反应详情

To a mixture of 0.97 g of sodium hydride and 5.7 g of methyl iodide in 40 ml of dried dimethylformamide was added dropwise a solution of 2.4 g of 6-[4-(1,3-dithiolan-2-ylideneamino)phenyl]hexanol in 25 ml of dimethylformamide. The resulting mixture was stirred at room temperature for 16 hours and then poured into an aqueous solution containing 0.2 M potassium hydrogen phosphate/potassium dihydrogen phosphate buffer solution (pH 7) with a few crystals of sodium thiosulfate added. This aqueous mixture was extracted with diethyl ether and the organic extract was then washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was then removed to leave a crude orange oil which was purified by flash chromatography using 15 cm of silica gel and ethyl acetate/hexane as the eluant. The yellow oil obtained was N-(1,3-dithiolan-2-ylidene)-4-(6-methoxyhexyl)-aniline and 1.76 g of the oil was dissolved in 75 ml of diethyl ether. To this solution was added dropwise a solution of 0.6 g of sulfuric acid in 35 ml of diethyl ether. When the addition was complete, the mixture was placed in the freezer. The precipitate which formed was separated by filtration and crystallized from acetonitrile to give N-(1,3-dithiolan-2-ylidene)-4-(6-methoxyhexyl)aniline dihydrogen sulfate as white crystals melting at about 141°-142.5° C.

1. additionpoured into an aqueous solution
2. additionadded
3. extractionThis aqueous mixture was extracted with diethyl ether
4. extractionthe organic extract
5. washwas then washed with water and aqueous saturated sodium chloride solution
6. dry with materialdried over magnesium sulfate
7. customThe solvent was then removed
8. customto leave a crude orange oil which
9. customwas purified by flash chromatography
10. customThe yellow oil obtained
11. additionWhen the addition
12. customThe precipitate which formed
13. customwas separated by filtration
14. customcrystallized from acetonitrile