Hydrochloric Acid → HCID 178515713, compound

HRID 1289847Notes

Reaction equation

HRID 1289847 reaction equation
[F:1][C:2]1[C:7]([C:8]([CH2:10][C:11]([O:13]CC)=O)=O)=[C:6]([F:16])[C:5]([F:17])=[C:4]([F:18])[C:3]=1[F:19].[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>CO>[C:20]1([N:26]2[C:11]([OH:13])=[CH:10][C:8]([C:7]3[C:6]([F:16])=[C:5]([F:17])[C:4]([F:18])=[C:3]([F:19])[C:2]=3[F:1])=[N:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 2760255Ethyl (pentafluorobenzoyl)acetate

Product 1

HCID 178515713HCID 178515713, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.82 g (10 mmol) of ethyl pentafluorobenzoylacetate, phenylhydrazine (1.08 g; 10 mmol), and 0.33 ml of conc. HCl in 10 ml of methanol was refluxed for 18 hours. The mixture was concentrated in vacuo, the residue was diluted with toluene and heated at 110° C. for 20 hours and cooled. The mixture was diluted with sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 20-50% ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to afford 1.76 g (54%) of 1-phenyl-3-(pentafluorophenyl)-5-hydroxypyrazole as a white solid, mp 149-151° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted with toluene
  4. temperaturecooled
  5. additionThe mixture was diluted with sodium bicarbonate solution
  6. extractionextracted with ethyl acetate (3×)
  7. dry with materialThe combined organic layer was dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica gel; 20-50% ethyl acetate/hexane)
  10. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-01ebe27b42914b6d971aa3d62eff5ff8
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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