Triethylamine → 2-Chloro-5-[5-(4-isobutylphenyl)-1,3,4-oxadiazol-2-yl]pyridine

Participants

Reaction Steps

N,N-Dimethyl(chlorosulphonyl)methaniminium chloride (1.57 g, 0.01 mol) was added to a solution of 6-chloronicotinic acid (1.58 g, 0.01 mol) and dichloromethane (20 mL) at 0° C. and stirred for 10 minutes. 4-isobutylbenzohydrazide (5.29 g, 0.03 mol) was added to the reaction mixture, followed by the dropwise addition of a solution of triethylamine (12.3 mL, 0.09 mol) in dichloromethane (30 mL). The resulting mixture was stirred at room temperature for 12 hours, quenched with water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo. The resulting residue was recrystallized from methanol:acetone (10:1) to give the title compound (2.57 g, 82% yield) as a white solid.

Provenance & Evidence