Reacción #1528384

Ecuación de reacción

benzimidazole

potassium hydroxide

α,α′-dibromo-m-xylene

→

1-[3-(1H-benzimidazole-1yl-methyl)benzyl]-1H-benzimidazole

Rendimiento 18.8%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 1 L round bottom flask equipped with a stirbar
2. 2
   Temperaturaat reflux
3. 3
   Temperaturaat reflux for 6 hours
4. 4
   Otrofollowed by room temperature
5. 5
   workup.STIRRINGstirring for 72 hours
6. 6
   FiltraciónThe cloudy solution was filtered
7. 7
   Lavadothe white solids rinsed with acetone
8. 8
   OtroThe resulting filtrate was dried on silica
9. 9
   Otropartitioned on a silica gel column
10. 10
    OtroThe product fractions were evaporated of solvent

Procedimiento

To a 1 L round bottom flask equipped with a stirbar was added 26.8 g benzimidazole (227 mmol) and 12.7 g (227 mmol) finely pulverized potassium hydroxide. These were stirred in 500 mL acetone for 20 minutes at reflux. 20.0 g (78.5 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at reflux for 6 hours followed by room temperature stirring for 72 hours. The cloudy solution was filtered, and the white solids rinsed with acetone. The resulting filtrate was dried on silica and partitioned on a silica gel column using a gradient of 100% acetonitrile→90% acetronitrile/10% MeOH as eluent. The product fractions were evaporated of solvent to give 5 g 1-[3-(1H-benzimidazole-1yl-methyl)benzyl]-1H-benzimidazole as a white solid.

Fuente