反应详情

To a solution of 5.1 g of 4-[1-(methoxymethyl)propyl]aniline and 210 ml of dried dimethylformamide was added 7.25 g of triethylamine. Then, 8.8 g of methyl(1,3-dithiolan-2-ylidene)sulfonium iodide was added and the mixture was allowed to stir at room temperature for 3 hours. The mixture was then poured into water and the resulting aqueous mixture was extracted with 2:1 diethyl ether/ethyl acetate. The organic extract was washed with 0.2 N hydrochloric acid until all unreacted aniline had been removed as shown by thin-layer chromatography. The organic solution 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 yellow oil which was purified by flash chromatography using silica gel with ethyl acetate/hexane as eluant. The yellow oil obtained was N-(1,3-dithiolan-2-ylidene)-4-[1-(methoxymethyl)propyl]aniline and it was dissolved in 250 ml of diethyl ether. To this solution was added dropwise a solution of 2 g of sulfuric acid in 110 ml of diethyl ether. When the addition was complete, the resulting mixture was placed in a freezer. The solid which formed was separated by filtration and recrystallized from acetonitrile to give N-(1,3-dithiolan-2-ylidene)-4-[1-(methoxymethyl)propyl]aniline dihydrogen sulfate as small white crystals melting at about 134°-137.5° C.

1. extractionthe resulting aqueous mixture was extracted with 2:1 diethyl ether/ethyl acetate
2. extractionThe organic extract
3. washwas washed with 0.2 N hydrochloric acid until all unreacted aniline
4. customhad been removed
5. washThe organic solution was 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 yellow oil which
9. customwas purified by flash chromatography
10. customThe yellow oil obtained
11. additionWhen the addition
12. customThe solid which formed
13. customwas separated by filtration
14. customrecrystallized from acetonitrile