperature. 5.48 Parts of iodomethane were added dropwise slowly. Upon completion, stirring was continued overnight at roo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | C1CC[NH]CC1.c1ccc2scnc2c1 | HI | O | null | 1 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1.CI>O>CC(=O)N1CCC(CN(C)c2nc3ccccc3s2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c9b16aa6f74749a99eb7aab43a37c592 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1>>Br.c1ccc2sc(NCC3CCNCC3)nc2c1 | C(C)(=O)N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2.Br>>Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2 | CC(=O)[N:14]1[CH2:13][CH2:12][CH:11]([CH2:10][NH:9][c:8]2[s:7][c:6]3[cH:5][cH:4][cH:3][cH:19][c:18]3[n:17]2)[CH2:16][CH2:15]1>>[BrH:2].[cH:3]1[cH:4][cH:5][c:6]2[s:7][c:8]([NH:9][CH2:10][CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[n:17][c:18]2[cH:19]1 | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1 | Br.c1ccc2sc(NCC3CCNCC3)nc2c1 | null | null | O | Miscellaneous | Hydrogenolysis of tertiary amines | 9b929ebabc9d56e2ac499595af1f340b21610b5f71874bd02f1d8f46a982605e | 5ba542a97dd3ca917dd84dc29c99ae9b05b6ca96dbd806e22774484cf1a34b59 | c1ccc2sc(NCC3CCNCC3)nc2c1 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 79 | [{"value": 79.0, "product": "Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 140 parts of 1-acetyl-N-(2-benzothiazolyl)-4-piperidinemethanamine and 1500 parts of a hydrobromic acid solution 24% in water was stirred and refluxed for 5 hours. The reaction mixture was evaporated and the residue was suspended in boiling ethanol. After cooling, the product was filtered off and dried, yi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2scnc2c1.C1CCNCC1 | HO- | O | null | null | CC(=O)N1CCC(CNc2nc3ccccc3s2)CC1>O>Br.c1ccc2sc(NCC3CCNCC3)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-75690f0a653d4186828de4ecee7463a7 | Nc1ccccc1O.S=C=NCc1ccncc1>>Oc1ccccc1NC(=S)NCc1ccncc1 | N(=C=S)CC1=CC=NC=C1.NC1=C(C=CC=C1)O>>OC1=C(C=CC=C1)NC(=S)NCC1=CC=NC=C1 | [OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8].[C:9](=[S:10])=[N:11][CH2:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][C:9](=[S:10])[NH:11][CH2:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | Nc1ccccc1O.S=C=NCc1ccncc1 | Oc1ccccc1NC(=S)NCc1ccncc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | S=C(NCc1ccncc1)Nc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[C:8]-[c:9]>>[S;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[C:8]-[c:9])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | A mixture of 15 parts of 4-(isothiocyanatomethyl)pyridine, 9.5 parts of 2-aminophenol and 160 parts of acetonitrile was stirred for 3 hours at room temperature. The precipitated product was filtered off, washed with 2,2'-oxybispropane and crystallized from acetonitrile, yielding 8.22 parts of N-(2-hydroxyphenyl)-N'-(4-... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccncc1 | null | C(C)#N | null | 3 | Nc1ccccc1O.S=C=NCc1ccncc1>C(C)#N>Oc1ccccc1NC(=S)NCc1ccncc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1f8d4057264749fe934f5d65ae0c3eaf | Oc1ccccc1NC(=S)NCc1ccncc1>>c1ccc2oc(NCc3ccncc3)nc2c1 | OC1=C(C=CC=C1)NC(=S)NCC1=CC=NC=C1.[S].CC(C)O>>N1=CC=C(C=C1)CNC=1OC2=C(N1)C=CC=C2 | S=[C:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[NH:15][c:16]1[c:4]([OH:5])[cH:3][cH:2][cH:1][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]2[o:5][c:6]([NH:7][CH2:8][c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[n:15][c:16]2[cH:17]1 | Oc1ccccc1NC(=S)NCc1ccncc1 | c1ccc2oc(NCc3ccncc3)nc2c1 | null | [Hg]=O | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | e5161dad16ba0de611bb88bf71727cf43a1a35a2554fa1428c27f381c2392622 | 5b50b5990b44a3b8932dd42e9875f76813cd6ae8ffd0db2c3ea135be28fae54d | c1ccc2oc(NCc3ccncc3)nc2c1 | S=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:1 | 56 | [{"value": 56.0, "product": "N1=CC=C(C=C1)CNC=1OC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 14 parts of N-(2-hydroxyphenyl)-N'-(4-pyridinylmethyl)thiourea, 20 parts of mercury(II) oxide, 1 part of sulfur, 160 parts of 2-propanol and 160 parts of acetonitrile was stirred and refluxed for 14 hours. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The oily r... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Aromatic alcohol | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccncc1 | Other | [Hg]=O.C(C)#N | null | null | Oc1ccccc1NC(=S)NCc1ccncc1>[Hg]=O.C(C)#N>c1ccc2oc(NCc3ccncc3)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e920b357190a42caa0fed114a232849c | c1ccc2oc(NCc3ccncc3)nc2c1>>c1ccc2oc(NCC3CCNCC3)nc2c1 | N1=CC=C(C=C1)CNC=1OC2=C(N1)C=CC=C2.[H][H]>>N1CCC(CC1)CNC=1OC2=C(N1)C=CC=C2 | [cH:1]1[cH:2][cH:3][c:4]2[o:5][c:6]([NH:7][CH2:8][c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[n:15][c:16]2[cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]2[o:5][c:6]([NH:7][CH2:8][CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15][c:16]2[cH:17]1 | c1ccc2oc(NCc3ccncc3)nc2c1 | c1ccc2oc(NCC3CCNCC3)nc2c1 | null | null | CO | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2oc(NCC3CCNCC3)nc2c1 | [#7:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1>>[#7:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[NH;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1 | null | [] | null | null | null | null | A mixture of 4.5 parts of N-(4-pyridinylmethyl)-2-benzoxazolamine and 120 parts of methanol was hydrogenated at normal pressure at about 50° C. with 2 parts of rhodium-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 4... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | c1ccc2ocnc2c1.C1CCNCC1 | null | CO | null | null | c1ccc2oc(NCc3ccncc3)nc2c1>CO>c1ccc2oc(NCC3CCNCC3)nc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-254beb3cf13148c9862feb5a4f049125 | CC(=O)c1ccc(F)cc1O.ClCc1ccccc1>>CC(=O)c1ccc(F)cc1OCc1ccccc1 | FC1=CC(=C(C=C1)C(C)=O)O.ClCC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>FC1=CC(=C(C=C1)C(C)=O)OCC1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[OH:11].Cl[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(=O)c1ccc(F)cc1O.ClCc1ccccc1 | CC(=O)c1ccc(F)cc1OCc1ccccc1 | null | null | CC(C)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | 58 | [{"value": 58.0, "product": "FC1=CC(=C(C=C1)C(C)=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 13 parts of 1-(4-fluoro-2-hydroxyphenyl)ethanone, 14.9 parts of (chloromethyl)benzene, 16.4 parts of potassium carbonate, 0.1 parts of potassium iodide and 120 parts of 2-propanone was stirred overnight at reflux temperature. The reaction mixture was evaporated. The reaction mixture was poured into water. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | CC(C)=O | null | 8 | CC(=O)c1ccc(F)cc1O.ClCc1ccccc1>CC(C)=O>CC(=O)c1ccc(F)cc1OCc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0d9543b504514c609d822aa97a645569 | ClCCCBr.Oc1ccc(F)cc1OCc1ccccc1>>Fc1ccc(OCCCCl)c(OCc2ccccc2)c1 | [OH-].[Na+].FC1=CC(=C(C=C1)O)OCC1=CC=CC=C1.BrCCCCl>>ClCCCOC1=C(C=C(C=C1)F)OCC1=CC=CC=C1 | Br[CH2:7][CH2:8][CH2:9][Cl:10].[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][Cl:10])[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20]1 | ClCCCBr.Oc1ccc(F)cc1OCc1ccccc1 | Fc1ccc(OCCCCl)c(OCc2ccccc2)c1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | 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] | 100 | [{"value": 100.0, "product": "ClCCCOC1=C(C=C(C=C1)F)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | To a stirred mixture of 2.5 parts of 4-fluoro-2-(phenylmethoxy)phenol, 2.3 parts of 1-bromo-3-chloropropane, 10 parts of water and 0.39 parts of tetrabutylammonium hydrogen sulfate was added dropwise a solution of 0.7 parts of sodium hydroxide in 5 parts of D at 60° C. (exothermic reaction: temperature rose to 70°). Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | 70 | 2 | ClCCCBr.Oc1ccc(F)cc1OCc1ccccc1>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>Fc1ccc(OCCCCl)c(OCc2ccccc2)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8dcd6c4737cf4236a7025063f5be88e5 | NCC1CCN(CC2COc3ccccc3O2)CC1.O=Cc1ccc(F)cc1>>Fc1ccc(CNCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | [H][H].Br.Br.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CN.FC1=CC=C(C=O)C=C1.S1C=CC=C1.[O-2].[Ca+2]>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNCC2=CC=C(C=C2)F | [NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH:14]2[CH2:15][O:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[O:23]2)[CH2:24][CH2:25]1.O=[CH:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]3[CH2:15][O:16][c:17]4[cH:18]... | NCC1CCN(CC2COc3ccccc3O2)CC1.O=Cc1ccc(F)cc1 | Fc1ccc(CNCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 98.3 | [{"value": 98.3, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNCC2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinmethanamine dihydrobromide, 1.6 parts of 4-fluorobenzaldehyde, 3 parts of a solution of thiophene in methanol 4%, 200 parts of methanol and 4 parts of calcium oxide was hydrogenated at normal pressure and at room temperature with 2 parts of... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | Other | [Pd].CO | null | null | NCC1CCN(CC2COc3ccccc3O2)CC1.O=Cc1ccc(F)cc1>[Pd].CO>Fc1ccc(CNCC2CCN(CC3COc4ccccc4O3)CC2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b827a6a6c42e4114b2f5cab02191890a | CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1>>CC(N)C1CCN(CC2COc3ccccc3O2)CC1 | [H][H].O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(NCC2=CC=CC=C2)C>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(N)C | c1ccc(C[NH:3][CH:2]([CH3:1])[CH:4]2[CH2:5][CH2:6][N:7]([CH2:8][CH:9]3[CH2:10][O:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[O:18]3)[CH2:19][CH2:20]2)cc1>>[CH3:1][CH:2]([NH2:3])[CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[O:18]2)[CH2:19][CH2:20]1 | CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1 | CC(N)C1CCN(CC2COc3ccccc3O2)CC1 | null | [Pd] | CO | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc2c(c1)OCC(CN1CCCCC1)O2 | [C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4] | 80.4 | [{"value": 80.4, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 13.2 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-α-methyl-N-(phenylmethyl)-4-piperidinemethanamine and 160 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | Other | [Pd].CO | null | null | CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1>[Pd].CO>CC(N)C1CCN(CC2COc3ccccc3O2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ce4481d3c1e949b698e956653885160d | CC1(C2CCNCC2)OCCO1.OCC1COc2ccccc2O1>>CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1 | O1C(COC2=C1C=CC=C2)CO.CC1=CC=C(C=C1)S(=O)(=O)[O-].CC1(OCCO1)C1CCNCC1.C([O-])([O-])=O.