Benzenesulfonyl chloride → Benzenesulfonamide, N-dodecyl-

Participants

Reaction Conditions

Reaction Steps

Benzenesulfonyl chloride (353 g, 2 mol) was added dropwise to a toluene (2000 mL) solution of dodecylamine (371 g, 2 mol) and triethylamine (203 g, 2 mol) with ice bath cooling. During the one hour addition period, the temperature increased to about 40° C. After filtration of the triethylamine hydrochloride, the toluene solution was washed with dilute HCl, dilute NaOH and water. After drying over magnesium sulfate, the toluene was removed in vacuo and the precipitate slurried in hexane and filtered to give 539 g of product. Melting point 57-60° C. Calculated for C18H32NO2S 326, found 326. 1H NMR (CDCl3) δ0.88 (t, 3, CH3), 1.24 (d, 18, CH2), 1.45 (s, 2, CH2), 4.66 (sb, 1, NH), 7.49-7.84 (m, 5, arom.).

Provenance & Evidence