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

HRID 1266330Notes

Reaction equation

HRID 1266330 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-79db81ffe7714050b073a81e99ce3197
Source dataset
uspto-grants-2003_04
Patent number
US06548525B2

Reaction notes

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