Reacción #5136

Ecuación de reacción

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

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente