Hydrochloric Acid → Sulfabenz

Beteiligte Stoffe

Reaktionsschritte

An aqueous 6N solution of HCl (40 mL) was cautiously added with stirring to a solution of 3 (20 g, 68 mmol) in ethanol (80 mL). After heating under reflux for 3 h, the reaction mixture was evaporated to dryness in vacuo and the residue was dissolved in water. The pH of the solution was adjusted to 8-9 using 1N aq. NH4OH. 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 to give 4-amino-N-phenyl-benzenesulfonamide (4) (also called 207-33 or LED207) (10.9 g, 65%) as a white solid, mp 194-195° C. 1H NMR (CD3COCD3, 300 MHz) δ 8.64 (br s, 1H), 7.50-7.45 (m, 2H), 7.25-7.18 (m, 4H), 7.04-6.98 (m, 1H), 6.67-6.62 (m, 2H), 5.44 (br s, 2H); 13C NMR (CD3COCD3, 75 MHz) δ 152.9, 138.8, 129.3 (2C), 129.1 (2C), 126.3, 124.0, 120.5 (2C), 113.1 (2C).

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