1911 Encyclopædia Britannica/Thiazoles

THIAZOLES, in organic chemistry, a series of hetero cyclic compounds containing the grouping shown below; the replaceable hydrogen atoms in which are designated o., 5 and /L They are prepared by condensing thio-amides with a.-haloid ketones or aldehyde's, the thio-amide reacting as the tautomeric thio-imino acid. Amino derivatives similarly result from thio-ureas and a-haloid ketones; the oxy derivatives from o.-sulphocyanoketones by the action of caustic alkali; and the carboxylic acids from chloro-aceto-acetic ester, &c. and thioamides. The thiazoles are somewhat basic in character, and combine with the alkyl iodides to form thiazolium iodides. Dihydrothiazoles, or thiazolines, are obtained by condensing ethylene dibromides with thio-amides; by the action of /3-haloid alkylamines on thio-amides (S. Gabriel, Bef., 1891, 24, p. LS? 1896, 29, p. 2610); and by the action of phosphorus pentasulp i e on acyl-B-bromalkylamides (A. Salomon, Bef., 1893, 26, p. 1328). They are much less stable than the thiazoles. The benzothiazoles are a series of weak bases formed by condensing carboxylic acids with ortho-aminothiophenols (A. W. Hofmann, Ber., 1880, 13, p. 1224), b heating the acid anilides with sulphur or by the oxidation oly thio-anilides. On fusion with caustic alkalis they decompose into their constituent aminothiophenol and acid. Derivatives of this group are important as substantive cotton dyestuffs. oo S

s- cH'N /

HC: CH> / CH

KB) (11) N/

Thia zole. Benzothiazole.