Réaction #586104

Équation de réaction

3-tert-butyl-2-vinyl-phenylamine

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid

triethylamine

dimethylformamide

→

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3-tert-butyl-2-vinylphenyl)amide

Solvants

methylenechloride

methylenechloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter this the solution is slowly added to a solution
2. 2
   AutreThe resulting reaction mixture
3. 3
   AutreAfter removal of the solvent in a water jet vacuum
4. 4
   Autrethe residue is purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 2:1)

Mode opératoire

197 mg (1,01 mmol) 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid and 135 mg (1,07 mmol) oxalylic acid chloride are dissolved in 8 ml methylenechloride. The solution is stirred for 3 hours at room temperature in the presence of a catalytic amount of dimethylformamide (DMF). After this the solution is slowly added to a solution consisting of 180 mg (1,01 mmol) 3-tert-butyl-2-vinyl-phenylamine, 155 mg (1,52 mmol) triethylamine and 7 ml methylenechloride. The resulting reaction mixture is then stirred at room temperature for 16 hours. After removal of the solvent in a water jet vacuum, the residue is purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 2:1). This gives 0,27 g 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3-tert-butyl-2-vinylphenyl)amide in the form of a colourless solid (m.p. 118-119° C.; 76% of theory).

Source