Thionyl Chloride → 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)(O)=[O:2].S(Cl)([Cl:19])=O>>[Cl:19][C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)=[O:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 869254-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

Product 1

HCID 133654044-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Procedure

A mixture of one molar equivalent of N-(4-carboxyphenyl)maleimide is reacted with excess thionyl chloride at 50° C. for three hours. The excess thionyl chloride is distilled off, and the residual product recrystallized from benzene to obtain pure N-(4-(chlorocarbonyl)phenyl)maleimide.

Workup

distillationThe excess thionyl chloride is distilled off
customthe residual product recrystallized from benzene

Sources & evidence

ORD record: ord-bdb1cfcabb644ebd9d6fb1decc9614cd
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300456B1

Reaction notes

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