Methyl iodide → 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

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Reaction Steps

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole (2.0 g, 3.6 mmol) in tetrahydrofuran at 20° C. under nitrogen, was added sodium hydride (0.461 g, 60% in oil, 11.5 mmol), and stirred for 0.5 hour. Iodomethane (2.065 g, 14.4 mmol) was added and the mixture stirred for 4.5 hours at 20° C., then allowed to stand for 2.5 days. The mixture was added to ethyl acetate and saturated ammonium chloride solution. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated and chromatographed on silica gel eluting with heptane-ethyl acetate (3:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a light brown solid (Compound number 2-14, 1.3 g, 57% yield), mp 89° C.

Provenance & Evidence