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

HRID 357193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357193
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O: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])[C:5]=12.[CH:22](=O)[CH2:23][CH2:24][CH3:25].N1CCCC1>C(O)C>[CH:22](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6]2[C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=[CH:8][CH:7]=2)[C:19]1=[O:20])[CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 261Butanal2×HCID 31268Pyrrolidine2×HCID 189368403-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Produkt 1

HCID 572057075-Butylidene-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1.25 g (4.32 mmol) of 3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 0.39 ml (4.32 mmol) of 1-butanal in 20 ml of ethanol, 0.036 ml (0.43 mmol) of pyrrolidine was added at 60° C., followed by refluxing for 19 hours (1 and 2 hours later, 0.39 ml (4.32 mmol) was further added; 3 hours later, 0.39 ml (4.32 mmol) of 1-butanal and 0.036 ml (0.43 mmol) of pyrrolidine were further added). After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4), after which the solvent was distilled off, to yield 0.17 g (11.5%, yellow oily substance) of the desired product.

Aufarbeitung

  1. temperatureby refluxing for 19 hours (1 and 2 hours later
  2. addition0.39 ml (4.32 mmol) was further added
  3. temperatureAfter the reaction mixture was cooled
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with purified water
  7. customdried
  8. distillationafter which the solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4)
  10. distillationafter which the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-f5f6c629edd142e69c040bd38c16b828
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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