Trifluoroacetic acid → ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

HRID 351655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351655
[Na].[C:2]([CH2:4][C:5](=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:3].FC(F)(F)C(O)=O.[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[CH2:22][NH:23][NH2:24]>O1CCOCC1>[NH2:3][C:2]1[N:23]([CH2:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[F:19])[N:24]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 10374537(2-Fluorobenzyl)hydrazineHCID 11309560Ethyl 3-cyano-2-oxopropanoate

Produkt 1

HCID 11391384ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under argon, 100 g (0.613 mol) of the sodium salt of ethyl cyanopyruvate (preparation analogously to Borsche and Manteuffel, Liebigs Ann. 1934, 512, 97) in 2.5 l of dioxane are admixed, with efficient stirring and at room temperature, with 111.75 g (75 ml, 0.98 mol) of trifluoroacetic acid, and the mixture is stirred for 10 min, during which a large proportion of the starting material dissolves. 85.93 g (0.613 mol) of 2-fluorobenzylhydrazine are then added, and the mixture is boiled overnight. After cooling, the precipitated sodium trifluoroacetate crystals are filtered off with suction and washed with dioxane, and the crude solution is reacted further.

Aufarbeitung

  1. dissolutiondissolves
  2. waitthe mixture is boiled overnight
  3. temperatureAfter cooling
  4. filtrationthe precipitated sodium trifluoroacetate crystals are filtered off with suction
  5. washwashed with dioxane
  6. customthe crude solution is reacted further

Quellen und Nachweise

ORD-Eintrag
ord-cd147afe3d784b688ddc7af8a4c6cf13
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743798B1

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