Ethyl Acetate → 4,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine

HRID 654774

Reaktionsgleichung

Reaktionsgleichung von HRID 654774
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[Na].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]#[N:23])=[CH:16][CH:15]=1.C(OCC)(=O)C>C(O)C.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:20]([C:17]3[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=3)[CH2:21][C:22]([NH2:23])=[N:10]2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 42396803-[4-(Methylthio)phenyl]acrylonitrileHCID 5360545Sodium

Produkt 1

HCID 104945294,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Fluorophenylhydrazine hydrochloride 4 g) was added to a solution of sodium (1.13 g) in ethanol (50 ml), and the mixture was refluxed for 1 hour. To the cooled mixture was added 3-[4-(methylthio)phenyl]acrylonitrile (4.3 g), and the resulting mixture was refluxed overnight. Ethyl acetate and water were added, and the organic layer was separated, dried and concentrated. The oily residue (7.6 g) was purified by column chromatography on silica gel (76 g) eluting with a mixture of toluene and ethyl acetate (2:1) to give brown crystals of 4,5-dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine (5 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturethe resulting mixture was refluxed overnight
  3. customthe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe oily residue (7.6 g) was purified by column chromatography on silica gel (76 g)
  7. washeluting with a mixture of toluene and ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-2425888f196f492396fa15bd73dac99d
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134142

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