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

HRID 1504112Notes

Reaction equation

[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH2:17][C:16](=[O:21])[N:15]([CH3:22])[C:14]=2[CH:23]=1.[CH2:24](I)[CH3:25]>O>[CH2:24]([N:19]1[C:18](=[O:20])[CH2:17][C:16](=[O:21])[N:15]([CH3:22])[C:14]2[CH:23]=[C:10]([O:9][CH3:8])[CH:11]=[CH:12][C:13]1=2)[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% in oil, 44 mg) was suspended in of DMF (8 ml), and was cooled to 0° C. in an ice water bath. 8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (220 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. Ethyl iodide (187 mg) was added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction liquid, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1→1:1). The purified product was condensed to dryness to give the title compound (190.2 mg) as a yellow solid.

Workup

stirringthe mixture was stirred at room temperature overnight
extractionfollowed by extraction by ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1→1:1)
customcondensed to dryness

Sources & evidence

ORD record: ord-520dd7c2c3254add87a77720bd94eefc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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