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.
ASJC Scopus subject areas
- Organic Chemistry