Reaction #470390

Reaction equation

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

→

desired product

Yield 58.2%

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

Yield 58.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 3 hours
2. 2
   TemperatureThe reaction mixture was heated up again
3. 3
   Temperatureto reflux overnight
4. 4
   OtherAir was bubbled through the reaction
5. 5
   Temperaturewhile reflux
6. 6
   OtherThe solvent was evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
8. 8
   OtherThe crude product was purified by column chromatography
9. 9
   OtherThe product was further purified
10. 10
    Otherby recrystallizing form ethanol

Procedure

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.

Source