Modified Lossen Rearrangement of Malonohydroxamic Acid. Preparation and Properties of 3-(p-Toluenesulfonoxy)hydantoin

3-(p-Toluenesulfonoxy)hydantoin (2) was obtained by the reaction of malonohydroxamic acid (1) with ptoluenesulfonyl chloride. Acid hydrolysis and acid alcoholysis of 2 afforded 5-(p-toluenesulfonoxy)hydantoic acid (3) and alkyl 5-(p-toluenesulfonoxy)hydantoate (4), respectively. On treatment with ammonia and amines, methylenediurea and its alkyl derivatives (5) were obtained. Compound 2 yielded with aniline also ω-phenylsemicarbazidoacetanilide (6). Mechanisms of formation and structure of these compounds were studied. When it was necessary for confirmation of structures, some compounds were prepared in alternatives routes.