Water → 1-Ethyl-7-methoxy-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1504210Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[N:8]([CH3:15])[C:7]=2[CH:16]=1.[CH2:17](I)[CH3:18].O>C(OCC)(=O)C>[CH2:17]([N:12]1[C:11](=[O:13])[CH2:10][C:9](=[O:14])[N:8]([CH3:15])[C:7]2[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]1=2)[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (220 mg) was added to the suspension at the same temperature, and stirred at 0° C. for 1 hour. Ethyl iodide (187 mg) was added to the mixture and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1). The purified product was concentrated to dryness under reduced pressure to give the title compound(190.2 mg) as a yellow solid.

Workup

stirringstirred at room temperature overnight
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1)
concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-f1cb18a2488a4c4d980def2d8d83569e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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