Methyl iodide → N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]-N-methylphenylacetamide

Participants

Reaction Steps

Sodium hydride (60% paraffin dispersion, 58 mg, 1.5 mmol) was added to a solution of N-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]phenylacetamide (0.50 g, 1.2 mmol) in dimethyl sulfoxide (5 mL) and the mixture was stirred at room temperature for 1 hour. Methyl iodide (0.09 mL, 1.5 mmol) was added to this reaction solution and the mixture was stirred at room temperature for 1 hour. A 10% aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 7:1→4:1) and washed with hexane to obtain 0.18 g (yield 35%) of the title compound.

Provenance & Evidence