Reaktion #470390

Reaktionsgleichung

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

→

desired product

Ausbeute 58.2%

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

Ausbeute 58.2%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 3 hours
2. 2
   TemperaturThe reaction mixture was heated up again
3. 3
   Temperaturto reflux overnight
4. 4
   SonstigeAir was bubbled through the reaction
5. 5
   Temperaturwhile reflux
6. 6
   SonstigeThe solvent was evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
8. 8
   SonstigeThe crude product was purified by column chromatography
9. 9
   SonstigeThe product was further purified
10. 10
    Sonstigeby recrystallizing form ethanol

Vorschrift

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.

Quelle