Imidazole → N-p-methoxybenzylimidazole

HRID 1586325Notes

Reaction equation

HRID 1586325 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-027d982006c443b2a642d4059f039a13
Source dataset
uspto-grants-1999_08
Patent number
US05942530

Reaction notes

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