5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione → Pioglitazone

HRID 377123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377123
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>O1CCOCC1.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 533948925-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

Produkt 1

HCID 4829Pioglitazone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (10 g) in dioxane (200 ml) was added 5% palladium on carbon (5 g). The mixture was heated at 100° C. under 50 kg/cm2 for 2 hours. The catalyst was filtered off, and the filtrate was concentrated to about 70 ml under reduced pressure. The resulting crystals were collected by filtration and dried at 50° C. under a reduced pressure to give 7.2 g of crude crystals. Recrystallization from acetic acid-water gave crystals of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione. Yield: 6.42 g (63.8%).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to about 70 ml under reduced pressure
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried at 50° C. under a reduced pressure
  5. customto give 7.2 g of crude crystals
  6. customRecrystallization from acetic acid-water

Quellen und Nachweise

ORD-Eintrag
ord-a31e0af1c2bc4d87a73bd25751bd09f9
Quelldatensatz
uspto-grants-2000_02
Patentnummer
USRE036575

Notizen zur Reaktion

Wird geladen…