Abstract
The reactions of 1,3-diazepane-2-thione with α-halocarboxylic acids and their esters have been studied in detail. On alkylation of butylenethiourea with chloroacetic acid and ethyl chloro(bromo)acetate in anhydrous acetone at room temperature the hydrogen chloride of the S-carboxymethyl and the hydrogen halides of the S-ethoxycarbonylmethyl derivatives respectively of the cyclic substrate were formed initially. When butylenethiourea was alkylated with chloroacetic acid in boiling ethanol in the presence of sodium acetate the neutral (zwitterionic) form of its S-carboxymethyl derivative was also formed. Our results and the literature data on the alkylation of 5-, 6-, and 7-membered cyclic thioureas with α-halocarboxylic acids and their esters have been reviewed and interpreted.
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