Trifluoroacetic acid → HCID 18624094, Verbindung

HRID 1860581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860581
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][N:5]=1)[NH2:3].C(O)(C(F)(F)F)=O.[F:21][CH:22]([F:34])[C:23](=O)[CH2:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=O>C(O)C(F)(F)F>[CH:27]1([C:25]2[N:2]([C:4]3[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:11])=[O:12])=[CH:6][N:5]=3)[N:3]=[C:23]([CH:22]([F:21])[F:34])[CH:24]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochlorideHCID 230055004,4-Difluoro-1-cyclohexyl-1,3-butanedione

Produkt 1

HCID 18624094HCID 18624094, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64092,2,2-TrifluoroethanolLösungsmittel

Versuchsvorschrift

2-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride (448 mg, 2 mmol) and TFA (1.38 mL, 18 mmol) were mixed in trifluoroethanol (10 mL) and stirred for 5 minutes 4,4-Difluoro-1-cyclohexyl-1,3-butanedione (408 mg, 2 mmol) was added. The resulting reaction mixture was heated at reflux temperature for 60 hours. The solvent was then removed in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was washed with brine and concentrated in vacuo. The product was purified by recrystallization from 3:1 of isooctane:methylene chloride to give the title compound (346 mg, 49%).

Aufarbeitung

  1. additionwas added
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux temperature for 60 hours
  5. customThe solvent was then removed in vacuo
  6. customthe residue was partitioned between EtOAc and water
  7. washThe organic layer was washed with brine
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by recrystallization from 3:1 of isooctane

Quellen und Nachweise

ORD-Eintrag
ord-979f70b49e014e379a3dca779c310276
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531492B1

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