3-Aminobenzyl alcohol → 1-(3-Hydroxymethylphenyl)-3-(2,2,2-trifluoroethyl)thiourea

Participants

Reaction Steps

m-Aminobenzyl alcohol (0.123 g.) and 2,2,2-trifluoroethylisothiocyanate (0.141 g.) were heated under reflux in acetone (5 ml.) for 2 hours. Volatile material was evaporated in vacuo and the crude residue was fractionated on a silica gel column (20 cm.×1 cm. diameter) eluted with ethyl acetate to give 1-(3-hydroxymethylphenyl)-3-(2,2,2-trifluoroethyl)thiourea. The n.m.r. spectrum in CDCl3 using tetramethylsilane as internal standard (δ=0) had the following resonances (δ): 7.2 (4H, multiplet); 4.6 (2H, singlet); 4.3 (2H, multiplet).

Provenance & Evidence