Disulfide 2-Mercapto-5-aminothiazole Derivatives

TABLE II-34a. 2-MERCAPTO-5-AMINOTH1AZOLE DERIVATJVES FROM a-AMINONITRUJES and carbon disulfide 

Acetone reacts similarly to give the corresponding 2-mercapto-5-isopropylideneaminothiazoles (68, 293, 304). 

Genera Synthetic Methcxis for Thiazole and Thiazolium Salts 

TABLE 11-35 2-HYDROXV-5-AMINOTHIAZOLES DERIVATIVES FROM o-AMINONITRILE AND CARBON OXYSULnOE- 

Methyl (299), phenyl (299), acetyl (394). benzoyl (299, 394), and carbethoxy (292) isothiocyanates (221), R, = Me, Ph, Ac, PhCO, COjEt. have been successfully used. In some cases, a 2,5-disubstituted aminothiazole (224) was isolated as by-product (292). 

---

Carbon disulfide readily reacts with a-aminonitriles giving 2-mercapto-5-aminothiazoles (213), (271, 293) which can be converted to 5-aminothiazoles unsubstituted in the 2-position (Scheme 110 and Table II-34a). If this reaction is carried out in the presence of benzyl chloride in phosphorus tribromide, a 2-S-substituted thiazole derivative (214) is obtained in quantitative yield (Scheme 111), with R = hydrogen or phenyl (68, 304). 

---