Water → HCID 86687446, compound

Participants

Reaction Steps

A round-bottom flask was charged with 6-(benzylthio)-1-chlorophthalazine (2.20 g, 7.67 mmol), acetonitrile (72.2 ml), acetic acid (2.71 ml), and water (1.805 ml) to give a clear, orange solution. The flask was cooling in an ice-bath for 10 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (3.02 g, 15.34 mmol) was added in one portion. After 30 min, 2,3,4,5,6-pentafluorophenol (2.82 g, 15.34 mmol) and triethylamine (4.28 ml, 30.7 mmol) were added in sequence. After 30 min, the mixture was diluted with EtOAc (100 mL), washed with water (50 ml), washed with 0.5 N aq. HCl (100 mL), washed with brine, and dried over sodium sulfate. The residue was dissolved in DCM and loaded onto a chilled 25-g silica gel loading column. The column was dried with a vacuum hose, then eluted onto a pre-equilibrated 80-g column with 0 to 50% EtOAc/Heptane to give perfluorophenyl 1-chlorophthalazine-6-sulfonate (2.134 g, 5.20 mmol, 67.7% yield) as a yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=9.64 (d, J=0.7 Hz, 1H), 8.72 (d, J=1.8 Hz, 1H), 8.65-8.59 (m, 1H), 8.56-8.50 (m, 1H); m/z (ESI) 411.2 (M+H)+.

Provenance & Evidence