Methyl iodide → HCID 22563398, compound

HRID 1716558Notes

Reaction equation

HRID 1716558 reaction equation
[CH3:1]I.[CH3:3][C:4]([N+:18]([O-:20])=[O:19])([CH3:17])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][CH:10]=1.[OH-].[K+]>CN(C=O)C>[CH3:1][N:9]1[CH:10]=[C:6]([CH2:5][C:4]([CH3:3])([N+:18]([O-:20])=[O:19])[CH3:17])[N:7]=[C:8]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178441347HCID 178441347, compound

Product 1

HCID 22563398HCID 22563398, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyliodide (1.4 g) was added dropwise to a mixture of 4-(2-methyl-2-nitro-propyl)-2-phenyl-1H-imidazole (1.6 g) and fine powdered potassium hydroxide (2.19 g) in DMF (20 ml) at 20-25° C. The reaction mixture was stirred at RT for 4 h, quenched with ice/water and extracted with ethyl acetate. The organic phase washed with water and brine, dried over magnesium sulphate and concentrated. The residue was purified on silica gel using methylene chloride/methanol 2 and 5% as eluent to obtain the desired product (1.40 g) as a light yellow solid.

Workup

  1. customquenched with ice/water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-b5f6c9a27b1b49f89d2126ad4057d7a1
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

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