Hydrochloric Acid → HCID 12852930, compound

Participants

Reaction Steps

After 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid in 225 ml of warm (65° C.) water and 83.0 (0.61 mole) of sodium acetate trihydrate in 75 ml of acetonitrile was combined and the temperature stabilized at approximately 68°-70° C., 43.2 g (0.20 mole) of 4-nitrobenzyl bromide in 85 ml of warmed acetonitrile was added dropwise over 70 minutes. The orange-red solution was then refluxed for 2 hrs, then acidified with 42 ml of conc. HCl over 40 minutes while simultaneously distilling off 110 ml of acetonitrile. The mixture was filtered hot (70° C.) which gave a light yellow powder. The powder was slurried in 275 ml of hot (75° C.) water for 20 minutes and then filtered. The slurrying process was repeated with water and then with methanol which gave a cream-colored powder. The cream-colored powder was dried in vacuo overnight at 50° C. to afford 35.33 g (57.3% yield) of purified 3-(((4-nitrophenyl)methyl)amino)benzenesulfonic acid as a cream-colored powder having a melting point greater than 275° C.

Provenance & Evidence