Aniline → 4-Acetamidobenzenesulfonanilide

Participants

Reaction Steps

N-Acetylsulfanilyl chloride 1 (55 g, 236 mmol) was added in portion to a stirring, 0° C. suspension of sodium acetate (48.4 g, 590 mmol) and aniline 2 (22 mL, 236 mmol) in ethanol (300 mL). The reaction mixture was stirred at room temperature overnight and then poured into ice-cold water (1.5 L) with vigorous stirring. After stirring for 1 h, the white solid that gradually precipitated was collected by filtration. The filter cake was washed with ice-cold water, dried under vacuum, and recrystallized from hot ethanol to give N-[4-[(phenylamino)sulfonyl]phenyl]acetamide (3) (also called 137-19 or LED137) (41 g, 60%) as a white solid, mp 209-210° C. 1H NMR (CD3OD, 400 MHz) δ 7.64 (br s, 4H), 7.18 (t, J=7.6 Hz, 2H), 7.06-7.00 (m, 3H), 2.10 (s, 3H).

Provenance & Evidence