Reacción #470390

Ecuación de reacción

N1-(2-isopropylphenyl)benzene-1,2-diamine

→

desired product

Rendimiento 58.2%

1-(2-isopropylphenyl)-2-phenyl-1H-benzo[d]imidazole

Rendimiento 58.2%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 3 hours
2. 2
   TemperaturaThe reaction mixture was heated up again
3. 3
   Temperaturato reflux overnight
4. 4
   OtroAir was bubbled through the reaction
5. 5
   Temperaturawhile reflux
6. 6
   OtroThe solvent was evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
8. 8
   OtroThe crude product was purified by column chromatography
9. 9
   OtroThe product was further purified
10. 10
    Otroby recrystallizing form ethanol

Procedimiento

N1-(2-isopropylphenyl)benzene-1,2-diamine (20 g, 88 mmol) and benzldehyde (8.5 g, 80 mmol) were reacted in acetonitrile (100 mL) under reflux for 3 hours. The reaction mixture was cooled to room temperature. Ferric chloride (0.13 g, 0.8 mmol) was added. The reaction mixture was heated up again to reflux overnight. Air was bubbled through the reaction while reflux. The solvent was evaporated. The residue was dissolved in dichloromethane (200 mL) and ran through a short silica gel plug. The crude product was purified by column chromatography using dichloromethane to 3% of ethyl acetate in dichloromethane. The product was further purified by recrystallizing form ethanol. 8 g of desired product was obtained.

Fuente