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

HRID 2196053

Reaktionsgleichung

[H-].[Na+].[CH2:3]([C:5]1([CH2:20][CH3:21])[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16]C=2NC1=O)[CH3:4].[CH3:22]I.O.[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>C(OCC)(=O)C>[CH2:20]([C:5]1([CH2:3][CH3:4])[C:11](=[O:12])[N:10]([CH3:22])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:25]=2[N:26]([CH3:27])[C:28]1=[O:29])[CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Sodium hydride (60% in oil, 170 mg, 4.3 mmol) was suspended in DMF (15 ml). 3,3-Diethyl-7-methoxy-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (452 mg, 1.7 mmol) was added thereto at 0° C., and stirring was conducted at the same temperature for 1 hour. Methyl iodide (0.42 ml, 6.8 mmol) was added to the mixture, and stirred at room temperature for 3 days. 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=2:1→1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 373 mg (yield: 76%) of 3,3-diethyl-7-methoxy-1,5-dimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a white powder.

Aufarbeitung

stirringstirred at room temperature for 3 days
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=2:1→1:1)
concentrationThe purified product was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-23ff7ecae9684bd4a4b1d8e389494ada
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08338406B2

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