1,1'-Carbonyldiimidazole → 3-(3-(4-Methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)cyclobutanone

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-oxocyclobutanecarboxylic acid (595 mg, 5.12 mmol) in 1-methyl-2-pyrrolidinone (6 mL) was added 1,1′-carbonyldiimidazole (831 mg, 5.12 mmol). The reaction was stirred for 5 minutes. Then, N′-hydroxy-4-methyl-3-nitrobenzimidamide (27) (500 mg, 2.56 mmol) was added and the reaction was stirred for 15 minutes. Next, the reaction was heated in the microwave at 130° C. for 10 minutes. The crude product was taken in ethyl acetate and water. The organic was washed with 2× water/brine mixture and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography to afford 3-(3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)cyclobutanone (122). MS m/z 274.07 (M+1)+.

Provenance & Evidence