Acetonitrile → 1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Participants

Reaction Steps

A mixture of 4-nitro-imidazole (2.75 g, 24.3 mmol), benzyl chloride (4.3 g, 26.8 mmol), potassium carbonate (4 g, 29.2 mmol), and acetonitrile (50 mL) was stirred for 2 h at rt, warmed to 55° C., stirred for 16 h, allowed to cool to rt, concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 4:1) to afford 5.6 g of the title compound. tR: 0.93 min (LC-MS 4); ESI-MS: 234.3 [M+H]+ (LC-MS 4); Rf=0.25 (hexane/EtOAc, 4:1).

Provenance & Evidence