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2,4-Dichlorobenzoyl chloride → HCID 178434070, Verbindung

HRID 461588
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 461588
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[NH:3]1.[OH-].[Ca+2].[OH-].[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>C(O)(C)C>[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:13]=2[Cl:12])[C:4]([CH3:8])=[N:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 27668471,3-dimethyl-1H-pyrazol-5-olHCID 6093208Calcium Hydroxide

Produkt 1

HCID 178434070HCID 178434070, VerbindungAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

In 65 ml. of isopropanol are suspended 4.48 g. of 1,3-dimethyl-5-pyrazolone and 3 g. of calcium hydroxide and the resulting suspension is heated under reflux for 30 minutes with stirring. After cooling, 8.4 g. of 2,4-dichlorobenzoyl chloride is added dropwise thereto. After completion of the dropwise addition, the mixture is heated under reflux for 2 hours. The solvent is distilled off from the reaction mixture and 15 ml. of water is added to the residue. The mixture is made acidic with 23 ml. of a 2N hydrochloric acid solution and extracted with 60 ml. of chloroform. The chloroform layer is washed with water and the organic phase is separated and dried. The chloroform is distilled off. The residue is recrystallized from ethanol to give 7.6 g. of the desired product as colorless prisms of mp. 165°-166° C. Yield 66.7%

Aufarbeitung

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling
  3. additionAfter completion of the dropwise addition
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 2 hours
  6. distillationThe solvent is distilled off from the reaction mixture and 15 ml
  7. additionof water is added to the residue
  8. extractionof a 2N hydrochloric acid solution and extracted with 60 ml
  9. washThe chloroform layer is washed with water
  10. customthe organic phase is separated
  11. customdried
  12. distillationThe chloroform is distilled off
  13. customThe residue is recrystallized from ethanol
  14. customto give 7.6 g

Quellen und Nachweise

ORD-Eintrag
ord-cc4040e319714a53b34a3d932dd15b17
Quelldatensatz
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04063925

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