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

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-NO₂·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.