Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → 2-Chloro-5-(2-[p-chlorophenyl)ethylaminosulfonyl)benzoic Acid

Participants

Reaction Steps

2-Chloro-5-chlorosulfonyl benzoic acid, 3.5 g. (0.014 mole), is added to a solution of 2-(p-chlorophenyl)ethylamine, 6.5 g. (0.042 mole) in 25 ml. methylene chloride. The resulting slurry is stirred overnight and filtered to recover 9.7 g. of residue. This is recrystallized three times from aqueous isopropanol, then dissolved in 1N aqueous sodium hydroxide, washed three times with ether, and then acidified with conc. hydrochloric acid. The resulting precipitate is recrystallized twice from aqueous isopropanol to yield the desired product, m.p. 176°-178° C.

Provenance & Evidence