Reaktion #446180

Reaktionsgleichung

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

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle