Methyl iodide → HCID 22563276, compound

HRID 2249612Notes

Reaction equation

HRID 2249612 reaction equation
[CH3:1]I.[CH3:3][C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][C:16]([CH3:21])([N+:18]([O-:20])=[O:19])[CH3:17].[OH-].[K+]>CN(C=O)C>[CH3:1][N:8]1[C:4]([CH3:3])=[C:5]([CH2:15][C:16]([CH3:21])([N+:18]([O-:20])=[O:19])[CH3:17])[N:6]=[C:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 22563381HCID 22563381, compound

Product 1

HCID 22563276HCID 22563276, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyliodide (1.4 g) was added dropwise to a stirred mixture of 5-methyl-4-(2-methyl-2-nitro-propyl)-2-phenyl-1H-imidazole (2.0 g) and fine powdered potassium hydroxide (2.0 g) in DMF (30 ml) at 10-20° C. The reaction mixture was stirred at RT for 2 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 (0.98 g) as a light yellow amorphous compound.

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-dbbb4a0c03b4432d82318d8e821f04ff
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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