Reactions of diphenylsulfanuric chloride with amines

Article abstract of DOI:10.1021/ic50194a002

Diphenylsulfanuric chloride (1-chloro-3,5-diphenyl-1H,3H,5H-1,3,5,2,4,6-trithiatriazine 1,3,5-trioxide), (NSO)₃(C₆H₅)₂Cl, reacts with secondary amines by nucleophilic substitution to give diphenylsulfanuric amides without cleavage of the trithiatriazine ring. Reaction with triethylamine or pyridine in the presence of water gives amine salts of diphenylsulfanuric acid, which hydrolyze to ring-opened products. Diphenylsulfanuric chloride also reacts with trimethylamine in the presence or absence of water to give the diphenylsulfanuric amide of dimethylamine, but with methanol and trimethylamine the tetramethylammonium salt of diphenylsulfanuric acid is formed.