Réaction #59825

Équation de réaction

1.8-diazabicyclo[5,4,0]undec-7-ene

potassium carbonate

1-chloro-2-bromoethane

compound

1H-Benzimidazol-2-yl(4-methylphenoxy)methanone

hydrochloric acid

→

title compound

Rendement 65.0%

(4-Methylphenyl)(1-vinyl-1H-benzimidazol-2-yl)methanone

Rendement 65.0%

Solvants

water

isopropanol

Conditions de réaction

Traitement

1. 1
   Températureto cool to room temperature
2. 2
   ExtractionThe mixture was extracted with ethyl acetate
3. 3
   LavageThe organic layer was washed with water and saturated saline
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Autrethe solvent was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe concentrated residue was dissolved in dimethylsulfoxide (30 ml)
7. 7
   workup.STIRRINGthe mixture was stirred at 100° C. for 4 hours
8. 8
   Extractionthe mixture was extracted with ethyl acetate
9. 9
   LavageThe organic layer was washed with 1N diluted hydrochloric acid, water and saturated saline
10. 10
    Séchagedried over magnesium sulfate
11. 11
    AutreThe solvent was evaporated under reduced pressure
12. 12
    Autrethe resultant was purified by silica gel column chromatography

Mode opératoire

The compound of Example 25-1 (6.25 g, 26.5 mmol) was dissolved in isopropanol (100 ml), and thereto were added potassium carbonate (7.31 g, 52.9 mmol) and 1-chloro-2-bromoethane (19.0 g, 133 mmol), and the mixture was stirred at 70° C. for 16 hours. The reaction solution was allowed to cool to room temperature, and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The concentrated residue was dissolved in dimethylsulfoxide (30 ml), and thereto was added 1.8-diazabicyclo[5,4,0]undec-7-ene (DBU) (15.2 g, 100 mmol), and the mixture was stirred at 100° C. for 4 hours. To the mixture was added 1N diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N diluted hydrochloric acid, water and saturated saline, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the resultant was purified by silica gel column chromatography to give the title compound (4.23 g, 65%).

Source