3-Chlorophenyl isothiocyanate → HCID 178446857, compound

Participants

Reaction Steps

To a stirred, ice bath chilled solution of 5.4 g. of sodium methoxide in 100 ml. of absolute ethyl alcohol was added slowly 13.69 g. of valeramidine hydrochloride. Stirring was continued for ten minutes and then 16.9 g. of 3-chlorophenyl isothiocyanate was added dropwise and stirring was continued an additional hour. The solvent was evaporated under reduced pressure, the resulting residue was taken up in 100 ml. of dry ether and the ether solution was extracted several times with water and the combined water wash was extracted with 50 ml. dry ether. The combined ether extract was dried and then acidified by addition of 50 ml. 2-N ethereal hydrogen chloride. The resulting precipitate was filtered to give, after recrystallization from acetonitrile, 9.6 g. of 1-(3-chlorophenyl)-3-(pentanimidoyl)-2-thiourea hydrochloride; m.p. 142°-145°C.

Provenance & Evidence