Sodium hydride → HCID 16732293, compound

Participants

Reaction Steps

A solution of 6-oxo-1,6-dihydropyridazine-3-carboxylic acid (1.4 g) and 1,1′-carbonylbis(1H-imidazole) (2.1 g) in N,N-dimethylformamide (80 mL) was stirred at 60° C. for 1 hr. The mixture was cooled to room temperature, and N′-hydroxyethanimidamide (963 mg) was added. Sodium hydride (520 mg) was slowly added, and the mixture was stirred at 100° C. for 8 hr. The mixture was cooled to room temperature, diluted with saturated aqueous ammonium chloride solution (100 mL) and saturated aqueous sodium chloride solution (100 mL), and the mixture was extracted 3 times with ethyl acetate-tetrahydrofuran (1:1, v/v, 100 mL). The organic layers were combined, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was suspended in diethyl ether and diisopropyl ether and the precipitate was collected by filtration to give the object product (1.1 g, 60%).

Provenance & Evidence