反应详情

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##

1. washIt was then washed with 0.1 N hydrochloric acid, twice with water
2. dry with materialonce with aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate
3. customThe solvent was then removed
4. customto give a crude yellow oil which
5. customwas purified by flash chromatography
6. customThis gave a colorless oil which
7. additionWhen the addition
8. customThe precipitate which formed
9. customwas separated by filtration
10. customrecrystallized from acetonitrile/ethyl acetate