Réaction #470390

Équation de réaction

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

→

desired product

Rendement 58.2%

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

Rendement 58.2%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 3 hours
2. 2
   TempératureThe reaction mixture was heated up again
3. 3
   Températureto reflux overnight
4. 4
   AutreAir was bubbled through the reaction
5. 5
   Températurewhile reflux
6. 6
   AutreThe solvent was evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
8. 8
   AutreThe crude product was purified by column chromatography
9. 9
   AutreThe product was further purified
10. 10
    Autreby recrystallizing form ethanol

Mode opératoire

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