3-(Trifluoromethyl)aniline → N,N'-Di-(m-trifluoromethylphenyl)urea

Participants

Reaction Conditions

Reaction Steps

3-(Trifluoromethyl)aniline 10 g (62.1 mmol) was added to 500 ml of anhydrous dichloromethane in a 500 ml round bottomed flask. This stirred solution was cooled to 0° C. using an ice water bath. 3-(Trifluoromethyl)phenyl isocyanate 15 g (80.1 mmol) was added drop-wise over a period of 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred at ambient temperatures for 18 hours. During this time a heavy precipitate was formed. This solid was collected by filtration on a Buchner funnel, and was re-suspended in 250 ml of dichloromethane. After approximately 30 minutes of stirring, the solid was again filtered on a Buchner funnel and then placed under vacuum at 40° C. to dry for a period of 24 hours to give 20 g of a white solid (92.5% yield). 1H NMR (400 MHz DMSO) δ 9.20 (s 2H) 8.04 (s 2H) 7.61 (m 2H) 7.54 (t 2H) 7.34 (m 2H). MS: M+1 found 349.

Provenance & Evidence