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

HRID 1365597Notes

Reaction equation

HRID 1365597 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1)([O-:9])=[O:8].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>O>[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 5858191-(4-Nitrobenzyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (3.1 g, 23 mmol) is added to a solution of 4-nitrobenzylbromide (5 g, 23 mmol) and imidazole (1.6 g, 23 mmol) and the reaction mixture is stirred at RT. After the reaction has been completed according to HPLC-MS the suspension is poured into 800 mL water and extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried on sodium sulphate and evaporated down. The residue is purified by chromatography on silica gel with dichloromethane/methanol. Yield: 2.1 g.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. customdried on sodium sulphate
  4. customevaporated down
  5. customThe residue is purified by chromatography on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-91e892ed10d74592b3f173d1fcf866c6
Source dataset
uspto-grants-2011_02
Patent number
US07893049B2

Reaction notes

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