Hydrochloric Acid → HCID 17862340, Verbindung

HRID 644827

Reaktionsgleichung

Reaktionsgleichung von HRID 644827
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[OH:17][C:18]1[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=1.Cl>CN(C=O)C>[CH3:23][C:21]1[NH:20][N:19]=[C:18]([O:17][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:22]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Produkt 1

HCID 17862340HCID 17862340, VerbindungAusbeute 182,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (0.5 g, 3.6 mmol) and 4-fluoronitrobenzene (1.6 g, 1.0 mmol) were added to a solution of 3-hydroxy-5-methylpyrazole (0.33 g, 3.4 mmol) in DMF (50 ml) at room temperature, and further, the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (100 ml) and extracted with ethyl acetate (30 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/3), to give a white solid of 5-methyl-3-(4-nitrophenyloxy)pyrazole (0.4 g, yield: 63.3%) mp: 124-125° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.33 (s, 3H), 5.75 (s, 1H), 7.20 (dd, J=2.2 and 7.1 Hz, 2H), 8.22 (dd, J=2.2 and 7.1 Hz, 2H), 9.30-9.90 (br s, 1H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (30 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/3)

Quellen und Nachweise

ORD-Eintrag
ord-792389413d7142dcb52a0dcce6ee5a47
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700786B2

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