Hydrochloric Acid → HCID 178522079, compound

Participants

Reaction Steps

To a solution of 4-chloro-3-(trifluoromethyl)phenyl isocyanate (5 g, 22.6 mmol) in DMF (35 mL) were added trans-4-aminocyclohexanol hydrochloride (3.8 g, 24.8 mmol) and Et3N (3.5 mL, 24.8 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. After adding 1N HCl (40 mL) and water, the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. White powers collected were dissolved in EtOH (200 mL) then aqueous 30% NaOH (25 mL) was added. The reaction mixture was refluxed overnight. EtOH was removed in vacuo. The precipitates were filtered and washed with water. Recrystallization from methanol afforded 9.5 g (42%) of the title compound as a white solid. Mp: 239.5-241.1° C. NMR (DMSO-d6): δ 8.79 (s, 1H), 8.06 (d, J=2 Hz, 1H), 7.55-7.47 (m, 2H), 6.20 (d, J 8 Hz, 1H), 4.54 (d, J=4 Hz, 1H), 3.45-3.34 (m, 2H), 1.86-1.75 (m, 4H), 1.28-1.11 (m, 4H).

Provenance & Evidence