تفاعل #1161630
ord-81864ef33db448e598a4831ec28dd92f
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1استخلاصthe resulting aqueous mixture was extracted with 2:1 diethyl ether/ethyl acetate
- 2استخلاصThe organic extract
- 3غسيلwas washed with 0.2 N hydrochloric acid until all unreacted aniline
- 4أخرىhad been removed
- 5غسيلThe organic solution was then washed with water and aqueous saturated sodium chloride solution
- 6تجفيفdried over magnesium sulfate
- 7أخرىThe solvent was then removed
- 8أخرىto leave a crude yellow oil which
- 9أخرىwas purified by flash chromatography
- 10أخرىThe yellow oil obtained
- 11workup.ADDITIONWhen the addition
- 12أخرىThe solid which formed
- 13أخرىwas separated by filtration
- 14أخرىrecrystallized from acetonitrile
الإجراء التجريبي
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.