Imidazole → N-p-methoxybenzylimidazole

HRID 1276954Notes

Reaction equation

HRID 1276954 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Cl)=[CH:10][CH:9]=1>C(#N)C>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 578587N-p-methoxybenzylimidazoleYield 69.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of imidazole (25.53 g, 375 mmole) in acetonitrile (625 ml) was added p-methoxybenzyl chloride (16.95 ml, 125 mmole). The reaction was refluxed for 16 hours, evaporated to dryness, and redissolved in methylene chloride and saturated sodium bicarbonate. The organic layer was extracted with water twice. Standard acid/base workup gave N-p-methoxybenzylimidazole (16.3 g, 69%) which was used without further purification:

Workup

  1. temperatureThe reaction was refluxed for 16 hours
  2. customevaporated to dryness
  3. dissolutionredissolved in methylene chloride
  4. extractionThe organic layer was extracted with water twice

Sources & evidence

ORD record
ord-0d64a439fc3147089f9e8accce022dbb
Source dataset
uspto-grants-2000_12
Patent number
US06166216

Reaction notes

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