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

Gury Zvilichovsky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)486-489
Number of pages4
JournalJournal of Organic Chemistry
Volume34
Issue number3
DOIs
StatePublished - 1 Mar 1969

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