Acetic Acid → 3,5-Dimethyl-1-(alpha,alpha,alpha-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl ester

HRID 615004

Reaktionsgleichung

Reaktionsgleichung von HRID 615004
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=O)[CH3:11])[C:7](=O)[CH3:8])[CH3:2].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][NH2:23])[CH:17]=1.C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:10]([CH3:11])=[N:23][N:22]([C:18]2[CH:17]=[C:16]([C:15]([F:14])([F:25])[F:24])[CH:21]=[CH:20][CH:19]=2)[C:7]=1[CH3:8])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 98650(3-(Trifluoromethyl)phenyl)hydrazine

Produkt 1

HCID 705469613,5-Dimethyl-1-(alpha,alpha,alpha-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl esterAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

14.9 grams 3,3-diacetyl-propionic acid-ethyl ester, 14.1 grams (α,α,α-trifluoro-m-tolyl)-hydrazine, 4.8 grams glacial acetic acid and 100 milliliters ethanol were mixed, and the mixture heated to boiling temperature under reflux for 1 hour. The reaction mixture was evaporated and the residue distilled to produce 22.3 grams of crude 3,5-dimethyl-1-(α,α,α-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl ester. This ester was saponified as and worked up in accordance with the method described in Example (1b), using 4.0 grams sodium hydroxide as the base. The free acid was precipitated from the alkaline solution obtained in this manner by the addition of 2% acetic acid and of sufficient aqueous hydrochloric acid to complete the precipitation.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated
  4. distillationthe residue distilled

Quellen und Nachweise

ORD-Eintrag
ord-312da3908e114012abd82082816a6a65
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04146721

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