Triethylamine → N-(tert-butyl)-N'-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea

Participants

Reaction Conditions

Reaction Steps

The process is performed as in Example 2, starting with 5.65 g of (2S)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride, 3.7 cm3 of tert-butyl isothiocyanate and 3.41 cm3 of triethylamine in 60 cm3 of ethanol. After stirring for 3 days at a temperature in the region of 20° C. and then heating for 30 minutes at a temperature in the region of 60° C., 3.7 cm3 of tert-butyl isothiocyanate are added to the reaction medium and heating is then continued for a further 3 hours at the same temperature. After an identical work-up, 6.45 g of N-(tert-butyl)-N′-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea are obtained in the form of a yellow foam. (Rf=0.61 in a 40/5/0.5 by volume mixture of dichloromethane/methanol/aqueous ammonia, on a Merck 60F254R silica plate).

Provenance & Evidence