Hydrochloric Acid → (4-Methylphenyl)(1-vinyl-1h-benzimidazol-2-yl)methanone

HRID 31547Notes

Reaction equation

HRID 31547 reaction equation
N1C2C=CC=CC=2N=C1C(O[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O.[C:20](=[O:23])([O-])[O-].[K+].[K+].ClCCBr.[N:30]12[CH2:40][CH2:39][CH2:38][N:37]=[C:36]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2.Cl>C(O)(C)C.O>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:20]([C:36]2[N:30]([CH:40]=[CH2:39])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:38]=3[N:37]=2)=[O:23])=[CH:14][CH:15]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 231169711h-Benzimidazol-2-yl(4-methylphenoxy)methanone

Product 1

HCID 23116964(4-Methylphenyl)(1-vinyl-1h-benzimidazol-2-yl)methanoneYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe concentrated residue was dissolved in dimethylsulfoxide (30 ml)
  7. stirringthe mixture was stirred at 100° C. for 4 hours
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with 1N diluted hydrochloric acid, water and saturated saline
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe resultant was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-07aa9139f8844ea7a1b1e9a6f6b4c42b
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Reaction notes

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