Rearrangement reactions of phenyl chloroformate derivatives of 2-Hydroxyaminoacetanilides to hydantoins, ureas and hydantoie acid derivatives

Alkaline treatment of 2′-benzoyl-2-(N-carbophenoxy-N-hydroxyamino)-4′-chloroacetanilide (10) and its corresponding acetate 6 afforded respectively 5-(2-benzoyl-4-chlorophenyl)-3-hydroxy-hydantoic acid (12) and 6-chloro-4-phenylquinazolone (13). A study of the course of the reaction was carried out with the corresponding compounds that are devoid of the 2-benzoyl group. An elucidation of the rearrangement is based on the isolation and independent synthesis of the heterocyclic intermediates.