Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)

George R. Pettit, Joseph A. Settepani

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A Mannich-type reaction involving bis(2-chloroethyl)amine, formaldehyde, and several amides has been investigated. Bis(2-chloroethyl)amine was shown to condense in ethanol-formalin solution with phthalimide, saccharin, isatin, and isatin thiosemicarbazone to yield (51-89%) the corresponding nitrogen mustard Mannich bases II, IV, and VI. The reaction was found to follow other courses under acidic conditions. Formation of V-methylbis(2-chloroethyl)amine and conversion of saccharin to alkoxymethylene (VII) and bismethylene (VIII) derivatives occurred in acidic media.

Original languageEnglish (US)
Pages (from-to)1714-1717
Number of pages4
JournalJournal of Organic Chemistry
Volume27
Issue number5
DOIs
StatePublished - May 1 1962
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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