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

HRID 1183069ノート

反応式

HRID 1183069 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[N:10]([CH3:17])[C:9]=2[CH:18]=1.[CH2:19](I)[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:14]1[C:13](=[O:15])[CH2:12][C:11](=[O:16])[N:10]([CH3:17])[C:9]2[CH:18]=[C:5]([O:4][CH3:3])[CH:6]=[CH:7][C:8]1=2)[CH3:20]

参加物

7

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 669610818-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

生成物 1

HCID 686748151-Ethyl-7-methoxy-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione収率 77%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% in oil, 44 mg, 1.1 mmol) was suspended in dimethylformamide (DMF) (8 ml), and cooled in an ice water bath to 0° C. 8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (220 mg, 1.0 mmol) was added to the suspension at the same temperature, and stirred at 0° C. for 1 hour. Ethyl iodide (187 mg, 1.2 mmol) 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 thereby obtain 190.2 mg (yield: 77%) of 1-ethyl-7-methoxy-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow solid.

後処理

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

出典と根拠

ORDレコード
ord-c3051c61373e43659d3c48d89d58de8e
出典データセット
uspto-grants-2014_03
特許番号
US08664217B2

反応ノート

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