4-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid → HCID 12985694, Verbindung

HRID 2119616

Reaktionsgleichung

Reaktionsgleichung von HRID 2119616
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:8][C:9]3[CH:10]=[N:11][N:12]([CH3:17])[C:13]=3[C:14](=[O:16])[C:6]=2[CH:7]=1

Komponenten

3

Edukt 1

HCID 129856934-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid

Produkt 1

HCID 12985694HCID 12985694, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A suspension of 4-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 1, step 1, 280 mg, 1.19 mmol) in phosphorus oxychloride (6 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated and dried in vacuo. The residue was dissolved in 50% aqueous acetic acid (6 ml) and refluxed for 8 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 ml), washed with saturated aqueous sodium bicarbonate (100 ml) and dried over magnesium sulfate. Removal of solvent and recrystallization from ethyl acetate gave 98 mg (38%) of the title compound as a solid.

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated
  3. customdried in vacuo
  4. dissolutionThe residue was dissolved in 50% aqueous acetic acid (6 ml)
  5. temperaturerefluxed for 8 h
  6. temperatureAfter cooling to room temperature
  7. additionthe mixture was diluted with ethyl acetate (200 ml)
  8. washwashed with saturated aqueous sodium bicarbonate (100 ml)
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of solvent and recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-62a4b5f19fdf44ce848d22e826021974
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686373B2

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