[Na+].[Na+].CN(C(C)=O)C>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C2(OCCO2)C | [CH3:1][C:2]1([CH:3]2[CH2:4][CH2:5][NH:6][CH2:18][CH2:19]2)[O:20][CH2:21][CH2:22][O:23]1.O[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][C:2]1([CH:3]2[CH2:4][CH2:5][N:6]([CH2:7][CH:8]3[CH2:9][O:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[O:17]3)[CH2:18][CH2:19]2)[O:20][CH2:21][C... | CC1(C2CCNCC2)OCCO1.OCC1COc2ccccc2O1 | CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 511913fc601efdcc18555347fcfe0c2354215793b65f509995496ee3f61c9425 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc2c(c1)OCC(CN1CCC(C3OCCO3)CC1)O2 | O-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:6]-[C:5]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11])-[#8:3]-[c:4] | 100 | [{"value": 100.0, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C2(OCCO2)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 22.5 parts of 2,3-dihydro-1,4-benzodioxin-2-methanol 4-methylbenzenesulfonate (ester), 11.1 parts of 4-(2-methyl-1,3-dioxolan-2-yl)piperidine, 15 parts of sodium carbonate and 135 parts of N,N-dimethylacetamide was stirred overnight at 75° C. Water was added. The product was extracted with 4-methyl-2-penta... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)OCCO2.C1COCO1 | HO- | O | 75 | 8 | CC1(C2CCNCC2)OCCO1.OCC1COc2ccccc2O1>O>CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6e6cbc22abe547e39f9456ddca12ca59 | CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1>>CC(=O)C1CCN(CC2COc3ccccc3O2)CC1 | [OH-].[Na+].O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C2(OCCO2)C.Cl>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(C)=O | C1C[O:3][C:2]([CH3:1])([CH:4]2[CH2:5][CH2:6][N:7]([CH2:8][CH:9]3[CH2:10][O:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[O:18]3)[CH2:19][CH2:20]2)O1>>[CH3:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[O:18]2)[CH2:19][CH2:20]1 | CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1 | CC(=O)C1CCN(CC2COc3ccccc3O2)CC1 | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | c1ccc2c(c1)OCC(CN1CCCCC1)O2 | [C:1]-[C:2](-[C;H0;D4;+0:3]1(-[C;D1;H3:4])-O-C-C-[O;H0;D2;+0:5]-1)-[C:6]>>[C:1]-[C:2](-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5])-[C:6] | 55.8 | [{"value": 55.8, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 20.6 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-(2-methyl-1,3-dioxolan-2-yl)piperidine and 200 parts of a hydrochloric acid solution 2N was stirred and refluxed for 15 hours. After cooling, crushed ice was added. The whole was treated with a sodium hydroxide solution. The product was extracted... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CC1(C2CCN(CC3COc4ccccc4O3)CC2)OCCO1>>CC(=O)C1CCN(CC2COc3ccccc3O2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9ef0208a4e5b43b2b7f150bae866db41 | CC(=O)C1CCN(CC2COc3ccccc3O2)CC1.NCc1ccccc1>>CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1 | [H][H].O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(C)=O.C1(=CC=CC=C1)CN.S1C=CC=C1>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(NCC2=CC=CC=C2)C | O=[C:2]([CH3:1])[CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH:16]2[CH2:17][O:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[O:25]2)[CH2:26][CH2:27]1.[NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][CH:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH:16]2[CH2:17]... | CC(=O)C1CCN(CC2COc3ccccc3O2)CC1.NCc1ccccc1 | CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:4]-[C:3](-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:6]-[C:7]-[c:8])-[C:5] | 100 | [{"value": 100.0, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(NCC2=CC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10 parts of 1-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]ethanone, 3.8 part of benzenemethanamine, 1 part of a solution of thiophene in methanol 4% and 160 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calc... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | Other | [Pd].CO | null | null | CC(=O)C1CCN(CC2COc3ccccc3O2)CC1.NCc1ccccc1>[Pd].CO>CC(NCc1ccccc1)C1CCN(CC2COc3ccccc3O2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c88b668ea68341bc8637a8183b3a01fe | BrCC1COc2ccccc2O1.CC(=O)NCC1CCNCC1>>CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1 | BrCC1COC2=C(O1)C=CC=C2.C(C)(=O)O.N1CCC(CC1)CNC(C)=O.C([O-])([O-])=O.[Na+].[Na+].[I-].[Na+]>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC(C)=O | Br[CH2:10][CH:11]1[CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20]1.[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:21][CH2:22]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][CH:11]2[CH2:12][O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[O:20]2)[CH2:21][CH2:22]1 | BrCC1COc2ccccc2O1.CC(=O)NCC1CCNCC1 | CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1 | null | null | O.CN(C(C)=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)OCC(CN1CCCCC1)O2 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:6]-[C:5]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11])-[#8:3]-[c:4] | 21 | [{"value": 21.0, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 12.6 parts of 2-(bromomethyl)-2,3-dihydro-1,4-benzodioxin, 11 parts of N-(4-piperidinylmethyl)acetamide acetate (1:1), 15 parts of sodium carbonate, 0.1 parts of sodium iodide and 135 parts of N,N-dimethylacetamide was stirred overnight at 75° C. The reaction mixture was poured into water. The product was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | HBr | O.CN(C(C)=O)C | 75 | 8 | BrCC1COc2ccccc2O1.CC(=O)NCC1CCNCC1>O.CN(C(C)=O)C>CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-665d6e5a8cd442d9a9c1be826d85823b | CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1>>Br.NCC1CCN(CC2COc3ccccc3O2)CC1 | O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC(C)=O.Br>>Br.Br.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CN | CC(=O)[NH:3][CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH:10]2[CH2:11][O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[O:19]2)[CH2:20][CH2:21]1>>[BrH:2].[NH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH:10]2[CH2:11][O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[O:19]2)[CH2:20][CH2:21]1 | CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1 | Br.NCC1CCN(CC2COc3ccccc3O2)CC1 | null | null | O | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 707d862673494df308d0498876d0cad3507dbc14401d385dbef5e48e25cb04ab | 9a852660e38a73253f286565bb98edc48afeded5895ee8b4d0c2bc8a5eeae729 | c1ccc2c(c1)OCC(CN1CCCCC1)O2 | C-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 4 | HOUR | A mixture of 2 parts of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]acetamide, 15 parts of a hydrobromic acid solution 48% in water and 10 parts of water was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated. The residue was crystallized from a mixture of ethanol a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | HO- | O | null | 4 | CC(=O)NCC1CCN(CC2COc3ccccc3O2)CC1>O>Br.NCC1CCN(CC2COc3ccccc3O2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-14205214171c4d26b4456f89ea25af7d | COc1ccc(N=C=S)cc1.NCC1CCN(CC2COc3ccccc3O2)CC1>>COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | Br.Br.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CN.[O-2].[Ca+2].N(=C=S)C1=CC=C(C=C1)OC>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC(=S)NC2=CC=C(C=C2)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]=[S:9])[cH:29][cH:30]1.[NH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH:17]2[CH2:18][O:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[O:26]2)[CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[S:9])[NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH... | COc1ccc(N=C=S)cc1.NCC1CCN(CC2COc3ccccc3O2)CC1 | COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | S=C(NCC1CCN(CC2COc3ccccc3O2)CC1)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[S;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[S;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 3 | HOUR | A mixture of 6.4 parts of (1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromide, 4 parts of calcium oxide and 80 parts of methanol was stirred for 3 hours at room temperature. Then there were added 5 parts of 1-isothiocyanato-4-methoxybenzene and the whole was stirred for 3 hours at room ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | null | CO | null | 3 | COc1ccc(N=C=S)cc1.NCC1CCN(CC2COc3ccccc3O2)CC1>CO>COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cedeedf2881343c2aac2758f88e3644b | BrCC1COc2ccccc2O1.c1ccc2sc(NCC3CCNCC3)nc2c1>>c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | BrCC1COC2=C(O1)C=CC=C2.Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2.C([O-])([O-])=O.[Na+].[Na+].[I-].[Na+]>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=CC=C1 | Br[CH2:10][CH:9]1[CH2:8][O:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)[O:28]1.