2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone

HRID 1404948Notes

Reaction equation

HRID 1404948 reaction equation
[CH3:1][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=2[S:5][C:6]=1[SH:7].Cl[CH2:13][C:14]([N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1)=[O:15].S1C(SCC(N2C3C(=CC=CC=3)CCC2)=O)=CC2C=CC=CC1=2>>[N:16]1([C:14](=[O:15])[CH2:13][S:7][C:6]2[S:5][C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[C:2]=2[CH3:1])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 130056393-Methyl-1-benzothiophene-2-thiolHCID 59467886HCID 59467886, compound

Product 1

HCID 594679041-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanoneYield 11.7%

Procedure

Crude compound 75 (0.55 g, 3.0 mmol) was coupled with compound 4 (0.48 g, 2.3 mmol) according to procedure used to synthesize compound 73. The product was purified by column chromatography to yield compound 76 (95 mg, 5% for two steps): MS: m/z+ 354.1 [M+H]+; Anal. Calcd (found) for C20H19NOS2.0.1H2O: C, 67.61 (67.59); H, 5.45 (5.48); N, 3.94 (3.94); S, 18.05 (17.75).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-33bd4f80a4fa4884b071bf1681bf5c5a
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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