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

HRID 2039468Notes

Reaction equation

HRID 2039468 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>[N:2]1([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][N:4]=[CH:3]1

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 mmol) of sodium are added slowly to 2.5 litres of ethanol. 350.0 g (5.1 mol) of imidazole and 570 ml (858.6 g, 5.1 mol) of ethyl bromoacetate are added dropwise at an internal temperature of 20-25° C. The mixture is stirred at RT for 24 h. The precipitated solid is filtered off, the ethanol is removed under reduced pressure and the mixture is filtered again. The residue is purified by column chromatography on silica gel (mobile phase ethyl acetate). Yield: 639.0 g (81% of theory)

Workup

  1. filtrationThe precipitated solid is filtered off
  2. customthe ethanol is removed under reduced pressure
  3. filtrationthe mixture is filtered again
  4. customThe residue is purified by column chromatography on silica gel (mobile phase ethyl acetate)

Sources & evidence

ORD record
ord-4dc5c349ee824dfcbf97ea2f02f4f5dc
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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