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Lawesson's reagent → 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

HRID 504655
Notes
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Reaction equation

HRID 504655 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([NH2:23])=O)[NH:6]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21](=[S:33])[NH2:23])[NH:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 574760064-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

Product 1

HCID 574760084-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.78 g), Lawesson's reagent (2.26 g) and tetrahydrofuran (120 ml) was stirred at 60° C. for 2 hr. The reaction solution was concentrated under reduced pressure, and the obtained oil was crystallized from dichloromethane-toluene to give the title compound (1.56 g, yield 84%) as pale-yellow crystals. MS: 366 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained oil was crystallized from dichloromethane-toluene

Sources & evidence

ORD record
ord-f2f6652c9f1248049672882dda6c08c3
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07777047B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes