2-Methylimidazole → 1-(4-chloro-2-methoxybenzyl)-2-methyl-1H-imidazole

HRID 272745Notes

Reaction equation

HRID 272745 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[O:18][CH3:19]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[C:12]([O:18][CH3:19])[CH:13]=1

Participants

6

Reactant 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Product 1

HCID 570132771-(4-chloro-2-methoxybenzyl)-2-methyl-1H-imidazoleYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl imidazole (45 mg, 0.55 mmol) was dissolved in DMF. Sodium hydride (60 mg, 1.5 mmol) was added slowly. The mixture was stirred at room temperature until bubbling ceased. 1-Bromomethyl-4-chloro-2-methoxy-benzene (117 mg, 0.5 mmol) was added and the mixture was heated to 100° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and with brine. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate) to provide 47 mg (40%) of the title compound. MS (ESI) m/e 237 (M+H)+.

Workup

  1. customuntil bubbling
  2. temperaturethe mixture was heated to 100° C. for 16 hours
  3. temperatureThe mixture was cooled to room temperature
  4. washwashed with water and with brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-499cdbbb45b546f9b3dd8b3932a6f146
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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