Sodium Methoxide → HCID 24988168, compound

Participants

Reaction Steps

To a liquid prepared by dissolving with stirring 7.8 g (0.052 mol, 0.95 eq.) of 2-mercaptobenzimidazole and 61.5 g (0.319 mol, 5.8 eq.) of a 28% sodium methoxide solution in 360 mL of methanol, a liquid prepared by dissolving the whole amount of 4-hexyloxy-2-chloromethyl-3-methylpyridine in 180 mL of methanol was added at 30° C. Subsequently, the mixture was heated to reflux for 30 minutes and cooled, and then methanol was solid dried under reduced pressure. A yellow brown oily residue resulting therefrom was dissolved in 200 mL of ethyl acetate, and then the organic layer was washed with 80 mL of water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated to dryness. The resulting residue was purified by silica gel column chromatography, and then was concentrated to dryness, to obtain 15.2 g of an orange-colored oily matter. The product was recrystallized from ethyl acetate (5 vol.), to obtain 5.0 g of colorless crystals (HPLC: 99.1 Area %, yield 25.5%).

Provenance & Evidence