Water → HCID 22482281, compound

A stirred suspension of 5-[(4-methoxyphenyl)sulfonyl]-6-phenyl-5,6-dihydrophenanthridine (4.27 g, 10 mmol) was heated to 50° C. in glacial acetic acid (20 mL) and treated drop-wise over three hours with excess bromine (8.0 g, 50 mmol). After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, and the precipitate filtered. The organic phase filtrate was washed sequentially with a saturated, aqueous, sodium thiosulfate solution, a 1 N hydrochloric acid solution, and water. The organic phase was further washed sequentially with a 2.5 N aqueous sodium hydroxide solution until a basic extract was obtained, water, and a saturated, aqueous, sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered through a short column of silica gel, and the solvent removed in vacuo to afford a crude yellow solid (4.0 g, 7.9 mmol, 79%). The crude solid was purified by repetitive preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with dichloromethane at a flow rate of 25 mL/min; to afford, after evaporation of the appropriate fractions, a monobromo compound and a dibromo compound, both as solids. Crystallization of the monobromo compound from a mixture of dichloromethane-diethyl ether-hexane yielded the title compound (1.4 g, 2.76 mmol, 28%) as a homogeneous, colorless, crystalline solid, m.p. 209-211° C.;

1. filtrationthe precipitate filtered
2. washThe organic phase filtrate was washed sequentially with a saturated, aqueous, sodium thiosulfate solution
3. washThe organic phase was further washed sequentially with a 2.5 N aqueous sodium hydroxide solution until
4. extractiona basic extract
5. customwas obtained
6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
7. filtrationfiltered through a short column of silica gel
8. customthe solvent removed in vacuo
9. customto afford a crude yellow solid (4.0 g, 7.9 mmol, 79%)
10. customThe crude solid was purified by repetitive preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g)
11. washeluting with dichloromethane at a flow rate of 25 mL/min
12. customto afford
13. customafter evaporation of the appropriate fractions
14. customCrystallization of the monobromo compound
15. additionfrom a mixture of dichloromethane-diethyl ether-hexane

ORD record

ord-1e14ed0c31dc42d5a62cd56217a1ac96

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894061B2