Imidazole → 1-(4-Nitrobenzyl)-1H-imidazole

HRID 1091651Notes

Reaction equation

HRID 1091651 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>C(#N)C>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 5858191-(4-Nitrobenzyl)-1H-imidazoleYield 42.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (2.00 g; 14.6 mmol) was added to a stirred solution of 1-(bromomethyl)-4-nitrobenzene (3.20 g; 14.8 mmol) and imidazole (1.00 g; 14.7 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 17 hr and then concentrated under reduced pressure. The residue was partitioned between EA and water and the phases separated. The aqueous phase was extracted twice with EA; and the combined organic layers washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-(4-nitrobenzyl)-1H-imidazole (1.27 g) as a red/brown oil. A solution of 1-(4-nitrobenzyl)-1H-imidazole (2.67 g; 13.1 mmol) in ethanol (100 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.285 g) at room temperature for 4.5 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[(1H-imidazol-1-ylmethyl]benzenamine (2.24 g) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EA and water
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted twice with EA
  5. washand the combined organic layers washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94d34be2bbda44faaf27ba4f200b122d
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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