Collect. Czech. Chem. Commun. 1981, 46, 3097-3103

Solvolysis kinetics and mechanism of 3-methyl-1,3-thiazolidine-2,4-dione

Vladimír Macháček, Vojeslav Štěrba and Helena Zahradníčková

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


The hydrolysis kinetics of 3-methyl-1,3-thiazolidine-2,4-dione have been studied in aqueous buffers and dilute NaOH solutions. The reaction proceeds via two base-catalyzed steps having different rates. In sodium methoxide solutions 3-methyl-1,3-thiazolidine-2,4-dione undergoes one-step methanolysis giving methyl thioglycolate anion as the final product. The rate-limiting step consists in decomposition of the anion CH3NCOSCH2COOCH3.