Hydrochloric Acid → HCID 12852929, compound

Participants

Reaction Conditions

Reaction Steps

To 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid in 225 ml of water was added 83.0 g (0.61 mole) of sodium acetate trihydrate and 75 ml of acetonitrile. The solution was stabilized at about 70° C. and a solution of 38.92 g (0.20mole) of 3-(trifluoromethyl)benzyl chloride in 75 ml of acetonitrile was added dropwise. The resulting orange solution was refluxed for 4 hrs, then acidified by the dropwise addition of 42 ml of conc. HCl while simultaneously removing 105 ml of acetonitrile by distillation. After standing overnight, a flocculent cream-colored solid crystalized which was removed by vacuum filtration. The collected solids were then slurried in 300 ml of warm (60° C.) water for 20 minutes and then filtered. The slurrying process was repeated using 300 ml of boiling methanol and the solids isolated by vacuum filtration. Air-drying in vacuo at about 60° C. gave 15.4 g (23.2% yield) of purified 3-(((3-(trifluoromethyl)phenyl)methyl)amino)benzenesulfonic acid as a white powder having a melting point greater than 275° C.

Provenance & Evidence