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

Article abstract of DOI:10.1248/cpb.44.639

1-n-Butyl-3-p-tosylurea (tolbutamide) does not incorporate the secondary amines, piperidine, diethylamine, dimethylamine, dipropylamine, pyrrolidine and morpholine, to any significant extent in its normal Mannich reaction under alkaline conditions in refluxing methanol, accetonitrile and dioxane. Instead 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 are mainly formed usually in good yields. These triazines have been isolated and characterized, and a mechanism is proposed for their formation.

Full text of DOI:10.1248/cpb.44.639

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