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

HRID 1404924Notes

Reaction equation

HRID 1404924 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].[C:15]([C:19]1[N:20]=[C:21]([SH:24])[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16]>>[C:15]([C:19]1[N:20]=[C:21]([S:24][CH2:2][C:3]([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][CH2:6]2)=[O:4])[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 178441426HCID 178441426, compound

Product 1

HCID 50036102-(4-tert-butylthiazol-2-ylthio)-1-(3,4-dihydroquinolin-1(2H)-yl)ethanoneYield 37%

Procedure

The title compound was synthesized according to General Procedure A using compound 4 as the electrophile and 4-tert-butylthiazole-2-thiol as the nucleophile to yield 34 (37%): MS: m/z+ 347.2 [M+H]+. Anal. Calcd (found) for C18H22N2OS2: C, 62.39 (62.60); H, 6.40 (6.43); N, 8.08 (8.06); S, 18.50 (18.39).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-f9305aa549684cb7885f984118dadb08
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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