Thiazolidinedione → HCID 86606241, Verbindung

HRID 1864563

Reaktionsgleichung

Reaktionsgleichung von HRID 1864563
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=1)=O.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[O:30]=[C:25]1[NH:26][C:27](=[O:29])[C:28](=[CH:1][C:3]2[S:7][C:6]([C:8]3[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=3)[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=2)[S:24]1

Komponenten

5

Edukt 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 86606242Tert-butyl[3-(5-formylthiophen-2-yl)benzyl]methylcarbamate

Produkt 1

HCID 86606241HCID 86606241, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2.4 g (7.2 mmol) of tert-butyl [3-(5-formylthiophen-2-yl)benzyl]methylcarbamate, 0.85 g (7.2 mmol) of 2,4-thiazolidinedione and 0.2 g (1.4 mmol) of piperidinium acetate in 50 ml of toluene is refluxed for 4 hours in Dean-Stark apparatus. After cooling, the product precipitates. The precipitate is filtered off and washed with ethyl ether. 2.3 g (76%) of tert-butyl {3-[5-(2,4-dioxothiazolidin-5-ylidenemethyl)thiophen-2-yl]benzyl}methylcarbamate are obtained.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe product precipitates
  3. filtrationThe precipitate is filtered off
  4. washwashed with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-fe8df232445e4730bf42fb93d6c3bb64
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625914B2

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