Thionyl Chloride → HCID 24988167, compound

Participants

Reaction Steps

8.3 g of 2-acetoxymethyl-3-methyl-4-butoxy-pyridine was dissolved in chloroform, and 21.6 g (4 eq.) of thionyl chloride was added. The mixture was heated to reflux for one hour and then concentrated, and a residue resulting therefrom was dissolved in methanol. The solution was added in advance to 6.1 g (1 eq.) of 2-mercaptobenzimidazole, 230 mL of a 28% sodium methoxide solution, and 120 mL of methanol, and the mixture was heated to reflux for one hour. Methanol was distilled off, ice was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate. Subsequently, the ethyl acetate solution was concentrated to dryness, and the resulting residue was purified by silica gel column chromatography, and then was concentrated to dryness, to obtain 12.2 g of yellow crystals. 12.2 g of the crystals were recrystallized from ethyl acetate/1-hexane, to obtain 4.2 g of colorless crystals. Total yield 10.8% (purity by HPLC: 97.0%).

Provenance & Evidence