Sodium Chloride → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-3-pyrazolecarboxamide oxime

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole (0.86 g, 1.90 mmol) was dissolved in 10 ml of 1,4-dioxane and hydroxylamine hydrochloride (0.22 g, 3.17 mmol) and triethylamine (0.45 ml, 3.24 mmol) were added, and then the mixture was stirred at room temperature. Ten hours after stirring, hydroxyamine hydrochloride (0.08 g, 1.2 mmol) and triethylamine (0.14 ml, 1.01 mmol) were further added. After the completion of adding, the solution was stirred at room temperature for 23 hours. Thirty milliliters of water and 15 ml of an aqueous saturated sodium chloride solution were added and then the reaction mixture was extracted twice with 30 ml of ethyl acetate. The ethyl acetate layer was washed with 20 ml of an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a colorless crystal. This crystal was washed with a hexane-ethyl acetate mixed solvent (volume ratio=1:1) to obtain 0.82 g (1.68 mmol) of the title compound as a colorless crystal. Yield 89%.

1. stirringTen hours after stirring
2. additionAfter the completion of adding
3. stirringthe solution was stirred at room temperature for 23 hours
4. extractionthe reaction mixture was extracted twice with 30 ml of ethyl acetate
5. washThe ethyl acetate layer was washed with 20 ml of an aqueous saturated sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off
8. customto obtain a colorless crystal
9. washThis crystal was washed with a hexane-ethyl acetate mixed solvent (volume ratio=1:1)

ORD record

ord-278fc0619bb944438fd60e866b1fe943

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06316477B1