Reaction #2186221

Reaction equation

5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-I H-pyrazole-3-carboxylic acid propargylamide

m-chloroperbenzoic acid

sodium sulfite sodium hydrogen carbonate

→

title compound

Yield 86.0%

5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboxylic acid propargylamide

Yield 86.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 15 minutes
3. 3
   ExtractionThe aqueous phase was extracted with dichloromethane
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherevaporated
6. 6
   Otherpurified by flash chomatography (silica, heptane/ethyl acetate)

Procedure

To a suspension of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-I H-pyrazole-3-carboxylic acid propargylamide (0.71 g, 1.43 mmol) in dichloromethane was slowly added a solution of m-chloroperbenzoic acid (70%, 0.41 g, 1.68 mmol) in dichloromethane. After stirring for 17 hours at 20° C., an aqueous solution of sodium sulfite/sodium hydrogen carbonate (5%:5%, 25 ml) was added and stirring continued for 15 minutes. The aqueous phase was extracted with dichloromethane, dried over magnesium sulfate, evaporated and purified by flash chomatography (silica, heptane/ethyl acetate) to give the title compound (0.604 g, yield 86%) as white crystals, mp 207° C., 1H NMR (CDCl3): 2.28 (t, 1H, propargyl), 4.20 (m, 2H, propargyl), 5.17 (bs, 2H, NH2), 6.88 (bt, 1H, C(O)NH), and 7.83 (s, 2H, Ar—H).

Source