Base catalysed methanolysis of 4-anilinomethylene-2-phenyl-2-oxazolin-5-one: Unexpected formation of N-benzoylaminoacetanilide

Abstract

The reaction of 4-anilinomethylene-2-phenyl-2-oxazolin-5-one 1 with 3.0 equivalents of sodium methoxide in methanol affords N-benzoylaminoacetanilide 3. Further, methyl 3-anilino-2-benzoylaminopropenoate 2 also affords product 3, when treated with sodium methoxide in methanol at reflux temperature. A plausible mechanism for this conversion has been proposed.