N-Methylacetamide → N-(3,5-dichloro-4-chloromethyl-pyridin-2-yl)-N-methyl-acetamide

Participants

Reaction Steps

Oxalyl dichloride (45 μL, 0.47 mmol) was added dropwise to a solution of N-methylacetamide (36 μL, 0.47 mmol) and 2,6-dimethyl-pyridine (55 μL, 0.47 mmol) in anhydrous DCM (10 mL) at 0° C. After stirring for 20 min, 3,5-dichloro-4-chloromethyl-pyridine 1-oxide (10 mg, 0.047 mmol) was added to it and stirring was continued overnight at 45° C. Saturated aqueous Na2CO3 solution (20 mL) and DCM (40 mL) were added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with EA/hexane 1:3) to give the title compound. MS (m/z): 267.4 [M+H+].

Provenance & Evidence