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

HRID 1183069노트

반응식

HRID 1183069 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c3051c61373e43659d3c48d89d58de8e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664217B2

반응 노트

불러오는 중…