[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([CH2:15][N:16]=[N+:17]=[N-:18])=[CH:13][C:12]=1[C:21]#[N:22]>C(O)C>[NH2:2][C:1]1[N:16]([CH2:15][C:14]2[CH:19]=[CH:20][C:11]([Cl:10])=[C:12]([C:21]#[N:22])[CH:13]=2)[N:17]=[N:18][C:3]=1[C:4]([NH2:6])=[O:5]A stirred suspension of 2-cyanoacetamide (790 mg, 9.4 mmol) in absolute ethanol (40 ml) was treated with sodium methoxide (495 mg, 9.2 mmol) and refluxed 10 minutes. The mixture was cooled lightly, a solution of 4-chloro-3-cyanobenzyl azide (1.35 g, 7.0 mmol) in absolute ethanol was added, and the mixture was refluxed 2.5 hours. The mixture was filtered hot and the filtrate evaporated under vacuum. The residue was triturated with diethyl ether, filtered and washed twice with diethyl ether. The solid was crystallized from refluxing methanol, filtered, washed twice with methanol and once with diethyl ether, and dried at 65° C. under vacuum to provide 635 mg (33%) 5-amino-1-(4-chloro-3-cyanobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 172°-175° C.
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