Water → HCID 9859623, Verbindung

HRID 1825724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825724
C[O-].[Na+].[S:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:14])[CH2:5]1.[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.O>CN(C)C=O>[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1/[CH:20]=[C:5]1\[S:4][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]\1=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 13854Pyrrole-2-carboxaldehydeHCID 213964H-1,4-Benzothiazin-3-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 9859623HCID 9859623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Sodium methoxide (0.28 g, 5.2 mmol) was added to a solution of 2H-1,4-benzothiazin-3(4H)-one (0.60 g, 4 mmol) and pyrrol-2-carboxaldehyde (0.49 g, 5.2 mmol) in dry N,N-dimethylformamide (3.5 ml) (hereinafter “DMF”). The mixture was heated at 120° C. for 6.5 h, allowed to cool and poured into water (60 ml). The precipitate was collected by filtration and washed with water. The precipitate was dissolved in ethyl acetate and the insoluble black residue was filtered out. The filtrate was concentrated, then chromatographed on a silica column using a gradient of 100% dichloromethane to (100:1) dichloromethane:ethanol as the mobile phase. The first eluted product was the (E)-isomer.

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dissolutionThe precipitate was dissolved in ethyl acetate
  5. filtrationthe insoluble black residue was filtered out
  6. concentrationThe filtrate was concentrated
  7. customchromatographed on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-3346707bb3e24281ae5e5faf76f49391
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049312B1

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