Chloromethyl methyl sulfide → 1-methylsulfanylmethyl-3-nitro-1H-pyrazole

Participants

Reaction Steps

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 50 mg, 4.42 mmol) in anhydrous N,N-dimethylformamide (5 mL), a 60% dispersion of sodium hydride in mineral oil (230 mg, 5.75 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 30 min, chloro-methylsulfanyl-methane (555 mg, 5.75 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 1-methylsulfanylmethyl-3-nitro-1H-pyrazole (514 mg, 67%) as a white solid.

Provenance & Evidence