[NH:11]1[CH2:12][CH2:13][CH:14]([CH2:15][NH:16][c:17]2[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[s:25]2)[CH2:26][CH2:27]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][CH:9]([CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][NH:16][c:1... | BrCC1COc2ccccc2O1.c1ccc2sc(NCC3CCNCC3)nc2c1 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:6]-[C:5]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11])-[#8:3]-[c:4] | null | [] | 70 | CELSIUS | 48 | HOUR | A mixture of 3.8 parts of 2-(bromomethyl)-2,3-dihydro-1,4-benzodioxin, 6.3 parts of N-(4-piperidinylmethyl)-2-benzothiazolamine dihydrobromide, 10 parts of sodium carbonate, 0.1 parts of sodium iodide and 68 parts of N,N-dimethylformamide was stirred for 48 hours at 70° C. The reaction mixture was poured into water and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)OCCO2.C1CC[NH]CC1.c1ccc2scnc2c1 | HBr | O.CN(C=O)C | 70 | 48 | BrCC1COc2ccccc2O1.c1ccc2sc(NCC3CCNCC3)nc2c1>O.CN(C=O)C>c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-29a97bcfac644df88361595b25c59427 | BrCC1COc2ccccc2O1.Clc1ccc2nc(NCC3CCNCC3)sc2c1>>Clc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 | BrCC1COC2=C(O1)C=CC=C2.Br.Br.ClC1=CC2=C(N=C(S2)NCC2CCNCC2)C=C1.C([O-])([O-])=O.[Na+].[Na+].[I-].[Na+]>>ClC1=CC2=C(N=C(S2)NCC2CCN(CC2)CC2COC3=C(O2)C=CC=C3)C=C1 | Br[CH2:14][CH:15]1[CH2:16][O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[O:24]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][CH2:9][CH:10]3[CH2:11][CH2:12][NH:13][CH2:25][CH2:26]3)[s:27][c:28]2[cH:29]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][CH2:9][CH:10]3[CH2:11][CH2:12][N:13]([CH2:14][CH:15]4[CH2:16][O:... | BrCC1COc2ccccc2O1.Clc1ccc2nc(NCC3CCNCC3)sc2c1 | Clc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 | null | null | CN(C(C)=O)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:6]-[C:5]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11])-[#8:3]-[c:4] | 59.8 | [{"value": 59.8, "product": "ClC1=CC2=C(N=C(S2)NCC2CCN(CC2)CC2COC3=C(O2)C=CC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 1.9 parts of 2-(bromomethyl)-2,3-dihydro-1,4-benzodioxin, 3.3 parts of 6-chloro-N-(4-piperidinylmethyl)-2-benzothiazolamine dihydrobromide, 5 parts of sodium carbonate, 0.1 parts of sodium iodide and 67.5 parts of N,N-dimethylacetamide was stirred overnight at about 75° C. Water was added to the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2scnc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | HBr | CN(C(C)=O)C.O | 75 | 8 | BrCC1COc2ccccc2O1.Clc1ccc2nc(NCC3CCNCC3)sc2c1>CN(C(C)=O)C.O>Clc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b15535aa13964aff82f7738b038b6fa8 | Fc1ccc(OCCCCl)c(OCc2ccccc2)c1.c1ccc2sc(NCC3CCNCC3)nc2c1>>Fc1ccc(OCCCN2CCC(CNc3nc4ccccc4s3)CC2)c(OCc2ccccc2)c1 | ClCCCOC1=C(C=C(C=C1)F)OCC1=CC=CC=C1.Br.Br.N1CCC(CC1)CNC=1SC2=C(N1)C=CC=C2.C([O-])([O-])=O.[Na+].[Na+].[I-].[Na+]>>FC1=CC(=C(OCCCN2CCC(CC2)CNC=2SC3=C(N2)C=CC=C3)C=C1)OCC1=CC=CC=C1 | Cl[CH2:9][CH2:8][CH2:7][O:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:36][c:27]1[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.[NH:10]1[CH2:11][CH2:12][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[s:24]2)[CH2:25][CH2:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]... | Fc1ccc(OCCCCl)c(OCc2ccccc2)c1.c1ccc2sc(NCC3CCNCC3)nc2c1 | Fc1ccc(OCCCN2CCC(CNc3nc4ccccc4s3)CC2)c(OCc2ccccc2)c1 | null | null | CN(C(C)=O)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(COc2ccccc2OCCCN2CCC(CNc3nc4ccccc4s3)CC2)cc1 | Cl-[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] | 65.2 | [{"value": 65.2, "product": "FC1=CC(=C(OCCCN2CCC(CC2)CNC=2SC3=C(N2)C=CC=C3)C=C1)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 3.2 parts of 1-(3-chloropropoxy)-4-fluoro-2-(phenylmethoxy)benzene, 4.1 parts of N-(4-piperidinylmethyl)-2-benzothiazolamine dihydrobromide, 6 parts of sodium carbonate, 0.1 parts of sodium iodide and 67.5 parts of N,N-dimethylacetamide was stirred overnight at 75° C. Water was added and the product was ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C(C)=O)C.O | 75 | 8 | Fc1ccc(OCCCCl)c(OCc2ccccc2)c1.c1ccc2sc(NCC3CCNCC3)nc2c1>CN(C(C)=O)C.O>Fc1ccc(OCCCN2CCC(CNc3nc4ccccc4s3)CC2)c(OCc2ccccc2)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e5b173451e7142968c31ab748f8e6b09 | CC(=O)N(C)C.COc1cc2nc(NCC3CCNCC3)sc2c(OC)c1OC.CS(=O)(=O)OCC1COc2ccccc2O1.O=C([O-])[O-]>>COc1cc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c(OC)c1OC.O=C(O)/C=C/C(=O)O | CS(=O)(=O)OCC1COC2=C(O1)C=CC=C2.COC=1C(=C(C2=C(N=C(S2)NCC2CCNCC2)C1)OC)OC.C([O-])([O-])=O.[Na+].[Na+].CN(C(C)=O)C>>C(\C=C\C(=O)O)(=O)O.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=C(C(=C1OC)OC)OC | CN(C)[C:40]([CH3:39])=[O:41].[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([NH:8][CH2:9][CH:10]3[CH2:11][CH2:12][NH:13][CH2:25][CH2:26]3)[s:27][c:28]2[c:29]([O:30][CH3:31])[c:32]1[O:33][CH3:34].O=S(=O)([CH3:38])[O:42][CH2:14][CH:15]1[CH2:16][O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[O:24]1.[O-][C:36](=[O:35])[O-:37]>>... | CC(=O)N(C)C.COc1cc2nc(NCC3CCNCC3)sc2c(OC)c1OC.CS(=O)(=O)OCC1COc2ccccc2O1.O=C([O-])[O-] | COc1cc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c(OC)c1OC.O=C(O)/C=C/C(=O)O | null | null | O | C-C Coupling | OtherReaction | c0b9b32cc0d0e92c4a163b6990a02d376ad04552d535ae7e12787c7251090f66 | fc8c326d38ab0e2894800f133c978339a31cf8467e0f147ca1c863a787660d0f | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | C-N(-C)-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].O=S(=O)(-[CH3;D1;+0:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[C:7](-[#8:8]-[c:9])-[C:10]-[#8:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16].[O-;H0;D1:17]-[C;H0;D3;+0:18](-[O-])=[O;D1;H0:19]>>[#8:11]-[C:10]-[C:7](-[CH2;D2;+0:6]-[N;H0;D3;+0:14](-[C:13]-[C:12])-[C:15]-[C:16])-[#8:... | 48.5 | [{"value": 48.5, "product": "C(\\C=C\\C(=O)O)(=O)O.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=C(C(=C1OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 2.8 parts of 2,3-dihydro-1,4-benzodioxin-2-methanol methanesulfonate (ester), 3.4 parts of 5,6,7-trimethoxy-N-(4-piperidinylmethyl)-2-benzothiazolamine, 3 parts of sodium carbonate and 67.5 parts of N,N-dimethylacetamide was stirred overnight at about 75° C. Water was added. The product was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Tertiary amide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2scnc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | MsOH.HO- | O | 75 | 8 | CC(=O)N(C)C.COc1cc2nc(NCC3CCNCC3)sc2c(OC)c1OC.CS(=O)(=O)OCC1COc2ccccc2O1.O=C([O-])[O-]>O>COc1cc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c(OC)c1OC.O=C(O)/C=C/C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0701af8e90954ddcb99b613811caad29 | CS(=O)(=O)c1nc2cnccc2s1.NCC1CCN(CC2COc3ccccc3O2)CC1>>c1ccc2c(c1)OCC(CN1CCC(CNc3nc4cnccc4s3)CC1)O2 | Br.Br.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CN.CS(=O)(=O)C=1SC2=C(C=NC=C2)N1.C([O-])([O-])=O.[Na+].[Na+]>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(C=NC=C1)N2 | CS(=O)(=O)[c:17]1[n:18][c:19]2[cH:20][n:21][cH:22][cH:23][c:24]2[s:25]1.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][CH:9]([CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][NH2:16])[CH2:26][CH2:27]1)[O:28]2>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][CH:9]([CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][N... | CS(=O)(=O)c1nc2cnccc2s1.NCC1CCN(CC2COc3ccccc3O2)CC1 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4cnccc4s3)CC1)O2 | null | null | CN(C(C)=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 66df03e7c79caa9950bf46712c3292329d3797faeace235d09531e13fa57c7e8 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4cnccc4s3)CC1)O2 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4](:[#7;a:5]:1):[c:6]:[#7;a:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:7]:[c:6]:[c:4]1:[#7;a:5]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:9]-[C:8]):[#16;a:2]:[c:3]:1 | 20 | [{"value": 20.0, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(C=NC=C1)N2", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 2 | HOUR | A mixture of 6.7 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromide, 3.26 parts of 2-(methylsulfonyl)thiazolo[4,5-c]pyridine, 4.25 parts of sodium carbonate and 18 parts of N,N-dimethylacetamide was stirred for 2 hours at 150° C. The reaction mixture was poured into ice water. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cc2scnc2cn1 | c1cc2scnc2cn1 | c1ccc2c(c1)OCCO2.C1CC[NH]CC1.c1cc2scnc2cn1 | HO- | CN(C(C)=O)C | 150 | 2 | CS(=O)(=O)c1nc2cnccc2s1.NCC1CCN(CC2COc3ccccc3O2)CC1>CN(C(C)=O)C>c1ccc2c(c1)OCC(CN1CCC(CNc3nc4cnccc4s3)CC1)O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-45b8253e9c01479cbece5ecd18a962aa | CC(=O)N(C)C.CC(N)C1CCN(CC2COc3ccccc3O2)CC1.Clc1nc2ccccc2s1.[O-2]>>CC(Nc1nc2ccccc2s1)C1CCN(CC2COc3ccccc3O2)CC1.O=C(O)C(=O)O | O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(N)C.ClC=1SC2=C(N1)C=CC=C2.[O-2].[Ca+2].CN(C(C)=O)C>>C(C(=O)O)(=O)O.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(C)NC=2SC1=C(N2)C=CC=C1 | CN(C)[C:33]([CH3:31])=[O:34].[CH3:1][CH:2]([NH2:3])[CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH:18]2[CH2:19][O:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[O:27]2)[CH2:28][CH2:29]1.Cl[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[s:12]1.[O-2:30]>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[s... | CC(=O)N(C)C.CC(N)C1CCN(CC2COc3ccccc3O2)CC1.Clc1nc2ccccc2s1.[O-2] | CC(Nc1nc2ccccc2s1)C1CCN(CC2COc3ccccc3O2)CC1.O=C(O)C(=O)O | null | null | null | Acylation | OtherReaction | 0c8075d2d1fe29c7f41c41bf76a14390f86cda55b48fbbc231d49ce5c010f6d7 | ea2fa6358c9b24db3f2c985013e3a1847fb8d9c8a280d7bd27f4a04a4b83c055 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | C-N(-C)-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].Cl-[c;H0;D3;+0:4]1:[#16;a:5]:[c:6]:[c:7]:[#7;a:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12].[O-2;H0;D0:13]>>[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[c;H0;D3;+0:4]1:[#16;a:5]:[c:6]:[c:7]:[#7;a:8]:1.[O;D1;H0:3]=[C;H0;D3;+0:1](-[O;D1;H1:14])-[C;H0;D3;+0:2](-[O;D1;H1:... | 39.7 | [{"value": 39.7, "product": "C(C(=O)O)(=O)O.