Thiazolidinedione → 5-(4-Methoxybenzylidene)-thiazolidine-2,4-dione

HRID 1581648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1581648
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[S:11]1[CH2:15][C:14](=[O:16])[NH:13][C:12]1=[O:17].N1CCCCC1>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:15]2[S:11][C:12](=[O:17])[NH:13][C:14]2=[O:16])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 312444-Methoxybenzaldehyde

Produkt 1

HCID 2331125-(4-Methoxybenzylidene)-thiazolidine-2,4-dioneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Methoxybenzaldehyde (20.4 g, 150 mmol), thiazolidine-2,4-dione (21.1 g, 180 mmol), piperidine (12.8 g, 150 mmol) and ethanol (150 mL) were mixed and refluxed for 18 hours. After allowed to stand for cooling, the precipitated crystals were collected by filtration. These were washed with ethanol, and then dried to obtain 11.2 g (32%) of the title compound as yellow crystals. Moreover, the filtrate was made acidic with concentrated hydrochloric acid, and the precipitated crystals were collected by filtration, washed with ethanol and water, and then dried to additionally obtain 18.1 g (51%, totally 83%) of the title compound as yellow crystals.

Aufarbeitung

  1. temperaturerefluxed for 18 hours
  2. temperaturefor cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThese were washed with ethanol
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6d75d2ea75dd479499a05eb2ed78447d
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06730687B1

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