Hydrochloric Acid → 3-Chloro-4-iodobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (3.27 g) in water was added dropwise over 1 h to a stirred solution of 3-chloro-4-iodoaniline (10.0 g) in a mixture of THF (120 ml) and concentrated hydrochloric acid (50 ml) at −5 to −1° C. Magnesium chloride (6.39 g) was then added and the resulting mixture poured into a stirred solution of acetic acid (50 ml) saturated with sulfur dioxide and containing cuprous chloride (2.14 g). After heating at 34° C. for 30 min, the mixture was poured into brine, extracted with EtOAc, washed with aqueous sodium bicarbonate and brine, dried (MgSO4) and evaporated. The residue was dissolved in THF (100 ml), 0.880 ammonia (100 ml) added and stirred for 2 h. The mixture was diluted with brine, extracted with EtOAc, washed with brine, dried (MgSO4) and evaporated. The residue was treated with isohexane/ether (4:1) and filtered to give the subtitle compound. Yield 5.67 g.

Provenance & Evidence