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)C(C)NC=2SC1=C(N2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 4 | HOUR | A mixture of 4 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-α-methyl-4-piperidinemethanamine, 2.7 parts of 2-chlorobenzothiazole, 1.5 parts of calcium oxide and 18 parts of N,N-dimethylacetamide was stirred for 4 hours at 140° C. The whole was filtered and to the filtrate was added 4-methyl-2-pentanone. The wh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | HCl | null | 140 | 4 | CC(=O)N(C)C.CC(N)C1CCN(CC2COc3ccccc3O2)CC1.Clc1nc2ccccc2s1.[O-2]>>CC(Nc1nc2ccccc2s1)C1CCN(CC2COc3ccccc3O2)CC1.O=C(O)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8448f9365305453fbaf740a187d7bdeb | CI.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2>>CN(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 | IC.CN(C=O)C.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=CC=C1.CN(C=O)C.[H-].[Na+]>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CN(C=2SC1=C(N2)C=CC=C1)C | I[CH3:1].[NH:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[O:18]2)[CH2:19][CH2:20]1)[c:21]1[n:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[s:29]1>>[CH3:1][N:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][cH:16]... | CI.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | CN(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1 | null | [] | null | null | 30 | MINUTE | To a stirred solution of 11.85 parts of N-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinylmethyl]-2-benzothiazolamine in 72 parts of N,N-dimethylformamide were added portionwise 1.5 parts of a sodium hydride dispersion 50%. Upon completion, stirring was continued for 30 minutes. A solution of 4.6 parts of io... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | C1CC[NH]CC1.c1ccc2c(c1)OCCO2.c1ccc2scnc2c1 | HI | O | null | 0.5 | CI.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2>O>CN(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3c011460876e45b6b5bb44988893edcf | O=C(O)c1ccco1.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2>>Cl.O=C(c1ccco1)N(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 | O1C(=CC=C1)C(=O)O.C(C)N(CC)CC.O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=CC=C1.[I-].ClC1=[N+](C=CC=C1)C>>Cl.S1C(=NC2=C1C=CC=C2)N(C(=O)C=2OC=CC2)CC2CCN(CC2)CC2COC1=C(O2)C=CC=C1 | O[C:3](=[O:2])[c:4]1[cH:5][cH:6][cH:7][o:8]1.[NH:9]([CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH:16]2[CH2:17][O:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[O:25]2)[CH2:26][CH2:27]1)[c:28]1[n:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[s:36]1>>[ClH:1].[O:2]=[C:3]([c:4]1[cH:5][cH:6][cH:7][o:8]1)[N:9]([CH2:10][C... | O=C(O)c1ccco1.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | Cl.O=C(c1ccco1)N(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 | null | null | ClCCl.O.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccco1)N(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6])-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1 | 41.8 | [{"value": 41.8, "product": "Cl.S1C(=NC2=C1C=CC=C2)N(C(=O)C=2OC=CC2)CC2CCN(CC2)CC2COC1=C(O2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred mixture of 1.12 parts of 2-furancarboxylic acid, 2.02 parts of N,N-diethylethanamine and 195 parts of dichloromethane were added 2.55 parts of 2-chloro-1-methylpyridinium iodide. Stirring was continued for 30 minutes at room temperature. A solution of 3.93 parts of N-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccoc1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2.c1ccc2scnc2c1 | null | ClCCl.O.O1CCCC1 | null | 0.5 | O=C(O)c1ccco1.c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2>ClCCl.O.O1CCCC1>Cl.O=C(c1ccco1)N(CC1CCN(CC2COc3ccccc3O2)CC1)c1nc2ccccc2s1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d2176593c0e7446f81b8b594876307c6 | COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1>>COc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 | [OH-].[Na+].O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC(=S)NC2=CC=C(C=C2)OC.ClC(Cl)Cl.BrBr>>O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=CC(=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][CH:16]3[CH2:17][O:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[O:25]3)[CH2:26][CH2:27]2)=[S:28])[cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][CH2:10][CH:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH:... | COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1 | COc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 | null | null | ClC(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc2c(c1)OCC(CN1CCC(CNc3nc4ccccc4s3)CC1)O2 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[S;H0;D1;+0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C:1]-[#7:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[s;H0;D2;+0:4]:1 | 21 | [{"value": 21.0, "product": "O1C(COC2=C1C=CC=C2)CN2CCC(CC2)CNC=2SC1=C(N2)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred mixture of 8.3 parts of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N'-(4-methoxyphenyl)thiourea, 60 parts of trichloromethane and 240 parts of tetrachloromethane were added at once 3.1 parts of bromine. The whole was stirred and refluxed for 1 hour. After cooling, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCCO2 | null | ClC(Cl)(Cl)Cl | null | null | COc1ccc(NC(=S)NCC2CCN(CC3COc4ccccc4O3)CC2)cc1>ClC(Cl)(Cl)Cl>COc1ccc2nc(NCC3CCN(CC4COc5ccccc5O4)CC3)sc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0786b25dde1d411a93033313798ab033 | CCC(CCCCCl)OC.ClC1C=CCC1>>CCC(CCCCC1C=CCC1)OC | ClC1C=CCC1.[Cl-].[NH4+].[Mg].ClCCCCC(CC)OC>>COC(CCCCC1C=CCC1)CC | Cl[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:13][CH3:14].Cl[CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1)[O:13][CH3:14] | CCC(CCCCCl)OC.ClC1C=CCC1 | CCC(CCCCC1C=CCC1)OC | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1 | null | [] | -25 | CELSIUS | null | null | Magnesium metal turnings (7.2 g, 0.299 moles) are added to a three-necked, round-bottomed flask equipped with a Friedrich condenser and kept under nitrogen gas. Tetrahydrofuran (300 ml) is transferred to the flask and the contents stirred. A clear, colorless solution of 1-chloro-5-methoxyheptane (48.1 g, 0.292 moles) i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Other | O1CCCC1 | -25 | null | CCC(CCCCCl)OC.ClC1C=CCC1>O1CCCC1>CCC(CCCCC1C=CCC1)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c21ededa198241be8bfe0a31117ca8c5 | CCC(CCCCC1C=CCC1)OC.CCCCCC.CCCCCC.CCN(CC)CC.O=C(Cl)C(Cl)Cl>>CCC(CCC(C)C12CCCC1C(=O)C2(Cl)Cl)OC.CCC(CCCCC1CCC2C(=O)C(Cl)(Cl)C12)OC.CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC | ClC(C(=O)Cl)Cl.COC(CCCCC1C=CCC1)CC.CCCCCC.C(C)N(CC)CC.CCCCCC>>ClC1(C2CCC(C2C1=O)CCCCC(CC)OC)Cl.ClC1(C(C2CCCC12C(C)CCC(CC)OC)=O)Cl.ClC1(C(C2CCC(C12)CCCCC(CC)OC)=O)Cl | [CH3:39][CH2:40][CH:41]([CH2:42][CH2:43][CH2:44][CH2:45][CH:46]1[CH2:47][CH2:48][CH:49]=[CH:50]1)[O:56][CH3:57].[CH2:3]([CH2:4][CH2:5][CH2:6][CH3:7])[CH3:12].[CH3:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].N([CH2:2][CH3:1])([CH2:26][CH3:27])[CH2:53][CH3:51].[C:13](=[O:14])([CH:15]([Cl:16])[Cl:17])[Cl:34]>>[CH3:1][CH2:... | CCC(CCCCC1C=CCC1)OC.CCCCCC.CCCCCC.CCN(CC)CC.O=C(Cl)C(Cl)Cl | CCC(CCC(C)C12CCCC1C(=O)C2(Cl)Cl)OC.CCC(CCCCC1CCC2C(=O)C(Cl)(Cl)C12)OC.CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC | null | null | null | C-C Coupling | OtherReaction | 9f73c275c1d2644e37d7ac436393a1d4820702c5ea292d9ac31e9749814026ce | 619721e0a1ae47aa4c59b8686b40ef843f5a95b0374e4d345c70e6b8b4761eae | O=C1CC2CCCC12.O=C1CC2CCCC12.O=C1CC2CCCC12 | [C;D1;H3:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C;D1;H3:7]-[CH2;D2;+0:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[CH3;D1;+0:12].[C;D1;H3:13]-[C:14]-[CH2;D2;+0:15]-[C:16]-[C:17]-[CH3;D1;+0:18].[C:19]-[C:20]1-[C:21]-[C:22]-[CH;D2;+0:23]=[CH;D2;+0:24]-1.[Cl;D1;H0:25]-[CH;D3;+0:26](-[Cl;D1;H0:27]... | null | [] | null | null | null | null | To a 1,000 ml three-necked, round-bottomed flask, equipped with a reflux condenser containing 3-(5-methoxyhept-1-yl)cyclopentene {3-(5-methoxyheptyl)cyclopentene} (15.0 g, 0.076 moles) in 300 ml of hexane, freshly distilled dichloroacetyl chloride (35.1 g, 0.240 moles) is added and the solution is stirred by a mechanic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Secondary halide.Tertiary amine | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ketone.Ketone.Ketone.Ether.Ether | C1=CCCC1 | C1CC2CCC2C1.C1CC2CCC2C1.C1CC2CCC2C1 | C1CC2CCC2C1.C1CC2CCC2C1.C1CC2CCC2C1 | null | null | null | null | CCC(CCCCC1C=CCC1)OC.CCCCCC.CCCCCC.CCN(CC)CC.O=C(Cl)C(Cl)Cl>>CCC(CCC(C)C12CCCC1C(=O)C2(Cl)Cl)OC.CCC(CCCCC1CCC2C(=O)C(Cl)(Cl)C12)OC.CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f0be817ce3d042319adc6ba51ba5d29c | CCC(O)CCCC(=O)O.CCOC(OCC)OCC>>CCOC(=O)CCCC(CC)OCC | OC(CCCC(=O)O)CC.C(C)C1CCCC(O1)=O.[OH-].[Na+].Cl(=O)(=O)(=O)O.S(O)(O)(=O)=O.C(C)OC(OCC)OCC.C(C)OC(OCC)OCC>>C(C)OC(CCCC(=O)OCC)CC | [OH:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH:9]([CH2:10][CH3:11])[OH:12].CCOC(O[CH2:2][CH3:1])O[CH2:13][CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH:9]([CH2:10][CH3:11])[O:12][CH2:13][CH3:14] | CCC(O)CCCC(=O)O.CCOC(OCC)OCC | CCOC(=O)CCCC(CC)OCC | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a367edd36e7a6d4fc8bcf7d6eeb3291b269bea15b3edbb95c515f2124c66dff5 | bcb571b9242e6612bdc8f209381b773bf471f4584cc3238291f772a3f2b72931 | null | C-C-O-C(-O-[CH2;D2;+0:1]-[C;D1;H3:2])-O-[CH2;D2;+0:3]-[C;D1;H3:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8].[C:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2].[C:9]-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH2;D2;+0:3]-[C;D1;H3:4] | null | [] | null | null | 4 | HOUR | A mixture of 400 g 5-hydroxyheptanoic acid and 6-ethyltetrahydro-2H-pyran-2-one (400 g) is added to the reaction vessel containing ethanol (4000 ml) and triethylorthoformate (4000 ml). Perchloric acid (160 ml) is slowly added. The mixture is stirred at room temperature for 4 hours, after which time sodium hydroxide pel... