2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(4,5-dimethylthiazol-2-ylthio)ethanone

HRID 1404923Notes

Reaction equation

HRID 1404923 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][C:16]1[N:17]=[C:18]([SH:22])[S:19][C:20]=1[CH3:21]>>[N:5]1([C:3](=[O:4])[CH2:2][S:22][C:18]2[S:19][C:20]([CH3:21])=[C:16]([CH3:15])[N:17]=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 1784335624,5-dimethyl-1,3-thiazole-2-thiol

Product 1

HCID 594679131-(3,4-dihydroquinolin-1(2H)-yl)-2-(4,5-dimethylthiazol-2-ylthio)ethanoneYield 74%

Procedure

The title compound was synthesized according to General Procedure A using compound 4 as the electrophile and 4,5-dimethylthiazole-2-thiol as the nucleophile to yield 33 as a cream solid (690 mg, 74%). MS (APCI): m/z 319 [M+H]+. Anal. Calcd. for C16H18N2OS2: C, 60.34; H, 5.70; N, 8.80. Found: C, 60.51; H, 5.71; N, 8.72.

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-542ae99b91144d2eb7c46d819f54b2bd
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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