Benzimidazole → HCID 5242437, compound

HRID 1441202Notes

Reaction equation

HRID 1441202 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 1 L 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. customTo a 1 L round bottom flask equipped with a stirbar
  2. temperatureat reflux
  3. temperatureat reflux for 6 hours
  4. customfollowed by room temperature
  5. stirringstirring for 72 hours
  6. filtrationThe cloudy solution was filtered
  7. washthe white solids rinsed with acetone
  8. customThe resulting filtrate was dried on silica
  9. custompartitioned on a silica gel column
  10. customThe product fractions were evaporated of solvent

Sources & evidence

ORD record
ord-3527d38c8f0d414f9b57a68037486f59
Source dataset
uspto-grants-2010_02
Patent number
US07655322B2

Reaction notes

Loading…