Imidazole → HCID 11228701, compound

HRID 1441205Notes

Reaction equation

HRID 1441205 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[K+].Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]Br)[CH:11]=1>CC(C)=O>[N:1]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14797Potassium HydroxideHCID 69373Benzene, 1,3-bis(bromomethyl)-

Product 1

HCID 11228701HCID 11228701, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 500 mL round bottom flask equipped with a stirbar was added 11.6 g imidazole (170 mmol) and 9.55 g (170 mmol) finely pulverized potassium hydroxide. These were stirred in 200 mL acetone until the solution became yellow translucent. 15.0 g (56.8 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at room temperature overnight. 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 30/70 acetonitrile/methanol as eluent. The product fractions were evaporated of solvent and the resulting oil recrystallized from ethyl acetate/hexanes to give 8.65 g 1-[3-(1H-imidazole-1yl-methyl)benzyl]-1H-imidazole as a white solid.

Workup

  1. customTo a 500 mL round bottom flask equipped with a stirbar
  2. filtrationThe cloudy solution was filtered
  3. washthe white solids rinsed with acetone
  4. customThe resulting filtrate was dried on silica
  5. custompartitioned on a silica gel column
  6. customThe product fractions were evaporated of solvent
  7. customthe resulting oil recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4d78dc0764a84f049d0e1626a6b5e69c
Source dataset
uspto-grants-2010_02
Patent number
US07655323B2

Reaction notes

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