1-Amino-2-propanol → N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamide

Participants

Reaction Conditions

Reaction Steps

Ethanol (1.27 L) and ethyl oxo{[3-(trifluoromethyl)phenyl]amino}acetate (243.15 g, 1 eq) were heated to reflux. 1-Amino-2-propanol (73.2 g, 1.05 eq) in ethanol (0.29 L) was added to the reaction mixture over 1 hour. The reaction mixture was held at reflux for a further 3 hours and then cooled to 20-25° C. The solvent was removed on a rotary evaporator and the resulting white solid was dissolved in ethyl acetate (1.6 L). The solution was reduced in volume by 80% by distillation at atmospheric pressure. Heptane (1.29 L) was then added and the product precipitated. The mixture was cooled further to 0-5° C. and held at this temperature for 1 hour. The mixture was filtered and the filter cake washed with heptane (0.24 L). The damp product was dried at 50° C. for 16 hours in a vacuum oven. The title compound (227.88 g, 84.3%) was isolated as a white crystalline solid.

Provenance & Evidence