3-CHLORO-N-(1,5-DIMETHYL-3-OXO-2-PHENYL-2,3-DIHYDRO-1H-PYRAZOL-4-YL)PROPANAMIDE synthesis

Yield:19854-82-1 80 %

Reaction Conditions:

with potassium carbonate in chloroform at 60;Reflux;

Steps:

Synthesis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide (5) and 3-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)propenamide (6)

General procedure: In a 100 mL round-bottomed flask, 15 mL ofchloroform, 2.03 g, 0.01 mole of 4-aminoantipyrine,and 0.132 g, 0.01 mole of anhydrous potassiumcarbonate were added. To this mixture, 0.01 mole ofchloroacetyl chloride or 3-chloropropionyl chloridewas added, respectively, drop-wise with stirring for20 min. The reaction mixture was refluxed on a waterbath at 60°C for 3 h. Chloroform was flushed togive a viscous solution which washed with (5% w/v,35 mL) aqueous solution of sodium bicarbonate, theprecipitate formed was filtered and dried, then recrystallizedwith ethanol (22).

References:

Mohammad, Abeer Essa;Muhammad-Ali, Munther Abduljaleel;Shaheed, Dhurgham Qasim;Hameed, Basim Jasim [Acta poloniae pharmaceutica,2021,vol. 78,# 5,p. 627 - 634]