Organic reactions in melts and solids. Part VIII. Reactions of diacylanilines with monobasic and dibasic carboxylic acids

M. Michman*, M. Frenkel

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Transacylation reactions in molten mixtures of NN-diacetylaniline, NN-dibenzoylaniline, and N-acetyl-N-benzoylaniline with carboxylic acids RCO2H (R = Ph, p-MeO·C6H4, p-NO 2·C6H4, Me, Et, CH2Cl, or CHCl2) have been studied. Transacylation reactions with NN-diacylanilines proceeded more readily than with mono-N-acylanilines. In the reaction of N-acetyl-N-benzoylaniline with aromatic acids at 100°the benzoyl group was a better leaving group than acetyl. Reactions of NN-diacylanilines with phthalic acid gave low yields of N-phenylphthalimide at 170°, and none below 150°. Phthalic anhydride reacted with NN-diacylanilines only in the presence of aluminium chloride.

Original languageEnglish
Pages (from-to)3856-3859
Number of pages4
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
StatePublished - 1971

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