4-Fluorophenylhydrazine hydrochloride → HCID 23174220, compound

HRID 654806Notes

Reaction equation

HRID 654806 reaction equation
F[CH2:2][C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=O.[ClH:16].[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1>C(O)(=O)C>[Cl:16][CH2:2][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[N:24]([C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[N:25]=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 10537225HCID 10537225, compound

Product 1

HCID 23174220HCID 23174220, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-fluoro-1-[4-(methylthio)phenyl]butan-1,3-dione (2 g) and 4-fluorophenylhydrazine hydrochloride (1.6 g) in acetic acid (10 ml) was refluxed for 5 hours. The solvent was evaporated and the residue was dissolved in ethyl acetate. The resulting solution was washed with an aqueous solution of sodium bicarbonate, dried, and concentrated in vacuo. The residue (3 g) was purified by column chromatography on silica gel eluting with chloroform. An oil of 3-(chloromethyl)-1-(4-fluorophenyl) -5-[4-(methylthio)phenyl]pyrazole (1.3 g) was obtained from the first eluate.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with an aqueous solution of sodium bicarbonate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue (3 g) was purified by column chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-9e75cbdb44ea4c7da5f4dca89d7dcfb9
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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