Sodium Methoxide → HCID 86668349, compound

Participants

Reaction Conditions

Reaction Steps

4-Nitrophenyl 4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylcarbamate (1.90 g, 3.55 mmol) was slurried in MeOH (15 mL) and cooled in a −10° C. dry ice/acetone bath. Sodium methoxide (1.33 mL of a 30 wt % solution in MeOH, 7.10 mmol) was added dropwise over 10 min. The resulting bright yellow slurry was warmed to ambient temperature and poured into ice water (150 mL). After stirring vigorously for 10 min, the mixture was filtered on a Büchner funnel. The tan solid was rinsed with water and dried in air. Recrystallization from MeOH/water provided the title compound (0.989 g, 65%) as a tan solid: mp 183-184.5° C.; 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 8.14 (d, J=8.7 Hz, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.50 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.9 Hz, 2H), 6.79 (s, 1H), 3.80 (s, 3H); HRMS-FAB (m/z) [M+H]+ calcd for C18H13F5N4O3, 428.0908. found, 428.0903.

Provenance & Evidence