Piperidine → 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide

HRID 1840487

Reaktionsgleichung

Reaktionsgleichung von HRID 1840487
[NH2:1][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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[CH:24]=O.N1CCCCC1>C(O)C>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[CH:24]=[C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([S:2]([NH2:1])(=[O:4])=[O:3])[CH:6]=2)[NH:10][C:9]1=[O:14]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 96389Indole-2-carboxaldehydeHCID 101982322-Oxoindoline-5-sulfonamide

Produkt 1

HCID 542321283-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-aminosulfonyl-2-oxindole (106 mg) (prepared as described in Compound IN-02), indole-2-carbaldehyde (87 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (4 mg) in ethanol (2 mL) was heated in a sealed tube at 90° C. for 3 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in oven for overnight to give 140 mg (83% yield) of 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide as an orange solid.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with cold ethanol
  4. customdried in oven for overnight

Quellen und Nachweise

ORD-Eintrag
ord-6e454b9f1c7848cc8c88aa3574f4c59a
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680335B2

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