Chlorosuccinimide → HCID 89995598, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(5-methyl-1,3,4-oxadiazol-2-yl)aniline (0.220 g, 1.26 mmol) and anhydrous DMF (1.9 mL) was added N-chlorosuccinimide (0.168 g, 1.26 mmol). The reaction mixture was heated at 40° C. for 1.5 hours under argon before being allowed to cool to room temperature and partitioned between EtOAc (90 mL) and saturated aqueous NaHCO3 (15 mL). The organic layer was washed with saturated aqueous NaHCO3 (15 mL), dried (Na2SO4) and concentrated in vacuo. The brown residue was absorbed on silica gel (1.4 g), and purified using silica gel column chromatography eluting with a gradient of 0-30% EtOAc in CH2Cl2 to afford the title compound as a white solid (0.130 g, 49%).

Provenance & Evidence