Chloroacetyl chloride → 2-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)pyridine

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Reaction Steps

A solution of 2-chloroacetyl chloride (0.209 mL) in dichloromethane (3 mL) was added dropwise to a solution of (Z)—N′-hydroxypicolinamidine (0.300 g) in dichloromethane (7 mL). Triethylamine (0.366 mL) was added dropwise to the reaction solution and stirring at room temperature continued for 18 hours. The mixture was purified by column chromatography on silica gel (10-50% ethyl acetate in hexane). Desired fractions were evaporated in vacuo to a pale pink residue (0.21 g). This material was taken in toluene and refluxed for 18 hours. The solvent was evaporated in vacuo and the residue purified by column chromatography on silica gel (1-3% methanol in dichloromethane) to provide the title compound (0.085 g) having the following physical data.

Provenance & Evidence