Ethyl bromoacetate → Ammonia

HRID 20270

Reaction equation

HRID 20270 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[NH:9][CH:10]=[CH:11][N:12]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[NH3:9].[CH3:7][C:8]1[N:9]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:10]=[CH:11][N:12]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 127492-Methylimidazole

Product 2

HCID 222AmmoniaHCID 28940035Ethyl (2-methyl-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (8.42 g, 61 mmol) was added to a solution of 2-methylimidazole (5 g, 61 mmol) in tetrahydrofuran (100 mL) and the suspension was stirred for 30 minutes. Ethyl bromoacetate (6.75 mL, 61 mmol) was added and the reaction was stirred for a further 30 minutes at room temperature. The mixture was filtered, washing through with dichloromethane:methanol (90:10). The filtrate was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (93:7:0.5) as eluant to afford the title compound as an oil, 5.28 g.

Workup

  1. stirringthe reaction was stirred for a further 30 minutes at room temperature
  2. filtrationThe mixture was filtered
  3. washwashing through with dichloromethane:methanol (90:10)
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f852e7f1217c4842882dc23cfb56a9df
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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