Hydrochloric Acid → 5-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

HRID 49109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49109
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.N1C=CC=CC=1.Cl>ClCCl.C(OCC)(=O)C>[N:15]1([S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31268PyrrolidineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Produkt 1

HCID 220421535-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), pyrrolidine (0.701 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and made acidic with 1N hydrochloric acid (16 mL). The organic layer was then washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL). It was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9 to give 0.432 g (27%)-5-(pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one.

Aufarbeitung

  1. washThe organic layer was then washed with sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. washThe residue was washed with ethanol (3 mL)
  5. customIt was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9

Quellen und Nachweise

ORD-Eintrag
ord-58d6d32a81db491db7056d18bd9d5ada
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706709B2

Notizen zur Reaktion

Wird geladen…