Water → 4-(3-Hexyl-2-imidazolon-1-yl)phenylsulphonyl chloride

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Reaction Steps

To the amine (38.6 mmol, 7.3 g) in methylene chloride (100 ml) at 0° C. was added 4-(chlorosulphonyl)phenyl isocyanate (38.6 mmol, 8.4 g). The reaction mixture was stirred for 20 mins until a clear solution had formed, and 1:1 water:trifluoroacetic acid (100 ml total) was added. Vigorous stirring was continued for 16 h., the layers separated, the organic layer was diluted with ethyl acetate (500 ml) and washed with saturated sodium bicarbonate solution (4×50 ml), brine (50 ml), dried with anhydrous magnesium sulphate, and concentrated in vacuo. Column chromatrography (eluant 3 hexane/1 ethyl acetate) yielded the title compound as pale yellow crystals (8.8 g, 67%).

Provenance & Evidence