Unprecedented Property of 4,6-Di(substituted)amino-1,2-dihydro-1,3,5-triazines: Formation of Acid Salts by Simple Treatment with Alkali Metal Salts of Protic Acids

Treatment of 4,6-di(substituted)amino-1,2-dihydro-1,3,5-triazine derivative (5) with sodium chloride in a bilayer system consisting of toluene and water gave its hydrochloride (6) in the toluene layer and sodium hydroxide in the aqueous layer. Similarly, treatment of 5, 8 and 9 with an aqueous sodium acetate solution in organic solvents resulted in the formation of their corresponding acetates, 7, 12 and 13, respectively.