Benzamidine → 4-Dimethoxymethyl-2-phenyl-1H-imidazole

HRID 457394Notes

Reaction equation

HRID 457394 reaction equation
[C:1]([NH2:9])(=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18](=O)[CH:19]([O:22][CH3:23])[O:20][CH3:21].C(OCC)(=O)C>CN(C=O)C.O>[CH3:21][O:20][CH:19]([O:22][CH3:23])[C:18]1[N:8]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:9][CH:17]=1

Participants

7

Reactant 4

HCID 2332BenzamidineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 120035673-Bromo-1,1-dimethoxypropan-2-one

Product 1

HCID 1784995604-Dimethoxymethyl-2-phenyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of benzamidine 207 (1.44 g, 12 mmol) and potassium carbonate (4.1 g, 30 mmol) in anhydrous DMF (25 mL) is slowly added a solution of 3-bromo-1,1-dimethoxy-propan-2-one 206 (1.97 g, 10 mmol) in anhydrous DMF (10 mL) over 30 min. The mixture is then heated at 50–60° C. for 2 h. After cooling to room temperature, ethyl acetate (100 mL) and water (100 mL) were added. The organic phase is separated and the aqueous phase is extracted with ethyl acetate twice and the combined organic phase is washed with water (3×20 mL) and brine. Removal of solvents under reduced pressure and purification of the residue by column chromatography affords the desired product as a white solid. Yield: 2.08 g; LC-MS (MH+): 219. 1H NMR (300 MHz, CDCl3) δ 7.88–7.85 (m, 2H), 7.37–7.46 (m, 4H), 5.49 (s, 1H), 3.36 (s, 6H).

Workup

  1. temperatureThe mixture is then heated at 50–60° C. for 2 h
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate twice
  4. washthe combined organic phase is washed with water (3×20 mL) and brine
  5. customRemoval of solvents
  6. customunder reduced pressure and purification of the residue by column chromatography

Sources & evidence

ORD record
ord-b88563d8db2642da99aa95eb2e80af79
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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