Azane;hydrate → HCID 178474353, Verbindung

HRID 2404570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404570
C([O:4][C:5]1[CH:9]=[C:8]([N:10](C(=O)C)[C:11](=[O:13])[CH3:12])[N:7]([C:17]2[CH:22]=[C:21]([S:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:20]([CH3:29])=[CH:19][C:18]=2[F:30])[N:6]=1)(=O)C.O.N>C(O)C>[C:11]([NH:10][C:8]1[N:7]([C:17]2[CH:22]=[C:21]([S:23][CH2:24][C:25]([F:26])([F:27])[F:28])[C:20]([CH3:29])=[CH:19][C:18]=2[F:30])[N:6]=[C:5]([OH:4])[CH:9]=1)(=[O:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 12896473Azane;hydrateHCID 68488136HCID 68488136, Verbindung

Produkt 1

HCID 178474353HCID 178474353, VerbindungAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

10.6 g of 5-amino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole was dissolved in 200 mL of toluene, and to this solution, 20.0 g of acetyl chloride was added, followed by reflux with heating for 12 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 9.4 g of 3-acetoxy-5-(N,N-diacetylamino)-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole. Then, 9.4 g of the obtained 3-acetoxy-5-(N,N-diacetylamino)-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole was dissolved in 100 mL of ethanol, and 10 mL of a 25 mass % ammonia water was added, followed by stirring at room temperature for 30minutes. Then, the solvent was distilled off under reduced pressure, and the obtained solid was washed with diisopropyl ether to obtain 7.0 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole in the form of white crystals (melting point: 223-225° C.).

Aufarbeitung

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. washthe obtained solid was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a8301ba9b42d49c399cfa14996b93d3b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802713B2

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