Synthesis and Properties of S-Aminomethylthiamine and N-Hydroxymethylthiamine

抄録

S-Aminomethylthiamine : N-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-N-[1-methyl-2-(dialkylaminomethyl) thio-4-hydroxy-1-butenyl] formamide (IIIa-d) were successfully synthesized by the reaction of an alkaline solution of thiamine (I) with chloroform solution of chloromethyldialkylamine (VIa-d), which were freshly prepared from methylenebisdialkylamine (Va-d) and acetyl chloride. The compounds (IIIa-d) were soluble in organic solvents and also soluble in water with the exception of IIIb. When III was dissolved in water, III afforded a small amount of cyclobismethylenethiamine (II) and mostly decomposed to I. The behaviour of IIIa in water was confirmed by means of polarographic technique. N-Hydroxymethylthiamine : 3-[(2-Methyl-4-hydroxymethylamino-5-pyrimidinyl)-methyl]-4-methyl-5-(2-hydroxyethyl) thiazolium chloride (VII) was also prepared from thiamine monochloride (I-Cl) and formalin. Compound VII gave also II in the presence of diethylamine. The formation pathway of II from I was also discussed.