Benzylamine → N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide

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Reaction Steps

To a solution of benzylamine (10.92 ml, 100 mmol) in DCM (150 ml) was added triethylamine (13.67 ml, 100 mmol) followed by a solution of 2-nitrobenzene-1-sulfonyl chloride (22.16 g, 100 mmol) in DCM (70 ml) at 5-10° C. with stirring. The mixture was stirred for 1 hour, stirring continued for 1 hour, washed with water, brine, most of DCM removed under reduced pressure. Ethyl acetate (150 ml) was added, another 25-30 ml distilled off under reduced pressure. To the resulting solution potassium tert-butoxide (0.561 g, 5.00 mmol) was added followed by 1-hydroxybut-3-en-2-one (9.47 g, 110 mmol) with stirring in one portion at 20-25° C. The mixture was stirred for 1 hour at 20-25° C., diluted with heptane (70 ml), washed with brine and 1N HCl (5 ml), organic phase was dried (MgSO4), evaporated to dryness under reduced pressure. The resulting oil was purified on a column with ethyl acetate-petroleum ether mixture as eluent. Fractions containing the wanted product were collected and evaporated to dryness under reduced pressure to give N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide (29.1 g, 77 mmol, 77% yield).

Provenance & Evidence