Hydrochloric Acid → HCID 17862345, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.13 g, 1.3 mmol) was added to a solution of 5-methyl-3-phenyloxypyrazole (0.20 g, 1.2 mmol) in ethyl acetate (5 ml), and the mixture cooled to 0° C. Then, ethyl isocyanate (0.09 g, 1.3 mmol) was added, and the mixture was stirred for 30 minutes at an ambient temperature. And, the mixture was stirred for 4 hours while it was allowed to have room temperature gradually. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (10 ml) and extracted with ethyl acetate (10 ml×2). An organic layer was washed with water (10 ml×2), 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=1/15), to give a yellow viscous substance of N-ethyl-5-methyl-3-phenyloxypyrazole-1-carboxamide (0.16 g, yield: 56.4%). 1H-NMR (CDCl3, TMS, ppm): δ 1.22 (t, J=7.3 Hz, 3H), 2.58 (d, J=0.8 Hz, 3H), 3.38 (dq, J=1.3 and 7.3 Hz, 2H), 5.67 (q, J=0.8 Hz, 1H), 6.99-7.07 (br s, 1H), 7.12-7.19 (m, 3H), 7.33-7.39 (m, 2H).

Provenance & Evidence