p-Toluenesulfonic acid monohydrate → HCID 18354782, compound

HRID 429270Notes

Reaction equation

HRID 429270 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH3:19])=[C:16]([S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[C:15]([C:27](=[N:29][OH:30])[NH2:28])=[N:14]1.O.[C:32]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([NH:18][CH3:19])=[C:16]([S:20]([C:23]([F:25])([F:26])[F:24])(=[O:21])=[O:22])[C:15]([C:27]2[N:28]=[CH:32][O:30][N:29]=2)=[N:14]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136364250HCID 136364250, compound

Product 1

HCID 18354782HCID 18354782, compoundYield 2,396.7%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoromethylsulfonyl-3-pyrazolecarboxamide oxime 500 mg (1.00 mmol) was dissolved in 5 ml of trimethyl orthoformate, and then 5 mg of p-toluenesulfonic acid monohydrate was added. After the mixture was was stirred at room temperature for 6hrs, trimethyl orthoformate was distilled off in vacuo, and then added 20 ml of ethyl acetate. The ethyl acetate solution was washed once with 30 ml of aqueous saturated sodium hydrogencarbonate solution, and then four times with 30 ml of aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The resulting concentrated residue was purified by silica gel column chromatography [eluent: chloroform] to obtain 320 mg (0.63 mmol) of the title compound as a colorless crystal. Yield 63%.

Workup

  1. distillationtrimethyl orthoformate was distilled off in vacuo
  2. additionadded 20 ml of ethyl acetate
  3. washThe ethyl acetate solution was washed once with 30 ml of aqueous saturated sodium hydrogencarbonate solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting concentrated residue was purified by silica gel column chromatography [eluent: chloroform]

Sources & evidence

ORD record
ord-0eab794ad46f44a293f64eb9910ad77a
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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