Ethyl chloroacetate → ethyl (2-formyl-1H-imidazol-1-yl)acetate

HRID 1916376Notes

Reaction equation

HRID 1916376 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].CN1CCCC1=O.Cl[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>O>[CH:6]([C:2]1[N:1]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[CH:4][N:3]=1)=[O:7]

Participants

6

Reactant 4

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 62222097ethyl (2-formyl-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1H-imidazole-2-carboaldehyde (2.0 g), N-methylpyrrolidone (25 mL) was added, followed by dissolution with heating. To the resultant solution, ethyl chloroacetate (11.1 mL) and potassium carbonate (2.9 g) were added. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, water (30 mL) was added. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated saline and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration and the solvent was concentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane) to obtain the title compound having the following physical properties (1.3 g).

Workup

  1. dissolutionfollowed by dissolution
  2. temperaturewith heating
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe anhydrous sodium sulfate was removed by filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-0565e269818249d3a4ce5913ed66a94e
Source dataset
uspto-grants-2013_12
Patent number
US08618122B2

Reaction notes

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