Hydrochloric Acid → N-(2-furanylmethyl) 5-(2,4-dichloro-5-methylbenzenesulfonamido)-2-(3-chloro-5-pyridyloxy)benzamide

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Reaction Steps

To a 0.2 M solution of N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamide (2.6 g, 7.6 mmol, prepared in Example 35.3) in a 1:1 THF/CH2Cl2 solution was added pyridine (0.67 mL, 8.3 mmol) followed by 2,4-dichloro-5-methylbenzenesulfonyl chloride (2.16 g, 8.3 mmol). The resulting mixture was stirred for 21 hr. A 1 M aqueous solution of HCl (100 mL) was added and the crude reaction mixture was extracted 3× with EtOAc (100 mL). The organic layers were combined and washed once with a brine solution (200 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was purified by chromatography (10-40% EtOAc in hexane) to yield 3.86 g (90%) of product as an off white solid.

Provenance & Evidence