Reactions of Thioamides with Haloacids

概要

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The reactions of S-carboxymethylisothioamide RC(=NR′)SCHRCOOH with acetic anhydride proceeded through various courses depending on the reaction conditions and the structure of thioamides. When S-carboxymethylisothiobenzanilide (IIa) was treated with a mixture of acetic anhydride and triethylamine in the cold, an intermediate (A), presumably 2-hydroxy-2,3-diphenylthiazolidin-4-one (V), was isolated which was readily converted to benzoylthioacetanilide (IIIa). Attempts to convert A or IIIa to a mesoionic compound failed. Under the same reaction conditions as for IIa, S-carboxymethylisothiobenz-p-chloroanilide (IIb) afforded benz-p-chloroanilide, while corresponding p-anisidide (IIc) gave only tarry product. Attempts to obtain a mesoionic product from pyrrolidine-2-thione or thiocaprolactam and bromoacetic acid were unsuccessful. However, condensation of pyrrolidine-2-thione with α-chlorophenylacetic acid followed by treatment with a mixture of acetic anhydride and triethylamine gave eight-membered rearranged product (XII).
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