Chloride → HCID 426634, compound

HRID 1251907Notes

Reaction equation

HRID 1251907 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].[Cl-].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]=1.[CH3:1][C:2]1[N:3]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]=[N:5][CH:6]=1

Participants

8

Reactant 5

HCID 312ChlorideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178418800HCID 178418800, compound

Product 2

HCID 237336Ethyl (4-methyl-1H-imidazol-1-yl)acetateHCID 426634HCID 426634, compoundYield 163.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-methylimidazole (8.2 g, 0.1M), anhydrous potassium carbonate (13.8 g, 0.1M), potassium hydroxide (5.6 g, 0.1 M) and tetrabutylammonuim chloride (1.13 g, 3.51 mM) in methylene chloride (170 ml) at 0° C. was treated with ethyl 2-bromoacetate (8.35 g, 50 mM). The mixture was stirred at 0° C. for 1 hour and at ambient temperature, for 18 hours. It was then filtered and evaporated to dryness. The product was purified on silica using ethylacetate as eluant to give ethyl 4-methylimidazol-1-ylacetate and ethyl 5-methylimidazol-1-ylacteate (6.89 g, 82%) as a 2:1 mixture.

Workup

  1. filtrationIt was then filtered
  2. customevaporated to dryness
  3. customThe product was purified on silica

Sources & evidence

ORD record
ord-593515565e9c4763a7b9d8fa3b03a030
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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