Methylamine → 4-[1-Hydroxy-2-(methylamino)ethyl]benzenesulfonamide

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Reaction Steps

To a solution of methyl amine (20 mL, 40 mmol, 2.0 M in methanol) was added 4-oxiran-2-ylbenzenesulfonamide (Preparation 49)(0.52 g, 2.6 mmol) at 0° C. The clear solution was warmed to room temperature and stirred overnight. The solvent and excess of methyl amine was evaporated to yield an oil. The crude oil was dissolved in methanol (5 mL), and stirred with resin (BioRad 50W×2, 1 g) for 4 hours. The resin was collected by filtration and washed with methanol (3×15 mL). The product on the resin was washed off with NH4OH/CH3OH (20 mL, 10% ammonium hydroxide aqueous solution (Aldrich, 29.4% NH3) in methanol). The solution was concentrated to dryness, and treated with high vacuum to give the title compound (0.19 g) as a white solid.

Provenance & Evidence