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Lawesson's reagent → 3-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridine-2-thione

HRID 215977
Notes
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Reaction equation

HRID 215977 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[S:6][CH:7]=[C:8]([CH2:9][CH:10]3[N:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]4=[N:12][C:11]3=O)[C:4]=2[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:31]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[S:6][CH:7]=[C:8]([CH2:9][CH:10]3[N:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]4=[N:12][C:11]3=[S:31])[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 591767543-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one

Product 1

HCID 591767613-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridine-2-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 172 mg (0.55 mmol) of 3-(5-chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one and 110 mg (0.27 mmol) of 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide in 20 mL of toluene is heated at 160° C. for 90 min under microwave condition. The resulting mixture is concentrated in vacuo and the residue is purified by flash chromatography to give the desired compound.

Workup

  1. concentrationThe resulting mixture is concentrated in vacuo
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-8e6ab48350a44d6bad03b2b180df4834
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193214B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes