Pyridine → Phenyl (4-(trifluoromethyl)pyridin-2-yl)carbamate

Participants

Reaction Steps

A solution of the commerically available 2-amino-4-trifluoromethylpyridine (20.86 g, 128.7 mmol) in 250 mL CH2Cl2 was treated with phenylchloroformate (17.81 mL, 141.5 mmol) and pyridine (22.85 mL, 283 mmol). During addition of the pyridine a yellow precipitate formed and a considerable exotherm was observed. After 0.5 h the homogeneous reaction was diluted with 1 L Et2O and washed with 1N bisulfate buffer (pH 2) and sat. NaHCO3. The organic layer was dried with Na2SO4 and evaporated to yield a gray solid. Tritruration with Et2O:hexanes (1:5) gave the title compound as cottony white crystals (33.5 g, 92% Yield). 1H-NMR (DMSO-d6) 11.28 (s, 1H), 8.60 (d, J=5.1 Hz, 1H), 8.12 (bs, 1H), 7.40 to 7.48 (m, 3H), 7.22 to 7.31 (m, 3H); MS [M+H]+=283.1; LCMS RT=3.51.

Provenance & Evidence