Sodium hydride → HCID 22058664, compound

HRID 1828789Notes

Reaction equation

HRID 1828789 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[NH:5][C:6]=1[Br:7].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27733644,5-dibromo-2-methyl-1H-imidazole

Product 1

HCID 22058664HCID 22058664, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,5-Dibromo-2-methylimidazole (4.91 g) was dissolved in N,N-dimethylformamide (50 ml), and 60% sodium hydride (901 mg) was added gradually under ice-cooling. After stirring at room temperature for 1 hour, 2-(trimethylsilyl)ethoxymethyl chloride (3.75 g) was gradually added dropwise under ice-cooling, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure and ethyl acetate was added to the residue. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give 4,5-dibromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole (7.6 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight at room temperature
  4. customThe solvent was evaporated under reduced pressure and ethyl acetate
  5. additionwas added to the residue
  6. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-eef26281ce7041259814cfda2c6eacdd
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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