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ChemicalBook CAS DataBase List 5-Amino-2-chlorobenzenesulfonamide

5-Amino-2-chlorobenzenesulfonamide synthesis

6synthesis methods
-

Yield:2015-19-2 83%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 50; for 4 h;

Steps:

4.2.5. 5-Amino-2-chlorobenzenesulfonamide (5) [14]

The compound 4 (14.15 g, 59.8 mmol) and 300 mL of methanol were placed into a flask and stirred at 50 °C until dissolved completely and then 10% Pd/C (1.4 g) was added. The mixture was intensively stirred under H2 at 50 °C and monitored with TLC. After 4 h, the reaction was complete, and the suspension was filtered. The resulting solution was evaporated to give the crude product. It was dissolved in 30 mL of 9 mol/L hydrochloric acid solution and filtered. The filtrate was alkalified with 10 mol/L sodium hydroxide solution to pH 7. The suspension was filtered to afford the compound 5 (10.27 g, 83% yield, m.p. 166-167 °C). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.969 (d, 1H, JH = 8.8 Hz, Ar-H), 8.017 (s, 2H, SO2NH2), 8.414-8.442 (m, 1H, Ar-H), 8.671-8.677 (m, 1H, Ar-H).

References:

Pan, Li;Jiang, Ying;Liu, Zhen;Liu, Xing-Hai;Liu, Zhuo;Wang, Gang;Li, Zheng-Ming;Wang, Di [European Journal of Medicinal Chemistry,2012,vol. 50,p. 18 - 26] Location in patent:experimental part

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