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Ether.Secondary alcohol | Ester.Ether | null | null | null | HO- | C(C)O | null | 4 | CCC(O)CCCC(=O)O.CCOC(OCC)OCC>C(C)O>CCOC(=O)CCCC(CC)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4e55915b9af54cf3b59fbf584e4c51f2 | CCOC(=O)CCCC(CC)OCC>>CCOC(CC)CCCCO | C(C)OC(CCCC(=O)OCC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)OC(CCCCO)CC | CCO[C:10]([CH2:9][CH2:8][CH2:7][CH:4]([O:3][CH2:2][CH3:1])[CH2:5][CH3:6])=[O:11]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11] | CCOC(=O)CCCC(CC)OCC | CCOC(CC)CCCCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | -60 | CELSIUS | null | null | A solution of tetrahydrofuran (2000 ml) containing lithium aluminum hydride (46 g, 1.21 moles) is cooled in a -60° C. dry ice/ethanol bath. Ethyl 5-ethoxyheptanoate (302 g, 1.49 moles) is diluted in tetrahydrofuran (300 ml) and added dropwise to the stirring reaction. After the addition is complete the reaction is warm... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | HO- | O1CCCC1 | -60 | null | CCOC(=O)CCCC(CC)OCC>O1CCCC1>CCOC(CC)CCCCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-848bac7c24cc4261bb2073abefd468c5 | CCOC(CC)CCCCO.O=S(Cl)Cl>>CCOC(CC)CCCCCl | C(C)OC(CCCCO)CC.N1=CC=CC=C1.S(=O)(Cl)Cl>>ClCCCCC(CC)OCC | O[CH2:10][CH2:9][CH2:8][CH2:7][CH:4]([O:3][CH2:2][CH3:1])[CH2:5][CH3:6].O=S(Cl)[Cl:11]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][Cl:11] | CCOC(CC)CCCCO.O=S(Cl)Cl | CCOC(CC)CCCCCl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | 75.8 | [{"value": 75.8, "product": "ClCCCCC(CC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Ethoxyheptanol (238 g, 1.49 moles) is diluted in pyridine (128 g, 1.62 moles). The solution is stirred at room temperature and thionyl chloride (388 g, 3.22 moles) is added dropwise over 2 hours. After this time the mixture is heated in a 70° C. water bath for 2 additional hours. Water (700 ml) is added to the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | null | HCl | O | null | null | CCOC(CC)CCCCO.O=S(Cl)Cl>O>CCOC(CC)CCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40763d3e96f8401aa86089cd7aca46a8 | CCCCCCCBr.ClC1C=CCC1>>CCCCCCCC1C=CCC1 | [Mg].ClC1C=CCC1.BrCCCCCCC>>C(CCCCCC)C1C=CCC1 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].Cl[CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1 | CCCCCCCBr.ClC1C=CCC1 | CCCCCCCC1C=CCC1 | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1 | 51.8 | [{"value": 51.8, "product": "C(CCCCCC)C1C=CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure followed is the same as that described in Example 20 substituting 1-bromoheptane (100 g, 0.56 moles) diluted in tetrahydrofuran (100 ml), granular magnesium (25 g) in tetrahydrofuran (100 ml), 0.1 M solution of Li2CuCl4 (1.7 mmoles), and 3-chlorocyclopentene (57 g, 0.56 moles) diluted in tetrahydrofuran (... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Br- | O1CCCC1 | null | null | CCCCCCCBr.ClC1C=CCC1>O1CCCC1>CCCCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-829aaf2fa95e4efd9138f91fff56f06b | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl>>CCC(CCCl)O[Si](C)(C)CC(C)C | CN(C=O)C.ClCCC(CC)O.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>ClCCC(CC)O[Si](C)(C)CC(C)C | Cl[Si:8]([CH3:9])([CH3:10])[C:12]([CH3:11])([CH3:13])[CH3:14].[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][Cl:6])[OH:7]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][Cl:6])[O:7][Si:8]([CH3:9])([CH3:10])[CH2:11][CH:12]([CH3:13])[CH3:14] | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl | CCC(CCCl)O[Si](C)(C)CC(C)C | null | null | null | Protection | OtherReaction | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].[C:8]-[C:9](-[C:10])-[OH;D1;+0:11]>>[C:8]-[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH2;D2;+0:7]-[CH;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 19 substituting 5-chloropentan-3-ol (1-chloro-3-pentanol) (50 g, 0.41 moles), tert-butyldimethylsilyl chloride (71 g, 0.47 moles), imidazole (32.6 g, 0.48 moles), and dimethylformamide (150 ml). The crude product is fractionally distilled under vacuum leav... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | null | HCl | null | null | null | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl>>CCC(CCCl)O[Si](C)(C)CC(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-12c3c2d8e2cb4fb682b0b5844f5c681d | CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C.ClC1C=CCC1>>CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C.CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C | [Mg].ClC1C=CCC1.ClCCC(O[Si](C)(C)C(C)(C)C)CC.ClCCC(CC)O[Si](C)(C)CC(C)C>>C1(C=CCC1)CCC(O[Si](C)(C)C(C)(C)C)CC.CC(C)(C)[Si](OC(CCC1C=CCC1)CC)(C)C | Cl[CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:18])[CH3:36].Cl[CH2:23][CH2:22][CH:21]([CH2:20][CH3:19])[O:29][Si:30]([CH3:17])([CH3:28])[CH2:33][CH:35]([CH3:26])[CH3:27].Cl[CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][C... | CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C.ClC1C=CCC1 | CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C.CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | f7fbeb208eeb150a59a3d1aaf4d167c0f98de0c3a124ab5c5e2cdd448e417190 | 0dd17fb8382e7be43ae3d3a371180bc22450eab508f050be2cb0fdda2faeb419 | C1=CCCC1.C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:11].Cl-[CH2;D2;+0:12]-[C:13]-[C:14]-[#8:15]-[Si;H0;D4;+0:16](-[CH3;D1;+0:17])(-[CH3;D1;+0:18])-[CH2;D2;+0:19]-[CH;D3;+0:20](-[CH3;D1;+0:21])-[CH3;D1;+0:22].Cl-[CH;D3;+0:23]1-[C:24]-[C:25]-[C:26... | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 20 substituting (5-chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl) dimethylsilane,} (78 g, 0.33 moles) diluted in tetrahydrofuran (100 ml), granular magnesium (24 g, 1.00 moles) in tetrahydrofuran (100 ml),... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide.Primary halide.TMS ether protective group.Silyl protective group | TMS ether protective group.TMS ether protective group | C1=CCCC1 | C1=CCCC1.C1=CCCC1 | C1=CCCC1.C1=CCCC1 | null | O1CCCC1 | null | null | CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C.ClC1C=CCC1>O1CCCC1>CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C.CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-70d1a100986c414c97318dea1fbc40ac | CC(C)(C)[Si](C)(C)Cl.CN(C)C=O.OCCCCCCl.c1c[nH]cn1>>CC(C)(C)[Si](C)(C)OCCCCCCl.CC(C)C[Si](C)(C)OCCCCCCl | N1C=NC=C1.ClCCCCCO.[Si](C)(C)(C(C)(C)C)Cl.CN(C=O)C>>ClCCCCCO[Si](C)(C)C(C)(C)C.ClCCCCCO[Si](C)(C)CC(C)C | [CH3:1][C:2]([CH3:3])([Si:5]([CH3:6])([CH3:7])[Cl:28])[CH3:17].N([CH3:4])([CH:23]=[O:22])[CH3:26].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14].n1[cH:24][cH:25][nH][cH:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14].[CH3:15][CH:16]([CH3:17])[CH2:18]... | CC(C)(C)[Si](C)(C)Cl.CN(C)C=O.OCCCCCCl.c1c[nH]cn1 | CC(C)(C)[Si](C)(C)OCCCCCCl.CC(C)C[Si](C)(C)OCCCCCCl | null | null | O | C-C Coupling | OtherReaction | 362b97bd308e1674d119f00f7193eb661001ec8b391ea68feb0fdd105b74f0a6 | 41459d5f85371d21209ad2e99e4133e1a13552dd3bfaa7e9511c73964195a9b6 | null | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[Si;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[Cl;H0;D1;+0:8].[CH3;D1;+0:9]-N(-[CH3;D1;+0:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12].[C:13]-[C:14]-[OH;D1;+0:15].[cH;D2;+0:16]1:[cH;D2;+0:17]:[nH]:[cH;D2;+0:18]:n:1>>[C;D1;H3:19]-[C:20](-[CH3;D1;+0:4])-[C:21]-[#14:22](-[C;D1;... | null | [] | null | null | 6 | HOUR | 5-Chloropentanol (325 g, 2.65 moles) is added to a solution containing tert-butyldimethylsilyl chloride (439 g, 2.91 moles) and dimethylformamide (1.625 liters). Imidazole (199 g, 2.91 moles) is added in one portion and the solution is stirred at room temperature for 6 hours, after which time water (1 liter) is added a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary alcohol.Silyl protective group | Primary halide.TMS ether protective group.Silyl protective group | c1c[nH]cn1 | null | null | null | O | null | 6 | CC(C)(C)[Si](C)(C)Cl.CN(C)C=O.OCCCCCCl.c1c[nH]cn1>O>CC(C)(C)[Si](C)(C)OCCCCCCl.CC(C)C[Si](C)(C)OCCCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-572be6f88f034fd7920d4ba2775bac75 | CCC(CC=O)C1CC=CC1.O=CCCCCC1C=CCC1>>CCC(O)CCCCC1C=CCC1 | C=1CC(CC1)C(CC=O)CC.C(C)[Mg]Br.S(O)(O)(=O)=O.C1(C=CCC1)CCCCC=O>>OC(CCCCC1C=CCC1)CC | O=CCC(C1CC=CC1)[CH2:2][CH3:1].[CH:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1 | CCC(CC=O)C1CC=CC1.O=CCCCCC1C=CCC1 | CCC(O)CCCCC1C=CCC1 | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | f5b623078728746259c96d8d7e10451b72e36bdaf1d0f607dd894f0c133668e9 | a8a096ebbde9746ae0a48228da6e8add5c1838f16988a8681e93e688f2c97cf9 | C1=CCCC1 | O=C-C-C(-[CH2;D2;+0:1]-[C;D1;H3:2])-C1-C-C=C-C-1.[C:3]-[C:4]-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[C:3]-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | -30 | CELSIUS | null | null | All work is performed an inert atmosphere using anhydrous tetrahydrofuran. The starting material, 3-(5-cyclopenten-3-yl) valeraldehyde {2-cyclopentene-1-pentanal} (75 g, 0.493 moles) is diluted in tetrahydrofurar (750 ml) and cooled in a -30° C. ethanol/dry ice bath. Ethyl magnesium bromide (0.493 moles) is added dropw... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Secondary alcohol | C1=CCCC1 | null | C1=CCCC1 | HO- | O1CCCC1.O | -30 | null | CCC(CC=O)C1CC=CC1.O=CCCCCC1C=CCC1>O1CCCC1.O>CCC(O)CCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ff888ae3a7c44055b46ba6e76b9b5081 | CC(C)(C)[Si](C)(C)Cl.OCCCCCl>>CC(C)C[Si](C)(C)OCCCCCl | CN(C=O)C.ClCCCCO.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>ClCCCCO[Si](C)(C)CC(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13]>>[CH3:1][CH:2]([CH3:3])[CH2:4][Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13] | CC(C)(C)[Si](C)(C)Cl.OCCCCCl | CC(C)C[Si](C)(C)OCCCCCl | null | null | null | Protection | OtherReaction | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH2;D2;+0:7]-[CH;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 19 substituting 4-chlorobutanol (326 g, 3.00 moles), tert-butyldimethylsilyl chloride (500 g, 3.31 moles), imidazole (225 g, 3.30 mmoles), and dimethylformamide (1600 ml). The crude product is fractionally distilled under reduced vacuum leaving a clear, co... