Benzyl Bromide → Diethyl 1-benzyl-2-methylimidazole-4,5-dicarboxylate

HRID 265185Notes

Reaction equation

HRID 265185 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[NH:9][C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>CN(C)C(=O)C.O>[CH2:23]([N:12]1[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]=[C:8]1[CH3:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 653376ST4058398HCID 23665647Potassium tert-butoxide

Product 1

HCID 19036158Diethyl 1-benzyl-2-methylimidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

5.21 g of potassium t-butoxide were added to a solution of 10.0 g of diethyl 2-methylimidazole-4,5-dicarboxylate in 100 ml of N,N-dimethylacetamide, whilst ice-cooling and under a nitrogen atmosphere. The mixture was stirred for 30 minutes, until a homogeneous solution was obtained, and then 5.78 ml of benzyl bromide were added dropwise to this solution, whilst ice-cooling. The resulting mixture was stirred at room temperature for 1 hour, after which it was mixed with ethyl acetate and water and shaken. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 12.38 g of the title compound as a syrup.

Workup

  1. temperaturecooling and under a nitrogen atmosphere
  2. customwas obtained
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at room temperature for 1 hour
  5. stirringshaken
  6. customThe ethyl acetate layer was separated
  7. washwashed with an aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customthe resulting residue was purified by column chromatography through silica gel
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-87abba3b377a49a49e74aa89b688f7f4
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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