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

HRID 377121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377121
[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]>[Pd].CN(C)C=O>[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 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.

Aufarbeitung

  1. customwas carried out at 50° C.
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. dissolutionThe residue was dissolved in 6N-hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-63bd61ee1fea45c88b38bc64f7683a0a
Quelldatensatz
uspto-grants-2000_02
Patentnummer
USRE036575

Notizen zur Reaktion

Wird geladen…