Potassium Carbonate → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

HRID 1462395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462395
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[C:7]([CH3:13])=[N:8][N:9]([CH3:12])[C:10]=1[OH:11])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][N:28]([CH3:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[C:7]([CH3:13])=[N:8][N:9]([CH3:12])[C:10]=1[O:11][CH2:26][CH2:27][N:28]([CH3:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12522480N-(2-Bromoethyl)-N-methylanilineHCID 178434070HCID 178434070, Verbindung

Produkt 1

HCID 132775064-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazoleAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.85 g of 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole was dissolved in 50 ml of acetonitrile, and 1.38 g of potassium carbonate (anydrous) was added thereto. The resultant mixture was stirred at room temperature for 2 hours, 2.14 g of β-bromoethyl-N-methylaniline was added, and the mixture heated for 3 hours under reflux. After cooling, crystals were filtered off. The filtrate was distilled under reduced pressure and the residue was purified by silica gel chromatography (eluent, benzene:ethyl acetate at 8:1) to give 3.82 g of the desired product, Compound 2, having nD24 1.5975 (yield 91.4%).

Aufarbeitung

  1. temperaturethe mixture heated for 3 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationcrystals were filtered off
  5. distillationThe filtrate was distilled under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent, benzene:ethyl acetate at 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-113281265032450f84e2d9d5d0cacf69
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460597

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