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | null | HCl | null | null | null | CC(C)(C)[Si](C)(C)Cl.OCCCCCl>>CC(C)C[Si](C)(C)OCCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7706b324198043e6ac6221284bfb46e7 | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1>>OCCCCC1C=CCC1 | C1(C=CCC1)CCCCO[Si](C)(C)C(C)(C)C.F>>OCCCCC1C=CCC1 | CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1 | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1 | OCCCCC1C=CCC1 | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 23 substituting 3-(5-[(1,1-dimethylethyl)dimethylsiloxyl]but-1-yl)cyclopentene {[4-(2-cyclopenten-1-yl)butoxy](1,1-dimethylethyl)dimethylsilane} (100 g, 0.407 moles), 5% hydrofluoric acid (78 ml), and acetonitrile (1500 ml). The crude product is kugelrohre... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | C1=CCCC1 | Other | C(C)#N | null | null | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1>C(C)#N>OCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4312836202594ea2b2a1aafcadb9333b | CS(=O)(=O)Cl.OCCCCC1C=CCC1>>ClCCCCC1C=CCC1 | OCCCCC1C=CCC1.N1=CC=CC=C1.CS(=O)(=O)Cl>>ClCCCCC1C=CCC1 | CS(=O)(=O)[Cl:1].O[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1 | CS(=O)(=O)Cl.OCCCCC1C=CCC1 | ClCCCCC1C=CCC1 | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | C1=CCCC1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | 3-(4-Hydroxybut-1-yl)cyclopentene {2-cyclopentene-1-butanol} (51 g, 0.37 moles) is diluted in dimethylformamide (100 ml) and added to pyridine (38 g, 0.40 moles). The solution is stirred and methanesulfonyl chloride (46 g, 0.40 moles) is added dropwise over 10 minutes. The reaction is partitioned between hexane (500 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | C1=CCCC1 | HO- | CN(C=O)C | null | null | CS(=O)(=O)Cl.OCCCCC1C=CCC1>CN(C=O)C>ClCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1925490ceb67467592872507621e072d | CCC=O.ClCCCCC1C=CCC1>>CCC(O)CCCCC1C=CCC1 | C(CC)=O.ClCCCCC1C=CCC1.[Mg].O.ClCCCCC1C=CCC1>>OC(CCCCC1C=CCC1)CC | [CH3:1][CH2:2][CH:3]=[O:4].Cl[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1 | CCC=O.ClCCCCC1C=CCC1 | CCC(O)CCCCC1C=CCC1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | 983d8b8e9b89ba290d93feeffe843caf411eba49bd1aefb21a784058d86f3a30 | 3e80fe0b4a87df3724831714de4ab23fef101254d00d9b3074e300e6e8f4b9ea | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6](-[OH;D1;+0:7])-[C:5]-[C;D1;H3:4] | null | [] | 0 | CELSIUS | null | null | All reactions are carried out under an inert atmosphere. 3-(4-Chlorobut-1-yl)cyclopentene {3-(4-chlorobutyl)cyclopentene} (43 g, 0.27 moles) is diluted in tetrahydrofuran (50 ml) and added dropwise to a stirred, refluxing solution of tetrahydrofuran (200 ml) containing granular magnesium (30 g, 1.25 moles). After the a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Secondary alcohol | null | null | C1=CCCC1 | Other | O1CCCC1 | 0 | null | CCC=O.ClCCCCC1C=CCC1>O1CCCC1>CCC(O)CCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-658d441f736741cb9c772b3cd708c096 | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>>CCC(CCCCC1CCC2CC(=O)CC12)OC | ClC1(C2CCC(C2CC1=O)CCCCC(CC)OC)Cl>>COC(CCCCC1C2CC(CC2CC1)=O)CC | Cl[C:12]1(Cl)[CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:17][CH3:18])[CH:16]2[CH2:15][C:13]1=[O:14]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12)[O:17][CH3:18] | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC | CCC(CCCCC1CCC2CC(=O)CC12)OC | null | [Zn].[Cl-].[Cl-].[Zn+2] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | 96adc8577184d4d7f9d08648c84f095e8cfcbb983c5ca7b6ef569e3540d5d72d | 1a16202f689fbcf4c49583e05a4736360fc884dbe7bf9b78f3063aeae48ae6e3 | O=C1CC2CCCC2C1 | Cl-[C;H0;D4;+0:1]1(-Cl)-[C:2](-[C:3])-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7]>>[C:3]-[C:2]1-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | 6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichlorohexahydro-4-(5-methoxyheptyl)-2(lH)-pentalenone} or the isomer (45.9 g) are added to a single-neck 100 ml, round-bottom flask equipped with a condenser. The solution is stirred by a magnetic stirrer and powdered zinc metal (92 g) and glacial acet... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Ketone | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | [Zn].[Cl-].[Cl-].[Zn+2].C(C)(=O)O | null | null | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>[Zn].[Cl-].[Cl-].[Zn+2].C(C)(=O)O>CCC(CCCCC1CCC2CC(=O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a0fb30ee3b2c41b0b02c77836884e130 | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC>>CCC(CCCCC1CCC2CC(=O)C12)OC | ClC1(C2CCC(C2C1=O)CCCCC(CC)OC)Cl>>COC(CCCCC1C2C(CC2CC1)=O)CC | Cl[C:12]1(Cl)[CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:16][CH3:17])[CH:15]2[C:13]1=[O:14]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH:15]12)[O:16][CH3:17] | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC | CCC(CCCCC1CCC2CC(=O)C12)OC | null | [Zn] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | bfc3e020573e20351ad68954934065203460bc52bee5735cde0606376ab375d3 | 1a16202f689fbcf4c49583e05a4736360fc884dbe7bf9b78f3063aeae48ae6e3 | O=C1CC2CCCC12 | Cl-[C;H0;D4;+0:1]1(-Cl)-[C:2](-[C:3])-[C:4]-[C:5]-1=[O;D1;H0:6]>>[C:3]-[C:2]1-[C:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:1]-1 | null | [] | null | null | 1 | HOUR | Zinc (3 g) is added to a stirred solution of 6,6-dichloro-2(5-methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one} (2 g, 6 moles) in acetic acid (100 ml) under a nitrogen atmosphere. The solution is stirred at room temperature for one hour, then refluxed for 13 hours, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Ketone | C1CC2CCC2C1 | C1CC2CCC2C1 | C1CC2CCC2C1 | Other | [Zn].C(C)(=O)O | null | 1 | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC>[Zn].C(C)(=O)O>CCC(CCCCC1CCC2CC(=O)C12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b4f3d8c616a4a45ba2bbc193e565046 | CCC(CCCCC1CCC2CC(=O)CC12)OC>>CCC(CCCCC1CCC2CC(C)(O)CC12)OC | COC(CCCCC1C2CC(CC2CC1)=O)CC.COC(CCCCC1C2CC(CC2CC1)=O)CC.C(C)[Mg]Br>>COC(CCCCC1C2CC(CC2CC1)(O)C)CC | [CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:15])[CH2:16][CH:17]12)[O:18][CH3:19]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13]([CH3:14])([OH:15])[CH2:16][CH:17]12)[O:18][CH3:19] | CCC(CCCCC1CCC2CC(=O)CC12)OC | CCC(CCCCC1CCC2CC(C)(O)CC12)OC | null | null | CCOCC.C(C)OCC | Miscellaneous | OtherReaction | 1ecd181abde8298e671a9f4f1de0a680fd98e618629b4139d000f7403ddf00cd | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | C1CC2CCCC2C1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1>>[C;D1;H3:7]-[C;H0;D4;+0:2]1(-[OH;D1;+0:1])-[C:3]-[C:4]-[C:5]-[C:6]-1 | 39.9 | [{"value": 39.9, "product": "COC(CCCCC1C2CC(CC2CC1)(O)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone, (4 g, 0.0158 moles) diluted in ether is added dropwise to a stirring solution of ethyl magnesium bromide (0.0158 moles) dissolved with diethyl ether. The mixture is cooled in an ice bath during the addition. The ice bath is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | CCOCC.C(C)OCC | null | null | CCC(CCCCC1CCC2CC(=O)CC12)OC>CCOCC.C(C)OCC>CCC(CCCCC1CCC2CC(C)(O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-59112f48b25e446cb302058979b54590 | CCC(CCCCCl)OC.ClC1C=CCC1>>CCC(CCCCC1C=CCC1)OC | ClCCCCC(CC)OC.[Cl-].[NH4+].[Mg].ClC1C=CCC1>>COC(CCCCC1C=CCC1)CC | Cl[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:13][CH3:14].Cl[CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1)[O:13][CH3:14] | CCC(CCCCCl)OC.ClC1C=CCC1 | CCC(CCCCC1C=CCC1)OC | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1 | null | [] | -25 | CELSIUS | null | null | A three-neck, round-bottomed flask containing magnesium metal turnings (7.2 g, 0.299 moles), is equipped with a Friedrich condenser and kept under a nitrogen atmosphere. Tetrahydrofuran (300 ml) is added and the contents are allowed to stir. A solution of 1-chloro-5-methoxyheptane (48.1 g, 0.292 moles) is added in smal... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Other | O1CCCC1 | -25 | null | CCC(CCCCCl)OC.ClC1C=CCC1>O1CCCC1>CCC(CCCCC1C=CCC1)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-463df9a7378c4be6b53eb256f879c341 | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC>>CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC | ClC1(C2CCC(C2C1=O)CCCCC(CC)OC)Cl.[OH-].[K+].[N+](=[N-])=C.CN(S(=O)(=O)C1=CC=C(C=C1)C)N=O.[N+](=[N-])=C.ClC1(C(C2C(CCC12)CCCCC(CC)OC)=O)Cl>>ClC1(C2CCC(C2CC1=O)CCCCC(CC)OC)Cl | [CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH:12]1[C:14](=[O:15])[C:16]2([Cl:17])[Cl:18])[O:19][CH3:20]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH:12]1[CH2:13][C:14](=[O:15])[C:16]2([Cl:17])[Cl:18])[O:19][CH3:20] | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC | null | null | CCOCC.C(C)(=O)O.C(C)O | Miscellaneous | OtherReaction | 97d98f33c73f2831bc5bd487ce5dea0447a55d13adc3d8dc0ef940f61adf4799 | f394080031812a9c0cde55fa330311dfe42bea38dbdf0b4621700859838ffa32 | O=C1CC2CCCC2C1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[CH;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-2(-[Cl;D1;H0:10])-[Cl;D1;H0:11]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[CH;D3;+0:6]-1-[C:12]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-2(-[Cl;D1;H0:10])-[Cl;D1;H0:11] | null | [] | null | null | null | null | The starting material, 6,6-dichloro-2-(5-methoxyhept-1-yl) bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-(5-methoxyheptyl)bicyclo [3.2.0]heptan-6-one} (5 g), is dissolved in 100 ml of ether and transferred to a 500 ml, round-bottomed flask. An excess of diazomethane is generated in situ by reacting N-methyl-N-nitroso-p-to... