Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one

HRID 1363200

Reaktionsgleichung

Reaktionsgleichung von HRID 1363200
[OH-].[Na+].[O:3]=[C:4]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:8][CH:7]=[CH:6][C:5]1=2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl>[C:13]1([S:19]([N:8]2[C:9]3[CH2:10][CH2:11][CH2:12][C:4](=[O:3])[C:5]=3[CH:6]=[CH:7]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-one

Produkt 1

HCID 134377091-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of NaOH (4.44 g) in 1,2-dichloroethane (250 mL) was added 4-oxo-4,5,6,7-tetrahydroindole (5.0 g). The mixture was then cooled to 0° C. and stirred for 30 min, following which a solution of phenylsulfonyl chloride (5.7 mL) in 1,2-dichloroethane (50 mL) was added dropwise over a period of 30 min. After 30 min of stirring, the reaction mixture was allowed to come to room temperature and stirred overnight. The reaction was quenched by pouring onto distilled water (100 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic extract was washed with distilled water to neutrality, dried over MgSO4, and concentrated in vacuo to afford 7.0 g of the title compound.

Aufarbeitung

  1. additionwas added dropwise over a period of 30 min
  2. stirringAfter 30 min of stirring
  3. customto come to room temperature
  4. stirringstirred overnight
  5. customThe reaction was quenched
  6. additionby pouring
  7. distillationonto distilled water (100 mL)
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  10. extractionThe combined organic extract
  11. washwas washed with distilled water to neutrality
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-db1be117db264d6aa8a894f8482557ef
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884109B2

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