Methyl iodide → 1-(10-Methyl-10H-phenothiazin-2-yl)ethan-1-one

Participants

Reaction Steps

To a solution of 2-acetylphenothiazine (Aldrich) (2.41 g, 10 mmol) in dimethylformamide (25 mL) was added potassium t-butoxide (1.5 g, 13.4 mmol) and the mixture was stirred for 15 minutes. Methyl iodide (1.9 g, 13.4 mmol) was then added, dropwise, to the resulting solution and the mixture stirred for 30 minutes. Ice-water was added to the reaction mixture followed by ethyl acetate. The organic layer was decanted, washed with brine, dried over Na2SO4 and evaporated to dryness. The oily residue was chromatographed on flash silica gel eluting with 10% ethyl acetate/hexane to afford the pure title product (1.0 g, 39%).

Provenance & Evidence