Hydrochloric Acid → HCID 17862385, compound

Participants

Reaction Steps

Potassium hydroxide (0.42 g, 7.5 mmol) and 30% hydrogen peroxide (2.7 ml) were added to a solution of N-butyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carbothioamide (0.98 g, 2.5 mmol) in methanol (10 ml), and the mixture was stirred at room temperature for 3 hours. Concentrated hydrochloric acid was added to the reaction mixture up to a pH of 1, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (15 ml×3), and the 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=1/10→1/1), to give a colorless viscous substance of N-butyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.17 g, yield: 18.1%). 1H-NMR (CDCl3, TMS, ppm): δ 0.94 (t, J=7.3 Hz, 3H), 1.30-1.50 (m, 2H), 1.50-1.70 (m, 2H), 2.65 (s, 3H), 3.35 (dt, J=6.3 and 6.3 Hz, 2H), 6.04 (s, 1H), 6.90-7.20 (m, 1H), 8.02 (d, J=2.0 Hz, 1H), 8.35 (m, 1H).

Provenance & Evidence