Hydrochloric Acid → HCID 17862371, compound

Participants

Reaction Steps

Potassium carbonate (0.83 g, 6.0 mmol) and tert-butyl isocyanate (0.59 g, 6.0 mmol) were added to a solution of 5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)pyrazole (1.15 g, 4.0 mmol) in DMF (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 (20 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=1/5), to give a white solid of N-tert-butyl-5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)-pyrazole-1-carboxamide (0.80 g, yield: 51.8%). mp: 104-106° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.41 (s, 9H), 2.61 (s, 3H), 5.82 (s, 1H), 6.65-6.90 (br s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.82 (dd, J=2.1 and 8.7 Hz, 1H), 8.23 (d, J=2.1 Hz, 1H).

Provenance & Evidence