Hydrochloric Acid → 4-[N-(2,3-Epoxypropyl)sulphamoyl]nitrobenzene

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Reaction Steps

p-Nitrobenzene sulphonamide (6.06 g, 30 mmol) was added portionwise to a solution of sodium hydroxide (1.32 g, 33 mmol) in water (60 ml) at room temperature. Epibromohydrin (4.5 g, 33 mmol) was added quickly dropwise and the solution stirred at room temperature for 24 hours. The mixture was acidified to pH 1 with 2M hydrochloric acid and extracted with DCM (2×30 ml). The combined organic extracts were dried with sodium sulphate, filtered and the volatiles removed by evaporation. The resulting yellow oil was purified by chromatography on silica eluting with DCM/methanol (100:0) increasing in polarity to (99:1) to give the title compound as a pale yellow solid (2.5 g, 32%); NMR (CDCl3) 2.65 (m, 1H), 2.80 (t, 1H), 3.10 (m, 2H), 3.50 (m, 1H), 5.08 (brs, 1H), 8.08 (d, 2H), 8.38 (d, 2H); m/z: 257.

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