Potassium Hydroxide → 1,5-diamino-3-(4-fluorophenyl)-1H-pyrazole

HRID 733115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733115
[NH2:1]OS(O)(=O)=O.[NH2:7][C:8]1[NH:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:9]=1.[OH-].[K+]>>[NH2:1][N:12]1[C:8]([NH2:7])=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:11]1

Komponenten

4

Edukt 3

HCID 14797Potassium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acid2×HCID 178507289HCID 178507289, Verbindung

Produkt 1

HCID 230848951,5-diamino-3-(4-fluorophenyl)-1H-pyrazoleAusbeute 14,9 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Hydroxylamine-O-sulfonic acid (2.26 g, 20-0 nmol) was portionwise added to aqueous solution, (100 mL) containing 5-amino-3-(4-fluorophenyl)-1H-pyrazole (2.0 g, 11.3 mmol) and potassium hydroxide (2.52 g, 45 mmol) while stirring at 80° C. After the mixture was stirred at 80° C. for 30 minutes, potassium hydroxide (2.52 g, 45 mmol) was added thereto, hydroxylamine-O-sulfonic acid (2.26 g, 20.0 mmol) was portionwise added, and the mixture was stirred for further 1 hour. The reaction solution was cooled down to room temperature, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous potassium carbonate, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (C-300, hexane:ethyl acetate=1:2) to obtain the title compound (324 mg, 14.9%).

Aufarbeitung

  1. stirringAfter the mixture was stirred at 80° C. for 30 minutes
  2. stirringthe mixture was stirred for further 1 hour
  3. temperatureThe reaction solution was cooled down to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (C-300, hexane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-3dbfec5f7fd34ac78c6dfe77364910cd
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589096B2

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