[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C([NH+](CC)CC)C>C1COCC1>[C:13]([N:1]1[CH:5]=[N:4][N:3]=[N:2]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1To a stirring suspension of 1H-tetrazole (7.0 g, 0.1 mol) and triethylamine (15 ml, 0.12 mol) in anhydrous THF (300 ml), in a bath maintained at 0° C., was added benzoyl chloride (99%, 12.8 ml, 0.11 mol) slowly over 30 min. When addition was complete, the mixture was stirred for an additional 45 min. A precipitate formed, identified as triethylammonium hydrochloride (using NMR spectroscopy), was removed by filtration through a pad of Celite 545. The solvent was removed under reduced pressure while the bath temperature was maintained below 30° C. A residual oil was obtained. Crystallization of the residual oil in hexanes yielded N-benzoyltetrazole as colorless crystals. The crystals were removed by filtration, washed with hexanes (2×15 ml) and dried under vacuum for approximately 15 hours at room temperature. Yield: 15 g, 86%; m.p. 56-58iC; 1H NMR, (CDCl3) δ 9.43 (s, 1H), 8.26-8.22 (d, J=, 2H), 7.79-7.54 (m, 3H); 13C NMR, (CDCl3) 162.9, 143.7, 136.3, 132.7, 129.7 and 129.5. HRMS: (FAB) for C8H7N4O (MH+) 175.0620, found 175.0627.
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