Methyl iodide → HCID 22563398, compound

HRID 2249611Notes

Reaction equation

HRID 2249611 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 was 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 was 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-d4e87508118b452aabc35112bfa01bf2
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

Loading…