Benzenesulfonyl chloride → HCID 18765369, Verbindung

HRID 2423131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423131
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]([S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2608005-Benzyloxy-6-methoxyindole

Produkt 1

HCID 18765369HCID 18765369, VerbindungAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3 M NaOH (5 mL, 15 mmol) was added to a solution of 5-(benzyloxy)-6-methoxy-indole (1.0 g, 3.9 mmol), tetrabutylammonium hydrogen sulfate (0.400 g, 1.18 mmol) and benzenesulfonyl chloride (1.04 g, 5.92 mmol) in DCM (25 mL). The mixture was stirred overnight at room temperature and diluted with DCM and water. The organic phase was washed with water (1×), dried (MgSO4) and evaporated. The crude product was purified through a plug of silica gel using DCM as the eluent to give the title compound (1.1 g) as a white solid. MS m/z 394 [M+H]+.

Aufarbeitung

  1. washThe organic phase was washed with water (1×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product was purified through a plug of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c310c27a59d042328cd8f50961b437f0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960374B2

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