tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea

Participants

Reaction Steps

A solution of 3.54 g of 2-amino-2-(3-bromophenyl)-1-ethanol, in 20 cm3 of ethanol containing 0.18 cm3 of tert-butyl isothiocyanate is stirred at a temperature in the region of 20° C. for 5 hours. After concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 25 cm3 of petroleum ether. The resulting crystals are spin-filtered, washed with twice 25 cm3 of petroleum ether and then dried under reduced pressure (5 kPa) at a temperature in the region of 20° C. 4 g of N-(tert-butyl)-N′-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea are obtained in the form of a white solid (Rf=0.68 in a 40/5/0.5 by volume dichloromethane/methanol/aqueous ammonia mixture, on a Merck 60F254R silica plate)

Provenance & Evidence