Imidazole → Methyl 1H-imidazol-1-ylacetate

HRID 1244024Notes

Reaction equation

HRID 1244024 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:14][O:15][C:16](=[O:19])[CH2:17]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:14][O:15][C:16](=[O:19])[CH2:17][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 60984Methyl bromoacetate

Product 1

HCID 557332Methyl 1H-imidazol-1-ylacetateYield 27%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, combined 1.0 g of imidazole (14.7 mmol) with 824 mg of potassium hydroxide (14.7 mmol), 2.0 g of potassium carbonate (14.7 mmol) and 82 mg of benzyltriethylammonium chloride (7.34 mmol) in 40 ml of CH2Cl2. Added 695 μl of methylbromoacetate. Reaction is stirred at room temperature for 3 hours. Filtered off solids, rinsed with CH2Cl2, and evaporated the filtrate under reduced pressure to give colorless oil. Product is purified by flash chromatography on a Biotage Flash 40 (Eluent: 95:5 CH2Cl2/CH3OH), yielding 300 mg of a white solid (27%). 1H NMR (400 MHz, CD3OD) δ 3.75 (3H, s), 4.91 (2H, s), 6.96 (1H, s), 7.10 (1H, s), 7.64 (1H, s).

Workup

  1. customReaction
  2. filtrationFiltered off solids
  3. washrinsed with CH2Cl2
  4. customevaporated the filtrate under reduced pressure
  5. customto give colorless oil
  6. customProduct is purified by flash chromatography on a Biotage Flash 40 (Eluent: 95:5 CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-5dd9dd6aadef430d9a024f4bb32ccf29
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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