Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.C[N:19]([CH:21]=O)C.[C-:23]#[N:24].[Na+].CN>O>[C:23]([C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH:19][CH3:21])=[O:15])#[N:24]A 250 ml round bottom flask fitted with a mechanical stirrer was charged with 25.0 g (0.1 mol) of 92.33% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester and 60 ml of DMF. The mixture was stirred at room temperature for a short period and then 9.8 g (0.2 mol) of sodium cyanide was added. The resulting dark mixture was heated at approximately 100° C. for 6 hours and cooled to room temperature. The reaction mixture was stirred for approximately 12 hours at this temperature and then charged with 27.13 g (0.35 mol) of an aqueous solution of 40% methylamine by weight (hereinafter 40% aqueous methylamine, from Aldrich Chemical Co., Milwaukee Wis.). The reaction mixture was stirred for approximately 61/2 hours and 60 ml of water was added. The resulting suspension was stirred for approximately 10 minutes and the precipitated solid was collected by filtration. The solid was washed with water and vacuum dried to provide 18.36 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. A high pressure liquid chromatographic analysis of the final product indicated it to be 97.86% pure. Corrected yield 86.1%. m/e 226.
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