p-Toluenesulfonic acid monohydrate → HCID 18354785, compound

HRID 429269Notes

Reaction equation

HRID 429269 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]([N:18]([CH3:20])[CH3:19])=[C:16]([S:21]([C:23]([F:26])([F:25])[F:24])=[O:22])[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]([N:18]([CH3:20])[CH3:19])=[C:16]([S:21]([C:23]([F:25])([F:26])[F:24])=[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 136364249HCID 136364249, compound

Product 1

HCID 18354785HCID 18354785, compoundYield 4,375%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

1-(2,6-dichloro-4-trifluoromethylphenyl)-5-dimethylamino-4-trifluoromethylsulfinyl-3-pyrazolecarboxamide oxime 0.59 g (1.18 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 3 hrs, trimethyl orthoformate was distilled off in vacuo, and then added 40 ml of ethyl acetate. The ethyl acetate solution was washed twice with 15 ml of aqueous saturated sodium hydrogencarbonate solution, and then once with 15 ml of aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain 583 mg (1.15 mmol) of the title compound as a colorless crystal. Yield 97%.

Workup

  1. distillationtrimethyl orthoformate was distilled off in vacuo
  2. additionadded 40 ml of ethyl acetate
  3. washThe ethyl acetate solution was washed twice with 15 ml of aqueous saturated sodium hydrogencarbonate solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8a99254d41034eb5bff4a25a66f3e98d
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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