Hydrochloric Acid → HCID 17862392, compound

Participants

Reaction Steps

Potassium carbonate (0.61 g, 4.4 mmol) and propyl isocyanate (0.34 g, 4.0 mmol) were added to a solution of 5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole (1.15 g, 4.0 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (20 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered co 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=1/5), to give a yellow viscous substance of N-propyl-5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (1.08 g, yield: 72.5%). 1H-NMR (CDCl3, TMS, ppm): δ 0.97 (t, J=7.4 Hz, 3H), 1.62 (tq, J=7.4 and 7.4 Hz, 2H), 2.64 (d, J=0.7 Hz, 3H), 3.25-3.40 (m, 2H), 5.88 (q, J=0.7 Hz, 1H), 6.80-7.05 (m, 1H), 7.42 (d, J=9.2 Hz, 1H), 8.40 (dd, J=2.7 and 9.2 Hz, 1H), 8.59 (d, J=2.7 Hz, 1H).

Provenance & Evidence