Methyl iodide → 5-(3,5-Dimethylphenylthio)-4-ethyl-1,2-dimethyl-1H-imidazole

HRID 1415982Notes

Reaction equation

HRID 1415982 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][C:11]=2[CH2:16][CH3:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:20][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)=[C:11]([CH2:16][CH3:17])[N:12]=[C:13]1[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178437674HCID 178437674, compound

Product 1

HCID 4739135-(3,5-Dimethylphenylthio)-4-ethyl-1,2-dimethyl-1H-imidazoleYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dry dimethylformamide (4 ml)was dissolved 200 mg (0.8 mmol)of 5-(3,5-dimethylphenylthio)-4-ethyl-2-methylimidazole (5c), followed by addition of 49 mg (1.2 mmol)of 60% sodium hydride under ice-cooling, and the mixture was stirred for 5 minutes. Then, 138 mg (1.00 mmol)of methyl iodide was added and stirred for 30 minutes. The reaction mixture was poured in ice-water and extracted with diethyl ether, and the organic layer was dried over sodium sulfate. The solvent was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:1). From the first fraction, 40 mg (yield 19%)of positional isomer (6e')of the target compound was obtained as oil. From the latter fraction, 140 mg of 1,2-dimethyl-5-(3,5-dimethylphenylthio)-4-ethylimidazole (Compound I-5)was obtained as oil (yield 66%).

Workup

  1. temperaturecooling
  2. stirringstirred for 30 minutes
  3. extractionextracted with diethyl ether
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:1)
  7. customFrom the first fraction, 40 mg (yield 19%)of positional isomer (6e')of the target compound was obtained as oil

Sources & evidence

ORD record
ord-f6172f6e909a422d80cfa60fb1622256
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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