Реакция #470390

Уравнение реакции

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

→

desired product

Выход 58.2%

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

Выход 58.2%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Температураunder reflux for 3 hours
2. 2
   ТемператураThe reaction mixture was heated up again
3. 3
   Температураto reflux overnight
4. 4
   ДругоеAir was bubbled through the reaction
5. 5
   Температураwhile reflux
6. 6
   ДругоеThe solvent was evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
8. 8
   ДругоеThe crude product was purified by column chromatography
9. 9
   ДругоеThe product was further purified
10. 10
    Другоеby recrystallizing form ethanol

Методика

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.

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