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1CC2CCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | CCOCC.C(C)(=O)O.C(C)O | null | null | CCC(CCCCC1CCC2C1C(=O)C2(Cl)Cl)OC>CCOCC.C(C)(=O)O.C(C)O>CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7f3ea532b31d44c58d8e70e3fda794e9 | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>>CCC(CCCCC1CCC2CC(=O)CC12)OC | ClC1(C2CCC(C2CC1=O)CCCCC(CC)OC)Cl>>COC(CCCCC1C2CC(CC2CC1)=O)CC | Cl[C:12]1(Cl)[CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:17][CH3:18])[CH:16]2[CH2:15][C:13]1=[O:14]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12)[O:17][CH3:18] | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC | CCC(CCCCC1CCC2CC(=O)CC12)OC | null | [Zn] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | 96adc8577184d4d7f9d08648c84f095e8cfcbb983c5ca7b6ef569e3540d5d72d | 1a16202f689fbcf4c49583e05a4736360fc884dbe7bf9b78f3063aeae48ae6e3 | O=C1CC2CCCC2C1 | Cl-[C;H0;D4;+0:1]1(-Cl)-[C:2](-[C:3])-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7]>>[C:3]-[C:2]1-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | 6,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichlorohexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (45.9 g) is added to a 100 ml, round-bottomed flask fitted with a condenser. Powdered zinc metal (92 g) and glacial acetic acid (312 ml) are added to the flask and the solution allowed to reflux fo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Ketone | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | [Zn].C(C)(=O)O | null | null | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>[Zn].C(C)(=O)O>CCC(CCCCC1CCC2CC(=O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc943bb8137844e696e7511318aca43f | CCOC(CC)CCCCC1CCC2C1C(=O)C2(Cl)Cl>>CCOC(CC)CCCCC1CCC2C1CC(=O)C2(Cl)Cl | ClC1(C2CCC(C2C1=O)CCCCC(CC)OCC)Cl.C(C)OC(CCCCC1C=CCC1)CC.ClC1(C(C2C(CCC12)CCCCC(CC)OCC)=O)Cl.[N+](=[N-])=C.ClCCCCC(CC)OCC>>ClC1(C2CCC(C2CC1=O)CCCCC(CC)OCC)Cl | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH:14]2[CH:15]1[C:17](=[O:18])[C:19]2([Cl:20])[Cl:21]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH:14]2[CH:15]1[CH2:16][C:17](=[O:18])[C:19]2([Cl:20])[Cl:21] | CCOC(CC)CCCCC1CCC2C1C(=O)C2(Cl)Cl | CCOC(CC)CCCCC1CCC2C1CC(=O)C2(Cl)Cl | null | null | null | Miscellaneous | OtherReaction | 97d98f33c73f2831bc5bd487ce5dea0447a55d13adc3d8dc0ef940f61adf4799 | f394080031812a9c0cde55fa330311dfe42bea38dbdf0b4621700859838ffa32 | O=C1CC2CCCC2C1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[CH;D3;+0:6]-1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-2(-[Cl;D1;H0:10])-[Cl;D1;H0:11]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[CH;D3;+0:6]-1-[C:12]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-2(-[Cl;D1;H0:10])-[Cl;D1;H0:11] | null | [] | null | null | null | null | The corresponding 2-(5-ethoxyhept-1-yl) homologs are prepared by substituting an equivalent amount of 1-chloro-5-ethoxyheptane in the Grignard reaction of Example 1 in place of the 5-methoxy homolog and using the reaction sequence shown above to prepare first the 3-(5-ethoxyhept-1-yl)cyclopentene, which is then convert... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1CC2CCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | null | null | null | CCOC(CC)CCCCC1CCC2C1C(=O)C2(Cl)Cl>>CCOC(CC)CCCCC1CCC2C1CC(=O)C2(Cl)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f7eb1d9de728438c9f42db028e332833 | CCC(CCCCC1CCC2CC(=O)CC12)OC>>CCC(CCCCC1CCC2CC(C)(O)CC12)OC | COC(CCCCC1C2CC(CC2CC1)=O)CC.C(C)[Mg]Br>>COC(CCCCC1C2CC(CC2CC1)(O)C)CC | [CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:15])[CH2:16][CH:17]12)[O:18][CH3:19]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13]([CH3:14])([OH:15])[CH2:16][CH:17]12)[O:18][CH3:19] | CCC(CCCCC1CCC2CC(=O)CC12)OC | CCC(CCCCC1CCC2CC(C)(O)CC12)OC | null | null | CCOCC.C(C)OCC | Miscellaneous | OtherReaction | 1ecd181abde8298e671a9f4f1de0a680fd98e618629b4139d000f7403ddf00cd | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | C1CC2CCCC2C1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1>>[C;D1;H3:7]-[C;H0;D4;+0:2]1(-[OH;D1;+0:1])-[C:3]-[C:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | 2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (4 g, 0.0158 moles) diluted in ether is added dropwise to a stirring solution of ethyl magnesium bromide (0.0158 moles) dissolved with diethyl ether. The mixture is cooled in an ice bath during the addition. The ice bath i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | CCOCC.C(C)OCC | null | null | CCC(CCCCC1CCC2CC(=O)CC12)OC>CCOCC.C(C)OCC>CCC(CCCCC1CCC2CC(C)(O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bed3dee93a03496f83549f0ad35d1929 | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>>CCC(CCCCC1CCC2CC(O)CC12)OC | ClC1(C2CCC(C2CC1=O)CCCCC(CC)OC)Cl.ClC1(C2CCC(C2CC1O)CCCCC(CC)OC)Cl>>COC(CCCCC1C2CC(CC2CC1)O)CC | Cl[C:12]1(Cl)[CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:17][CH3:18])[CH:16]2[CH2:15][C:13]1=[O:14]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([OH:14])[CH2:15][CH:16]12)[O:17][CH3:18] | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC | CCC(CCCCC1CCC2CC(O)CC12)OC | null | [Zn] | C(C)(=O)O | Reduction | OtherReaction | 351c9b612406ce72847eab727b7250c3b9dbfef2aaf513caea6ec04764d30901 | 842aa4ebb60cfc8e76502bd50f3e0d33e0dc5566b03c89a81de612990dca6c8c | C1CC2CCCC2C1 | Cl-[C;H0;D4;+0:1]1(-Cl)-[C:2](-[C:3])-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=[O;H0;D1;+0:7]>>[C:3]-[C:2]1-[C:4]-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | The reactions of this example can also be conducted using an equivalent amount of 6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo [3.3.0]octan-7-one {1-1-dichlorohexahydro-4-(5-methoxyheptyl)-2 (1H)-pentalenone} to first prepare 6,6-dichloro-2-(5-methoxyhept-1-yl) bicyclo[3.3.0]octan-7-ol {1,1-dichlorooctahydro-4-(5-methoxy... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone | Secondary alcohol | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | [Zn].C(C)(=O)O | null | null | CCC(CCCCC1CCC2C1CC(=O)C2(Cl)Cl)OC>[Zn].C(C)(=O)O>CCC(CCCCC1CCC2CC(O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-642222c817f14c568dd170c84ef8109c | CC(C)(C)[Si](C)(C)Cl.OCCCCCCl>>CC(C)C[Si](C)(C)OCCCCCCl | N1C=NC=C1.ClCCCCCO.[Si](C)(C)(C(C)(C)C)Cl.CN(C=O)C>>ClCCCCCO[Si](C)(C)CC(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14]>>[CH3:1][CH:2]([CH3:3])[CH2:4][Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14] | CC(C)(C)[Si](C)(C)Cl.OCCCCCCl | CC(C)C[Si](C)(C)OCCCCCCl | null | null | O | Protection | OtherReaction | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH2;D2;+0:7]-[CH;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6] | null | [] | null | null | null | null | 5-Chloropentanol (325 g, 2.65 moles) is added to a solution containing tert-butyldimethylsilyl chloride (439 g, 2.91 moles) and dimethylformamide (1.625 liters). The solution is stirred and imidazole (199 g, 2.91 moles) is added at once. The solution is stirred at room temperature for 6 hours, after which time water (1... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | null | HCl | O | null | null | CC(C)(C)[Si](C)(C)Cl.OCCCCCCl>O>CC(C)C[Si](C)(C)OCCCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-44a89d079e1d4521b5a9c6a109d06cd9 | CC(C)(C)[Si](C)(C)OCCCCCCl.ClC1C=CCC1>>CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1 | [Mg].ClCCCCCO[Si](C)(C)CC(C)C.ClC1C=CCC1.ClCCCCCO[Si](C)(C)C(C)(C)C>>CC(C)(C)[Si](OCCCCCC1C=CCC1)(C)C | Cl[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].Cl[CH:14]1[CH:15]=[CH:16][CH2:17][CH2:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:15]=[CH:16][CH2:17][CH2:18]1 | CC(C)(C)[Si](C)(C)OCCCCCCl.ClC1C=CCC1 | CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1 | null | null | O1CCCC1.O | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | All reactions are carried out under an inert atmosphere. The starting material, (5-chloro-1-pentyloxy)(2,2-dimethylethyl) dimethylsilane {[(5-chloropentyl)oxy](1,1-dimethylethyl)dimethylsilane} (534 g, 2.26 moles), diluted in tetrahydrofuran (500 ml), is added portionwise to a refluxing solution of tetrahydrofuran and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Other | O1CCCC1.O | null | null | CC(C)(C)[Si](C)(C)OCCCCCCl.ClC1C=CCC1>O1CCCC1.O>CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7822be45e6a7487a81b1386880688f0e | CC(C)(C)[Si](C)(C)OCCCCCC1CCC2C1CC(=O)C2(Cl)Cl>>O=C1CC2CCC(CCCCCO)C2C1 | ClC1(C2CCC(C2CC1=O)CCCCCO[Si](C)(C)C(C)(C)C)Cl.ClC1(C(CC2C(CCC12)CCCCCO[Si](C)(C)C(C)(C)C)=O)Cl.CCOCC>>OCCCCCC1C2CC(CC2CC1)=O | CC(C)(C)[Si](C)(C)[O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:6][CH2:5][CH:4]2[C:3](Cl)(Cl)[C:2](=[O:1])[CH2:15][CH:14]21>>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:14]2[CH2:15]1 | CC(C)(C)[Si](C)(C)OCCCCCC1CCC2C1CC(=O)C2(Cl)Cl | O=C1CC2CCC(CCCCCO)C2C1 | null | [Zn] | C(C)(=O)O | Deprotection | OtherReaction | a6023071637a7a1fd55762c847d42bf9e4bf43a1deeb92c6f585037e3e1e93f6 | 134ea584ae06b324ee35fec219b8456a8da345492f4eb1044d490535f00a1b3e | O=C1CC2CCCC2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3].Cl-[C;H0;D4;+0:4]1(-Cl)-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[C:9]-1-[C:10]>>[C:3]-[C:2]-[OH;D1;+0:1].[C:10]-[C:9]1-[C:8]-[C:7]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:4]-1 | null | [] | 70 | CELSIUS | null | null | The starting material, 6,6-dichloro-2-(5-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichloro-4-[5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]pentyl]hexahydro-2(1H)-pentalenone}(12.1 g, 0.30 moles) is dissolved in glacial acetic acid (85 ml) and the solution is stirred while zinc (25 g) is s... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone.TMS ether protective group | Ketone.Primary alcohol | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | HCl | [Zn].C(C)(=O)O | 70 | null | CC(C)(C)[Si](C)(C)OCCCCCC1CCC2C1CC(=O)C2(Cl)Cl>[Zn].C(C)(=O)O>O=C1CC2CCC(CCCCCO)C2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-44bfa0d5f31a44aa9684818b80bf5a65 | CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1>>OCCCCCC1C=CCC1 | CC(C)(C)[Si](OCCCCCC1C=CCC1)(C)C.F.C([O-])(O)=O.