Sodium Sulfide → 4-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol

Participants

Reaction Steps

1.876 g of 4-chloro-3-nitrobenzyl alcohol was dissolved in 20 ml of dimethyl sulfoxide. After adding 820 mg of anhydrous sodium sulfide, the resulting mixture was stirred at room temperature for 15 hours. After adding 1.19 g of 2,3-dichloropyrazine thereto, the reaction mixture was stirred at 100° C. for 1 hour. After adding ice/water, the reaction mixture was extracted with ethyl acetate, washed successively with water, 1 N hydrochloric acid, water, 1 N sodium hydroxide, and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.60 g of the title compound as yellow crystals.

Provenance & Evidence