Diethyl Sulfate → HCID 67954048, compound

Participants

Reaction Steps

Sodium t-butoxide (330 mg, 3.43 mmol) was added to a N,N-dimethylformamide (5 mL) solution of 8-benzyloxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.01 g, 3.4 mmol) under ice cooling, and the mixture was stirred under ice cooling for 30 minutes. Thereafter, diethyl sulfate (0.51 mL, 3.69 mmol) was added, and the mixture was stirred for 6 hours under ice cooling. Water was added to the reaction solution, and ethyl acetate (20 mL) extraction was performed. The resulting organic layer was washed with water, and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from 50% ethanol (9 mL). Precipitated crystals were collected by filtration, washed with 50% ethanol, and dried at 60° C., thereby obtaining 760 mg of light-yellow, powdery 7-benzyloxy-1-ethyl-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (yield: 69%).

Provenance & Evidence