Réaction #2186220

Équation de réaction

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

Cyclopropylamine

→

title compound

Rendement 87.0%

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

Rendement 87.0%

Solvants

dioxane

water

Conditions de réaction

Traitement

1. 1
   Températurewas heated to
2. 2
   workup.WAITcontinued at 55° C. for 6 hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Lavagewashed with aqueous potassium hydrogensulfate (5%)
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Autreevaporated

Mode opératoire

A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (0.85 g, 1.83 mmol) and 1,1-dicarbonylimidazole (0.36 g, 2.20 mmol) in dioxane was heated to. 55° C. for 2 hours. Cyclopropylamine (0.20 ml, 2.83 mmol) was then added and stirring continued at 55° C. for 6 hours. The cooled mixture was diluted with water, extracted with ethyl acetate, washed with aqueous potassium hydrogensulfate (5%), dried over magnesium sulfate and evaporated to give the title compound (0.762 g, yield 87%) as off-white crystals, mp 193° C., 1H NMR (CDCl3): 0.64 (m, 2H, cyclopropyl), 0.83 (m, 2H, cyclopropyl), 2,87 (m,1H, cyclopropyl), 4.31 (bs, 2H, NH2), 6.82 (bs,1 H, C(O)NH), and 7.80 (s, 2H, Ar—H).

Source