[Na+]>>OCCCCCC1C=CCC1 | CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:9][CH2:10][CH2:11]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:9][CH2:10][CH2:11]1 | CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1 | OCCCCCC1C=CCC1 | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | 10 | MINUTE | 3-(5-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene (300 g, 1.170 moles) is diluted with acetonitrile (3000 ml) and a 40% stock solution of hydrofluoric acid (166 ml) is added. The reaction is stirred at room temperature for 10 minutes and then slowly neutralized with a saturated solution of sodium bicarbona... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | C1=CCCC1 | Other | C(C)#N | null | 0.166667 | CC(C)(C)[Si](C)(C)OCCCCCC1C=CCC1>C(C)#N>OCCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a798ca8805c3407eb1901260aed8dce8 | CCC(CC=O)C1C=CCC1.CCC(CC=O)C1CC=CC1>>CCC(O)CCCCC1C=CCC1 | C=1CC(CC1)C(CC=O)CC.C(C)[Mg]Br.S(O)(O)(=O)=O.C1=CC(CC1)C(CC=O)CC>>OC(CCCCC1C=CCC1)CC | CC[CH:8]([CH2:7]C=[O:4])[CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1.O=[CH:6][CH2:5][CH:3](C1CC=CC1)[CH2:2][CH3:1]>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][CH2:12][CH2:13]1 | CCC(CC=O)C1C=CCC1.CCC(CC=O)C1CC=CC1 | CCC(O)CCCCC1C=CCC1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | e36ded412ea1d7c6f9df5824d7ce6c857249051a6957dd698d740bd96921a6a1 | 8bfc6d7c0e522e7b1f11bf2b693fafd682d1ff34472ac7c26c6e3f71ef89dcf0 | C1=CCCC1 | C-C-[CH;D3;+0:1](-[CH2;D2;+0:2]-C=[O;H0;D1;+0:3])-[C:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1.O=[CH;D2;+0:9]-[C:10]-[CH;D3;+0:11](-[C:12]-[C;D1;H3:13])-C1-C-C=C-C-1>>[C;D1;H3:13]-[C:12]-[CH;D3;+0:11](-[OH;D1;+0:3])-[C:10]-[CH2;D2;+0:9]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1 | null | [] | -30 | CELSIUS | null | null | All work is performed in an inert atmosphere using anhydrous tetrahydrofuran. The starting material, 3-(5-cyclopenten-3-yl) valeraldehyde {2-cyclopentene-1-pentanal} (75 g, 0.493 moles) is dissolved in tetrahydrofuran (750 ml) and cooled in a -30° C. ethanol/dry ice bath. Ethyl magnesium bromide (0.493 moles) is added ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Secondary alcohol | C1=CCCC1 | null | C1=CCCC1 | HO- | O1CCCC1.O | -30 | null | CCC(CC=O)C1C=CCC1.CCC(CC=O)C1CC=CC1>O1CCCC1.O>CCC(O)CCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-34afba9a9704414cbb10f1ebd75ae625 | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCCC1C=CCC1.CCC(O)CCCCC1C=CCC1.c1c[nH]cn1>>CCC(CCCCC1C=CCC1)OCC(C)(C)[SiH](C)C.CCC(CCCCC1C=CCC1)O[Si](C)(C)C(C)(C)C | N1C=NC=C1.OC(CCCCC1C=CCC1)CC.C(C)C(CCCCC1C=CCC1)O.[Si](C)(C)(C(C)(C)C)Cl>>C1(C=CCC1)CCCCC(CC)OCC(C)(C)[SiH](C)C.CC(C)(C)[Si](OC(CCCCC1C=CCC1)CC)(C)C | Cl[Si:18]([C:15]([CH3:16])([CH3:17])[CH3:37])([CH3:19])[CH3:40].[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1)[OH:13].[CH3:21][CH2:22][CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[CH:29]=[CH:30][CH2:31][CH2:32]1)[OH:33].n1[cH:14][nH][cH:20][cH:36]1>>[CH3:1][CH2:2][CH:3]([CH2... | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCCC1C=CCC1.CCC(O)CCCCC1C=CCC1.c1c[nH]cn1 | CCC(CCCCC1C=CCC1)OCC(C)(C)[SiH](C)C.CCC(CCCCC1C=CCC1)O[Si](C)(C)C(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 94bbf83bb4e309c242af61604eb8d59215d1fad5e5a6fa3369286f414da72c62 | 12e47ce768a9e0b4fc42c8b8462594651faaf7fa9858d4c8019f2073451198b4 | C1=CCCC1.C1=CCCC1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[CH3;D1;+0:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].[C:8]-[C:9](-[C:10])-[OH;D1;+0:11].[C:12]-[C:13](-[C:14])-[OH;D1;+0:15].[cH;D2;+0:16]1:[nH]:[cH;D2;+0:17]:[cH;D2;+0:18]:n:1>>[C:12]-[C:13](-[C:14])-[O;H0;D2;+0:15]-[#14:19](-[C;D1;H3:20])(-[CH3;D1;+0:18])-[C;H0;D4;... | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 7 and 8 using 3-(5-hydroxyhept-1-yl)cyclopentene {alpha-ethyl-2-cyclopenten-1-pentanol} (32.5 g, 0.177 moles), t-butyldimethylsilylchloride (29.3 g, 0.194 moles), imidazole (13.3 g, 0.194 moles), and dimethylformamide (163 ml). The crude product is fractio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol.Silyl protective group | Ether.TMS ether protective group | c1c[nH]cn1 | null | C1=CCCC1.C1=CCCC1 | null | CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCCC1C=CCC1.CCC(O)CCCCC1C=CCC1.c1c[nH]cn1>CN(C=O)C>CCC(CCCCC1C=CCC1)OCC(C)(C)[SiH](C)C.CCC(CCCCC1C=CCC1)O[Si](C)(C)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5263750bf1284597acc5550363a196ee | CCC(O)CCCCC1CCC2CC(=O)CC12>>CCC(=O)CCCCC1CCC2CC(=O)CC12 | [Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.OC(CCCCC1C2CC(CC2CC1)=O)CC.OC(CCCCC1C2CC(CC2CC1)=O)CC.OC(CCCCC1C2CC(CC2CC1)=O)CC>>O=C(CCCCC1C2CC(CC2CC1)=O)CC | [CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]2[CH2:13][C:14](=[O:15])[CH2:16][CH:17]12>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]2[CH2:13][C:14](=[O:15])[CH2:16][CH:17]12 | CCC(O)CCCCC1CCC2CC(=O)CC12 | CCC(=O)CCCCC1CCC2CC(=O)CC12 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CC2CCCC2C1 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C;D1;H3:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 13 substituting the starting material from Example 3, 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (2.0 g, 8.4 mmoles) and pyridinium dichromate (4.7 g, 12.6 mmoles) in methylene chloride (10 ml). The cr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CC2CCCC2C1 | null | C(Cl)Cl | null | null | CCC(O)CCCCC1CCC2CC(=O)CC12>C(Cl)Cl>CCC(=O)CCCCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3dd62530494549a98c1c58849b00b4ae | CC(=O)O.CCC(O)CCCCC1CCC2CC(=O)CC12>>CCC(CCCCC1CCC2CC(=O)CC12)OC(C)=O | C(C)(=O)O.OC(CCCCC1C2CC(CC2CC1)=O)CC.OC(CCCCC1C2CC(CC2CC1)=O)CC.OC(CCCCC1C2CC(CC2CC1)=O)CC>>C(C)(=O)OC(CCCCC1C2CC(CC2CC1)=O)CC | [OH:17][C:18]([CH3:19])=[O:20].O[CH:3]([CH2:2][CH3:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12)[O:17][C:18]([CH3:19])=[O:20] | CC(=O)O.CCC(O)CCCCC1CCC2CC(=O)CC12 | CCC(CCCCC1CCC2CC(=O)CC12)OC(C)=O | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 55fde8dca0a408407bb776c4e1e9a22d6eeb5c734b0d7975d23baba4292968d2 | 505f7b4da8def84a80ac616845cb7b0566b14f3232b5b9d3480d84d3e0d284a0 | O=C1CC2CCCC2C1 | O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4]-[C:5].[C;D1;H3:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[C:5]-[C:4]-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[O;H0;D2;+0:9]-[C:7](-[C;D1;H3:6])=[O;D1;H0:8] | null | [] | 70 | CELSIUS | 4 | HOUR | The starting material from Example 3, 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (2.5 g, 10.5 mmoles) is diluted with glacial acetic acid (10 ml) and stirred in a 70° C. water bath for 4 hours. The reaction is cooled to room temperature and partitioned between ethe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1CC2CCCC2C1 | HO- | null | 70 | 4 | CC(=O)O.CCC(O)CCCCC1CCC2CC(=O)CC12>>CCC(CCCCC1CCC2CC(=O)CC12)OC(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a562188c5ed14659b721a63cea1485be | CC(=O)O.O=C1CC2CCC(CCCCCO)C2C1>>CC(=O)OCCCCCC1CCC2CC(=O)CC12 | C(C)(=O)O.OCCCCCC1C2CC(CC2CC1)=O.OCCCCCC1C2CC(CC2CC1)=O.O>>C(C)(=O)OCCCCCC1C2CC(CC2CC1)=O | [CH3:1][C:2](=[O:3])[OH:4].O[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH:13]2[CH2:14][C:15](=[O:16])[CH2:17][CH:18]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH:13]2[CH2:14][C:15](=[O:16])[CH2:17][CH:18]12 | CC(=O)O.O=C1CC2CCC(CCCCCO)C2C1 | CC(=O)OCCCCCC1CCC2CC(=O)CC12 | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | O=C1CC2CCCC2C1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[C:5](-[C;D1;H3:4])=[O;D1;H0:6] | null | [] | 75 | CELSIUS | null | null | The starting material 2-(5-hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxypentyl)-2(1H)-pentalenone} (0.8 g, 3.8 mmoles) is diluted with glacial acetic acid (7 ml). The reaction is stirred and heated in a 75° C. oil bath for 24 hours, after which time water (20 ml) is added and the reaction partition... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CC2CCCC2C1 | HO- | null | 75 | null | CC(=O)O.O=C1CC2CCC(CCCCCO)C2C1>>CC(=O)OCCCCCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6a2b05eb167f4a6fbf7b18ece3ffb063 | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl.CCC(O)CCCl.CN(C)C=O.c1c[nH]cn1>>CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C | N1C=NC=C1.ClCCC(CC)O.ClCCC(CC)O.CN(C=O)C.[Si](C)(C)(C(C)(C)C)Cl>>ClCCC(O[Si](C)(C)C(C)(C)C)CC.ClCCC(CC)O[Si](C)(C)CC(C)C | Cl[Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:14])[CH3:28].[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][Cl:6])[OH:7].[CH3:15][CH2:16][CH:17]([CH2:18][CH2:19][Cl:20])[OH:21].O=[CH:25]N([CH3:13])[CH3:24].n1[cH:23][nH][cH:26][cH:27]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][Cl:6])[O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:... | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl.CCC(O)CCCl.CN(C)C=O.c1c[nH]cn1 | CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C | null | null | null | C-C Coupling | OtherReaction | 1b5c9e6d22618862c0cf92ff421ed927a52f1a47e9c948a659dea2c61724f3a1 | e458a5c983718128b844b37d14f7422d92bf47d4d49e64ffe85804e9f4a928f4 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].O=[CH;D2;+0:8]-N(-[CH3;D1;+0:9])-[CH3;D1;+0:10].[C:11]-[C:12](-[C:13])-[OH;D1;+0:14].[C:15]-[C:16](-[C:17])-[OH;D1;+0:18].[cH;D2;+0:19]1:[nH]:[cH;D2;+0:20]:[cH;D2;+0:21]:n:1>>[C:15]-[C:16](-[C:17])-[O;H0;D2;+0:18]-[#... | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 7 substituting 5-chloropentan-3-ol {1-chloro-3-pentanol} (50 g, 0.41 moles), tert-butyldimethylsilyl chloride (71g, 0.47 moles), imidazole (32.6 g, 0.48 moles), and dimethylformamide (150 ml). The crude product is fractionally distilled under vacuum leavin... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Secondary alcohol.Secondary alcohol.Silyl protective group | TMS ether protective group.Silyl protective group | c1c[nH]cn1 | null | null | Other | null | null | null | CC(C)(C)[Si](C)(C)Cl.CCC(O)CCCl.CCC(O)CCCl.CN(C)C=O.c1c[nH]cn1>>CCC(CCCl)O[Si](C)(C)C(C)(C)C.CCC(CCCl)O[Si](C)(C)CC(C)C |
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