Triethylamine → 3,3-Diethyl-7-methoxy-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Participants

Reaction Steps

Diethylmalonyl dichloride (0.95 ml, 5.5 mmol) was added to a dichloromethane solution (20 ml) of 4-methoxy-o-phenylenediamine (691 mg, 5 mmol) and triethylamine (1.7 ml, 12.5 mmol) at 0° C., and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1→1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 452.3 mg (yield: 34%) of 3,3-diethyl-7-methoxy-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Provenance & Evidence