Trifluoroacetic acid methylene chloride → Trifluoroacetate

Participants

Reaction Steps

Tert-butyl 4-[2-({4-[(difluoromethyl)thio]phenyl}amino)-2-oxoethyl]phenylcarbamate (Example 27) (3.63 g) was stirred in 25% trifluoroacetic acid/dichloromethane at room temperature for 45 minutes. The mixture was diluted with 1,2-dichloroethane (25 mL) and evaporated down twice. The residue was recrystallized from ethyl acetate (15 mL) and hexane (15 mL). The product was obtained as the 1:1 trifluoroacetate salt, 2-(4-aminophenyl)-N-(4-(difluoromethylthio)phenyl)acetamide 2,2,2-trifluoroacetate: 1H NMR (300 MHz, DMSO-d6) δ ppm 3.45-4.13 (m, 2H) 3.62 (s, 2H) 7.03 (d, J=8.5 Hz, 2H) 7.38 (t, J=56.1 Hz, 1H) 7.28 (d, J=8.5 Hz, 2H) 7.47-7.55 (m, 2H) 7.64-7.72 (m, 2H) 10.36 (s, 1H) MS (DCI/NH3) m/z 309.0 (M+H)+; Anal. C15H14F2N2OS C2HF3O2: C, H, N.

Provenance & Evidence