Ammonia → HCID 59226972, compound

Participants

Reaction Conditions

Reaction Steps

Ammonia gas was added for 30 minutes to a solution of 4-cyano-3-fluoro-N-[2-methoxymethyl-6-methyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethyl-propyl)-phenyl]-benzamide (0.981 g, 1.90 mmol) (Example I1) in dimethylsulfoxide (20 ml). The reaction mixture was heated to 100° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and more ammonia gas was added. The reaction mixture was heated to 100° C. for a further 16 hours. The reaction mixture was allowed to cool to ambient temperature and then partitioned between water and ethyl acetate. The aqueous phase was extracted 3 times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give 3-amino-4-cyano-N-[2-methoxymethyl-6-methyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethyl-propyl)-phenyl]-benzamide (640 mg, 66% yield). 1H-NMR (400 MHz, CDCl3): 8.77 (s, 1H), 7.51 (m, 2H), 7.37 (m, 2H), 7.18 (d, 1H), 4.63 (s, 2H), 4.49 (s, 2H), 3.37 (s, 3H), 2.36 (s, 3H) ppm.

Provenance & Evidence