Thiazolidinedione → HCID 86606241, Verbindung

HRID 910311

Reaktionsgleichung

Reaktionsgleichung von HRID 910311
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[S:17][C:18]([CH:21]=O)=[CH:19][CH:20]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[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:21][C:18]2[S:17][C:16]([C:12]3[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=3)[CH2:9][CH2:8][NH:7][C:6](=[O:23])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:20][CH:19]=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-aca3e94273e8454b8e76efa263d0ab27
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022079B2

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