MANNICH REACTION OF 1-N-BUTYL-3-P-TOSYLUREA .1. SYNTHESES OF BUTYL-2-OXO-1,5-DI-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE AND DI-N-BUTYL-2-OXO-1-P-TOSYL-PERHYDRO-1,3,5-TRIAZINE

1-n-Butyl-3-p-tosylurea (tolbutamide) does not incorporate the seconda ry amines, piperidine, diethylamine, dimethylamine, dipropylamine, pyr rolidine and morpholine, to any significant extent in its normal Manni ch reaction under alkaline conditions in refluxing methanol, accetonit rile and dioxane, Instead -butyl-2-oxo-1,5-di-p-tosylperhydro-1,3,5-tr iazine and di-n-butyl-2-oxo-1-p-tosyl-perhydro-1,3,5-triazine are main ly formed usually in good yields, These triazines have been isolated a nd characterized, and a mechanism is proposed for their formation.