p-Toluenesulfonic acid → 1-(3-methyl-4-nitrobenzyl)-5-pentafluoroethyl-1H-pyrazole

HRID 2243270Notes

Reaction equation

HRID 2243270 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:5][NH:6][NH2:7].C(O[CH:17]=[CH:18][C:19](=O)[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:5][N:6]1[C:19]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[CH:18][CH:17]=[N:7]1.[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:5][N:6]1[CH:17]=[CH:18][C:19]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[N:7]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 37290855-Ethoxy-1,1,1,2,2-pentafluoro-4-penten-3-oneHCID 20367228[(3-Methyl-4-nitrophenyl)methyl]hydrazine

Product 2

HCID 860762991-(3-methyl-4-nitrobenzyl)-5-pentafluoroethyl-1H-pyrazoleHCID 860763011-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3-Methyl-4-nitrobenzyl)-hydrazine (1.81 g) and 5-ethoxy-1,1,1,2,2-pentafluoro-4-penten-3-one (2.18 g) were refluxed in ethanol (60 ml) for 8 hours, and p-toluenesulfonic acid (0.10 g) was added thereto and the mixture was further refluxed for 6 hours. After finishing the reaction, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography (mixed solvent of n-hexane and ethyl acetate) to obtain 1-(3-methyl-4-nitrobenzyl)-5-pentafluoroethyl-1H-pyrazole (0.96 g) as the first elution portion and 1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole (0.50 g) as the second elution portion.

Workup

  1. temperaturethe mixture was further refluxed for 6 hours
  2. customthe reaction
  3. distillationthe solvent was distilled off
  4. customthe obtained residue was purified by silica gel column chromatography (mixed solvent of n-hexane and ethyl acetate)

Sources & evidence

ORD record
ord-b0e3e501ad744800bac8c0722182f726
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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