Lawesson's reagent → (E)-3-(2-chloro-5-nitrophenyl)-2-propenethioamide

HRID 327563Notes

Reaction equation

HRID 327563 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13]([NH2:15])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13](=[S:25])[NH2:15]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19347587(E)-3-(2-chloro-5-nitrophenyl)-2-propenamide

Product 1

HCID 20084363(E)-3-(2-chloro-5-nitrophenyl)-2-propenethioamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution composed of 5.0 g of (E)-3-(2-chloro-5-nitrophenyl)-2-propenamide, 4.4 g of Lawesson's reagent and 100 ml of tetrahydrofuran was stirred under a positive argon atmosphere at room temperature for 16 hr. The volatiles were then removed in vacuo and the residual materials slurried with 100 ml of methylene chloride to yield (E)-3-(2-chloro-5-nitrophenyl)-2-propenethioamide as a orange solid; m.p. 236°-238° C. from acetonitrile.

Workup

  1. customThe volatiles were then removed in vacuo

Sources & evidence

ORD record
ord-f6d37bee613243ada4393e974b9ef767
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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