Bromine → N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

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Reaction Steps

Potassium thiocyanate (4.80 g, 49.2 mmol) was suspended in acetic acid (80 mL) and the mixture was stirred at room temperature for 10 min. To the obtained solution was added a is solution of N-[5-(4-aminophenoxy)-2-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide (5.00 g, 12.3 mmol) in acetic acid (80 mL), and the mixture was further stirred at room temperature for 20 min. To the obtained solution was added dropwise slowly a solution of bromine (2.46 g, 15.4 mmol) in acetic acid (50 mL) and, after the completion of the dropwise addition, the mixture was stirred at room temperature for 6 hr. The resulting yellow insoluble material was filtered off, and washed with acetic acid. The filtrate and the washing were combined and concentrated under reduced pressure. The obtained residue was suspended in ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogencarbonate solution (300 mL) and saturated brine (300 mL), successively, and dried over anhydrous sodium sulfate. Activated carbon was added, and the mixture was stood for a while. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.57 g, 66%) as a pale-yellow amorphous substance.

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