Toluene → HCID 86590247, Verbindung

HRID 2212578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2212578
C1(C)C=CC=CC=1.N1CCCCC1.[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([CH3:38])=[C:22]([C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=3[O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=O)[CH:23]=2)[C:18]([CH3:40])([CH3:39])[CH2:17][C:16]1=[O:41].[S:42]1[CH2:46][C:45](=[O:47])[NH:44][C:43]1=[O:48]>C(OCC)(=O)C.C(O)(=O)C>[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([CH3:38])=[C:22]([C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=3[O:33][C:34]([F:35])([F:37])[F:36])[CH:28]=[C:46]3[S:42][C:43](=[O:48])[NH:44][C:45]3=[O:47])[CH:23]=2)[C:18]([CH3:39])([CH3:40])[CH2:17][C:16]1=[O:41]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21966438HCID 21966438, Verbindung

Produkt 1

HCID 86590247HCID 86590247, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of toluene (80 mL), piperidine (380 μL), acetic acid (380 μL), 3-(1,4,4,6-Tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzaldehyde (7.5 g, 19.16 mmol) and 2,4-thiazolidinedione (2.25 g, 19.16 mmol) was heated at reflux overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine, dried over MgSO4. The residue was recrystallized successively from ethanol, dichloromethane/hexane and ethanol to afford 4.3 g (46%) of 5-[3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-trifluoromethoxy-benzylidene]-thiazolidine-2,4 dione. mp 182–184° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe residue was recrystallized successively from ethanol, dichloromethane/hexane and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-eed2d705dc59468faa6da20edeac562a
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07102000B2

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