85485-83-2Relevant academic research and scientific papers
The Synthesis and Hydrolysis of N-Benzyl-S-methylisothiazolidinium Salts
Swank, Darrel W.,Lambeth, David O.
, p. 1515 - 1520 (2007/10/02)
A series of N-benzyl-S-methylisothiazolidinium salts were obtained by iodinic oxidation of the corresponding N-benzyl-3-methylthiopropylamines at neutral pH followed by their isolation as the chloride salts.The parent N-benzyl-3-methylthiopropylamines were prepared by reacting substituted benzaldehydes with 3-methylthiopropylamine and sodium cyanoborohydride.Acid hydrolysis of the isothiazolidinium salts resulted in their quantitative conversion to the corresponding N-benzyl-3-methylsulfenylpropylamines.Although methylsulfenylpropylamine formation also predominated in alkaline solution, a significant fraction was converted to the parent benzaldehyde and presumably, 3-methylthiopropylamine.The latter conversion is believed to involve opening of the isothiazolidine ring via an elimination reaction followed by hydrolysis of the resulting Shiff's base.
