Benzene → 4-(2,4-Dichlorobenzoyl)-1-methyl-5-(p-acetylbenzyloxy)pyrazole

HRID 637595

Reaktionsgleichung

Reaktionsgleichung von HRID 637595
C1C=CC=CC=1.[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:18])[C:16]=1[OH:17])=[O:11].[C:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>C(N(CC)CC)C>[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:18])[C:16]=1[O:17][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([C:24](=[O:26])[CH3:25])=[CH:28][CH:29]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 5837851-[4-(Bromomethyl)phenyl]ethan-1-oneHCID 178481842HCID 178481842, Verbindung

Produkt 1

HCID 155907284-(2,4-Dichlorobenzoyl)-1-methyl-5-(p-acetylbenzyloxy)pyrazoleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

In 30 ml of dry benzene containing 0.50 g (0.005 mol) of triethylamine was dissolved 1.36 (0.005 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, and then 1.07 g (0.005 mol) of p-acetylbenzylbromide was added thereto. The resulting mixture was heated under reflux for 3 hours. After cooling the reaction mixture, the salt precipitated was filtered off and the solvent was distilled off therefrom under reduced pressure. The resulting oil was purified through column chromatography on silica gel using benzene/ethyl acetate 8:1 as an eluent to give 1.67 g of the title compound (yield 83%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. customthe salt precipitated
  5. filtrationwas filtered off
  6. distillationthe solvent was distilled off
  7. customThe resulting oil was purified through column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-70c3c8650efc4dc0acd3abc0a8cb70b0
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04557753

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