Sulfuric Acid → HCID 20496702, compound

Participants

Reaction Steps

To a mixture of 1 g of 6-[4-(1,3-dithiolan-2-ylideneamino)phenyl]hexanol and 0.38 g of triethylamine in 20 ml of dried methylene chloride was added dropwise a solution of 0.27 g of acetyl chloride in 10 ml of dried methylene chloride. The resulting solution was stirred at room temperature for 2 hours. It was then washed with 0.1 N hydrochloric acid, twice with water, and once with aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was then removed to give a crude yellow oil which was purified by flash chromatography using 15 cm of silica gel and ethyl acetate/hexane as the eluant. This gave a colorless oil which was 4-(6-acetoxyhexyl)N-(1,3-dithiolan-2-ylidene)aniline. This oil was dissolved in 40 ml of diethyl ether and there was added dropwise a solution of 0.29 g of sulfuric acid and 20 ml of diethyl ether. When the addition was complete, the reaction mixture was placed in a freezer. The precipitate which formed was separated by filtration and recrystallized from acetonitrile/ethyl acetate to give 4-(6-acetoxyhexyl)-N-(1,3-dithiolan-2-ylidene)-aniline dihydrogen sulfate as white needles melting at about 151.5°-153.5° C. The free base of this compound has the following structural formula ##STR6##

Provenance & Evidence