Methyl iodide → 5-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole

HRID 1415985Notes

Reaction equation

HRID 1415985 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][CH:13]=[N:12][C:11]=2[CH:15]([CH3:17])[CH3:16])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:20])[CH:13]=[N:12][C:11]=2[CH:15]([CH3:17])[CH3:16])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1784253375-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole

Product 1

HCID 221301155-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazoleYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dry N,N-dimethylformamide was dissolved 1.0 g (4.1 mmol)of 5-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole (X=Y=Me)(9), followed by addition of 330 mg (8.3 mmol)of 60% sodium hydride under ice-cooling. After 5 minutes, 690 mg (4.9 mmol)of methyl iodide was added and the mixture was stirred for 10 minutes. This reaction mixture was poured in ice-water and extracted with diethyl ether. The organic layer was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was fractionated by alumina chromatography (ethyl acetate:n-hexane,=1:1). From the first fraction, 833 mg (yield 79%)of 5-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole (X=Y=Me) (10)was recovered as oil.

Workup

  1. temperaturecooling
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-0185f45252164bb2a8dfede20075943b
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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