Methyl iodide → HCID 22563276, compound

HRID 1716559Notes

Reaction equation

HRID 1716559 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 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 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-a8e90c0a7dda4c4296dbaeeadda23bac
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

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