反应详情

To a solution of potassium thiocyanate (8.09 g, 83.2 mmol) in acetic acid (150 ml) was added a solution of N-[3-(4-aminophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide (7.34 g, 19.8 mmol) in acetic acid (150 ml), and the mixture was stirred at room temperature for 15 min. To the obtained solution was added dropwise a solution of bromine (4.0 g, 25.0 mmol) in acetic acid (100 mL) at room temperature over 30 min or longer and, after the completion of the dropwise addition, the mixture was stirred at room temperature for 4 hr. The resulting yellow solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL) and ethyl acetate (200 mL), and basified with 2N aqueous sodium hydroxide solution. The aqueous layer was separated and the organic layer was washed with saturated aqueous ammonium chloride solution (200 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (7.4 g, 87%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

1. additionafter the completion of the dropwise addition
2. stirringthe mixture was stirred at room temperature for 4 hr
3. filtrationThe resulting yellow solid was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in tetrahydrofuran (100 mL)
6. customThe aqueous layer was separated
7. washthe organic layer was washed with saturated aqueous ammonium chloride solution (200 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationThe insoluble material was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure