19412-46-5Relevant academic research and scientific papers
Synthesis of 2-Amino-4-imino-4,5-dihydrothiazoles from N-Sulfonyl-α-chloroamidines and Thiourea
Abdelaal, Salma,Bauer, Ludwig
, p. 1849 - 1856 (2007/10/02)
A number of new and interesting 2-amino-4-(N-substituted)imino-4,5-dihydrothiazoles were synthesized by reacting thiourea (or thiourea hydrochloride) with N-alkyl- or N,N-dialkyl-N'-p-toluenesulfonyl-α-chloroacetamidines, where the N-alkyl groups were ethyl, cyclohexyl, benzyl, β-phenethyl, (3,5-dimethyl-1-adamantyl)methyl, as well as N,N-dimethyl- and N,N-pentamethylene.Reactions of N-alkyl-N'-p-toluenesulfonyl-2-chloroacetamidines (substituents being N-ethyl, N-benzyl and N,N-dimethyl) with thiourea hydrochloride in hot 2-propanol furnished 2-amino-4-(p-toluenesulfonyl)imino-4,5-dihydrothiazole (in 51, 60 and 65percent yields, respectively) and the corresponding amine hydrochloride.In hot acetone or butanone, the reactions of these N-sulfonyl-2-chloroacetamidines with excess thiourea provided 2-amino-4-N-(alkyl or N,N-dialkyl)imminium-4,5-dihydrothiazole chlorides in 25-80percent yield.The by-product from these reactions was p-toluenesulfonamide.The structures of the products were established by chemical transformations and spectral methods (nmr and mass spectra).
