Methanesulfonyl chloride → HCID 85866249, compound

Diisopropylethylamine (585 μl, 3.36 mmol) followed by methane sulphonyl chloride (260 μl, 3.36 mmol) was added to a stirred solution of N-(2-hydroxyethyl)-4-iodobenzenesulphonamide (Method 45; 1 g, 3.06 mmol) in EtOAc (25 ml) at 5° C., under nitrogen. The reaction was allowed to warm to ambient temperature and stirred for 24 hours. The reaction mixture was washed with 1M hydrochloric acid (3×25 ml), saturated aqueous sodium hydrogen carbonate solution (3×25 ml), brine (2×25 ml), an then dried. The volatiles were removed by evaporation and the residue purified by chromatography on silica, eluting with DCM/MeOH (100:0 increasing in polarity to 99:1) to give the title compound (562 mg, 45%) as a white solid. NMR: 3.08 (m, 2H), 3.12 (s, 3H), 4.08 (t, 2H), 7.55 (d, 2H), 7.98 (d, 2H), 8.03 (t, 1H); m/z 405.

1. washThe reaction mixture was washed with 1M hydrochloric acid (3×25 ml), saturated aqueous sodium hydrogen carbonate solution (3×25 ml), brine (2×25 ml)
2. customan then dried
3. customThe volatiles were removed by evaporation
4. customthe residue purified by chromatography on silica
5. washeluting with DCM/MeOH (100:0 increasing in polarity to 99:1)

ORD record

ord-1ebc9192fe474f0aa18a619905c55317

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465728B2