Methanol → 5-(2-furyl)-1-(4-methoxy-phenyl)-3-(trifluoromethyl)-1H-pyrazole

HRID 890525

Reaction equation

HRID 890525 reaction equation
CO.Cl.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1.[F:14][C:15]([F:27])([F:26])[C:16](=O)[CH2:17][C:18]([C:20]1[O:21][CH:22]=[CH:23][CH:24]=1)=O.FC(F)(F)C(O)=O>C(O)(C)C.O>[O:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[C:18]1[N:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][CH:8]=2)[N:13]=[C:16]([C:15]([F:14])([F:26])[F:27])[CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 222405195-(2-furyl)-1-(4-methoxy-phenyl)-3-(trifluoromethyl)-1H-pyrazoleYield 97.3%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

Part A. In a flame-dried 1-L flask was combined anhydrous methyl alcohol (1.4 L), 4-methoxyphenylhydrazine hydrochloride (25 g, 140 mmol), 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (30 g, 140 mmol), and trifluoroacetic acid (1.1 mL, 14 mmol). The resulting red slurry was maintained at rt for 14 h. A 50% solution of isopropyl alcohol/water (500 mL) was then added, and the mixture was stirred vigorously for 5 min. The mixture was filtered; additional material precipitated from the filtrate upon standing, and the new mixture was filtered. After another 3 h, the resulting filtrate was filtered a third time, and the combined beige solid was oven dried under vacuum to afford 5-(2-furyl)-1-(4-methoxy-phenyl)-3-(trifluoromethyl)-1H-pyrazole (42 g, 96%) as a light brown solid. 1H NMR (CDCl3) δ 7.42(m, 1H), 7.35 (d, 2H), 6.98 (d, 2H), 6.89 (s, 1H), 6.33 (dd, 1H), 5.90 (d, 1H), 3.88 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customadditional material precipitated from the filtrate
  3. filtrationthe new mixture was filtered
  4. waitAfter another 3 h
  5. filtrationthe resulting filtrate was filtered a third time
  6. customdried under vacuum

Sources & evidence

ORD record
ord-eba3ad3408cd409eaedf611fd35ce596
Source dataset
uspto-grants-2006_02
Patent number
US06995172B2

Linked notes

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