Chloromethyl Methyl Ether → 4,5-Dibromo-2-ethyl-1-(methoxymethyl)imidazole

HRID 1828824Notes

Reaction equation

HRID 1828824 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:8][CH3:9])[NH:5][C:6]=1[Br:7].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][O:18][CH3:19]>CN(C)C=O.[Cl-].[Na+].O>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][CH3:9])[N:5]([CH2:17][O:18][CH3:19])[C:6]=1[Br:7]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 104674684,5-dibromo-2-ethyl-1H-imidazole

Product 1

HCID 220586624,5-Dibromo-2-ethyl-1-(methoxymethyl)imidazoleYield 87.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4,5-Dibromo-2-ethylimidazole (451.3 g) was dissolved in N,N-dimethylformamide (2.25 L), and potassium carbonate (368 g) was added. (Chloromethyl)methyl ether (200 g) was gradually added dropwise under ice-cooling and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice-cooled brine and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Hexane was added to the residue and the mixture was heated and allowed to cool. The precipitated crystals were collected by filtration and dried by heating under reduced pressure to give 4,5-dibromo-2-ethyl-1-(methoxymethyl)imidazole (461.7 g) as brown crystals.

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was poured into ice-
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue
  8. temperaturethe mixture was heated
  9. temperatureto cool
  10. filtrationThe precipitated crystals were collected by filtration
  11. customdried
  12. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-b78de2feae294d0dac0097cd6f6c634b
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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