反应详情

Triethylamine (0.13 g, 1.3 mmol) and methyl isocyanate (0.07 g, 1.2 mmol) were added to a solution of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.32 g, 1.1 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10), to give a white solid of N-methyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.22 g, yield: 56.9%). mp: 87-88° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.59 (s, 3H), 2.88 (d, J=5.0 Hz, 3H), 5.80 (s, 1H), 6.55-6.75 (m, 1H), 7.40 (dd, JHF=2.0 and 9.3 Hz, 1H), 7.56 (s, 1H).

1. customAfter completion of the reaction
2. extractionextracted with ethyl acetate (10 ml×3)
3. washAn organic layer was washed with water
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customto remove a desiccant, and the solvent
7. distillationwas distilled off from the filtrate under reduced pressure
8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10)