Phenylhydrazine hydrochloride → 5-(4-methylsulfanylphenyl)-1-phenyl-3-trifluoromethyl-1H-pyrazole

HRID 1394040Notes

Reaction equation

HRID 1394040 reaction equation
[F:1][C:2]([F:17])([F:16])[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.Cl.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:14][S:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:26]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 107301701,3-Butanedione, 4,4,4-trifluoro-1-[4-(methylthio)phenyl]-

Product 1

HCID 688847775-(4-methylsulfanylphenyl)-1-phenyl-3-trifluoromethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4,4-trifluoro-(4-methylsulfanylphenyl)-butane-1,3-dione (3.0 g) and phenyl hydrazine hydrochloride (1.18 g) in ethanol (20 mL) was refluxed for 7 h. The solvent was evaporated and the residue was chromatographed over silicagel using 20% ethyl acetate in petroleum ether as eluent yielding 2.25 g (% yield=83, Mol. Weight=334) of product as a gum.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed over silicagel
  3. customyielding 2.25 g (% yield=83, Mol. Weight=334) of product as a gum

Sources & evidence

ORD record
ord-ac4e6d0b8d1e4d04a13304b5c203e5c2
Source dataset
uspto-grants-2008_03
Patent number
US07348342B2

Reaction notes

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