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Butanal → 5-Butylidene-3-[4-(2-methyl-imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357070
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 357070
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])[N:5]2[CH:22]=1.[CH:23](=O)[CH2:24][CH2:25][CH3:26].N1CCCCC1>C(O)C>[CH:23](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:6]2[N:5]3[CH:22]=[C:2]([CH3:1])[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=2)[C:19]1=[O:20])[CH2:24][CH2:25][CH3:26]
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Komponenten

5

Edukt 3

HCID 261ButanalHCID 8082PiperidineHCID 189368353-[4-(2-Methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Produkt 1

HCID 572386885-Butylidene-3-[4-(2-methyl-imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 0.67 g (2.0 mmol) of 3-[4-(2-methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 0.18 ml (2.0 mmol) of n-butyraldehyde in 10 ml of ethanol, 0.02 ml (0.2 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=1/4) to yield 0.794 g (quant, light yellow oily 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=1/4)

Quellen und Nachweise

ORD-Eintrag
ord-cc04a157cad04296a22e59f67f2b4123
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05840732

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