Hydrochloric Acid → N-ethyl-4-azido-3-benzyloxybenzamide

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Reaction Steps

N-Ethyl-4-amino-3-benzyloxybenzamide (900 mg, 3.33 mmol) obtained in Example 312c) was dissolved in water (9 ml) and acetic acid (6 ml), 1N hydrochloric acid (3.33 ml, 1.0 eq.) was added. An aqueous solution (3 ml) of sodium nitrite (234 mg, 3.33 mmol, 1.0 eq.) was added at 0° C., and the mixture was stirred for 20 min. An aqueous solution (3 ml) of sodium azide (221 mg, 3.33 mmol, 1.0 eq.) was further added, and the mixture was stirred at 0° C. for 1.5 hr. The reaction mixture was diluted with ethyl acetate-hexane (3:1, 50 ml), washed sequentially with water, 0.1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (782 mg, 2.64 mmol, 79.2%).

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