Water → N-(6-t-butoxycarbonylamino-1-hexyl)-5-nitrobenzamide

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Reaction Steps

N-(6-aminohexyl)-5-nitroisobenzothiazol-3-one hydrochloride was synthesized as follows. A solution of 2.2 g (10 mmol) of 2-chloro-5-nitrobenzoyl chloride in 25 mL of CH2Cl2 was added dropwise to a mixture of 6-t-butoxycarbonylamino-1-hexylamine hydrochloride (Stahl, et al. J. Org. Chem., 43, 2285 (1978)). (2.5 g, 10 mmol) and triethylamine (2.0 g, 10 mmol) in 125 mL of CH2Cl2. After stirring overnight, 150 mL of H2O and 100 mL of CHCl3 were added. The organic phase was separated and the aqueous phase extracted three times with 100 mL of CHCl3. The combined organic extracts were dried (Na2SO4), filtered and the filtrate concentrated to yield 3.5 g (88%) of N-(6-t-butoxycarbonylamino-1-hexyl)-5-nitrobenzamide as a white solid, mp 157°-159° C.

Provenance & Evidence