Process for the production of thioamides

摘要

Thioamides are prepared by reacting a thionic ester with a metal (e.g. Li, Na or halomagnesium) derivative of a primary or secondary amine. The process is applicable particularly to the preparation of compounds of the general formula wherein R1 represents an alkyl, aralkyl, aryl or alkoxyaryl radical, R2 represents an alkyl, aralkyl, haloaryl, nitroaryl, alkaryl, alkoxyaryl or dialkylaminoalkyl radical, and R3 represents a hydrogen atom or an alkyl radical, from alkyl, aralkyl or aryl esters of acids R1.CS.OH. The N-disubstituted products of the aliphatic series form methyl iodide addition products of the general formula wherein R1 and R11 represent any aliphatic hydrocarbon residues and R111 any hydrocarbon residue. Thionic esters are prepared by reaction of H2S with imidoesters, preferably in the presence of a base, especially pyridine. Imidoesters are prepared by the action of alkali, especially anhydrous NH3, on their hydrochlorides obtained by reacting nitriles with absolute ethanol and dry HCl.