p-Toluenesulfonic acid → HCID 59210401, compound

HRID 2243266Notes

Reaction equation

HRID 2243266 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1)=O.[F:20][C:21]([F:26])([F:25])[CH2:22][NH:23][NH2:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][C:9]1[CH:8]=[C:7]([C:5]2[N:23]([CH2:22][C:21]([F:26])([F:25])[F:20])[N:24]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=2)[CH:12]=[CH:11][C:10]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 787402,2,2-TrifluoroethylhydrazineHCID 59210413HCID 59210413, compound

Product 1

HCID 59210401HCID 59210401, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution of 4,4,4-trifluoro-1-(3-methyl-4-nitro-phenyl)-butane-1,3-dione (1.8 g), 2,2,2-trifluoroethylhydrazine (1.2 g) and a catalytic amount of p-toluenesulfonic acid were refluxed for 6 hours. After cooling, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 3-(3-methyl-4-nitro-phenyl)-1-(2,2,2-trifluoro-ethyl)-5-trifluoro-methyl-1H-pyrazole (IX-5) (1.1 g) and 5-(3-methyl-4-nitro-phenyl)-1-(2,2,2-trifluoro-ethyl)-3-trifluoromethyl-1H-pyrazole (1-6) (0.5 g), respectively.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-833a14cd79774064af8c85f796b84755
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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