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0 °C

A solution of 3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)aniline (3.83 g, 19 mmol) in tetrahydrofuran was treated with 2,6-lutidine (2.17 mL, 19 mmol) and cooled to 0° C. A solution of phenyl chloroformate (2.36 mL, 19 mmol) in tetrahydrofuran was added dropwise. The mixture was stirred for 1 hour, then diluted with ethyl acetate and 0.1 N aqueous hydrochloric acid. The separated organic phase was washed twice with 0.1 N aqueous hydrochloric acid, then with saturated aqueous sodium chloride. The solution was dried over magnesium sulfate and concentrated under vacuum to provide a tan solid (6.00 g, quantitative). 1H NMR (300 MHz, CDCl3) δ7.86 (s, 1H), 7.5-7.3 (m, 5H), 7.3-7.1 (m, 3H), 4.17 (s, 3H), 2.71 (q, J=7 Hz, 2H), 1.27 (t, J=7 Hz, 3H).

1. washThe separated organic phase was washed twice with 0.1 N aqueous hydrochloric acid
2. dry with materialThe solution was dried over magnesium sulfate
3. concentrationconcentrated under vacuum
4. customto provide a tan solid (6.00 g, quantitative)