4-Toluenesulfonyl chloride → HCID 18406949, compound

Participants

Reaction Steps

To a suspension of 4-(2-fluorophenyl)-5-(hydroxymethyl)pyrazol-3-one (28.7 g, 0.138 mol) in dry dichloromethane (300 ml) was added p-toluenesulfonyl chloride (28.9 g, 0.152 mol) followed by triethylamine (21.2 ml, 0.152 mol) dropwise. The solution was stirred at room temperature for 2 days. Dichloromethane (300 ml) was then added to dilute and the solution was washed with brine (300 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography with 0%→40% ethyl acetate/dichloromethane as eluent to give the title compound (23.7 g). Data for the title compound: 1H NMR (360 MHz, DMSO) δ 2.34 (3H, s), 4.66 (2H, s), 6.94 (1H, t), 7.06 (3H, m), 7.17-7.25 (2H, m), 7.51 (2H, d); MS (ES+) m/e 362 [MH]+.

Provenance & Evidence