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

HRID 1942007Notes

Reaction equation

HRID 1942007 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1.CC[O-].[Na+].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1)[CH3:18]

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) 1H-imidazole-4-carbonitrile [Matthews et al., J. Org. Chem. 1986, 51, 3228-3231] are initially introduced into 13.2 ml (11.5 g, 35.3 mmol) 21% strength sodium ethylate solution in ethanol and 4.3 ml (6.5 g, 38.9 mmol) ethyl bromoacetate are added. The reaction mixture is stirred at RT for 16 h. For working up, the solid which has precipitated out is filtered off, the residue on the filter is washed with ethanol and the filtrate is concentrated in vacuo. Diisopropyl ether is added to the residue, the mixture is filtered again, the filtrate is concentrated again on a rotary evaporator and the residue is dried in vacuo.

Workup

  1. additionare added
  2. customthe solid which has precipitated out
  3. filtrationis filtered off
  4. washthe residue on the filter is washed with ethanol
  5. concentrationthe filtrate is concentrated in vacuo
  6. additionDiisopropyl ether is added to the residue
  7. filtrationthe mixture is filtered again
  8. concentrationthe filtrate is concentrated again on a rotary evaporator
  9. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-fe8fb8c58567492fb8546ff1476430e2
Source dataset
uspto-grants-2013_03
Patent number
US08389520B2

Reaction notes

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