Guanidine → 2-((Thiazol-5-ylmethyl)thio)ethanamine

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Conversion of the compounds of formula II to the pharmacologically active guanidine and thiourea products is accomplished in a variety of ways. When R2 is --SCH2CH2NH2, the 2-amino group of the 2-amino-5-(2-aminoethyl)thiomethylthiazole is removed, for example by reaction with ethylnitrite, to give the corresponding 5-(2-aminoethyl)thiomethylthiazole compound which is then treated with methyl isothiocyanate to give the corresponding N-methyl-N'-[2-(4-R1 -thiazolylmethylthio)ethyl]thioureas. Reaction of the same 5-(2-aminoethyl)thiomethylthiazole compound with N-cyano-N',S-dimethylisothiourea gives the corresponding N-cyano-N'-methyl-N"-[2-(4-R1 -thiazolylmethylthio)ethyl]guanidines. The guanidine products are also prepared by reaction of the 5-(2-aminoethyl)thiomethylthiazole with dimethyl-N-cyanoimidodithiocarbonate and subsequently reacting the resulting N-cyano-N'-[2-(4-R1 -thiazolylmethylthio)ethyl]-S-methylisothiourea with methylamine.

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