Ethyl bromoacetate → ethyl 2-(4-cyano-1H-imidazol-1-yl)acetate

HRID 562443Notes

Reaction equation

HRID 562443 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1.[O-]CC.[Na+].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[C:6]([C:4]1[N:3]=[CH:2][N:1]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1)#[N:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 178510437HCID 178510437, compound

Product 1

HCID 68753735ethyl 2-(4-cyano-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.3 g (35.3 mmol) of 1H-imidazole-4-carbonitrile [Matthews et al., J. Org. Chem. 1986, 51, 3228-3231] are initially charged in 13.2 ml (11.5 g, 35.3 mmol) of 21% strength sodium ethoxide solution in ethanol, and 4.3 ml (6.5 g, 38.9 mmol) of ethyl bromoacetate are added. The reaction mixture is stirred at RT for 16 h. For work-up, the precipitated solid is filtered off, the filter residue is washed with ethanol and the filtrate is concentrated under reduced pressure. Diisopropyl ether is added to the residue, the mixture is filtered again, the filtrate is once more concentrated on a rotary evaporator and the residue is dried under reduced pressure. Yield: 3.8 g (60% of theory)

Workup

  1. additionare added
  2. filtrationFor work-up, the precipitated solid is filtered off
  3. washthe filter residue is washed with ethanol
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. additionDiisopropyl ether is added to the residue
  6. filtrationthe mixture is filtered again
  7. concentrationthe filtrate is once more concentrated on a rotary evaporator
  8. customthe residue is dried under reduced pressure

Sources & evidence

ORD record
ord-4fb8941053864a6791eff61d297ffb7e
Source dataset
uspto-grants-2011_11
Patent number
US08067407B2

Reaction notes

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