2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 1-(3,4-Dihydro-2H-quinolin-1-yl)-2-(1-methyl-1H-benzoimidazol-2-ylsulfanyl)ethanone

HRID 1404910

Reaction equation

HRID 1404910 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[SH:25]>>[N:5]1([C:3](=[O:4])[CH2:2][S:25][C:17]2[N:16]([CH3:15])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 178481665HCID 178481665, compound

Product 1

HCID 406886931-(3,4-Dihydro-2H-quinolin-1-yl)-2-(1-methyl-1H-benzoimidazol-2-ylsulfanyl)ethanoneYield 77%

Procedure

The title compound was synthesized according to General Procedure A using compound 4 as the electrophile and 1-methyl-1H-benzo[d]imidazole-2-thiol as the nucleophile to yield 17 as a pale yellow solid (77%): MS m/z: 338 (M+H)+. Anal. Calcd. For, C19H19N3OS: C, 67.63; H, 5.68; N, 12.45; S, 9.50. Found: C, 67.45; H, 5.74; N, 12.25; S, 9.41.

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-1e1c574ae668488a8a196fb2dd41d802
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Linked notes

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