Mannich Reaction of 1-n-Butyl-3-p-tosylurea. I. Syntheses of 3-n-Butyl-2-oxo-1,5-di-p-tosyl-perhydro-1,3,5-triazine and 3,5-Di-n-butyl-2-oxo-1-p-tosyl-perhydro-1,3,5-triazine

摘要

l-n-Butyl-3-p-tosylurca (tolbutamide) does not incorporate the secondary amines, piperidine, diethylamine, dimethylamine, dipropylamine, pyrrolidine and morpholinc, to any significant extent in its normal Mannich reaction under alkaline conditions in refluxing methanol, accetonitrile and dioxane. Instead 3-n-butyl-2-oxo-l,5-di-p-tosyl-perhydro-l,3,5-triazine and 3,5~di-n-butyl-2-oxo-l-p-tosyl-perhydro-l,3,5-triazine are mainly formed usually in good yields. These' triazines have been isolated and characterized, and n mechanism is proposed for their formation.