Реакция #446180

Уравнение реакции

Compound 153a

Methyl 11-(5-mercapto-1,3,4-thiadiazol-2-yl)thio-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

octadecyl bromide

potassium carbonate

→

product

Methyl 11-(5-octadecylthio-1,3,4-thiadiazol-2-yl)thio-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
2. 2
   ЭкстракцияThe aqueous phase was extracted with 200 ml of methylene chloride
3. 3
   ПромывкаThe extract was washed with saturated sodium chloride aqueous solution
4. 4
   СушкаAfter drying over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   ПромывкаThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=15:1)

Методика

After 50 ml of an N,N-dimethylformamide solution containing a mixture of 2.0 g of Compound 153a obtained in Example 119, 2 ml of octadecyl bromide and 2.0 g of potassium carbonate was stirred at 80° C. at 1.5 hours, the solvent was distilled off under reduced pressure. The aqueous phase was extracted with 200 ml of methylene chloride. The extract was washed with saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=15:1) to give 0.8 g of the product.

Источник