Butanal → 5-Butylidene-3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357081
[C:1]1([C:7]2[N:8]=[C:9]3[C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[C:24](=[O:25])[CH2:23][S:22][C:21]4=[O:26])=[CH:13][CH:12]=[CH:11][N:10]3[CH:27]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:28](=O)[CH2:29][CH2:30][CH3:31].N1CCCCC1>C(O)C>[CH:28](=[C:23]1[S:22][C:21](=[O:26])[N:20]([CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[C:9]3[N:10]([CH:27]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH:11]=[CH:12][CH:13]=2)[C:24]1=[O:25])[CH2:29][CH2:30][CH3:31]

Komponenten

5

Edukt 3

HCID 261ButanalHCID 8082PiperidineHCID 189368343-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Produkt 1

HCID 570498025-Butylidene-3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1.91 g (5.0 mmol) of 3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 0.45 ml (5.0 mmol) of n-butyraldehyde in 20 ml of ethanol, 0.05 ml (0.5 mmol) of piperidine was added, followed by refluxing for 2 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1) to yield 1.70 g (78.0%, yellow foamy substance) of the desired product.

Aufarbeitung

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-f3531fa6dabf46ce89e81508e2b714cc
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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