[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]([NH2:9])=O.[OH-].COC(NS([NH3+])(=O)=O)=O.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]#[N:9]To a solution of 5-chloro-2-(1H-tetrazol-1-yl)benzamide (1.0 g, 4.5 mmol) in THF (29 mL) was added (methoxycarbonylsulfamoyl)ammonium hydroxide, inner salt (2.1 g, 8.8 mmol) in five portions over 5 h. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 5-chloro-2-tetrazol-1-yl-benzonitrile (0.83 g, 90%); 1H NMR (400 MHz, CDCl3): δ 9.26 (s, 1H), 7.90 (d, J=1.0 Hz, 1H,), 7.85 (m, 2H).
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