Methylation of 2-amino-δ2-thiazolin-4-one

It is shown that the nucleophilicity of the sodium salt of 2-amino-²-thiazolin-4-one with respect to dimethyl sulfate and methyl iodide is extremely low, regardless of the nature of the solvent. The anomalous (in the 4-thiazolidone series) behavior of this salt in methylation is explained by the low degree of heterolytic dissociation of the O-Na bond. The possible reasons for the inertness of the oxygen atom in the anions of 2-substituted 4-thiazolidones with respect to alkylating agents are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1046–1049, August, 1981.