Diethylcarbamoyl chloride (1.52 g, 7.8 mmol) was added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole (1.39 g, 5.0 mmol) and potassium carbonate (1.98 g, 14.3 mmol) in DMF (15 ml), the mixture was stirred at 70° C. for 9 hours and further stirred at room temperature for 2 days. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid, and the mixture was extracted with ethyl acetate (20 ml×3). An organic-layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant. 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=1/5), to give a colorless viscous substance of N,N-diethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.21 g, yield: 11.2%). 1H-NMR (CDCl3, TMS, ppm): δ 1.21 (t, J=7.0 Hz, 6H), 2.48 (d, J=0.6 Hz, 3H), 3.47 (q, J=7.0 Hz, 4H), 6.00 (q, J=0.6 Hz, 1H), 7.99 (d, J=2.1 Hz, 1H), 8.33 (m, 1H).
