p-Toluenesulfonic acid monohydrate → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfonylpyrazole

HRID 429260Notes

Reaction equation

HRID 429260 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=[N:21][OH:22])[NH2:20])[C:3]=1[S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24].O.[C:31]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]2[N:20]=[CH:31][O:22][N:21]=2)[C:3]=1[S:23]([C:26]([F:28])([F:29])[F:27])(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 1363642485-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-3-pyrazolecarboxamide oxime

Product 1

HCID 183547765-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfonylpyrazoleYield 658.2%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-3-pyrazolecarboxamide oxime (0.51 g, 1.87 mmol) was dissolved in 12 ml of trimethyl orthoformate and p-toluenesulfonic acid monohydrate (0.05 g) was added, and then the mixture was heated under reflux for 1 hour. Trimethyl orthoformate was distilled off and 80 ml of ethyl acetate was added to the residue. The ethyl acetate layer was washed twice with 50 ml of an aqueous saturated sodium hydrogencarbonate solution, and then washed once with 50 ml of an aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain a colorless crystal. This crystal was washed with a hexane-chloroform mixed solvent (volume ratio=2:1) to obtain 0.86 g (1.73 mmol) of the title compound as a colorless crystal. Yield 93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationTrimethyl orthoformate was distilled off
  4. addition80 ml of ethyl acetate was added to the residue
  5. washThe ethyl acetate layer was washed twice with 50 ml of an aqueous saturated sodium hydrogencarbonate solution
  6. washwashed once with 50 ml of an aqueous saturated sodium chloride solution
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customto obtain a colorless crystal
  10. washThis crystal was washed with a hexane-chloroform mixed solvent (volume ratio=2:1)

Sources & evidence

ORD record
ord-a0936c2b0c264df3ac098c93b4cb27c0
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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