Imidazole → 1H-Imidazole-1-propanoic acid, methyl ester

HRID 1934810Notes

Reaction equation

HRID 1934810 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]([O:10][CH3:11])(=[O:9])[CH:7]=[CH2:8]>C(#N)C>[N:1]1([CH2:8][CH2:7][C:6]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 7294Methyl Acrylate

Product 1

HCID 47375651H-Imidazole-1-propanoic acid, methyl esterYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.0 g(73.4 mmol) of imidazole and 12.6 g(148.6 mmol) of methyl acrylate were dissolved in 100 ml of acetonitrile, and then refluxed for 8 hours. Acetonitrile and the excess methyl acrylate was removed under reduced pressure. Then, 200 ml of ethyl acetate was added to the residue and the solution thus obtained was washed with saturated sodium chloride solution. Removal of ethyl acetate under reduced pressure provided 11.1 g(Yield: 90%) of the title compound.

Workup

  1. temperaturerefluxed for 8 hours
  2. customAcetonitrile and the excess methyl acrylate was removed under reduced pressure
  3. additionThen, 200 ml of ethyl acetate was added to the residue
  4. customthe solution thus obtained
  5. washwas washed with saturated sodium chloride solution
  6. customRemoval of ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-6991bf38e45346249e173b121eda5c4a
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

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