2,4-Dichlorobenzoyl chloride → HCID 178456657, Verbindung

HRID 1155359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155359
[CH2:1]([N:4]1[C:8](=[O:9])[CH2:7][C:6]([CH3:10])=[N:5]1)[CH:2]=[CH2:3].[OH-].[Ca+2].[OH-].[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C(O)(C)C>[CH2:1]([N:4]1[C:8]([OH:9])=[C:7]([C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:15]=2[Cl:14])[C:6]([CH3:10])=[N:5]1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 6093208Calcium HydroxideHCID 128940995-Methyl-2-(prop-2-en-1-yl)-2,4-dihydro-3H-pyrazol-3-one

Produkt 1

HCID 178456657HCID 178456657, VerbindungAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A suspension of 1.4 g of 1-allyl-3-methyl-2-pyrazolin-5-one and 0.74 g. of calcium hydroxide in 20 ml. of isopropanol is heated under reflux with stirring for 1.5 hours. After cooling, to the resulting mixture is added dropwise 2.3 g, 2,4-dichlorobenzoyl chloride. After completion of the dropwise addition, the resulting mixture is heated under reflux for 5.5 hours. After completion of the reaction, the solvent is distilled off from the reaction mixture and to the residue is added 3 ml. of 2 N hydrochloric acid to adjust pH to 3.0. Then, the mixture is extracted with chloroform and the extract solvent is distilled off from the extract. The residue is dissolved in a small amount of benzene and the solution is washed with water, dried over anhydrous sodium sulfate and the solvent is distilled off. The resulting residue is recrystallized from isopropyl ether containing a small amount of methylene chloride to give 1.18 g. of the desired product as white crystals melting at 161°-163° C. Yield 40.7%.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureAfter cooling, to the resulting mixture
  3. additionAfter completion of the dropwise addition
  4. temperaturethe resulting mixture is heated
  5. temperatureunder reflux for 5.5 hours
  6. customAfter completion of the reaction
  7. distillationthe solvent is distilled off from the reaction mixture and to the residue
  8. additionis added 3 ml
  9. extractionThen, the mixture is extracted with chloroform
  10. distillationthe extract solvent is distilled off from the extract
  11. dissolutionThe residue is dissolved in a small amount of benzene
  12. washthe solution is washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent is distilled off
  15. customThe resulting residue is recrystallized from isopropyl ether containing a small amount of methylene chloride
  16. customto give 1.18 g

Quellen und Nachweise

ORD-Eintrag
ord-25316956bd5c43d88be8dc455acb155a
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04301293

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