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 1716260Notes

Reaction equation

HRID 1716260 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].S1C(S)=CC2C=CC=CC1=2.[S].Cl[CH2:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][CH2:28]1)=[O:26].S1C(SCC(N2C3C(=CC=CC=3)CCC2)=O)=CC2C=CC=CC1=2>>[N:27]1([C:25](=[O:26])[CH2:24][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:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 5

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 5362487SulfurHCID 11073791Benzo[b]thiophene-2-thiolHCID 130056393-Methyl-1-benzothiophene-2-thiol2×HCID 59467886HCID 59467886, compound

Product 1

HCID 594679041-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanoneYield 5%

Procedure

Compound 75 was obtained according to the procedure used to synthesize compound 72, except the addition of sulfur was done at 40° C. in an attempt to avoid significant formation of disulfide. The obtained crude material (75) was used for the next step without further purification. 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone (76): 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. customwas done at 40° C. in an attempt
  2. customThe obtained crude material (75)
  3. customwas used for the next step without further purification
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-21689b75418c45a0a7179968ce311f60
Source dataset
uspto-grants-2010_09
Patent number
US07803790B2

Reaction notes

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