Thionyl Chloride → N-phenyl-3-(phenylsulphanyl)prop-2-enimidoyl chloride

HRID 2172536Notes

Reaction equation

HRID 2172536 reaction equation
[C:1]1([NH:7][C:8](=O)[CH:9]=[CH:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[C:1]1([N:7]=[C:8]([Cl:21])[CH:9]=[CH:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68865691N-phenyl-3-(phenylthio)acrylamide

Product 1

HCID 86702346N-phenyl-3-(phenylsulphanyl)prop-2-enimidoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thus, for example, IN 2003-MU444 describes the reaction of N-cyclohexyl-5-hydroxypentanamide with phosphorus pentachloride to give 5-chloro-N-cyclohexylpentaneimidoyl chloride. WO 2007/063702 provides the reaction of N-phenyl-3-(phenylsulphanyl)acrylamide with thionyl chloride and catalytical amounts of N,N-dimethylformamide to give N-phenyl-3-(phenylsulphanyl)prop-2-enimidoyl chloride.

Workup

  1. customWO 2007/063702 provides

Sources & evidence

ORD record
ord-6f41368e816f4109beacab54f612f492
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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