Sodium Carbonate → 5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

HRID 1360428

Reaktionsgleichung

Reaktionsgleichung von HRID 1360428
[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]O)=[CH:6][C:5]([C:13]([NH2:15])=O)=[N:4]1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([C:13]#[N:15])[CH:6]=1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 669587601-ethyl-5-(4-hydroxybutyl)-1H-pyrazole-3-carboxamide

Produkt 1

HCID 669589675-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A modification of the method described in Part E of Examples 1-4 was used to treat 1-ethyl-5-(4-hydroxybutyl)-1H-pyrazole-3-carboxamide (18.2 g, 86.1 mmol) with phosphorous oxychloride (60 mL). The reaction was heated for three hours before cooling to 0° C. and pouring into ice water. The mixture was adjusted to pH 12 with the addition of 2 N aqueous sodium carbonate and extracted with chloroform. The combined extracts were passed through a layer of silica gel (eluting first with chloroform and then with 1:1 hexane/ethyl acetate to provide 10.8 g of 5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile as a dark oil.

Aufarbeitung

  1. temperatureThe reaction was heated for three hours
  2. extractionextracted with chloroform
  3. washeluting first with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e477a59a51b04dcb8a0d84bb5f64c97b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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