Iodine → HCID 18670510, compound

Participants

Reaction Conditions

Reaction Steps

150 g of methyl 3-amino-4-mercaptobenzoate hydrochloride was suspended in 200 ml of diphenyl ether and heated to 100° C. After dropping 2-chloropyridine thereinto, 10.3 g of iodine was further added and the resulting mixture was reacted at 200° C. for 3 hours. After adding 20 ml of sulfuric acid and 300 ml of methanol at room temperature, the resulting mixture was heated under reflux for 3 hours. Then the reaction mixture was brought back to room temperature and poured into a cold saturated aqueous solution of sodium bicarbonate. Next, it was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The extract was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.3 g of the title compound as yellow crystals.

Provenance & Evidence