Unusual ammonolysis of a secondary amide assisted by unsubstituted vicinal amide group

Article abstract of DOI:10.1016/S0040-4020(96)00075-0

Evidence for the participation of neighboring -CONH₂ group in the ammonolysis of disubstituted amide was obtained. The surprising conversion of 1 into 3 in very mild conditions is a process formed by two consecutive first order reactions. Kinetics were performed in ethanol at various temperatures and NH₃ concentrations. The ammonolysis of the isolated intermediate 2 allowed the unambiguous attribution of k₁ and k₂ to steps 1 → 2 and 2 → 3, respectively. The thermodynamic parameters of activation for both steps of the process were evaluated.