Syntheses of Keterocyclic Compounds of Nitrogen. CI

5-Aminothiazolo-2-thiol Derivatives. (5)

Abstract

By the condensation of anisaldehyde and carbon disulfide with aminoacetonitrile in ethyl acetate, 5-p-methoxybenzylideneaminothiazolo-2-thiol was obtained. Application of alkyl halides, allyl bromide, benzyl chloride, β-hydroxy (methoxy, ethoxy, butoxy) ethyl halide, or phenacyl bromide, on the sodium salt of 5-(p-methoxy, o-hydroxy, p-dimethylamino) benzylideneaminothiazolo-2-thiols yielded the corresponding 2-alkyl (allyl or aryl) thin derivatives. Application of ethylene bromide to the sodium salt of 5-p-hydroxybenzylideneaminothiazolo-2-thiol (III) yielded 1, 2-bis (5-o-hydroxybenzylideneamino-2-thiothiazolyl) ethane. By the acetylation of (III) with hot acetic anhydride, the diacetate was obtained; By the acetylation of 5-p-hydroxybenzylideneamino-2-β- hydroxyethylthiothiazole (XXVI) with cold acetic anhydride, the monoacetate and with hot acetic anhydride, the diacetate were obtained.