Benzimidazole → HCID 5242437, compound

HRID 1441204Notes

Reaction equation

HRID 1441204 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[OH-].[K+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=1>CC(C)=O>[N:1]1([CH2:13][C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[CH2:20][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 14797Potassium HydroxideHCID 69373Benzene, 1,3-bis(bromomethyl)-

Product 1

HCID 5242437HCID 5242437, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 1L round bottom flask equipped with a stirbar was added 26.8 g benzimidazole (227 mmol) and 12.7 g (227 mmol) finely pulverized potassium hydroxide. These were stirred in 500 mL acetone for 20 minutes at reflux. 20.0 g (78.5 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at reflux for 6 hours followed by room temperature stirring for 72 hours. The cloudy solution was filtered, and the white solids rinsed with acetone. The resulting filtrate was dried on silica and partitioned on a silica gel column using a gradient of 100% acetonitrile→90% acetronitrile/10% MeOH as eluent. The product fractions were evaporated of solvent to give 5 g 1-[3-(1H-benzimidazole-1yl-methyl)benzyl]-1H-benzimidazole as a white solid.

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 6 hours
  3. customfollowed by room temperature
  4. stirringstirring for 72 hours
  5. filtrationThe cloudy solution was filtered
  6. washthe white solids rinsed with acetone
  7. customThe resulting filtrate was dried on silica
  8. custompartitioned on a silica gel column
  9. customThe product fractions were evaporated of solvent

Sources & evidence

ORD record
ord-9b63db91fce245f8939f72636696245d
Source dataset
uspto-grants-2010_02
Patent number
US07655323B2

Reaction notes

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