Water → 3-Acetamido-2-chloro-4-(4-fluorophenylsulphanyl)aniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-acetamido-2-chloro-4-(4-fluorophenylsulphanyl)nitrobenzene (Method 15) (0.1 g), ferric chloride hexahydrate (0.238 g) and zinc dust (0.192 g in DMF (1 ml) and water (1 ml) was stirred and heated (oil bath 100° C.) for 1 hour then cooled. Water (15 ml) was added and the mixture was basified to pH 11 with saturated aqueous sodium carbonate solution (3 ml) then extracted with DCM (3×15 ml). The extracts were washed with brine then dried. Volatile material was removed by evaporation and the residue was left under high vacuum (2 mm Hg) overnight to give the title compound (0.087 g) as a solid. NMR: 1.95 (s, 3H), 5.72 (brs, 2H), 6.73 (d, 1H), 7.05-7.20 (m, 5H), 9.54 (brs, 1H); m/z: 309.

Provenance & Evidence