904-04-1

Covatine,Bailly,France,1958

p-Butylmercaptobenzhydryl chloride was boiled with thiourea in alcohol thereby yielding p-butylmercaptobenzhydrylisothiouronium chloride which was then subjected to hydrolysis with dilute aqueous sodium hydroxide solution whereupon p-butylmercaptobenzhydryl mercaptan was formed.
p-Butylmercaptobenzhydryl mercaptan (28.5 g) was added to a solution of sodium (2.3 g) in absolute alcohol (75 ml), followed by the addition of a solution of diethylaminoethyl chloride (13.6 g) in toluene (50 ml). The mixture was boiled on a steam bath for 3 hours and the sodium chloride which separated out was removed by filtration. The filtrate was concentrated to one-third of its volume and dissolved in ether. The ether solution was shaken with 2N hydrochloric acid (100 ml), and the resulting middle oily layer was separated, dissolved in water and the resulting aqueous solution was washed with ether, then treated with aqueous sodium hydroxide solution to precipitate an oil. The latter was dissolved in ether, dried with anhydrous potassium carbonate, filtered and then treated with anhydrous hydrogen chloride whereupon the desired p-butylmercaptobenzhydryl 2-diethylaminoethyl sulfide hydrochloride precipitated as a white, crystalline substance which was filtered and dried in a desiccator. The melting point of the product was 124°C.

Sedative