Reaction #5136

Reaction equation

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

Solvents

toluene

Conditions

Workup

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

Procedure

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.

Source