Reaktion #5136

Reaktionsgleichung

methyl 11-chloroacetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

imidazole

→

product

Methyl 11-(1-imidazolyl)acetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
3. 3
   ExtraktionThe obtained residue was extracted with 300 ml of methylene chloride
4. 4
   WaschenThe extract was washed successively with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
5. 5
   TrocknenAfter drying over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   WaschenThe resulting residue was subjected to silica gel column chromatography (eluting solvent; chlororform:methanol=10:1)

Vorschrift

Crude methyl 11-chloroacetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate, 3.0 g, was heated to reflux for 4 hours in 100 ml of toluene together with 0.9 g of imidazole. After allowing to cool, the solvent was distilled off under reduced pressure. The obtained residue was extracted with 300 ml of methylene chloride. The extract was washed successively with saturated sodium bicarbonate aqueous solution and 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; chlororform:methanol=10:1) to give 1.6 g of the product.

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