Lawesson's reagent → 6,7-Dichloro-2,3-dimethoxy-5-thioacetamidoquinoxaline

HRID 842676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842676
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([O:19][CH3:20])[C:9]([O:17][CH3:18])=[N:10]2)(=O)[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1>C1(C)C=CC=CC=1>[Cl:15][C:14]1[C:5]([NH:4][C:1](=[S:30])[CH3:2])=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:16])[N:10]=[C:9]([O:17][CH3:18])[C:8]([O:19][CH3:20])=[N:7]2

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 22614897HCID 22614897, Verbindung

Produkt 1

HCID 226148756,7-Dichloro-2,3-dimethoxy-5-thioacetamidoquinoxalineAusbeute 135,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Acetamido-6,7-dichloro-2,3-dimethoxyquinoxaline (20.49 g, 64.8 mmol) was added to a stirred suspension of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent) (15.7 g, 38.9 mmol) in toluene (432 ml) at room temperature under nitrogen. The mixture was warmed to the reflux temperature 25 minutes and was maintained at that temperature for a further 90 minutes. After being cooled the mixture was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel, eluting with dichloromethane. 6,7-Dichloro-2,3-dimethoxy-5-thioacetamidoquinoxaline (17.54 g, 81%) was obtained as a yellow foam.

Aufarbeitung

  1. temperatureThe mixture was warmed to the reflux temperature 25 minutes
  2. temperaturewas maintained at that temperature for a further 90 minutes
  3. temperatureAfter being cooled the mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue purified by flash chromatography on silica gel
  6. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-654b969f0a0d4737966e464ba3df1b6d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376490B1

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