Methyl iodide → 6-chloro-7-methylsulfanyl-3-trifluoromethyl-1H-quinoxalin-2-one

HRID 584672

Reaktionsgleichung

Reaktionsgleichung von HRID 584672
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]=[C:7]([OH:13])[C:6]([C:14]([F:17])([F:16])[F:15])=[N:5]2.ClC1C=C2C(N=C(C(F)(F)F)C(O)=N2)=CC=1F.ClC1C(F)=CC(N)=C(N)C=1.FC(F)(F)C(=O)C(OCC)=O.O.[SH2:57].[Na].I[CH3:60]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:57][CH3:60])[NH:8][C:7](=[O:13])[C:6]([C:14]([F:17])([F:16])[F:15])=[N:5]2

Komponenten

8

Edukt 6

HCID 6328Methyl iodideHCID 7357734-Chloro-5-fluoro-1,2-phenylenediamineHCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoateHCID 53442613Sodium hydrogen sulfide hydrateHCID 178517239HCID 178517239, VerbindungHCID 178517316HCID 178517316, Verbindung

Produkt 1

HCID 223411506-chloro-7-methylsulfanyl-3-trifluoromethyl-1H-quinoxalin-2-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-7-fluoro-3-trifluoromethyl-quinoxalin-2-ol and 7-chloro-6-fluoro-3-trifluoromethyl-quinoxalin-2-ol (4.1 g, prepared similarly as described above from 4-chloro-5fluoro-1,2-diaminobenzene and ethyl trifluoropyruvate) was dissolved in DMF (140 ml) and sodium hydrogen sulfide monohydrate (3.5 g, 47 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and then iodomethane (3.5 ml) was added. Stirring was continued for 10 minutes and the reaction mixture was poured on ice/water (500 ml). The separated crystals were filtered, dried and recrystallised from ethanol to afford 1.73 g (38%) of 6-chloro-7-methylsulfanyl-3-trifluoromethyl-1H-quinoxalin-2-one.

Aufarbeitung

  1. customprepared similarly
  2. stirringStirring
  3. waitwas continued for 10 minutes
  4. additionthe reaction mixture was poured on ice/water (500 ml)
  5. filtrationThe separated crystals were filtered
  6. customdried
  7. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6c0033fd1fff4e99a6ba8ec915762f25
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927214B1

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