2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → 5-Amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole

HRID 1680959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1680959
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[NH:15][NH2:16].[C:17]([C:19](=[CH:25]OCC)[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].C(OCC)C.CCCCC>C(O)C>[NH2:18][C:17]1[N:15]([C:3]2[C:2]([F:1])=[C:7]([F:8])[C:6]([C:9]([F:12])([F:11])[F:10])=[C:5]([F:13])[C:4]=2[F:14])[N:16]=[CH:25][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

5

Edukt 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 298179(alpha,alpha,alpha,2,3,5,6-Heptafluoro-p-tolyl)hydrazineHCID 21877078Diethylether pentane

Produkt 1

HCID 139337085-Amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazoleAusbeute 8,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 15.7 grams (0.634 mole) of 2,3,5,6-tetrafluoro-4-trifluoromethylphenylhydrazine in 40 mL of anhydrous ethanol was added 10.7 grams (0.634 mole) of ethyl 2-cyano-3-ethoxyacrylate. The reaction mixture was heated at reflux for 21 hours, then cooled, and the solvent was removed by distillation under reduced pressure, leaving a residue. This residue was suspended in 80 mL of a 50:50 mixture of diethyl ether/n-pentane. A solid formed and was removed by filtration to yield 20.4 grams of ethyl 5-amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazol-4-ylcarboxylate, m.p. 166-168° C. The nmr spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 21 hours
  3. temperaturecooled
  4. customthe solvent was removed by distillation under reduced pressure
  5. customleaving a residue
  6. customA solid formed
  7. customwas removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-81f4c52acd6642549952368dcad2ac8d
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05167691

Notizen zur Reaktion

Wird geladen…