4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione → 2-(5-Furan-2-yl-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid

HRID 649817

Reaktionsgleichung

Reaktionsgleichung von HRID 649817
[F:1][C:2]([F:14])([F:13])[C:3](=O)[CH2:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[NH:15]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])[NH2:16]>C(O)(=O)C.CCOC(C)=O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[N:15]([C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])[N:16]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1

Komponenten

5

Edukt 2

HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 792232-Hydrazinobenzoic acid

Produkt 1

HCID 114159972-(5-Furan-2-yl-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4,4,4-Trifluoro-1-(2-furyl)-1,3-butanedione (2.4 mL, 16 mmol) was added to 2-hydrazinobenzoic acid (3.01 g, 16 mmol) in acetic acid (20 mL) and heated at reflux for 25 h. The reaction was cooled, diluted with EtOAc, and extracted twice with water. The organic layer was dried over Na2SO4, filtered, and evaporated to yield a thick red paste (5.71 g, >100%). 1H NMR (CDCl3) δ8.18 (dd, 1H, J=7.7, J′=1.8), 7.74 (td, 1H, J=7.7, J′=1.4), 7.65 (td, 1H, J=7.7, J′=1.5), 7.50 (dd, 1H, J=7.3, J′=1.1), 7.35 (m, 1H), 6.89 (s, 1H), 6.28 (m, 1H), 5.76 (d, 1H, J=3.3).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 25 h
  3. temperatureThe reaction was cooled
  4. extractionextracted twice with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a thick red paste (5.71 g, >100%)

Quellen und Nachweise

ORD-Eintrag
ord-db6e33ec60db41e0b3064a86bc5b5335
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271237B1

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