Hydrogen Sulfide → N-acetylformyl,N-(4-chlorophenyl)valine

Participants

Reaction Steps

To a mixture of the α-cyano-m-phenoxybenzyl ester of N-(4-chlorophenyl)valine (0.79 g) and about 20 ml of dry DMF is added about one ml of triethanolamine at RT. Into the mixture is slowly bubbled H2S gas for about 3 hours. The reaction is then stirred overnight. The reaction is worked up by partition with ether/water. The organic phase is washed with brine (3×), dried over sodium sulfate, filtered and evaporated. The residue is plated up on a prep. TLC plate eluting with 20% ethyl acetate/hexane to yield the desired thioamide, MS m/e 181.9 (100), IR (film) 3180 cm-1 (NH) and 1740 cm-1 (C=O). ##STR25##

Provenance & Evidence