Water → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]N-[[1-oxido-2-[4-(trifluoromethyl)phenyl]pyridin-1-ium-4-yl]methyl]prop-2-enamide

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Reaction Steps

3-Chloro perbenzoic acid (1.5 mol eq, 100 mg) was added to a solution of Example 1 (200 mg, 0.39 mmol) in CHCl3 (10 mL) and the mixture was stirred at r.t. for 24 hours. Then 10% water solution of K2CO3 was added to wash the organic phase that was then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (EtOAc 6/petroleum ether 4) to obtain a white solid (60 mg, 29% yield). 1HNMR (DMSO, 200 MHz) δ 1.09 (3H, t, J=7.2 Hz), 3.40 (2H, q, J=6.8 Hz), 4.40 (2H, d, J=6 Hz), 5.14 (1H, s), 6.10 (1H, s), 7.36 (1H, dd, J=4.8 Hz, J′=1.2 Hz), 7.46 (2H, t, J=8.8 Hz), 7.63 (1H, d, J=2.2 Hz), 7.83 (4H, m), 8.05 (2H, d, J=8 Hz), 8.34 (1H, d, J=6.8 Hz), 8.82 (1H, bt) [M+1] 524.6 (C24H21F4N3O4S requires 523.50).

Provenance & Evidence