Dimethyl Sulfoxide → 1H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-phenyl-

Participants

Reaction Conditions

Reaction Steps

A 500 ml 3-neck round bottom flask fitted with a mechanical stirrer was sequentially charged with 40.0 g (0.16 mol) of 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester, 15.68 g (0.32 mol) of sodium cyanide and 96 ml of dimethylsulfoxide. The reaction mixture was heated to about 125° C. and cooled to 100° C., at which temperature the reaction mixture was stirred for 6 hours. The mixture was stirred at room temperature overnight and charged with 43.4 g (0.56 mol) of 40% queous methylamine dropwise. The resulting mixture was stirred for 61/2 hours at room temperature and 96 ml of water was added thereto. The mixture was stirred for one hour and the precipitated solid was collected by vacuum filtration. The resulting solid was washed with water and vacuum dried to afford 27.5 g of 96.19% pure 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. Corrected yield 73.6%.

Provenance & Evidence