Imidazole → ethyl 2-(1H-imidazol-1-yl)acetate

HRID 876677Notes

Reaction equation

HRID 876677 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1)[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7748Ethyl bromoacetateHCID 5360545Sodium

Product 1

HCID 3798501ethyl 2-(1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

118.2 g (5.1 mol) sodium are slowly added to 2.5 liters ethanol. 350.0 g (5.1 mol) imidazole are then added and 570 ml (858.6 g, 5.1 mol) ethyl bromoacetate are added dropwise at an internal temperature of 20-25° C. The mixture is stirred at RT for 24 h. The solid which has precipitated out is filtered off, the ethanol is removed in vacuo and the mixture is filtered again. The residue is purified by column chromatography over silica gel (mobile phase: ethyl acetate).

Workup

  1. customThe solid which has precipitated out
  2. filtrationis filtered off
  3. customthe ethanol is removed in vacuo
  4. filtrationthe mixture is filtered again
  5. customThe residue is purified by column chromatography over silica gel (mobile phase: ethyl acetate)

Sources & evidence

ORD record
ord-6a5642b01146418998822b87b8a0627d
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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