2,5-Hexanedione → 3-(2,5-Dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazole

HRID 83488

Reaktionsgleichung

Reaktionsgleichung von HRID 83488
[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([NH2:12])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18]>C(O)(=O)C>[CH3:18][C:17]1[N:12]([C:9]2[CH:10]=[CH:11][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 80352,5-HexanedioneHCID 5943201-phenyl-1H-pyrazol-3-amine

Produkt 1

HCID 712878563-(2,5-Dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-1H-pyrazol-3-ylamine (32.7 g) in acetic acid (330 ml) was added 2,5-hexanedione (25 ml), and the mixture was stirred for 3 hours at reflux. This reaction solution was cooled to room temperature, and then acetic acid was concentrated under reduced pressure, and then toluene (100 ml) was added thereto, and the mixture was further concentrated. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate 100/1 to 20/1) to give the titled compound (41.8 g).

Aufarbeitung

  1. temperatureat reflux
  2. concentrationacetic acid was concentrated under reduced pressure
  3. additiontoluene (100 ml) was added
  4. concentrationthe mixture was further concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate 100/1 to 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-d6cc9c75209b44ca98adb1e56a69c812
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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