[CH3:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])[N:5]=[N:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](I)[CH3:23]>CC(C)=O.ClCCl>[CH3:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH2:22][CH3:23])=[O:10])[N:5]=[N:4][N:3]=1Under a nitrogen atmosphere, 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid (89.7 g, 0.44 mol) was dissolved in acetone (1 L) and cesium carbonate (214.7 g, 0.66 mol) was added with vigorous stirring. Ethyl iodide (70.3 ml, 0.88 mol) was added dropwise and the reaction was heated to reflux for 4 hours. The reaction was cooled to room temperature and filtered. The acetone was removed in vacuo to yield a yellow solid which was dissolved in dichloromethane (800 ml) and washed with saturated sodium bicarbonate (200 ml). The organic fraction was dried (Na2SO4), filtered, and concentrated to yield 92.7 g of ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate as a light yellow solid.
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