Imidazole → N-p-methoxybenzylimidazole

HRID 865954Notes

Reaction equation

HRID 865954 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 578587N-p-methoxybenzylimidazoleYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10.88 g (0.16 mol) of imidazole in 150 ml of dry DMF at 0° C. under argon was added 6.4 g (0.16 mol) of 60% NaH, and the mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. The mixture was cooled to 0° C., and 25 g (0.16 mol) of p-methoxybenzyl chloride was added, and the mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride and water. The organic layer was dried over sodium sulfate, concentrated in vacuo to yield 35.6 g of a crude product which was purified by chromatography on silica (methylene chloride/methanol 9:1) to afford 25.3 g (84.2%) of 1-(p-methoxybenzyl)-imidazole.

Workup

  1. waitat room temperature for 1 h
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringthe mixture was stirred at room temperature for 24 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was partitioned between methylene chloride and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield 35.6 g of a crude product which
  9. customwas purified by chromatography on silica (methylene chloride/methanol 9:1)

Sources & evidence

ORD record
ord-08e0df0f513b4728ad2ebd7516a38af8
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

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