1,3-Dichloro-5,5-dimethylhydantoin → Perfluorophenyl 4-chloroquinoline-7-sulfonate

Participants

Reaction Steps

A round-bottom flask was charged with 7-(benzylthio)-4-chloroquinoline (7.35 g, 25.7 mmol), acetonitrile (242 ml), acetic acid (9.08 ml), and water (6.05 ml), and after cooling the suspension in an ice bath for 10 minutes, 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (10.13 g, 51.4 mmol) was added in one portion to form a heterogeneous solution. After 20 minutes, conversion to 4-chloroquinoline-7-sulfonyl chloride was observed, and 2,3,4,5,6-pentafluorophenol (9.47 g, 51.4 mmol) was added, followed by drop wise addition of triethylamine (8.96 ml, 64.3 mmol). After 40 minutes, the mixture was diluted with EtOAc (200 mL) and washed with water (2×200 mL) and brine, and then dried over sodium sulfate. After filtration and concentration under a vacuum, the material was purified via silica gel chromatography (120-g column) eluting with 0 to 35% ethyl acetate in heptane to yield perfluorophenyl 4-chloroquinoline-7-sulfonate (10.54 g, 25.7 mmol, 100% yield) as a light yellow oily solid. m/z (ESI) 410.1 (M+H)+.

Provenance & Evidence