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

HRID 504732
Notes
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Reaction equation

HRID 504732 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([CH3:25])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([NH2:24])=O)=[CH:18]2)(=[O:11])=[O:10].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([CH3:25])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22](=[S:35])[NH2:24])=[CH:18]2)(=[O:11])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 574761777-[[(2-methoxyphenyl)sulfonyl](methyl)amino]-1H-indole-2-carboxamide

Product 1

HCID 591359767-[[(2-methoxyphenyl)sulfonyl](methyl)amino]-1H-indole-2-carbothioamideYield 154.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-[[(2-methoxyphenyl)sulfonyl](methyl)amino]-1H-indole-2-carboxamide (2.82 g), Lawesson's reagent (1.6 g) and tetrahydrofuran (250 mL) was stirred at 70° C. for 3 hr. The reaction solution was concentrated under reduced pressure, and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (2.3 g, yield: 78%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b815345e8d8e41c18deedb8c7cc44839
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