Sodium hydride → HCID 13934417, 화합물

HRID 868566노트

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HRID 868566 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13].Cl.[CH:15]([N:18]([CH:22]([CH3:24])[CH3:23])[CH2:19][CH2:20]Cl)([CH3:17])[CH3:16].[H-].[Na+]>CN(C)C=O>[CH:15]([N:18]([CH:22]([CH3:24])[CH3:23])[CH2:19][CH2:20][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6](=[O:13])[C:7]1=[O:12])([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 383335-MethoxyisatinHCID 779422-Chloroethyldiisopropylammonium chloride

생성물 1

HCID 13934417HCID 13934417, 화합물수율 64.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3.00 g of 5-methoxyisatin and 3.39 g of 2-diisopropylaminoethyl chloride hydrochloride in 50 ml of dry N,N-dimethylformamide was added 1.36 g of sodium hydride (60% dispersion in mineral oil) with stirring under ice-cooling. The mixture was stirred for 1 hour at room temperature and then heated at 80° C. for 13 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel flash column chromatography (eluent: chloroform) and recrystallized from hexane to obtain 3.33 g of 1-(2-diisopropylaminoethyl)-5-methoxyisatin having a melting point of 81°-82.5° C.

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hour at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel flash column chromatography (eluent: chloroform)
  10. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-f1d7984dd14848a890f3002eb183ef92
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04780477

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