Phosphorus oxychloride → (5-chloro-1-ethyl-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone

HRID 47620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47620
[CH2:1]([N:3]1[C:7](O)=[C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:5]([CH3:17])=[N:4]1)[CH3:2].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:17])[C:6]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178463090HCID 178463090, Verbindung

Produkt 1

HCID 22747496(5-chloro-1-ethyl-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone

Versuchsvorschrift

A solution of 2.6 g of (1-ethyl-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone in 4 ml of phosphorus oxychloride was stirred at 80° C. for 1.5 h. The mixture was poured into 300 ml of saturated sodium hydrogen carbonate and extracted three times with 70 ml of dichloromethane. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (bp 40-60° C.) (1:4) for the elution to give 1.74 g of (5-chloro-1-ethyl-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone as a pale yellow liquid. Mass spectrum (ES) m/z 249 [M+H]+, 290 [M+H+CH3CN]+.

Aufarbeitung

  1. extractionextracted three times with 70 ml of dichloromethane
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-91798ba2d11e4ae683983edf412bbac5
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699887B2

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