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

HRID 2196053Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-23ff7ecae9684bd4a4b1d8e389494ada
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338406B2

Reaction notes

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