Ethanolamine → 1-Butyl-3-(2-hydroxyethyl)urea

Participants

Reaction Conditions

Reaction Steps

61.7 grams (1 mole at 99% purity) of ethanolamine and 170 grams of dichloromethane were charged to a flask eguipped with stirrer, thermometer, feed tank, distillation head and condenser. 101 grams (1 mole at 98% purity) of butyl isocyanate were fed to the flask dropwise with stirring and cooling (utilizing a dry ice bath) over a period of 1.5 hours such that the temperature of the reaction mixture was maintained at about 30° C. At this time some solid had been formed and it was redissolved by heating to 46° C. The flask contents were stirred at 46° C. for an additional two hours and then freed of volatile materials by stripping at 90° C. and 2 mm Hg, leaving 181 g of solid product. This material was recrystallized from 2-butanone giving tiny white crystals melting at 67° C. The HLB value of N-(2-hydroxyethyl)-N'-1-butyl urea is 12.9.

Provenance & Evidence