Hexafluoroacetylacetone → HCID 23036563, Verbindung

HRID 1709696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1709696
[F:1][C:2]([F:13])([F:12])[C:3](=O)[CH2:4][C:5](=O)[C:6]([F:9])([F:8])[F:7].[Cl:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:16]=1[NH:25][NH2:26]>CO>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:6]([F:9])([F:8])[F:7])[N:25]([C:16]2[C:17]([Cl:24])=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[Cl:14])[N:26]=1

Komponenten

4

Edukt 2

HCID 73706HexafluoroacetylacetoneHCID 21179877(2,6-Dichloro-4-nitrophenyl)hydrazine

Produkt 1

HCID 23036563HCID 23036563, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1,1,1,5,5,5-Hexafluoro-2,4-pentanedione (0.56 g, 2.70 mmol) is added to a solution of 2,6-dichloro-4-nitrophenylhydrazine (0.30 g, 2.35 mmol) in 20 ml of methanol chilled in an ice bath. The mixture is stirred overnight at RT, after which the methanol is removed in vacuo. The residue is dissolved in toluene and a catalytic amount of p-toluenesulfonic acid (pTSOH) added. The mixture is heated under reflux and stirred for 2 hours, after which it is allowed to cool to RT and the solvent is removed in vacuo. The resulting crystals are dissolved in xylene, 40 mg of pTSOH is added and the mixture is heated under reflux for 2 hours. The resulting mixture is cooled, washed with methylene chloride, concentrated in vacuo and purified by flash chromatography to give 3,5-bis(trifluoromethyl)-1-(2,6-dichloro-4-nitrophenyl)pyrazole. Following the procedure of Example 5, the nitrophenylpyrazole is reduced by treatment with platinum dioxide and hydrogen to give 3,5-dichloro-4-[3,5-bis-(trifluoromethyl)-1-pyrazolyl]aniline.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. customafter which the methanol is removed in vacuo
  3. dissolutionThe residue is dissolved in toluene
  4. additiona catalytic amount of p-toluenesulfonic acid (pTSOH) added
  5. temperatureThe mixture is heated
  6. temperatureunder reflux
  7. stirringstirred for 2 hours
  8. temperatureto cool to RT
  9. customthe solvent is removed in vacuo
  10. dissolutionThe resulting crystals are dissolved in xylene
  11. addition40 mg of pTSOH is added
  12. temperaturethe mixture is heated
  13. temperatureunder reflux for 2 hours
  14. temperatureThe resulting mixture is cooled
  15. washwashed with methylene chloride
  16. concentrationconcentrated in vacuo
  17. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b8938db0d95e41869078690fb869ed87
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04950678

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