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

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Reaction Steps

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%).

Provenance & Evidence