Sodium Azide → 4-azidomethyl-5-methyl-2-phenyl-1H-imidazole

HRID 982845Notes

Reaction equation

HRID 982845 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:8]=1[CH3:9].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C>[N:16]([CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:8]=1[CH3:9])=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22563401HCID 22563401, compound

Product 1

HCID 225633704-azidomethyl-5-methyl-2-phenyl-1H-imidazoleYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloromethyl-5-methyl-2-phenyl-1H-imidazole hydrochloride (4.86 g) [CAS 58731-95-6] in DMF (50 ml) was added sodium azide (7.79 g). The reaction mixture was stirred at room temperature for 18 h under argon and concentrated without heating under high vacuum. To the residue was added ice/1 molar K2CO3 solution, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and concentrated. The residue was purified by chromatography on silica gel using methylene chloride/methanol 2% as eluent to obtain 4-azidomethyl-5-methyl-2-phenyl-1H-imidazole (3.70 g) as a light yellow amorphous powder.

Workup

  1. concentrationconcentrated
  2. temperaturewithout heating under high vacuum
  3. additionTo the residue was added ice/1 molar K2CO3 solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5602dd3fa09f413395ec7fa2e8511526
Source dataset
uspto-grants-2005_03
Patent number
US06861440B2

Reaction notes

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