Water → 1-Benzyl-4,5-dibromo-2-methyl-imidazole

HRID 2252031Notes

Reaction equation

HRID 2252031 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[NH:5][C:6]=1[Br:7].C(=O)([O-])[O-].[Na+].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([N:3]1[C:2]([Br:1])=[C:6]([Br:7])[N:5]=[C:4]1[CH3:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 27733644,5-dibromo-2-methyl-1H-imidazole

Product 1

HCID 3043081-Benzyl-4,5-dibromo-2-methyl-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-dibromo-2-methylimidazole (3.0 g, 12.5 mmol) in 25 mL DMF add sodium carbonate (2.0 g, 18.8 mmol) and benzyl bromide (1.64 mL, 13.8 mmol). Stir the solution at room temperature for 72 hours. Pour the reaction into water and extract with EtOAc. Wash the organic layer with water, saturated aqueous sodium chloride, and dry over sodium sulfate. Filter the mixture and concentrate to 3.8 g crude oil. Purify the oil by radial chromatography eluting with 40% EtOAc in hexanes. Concentrate the appropriate fractions to 3.1 g (75%) of the title compound as a colorless oil. MS(ES+): m/z=331.0 (M+H)+

Workup

  1. additionPour
  2. extractionextract with EtOAc
  3. washWash the organic layer with water, saturated aqueous sodium chloride
  4. dry with materialdry over sodium sulfate
  5. filtrationFilter the mixture
  6. concentrationconcentrate to 3.8 g crude oil
  7. customPurify the oil by radial chromatography
  8. washeluting with 40% EtOAc in hexanes
  9. concentrationConcentrate the appropriate fractions to 3.1 g (75%) of the title compound as a colorless oil

Sources & evidence

ORD record
ord-bdd8b35330444fe6948435b38cc9ba97
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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