Water → HCID 19076484, Verbindung

HRID 234535

Reaktionsgleichung

Reaktionsgleichung von HRID 234535
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[H-].[Na+].[CH3:30][C:31]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([CH3:34])[CH2:32][CH3:33].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:41]([C:38]1[CH:39]=[CH:40][C:35]([C:31]([CH3:30])([CH3:34])[CH2:32][CH3:33])=[CH:36][CH:37]=1)(=[O:43])=[O:42])[C:6](=[O:11])[C:5]2([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[NH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19076509HCID 19076509, VerbindungHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

Produkt 1

HCID 19076484HCID 19076484, VerbindungAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-[[2-(morpholin-4-yl)ethyl]amino]indol-2-one in 10 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.108 g of sodium hydride as a 60% dispersion in oil is added. After stirring for 30 minutes, 0.607 g of 4-(1,1-dimethylpropyl)benzenesulfonyl chloride is added and the reaction mixture is stirred for 2 hours, the temperature being allowed to rise to RT. It is poured into water and extracted with AcOEt, the organic phase is washed with water and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent to give 0.45 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=147° C.

Aufarbeitung

  1. stirringthe reaction mixture is stirred for 2 hours
  2. customto rise to RT
  3. extractionextracted with AcOEt
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-97821cec90dd424ebf695172d0a1d62e
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594023

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