Benzenesulfonyl chloride, 4-chloro-3-nitro- → 3-amino-4-chlorobenzenethiol

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Reaction Steps

To a cooled solution (0° C.) of tin(II) chloride (11.260 g, 59.40 mmol) in 10 ml concentrated hydrochloric acid was slowly added 4-chloro-3-nitro-benzenesulfonyl chloride (1.690 g, 6.60 mmol) portionwise. The resulting suspension was kept cool and stirred for 15 minutes before the mixture was heated to reflux for 1 hour. After cooling to room temperature the mixture was diluted with water (100 ml) and carefully neutralised using NaHCO3. The aqueous phase was extracted with chloroform (4×50 ml) and the organic phase separated and dried over Na2SO4. Removal of solvent under vacuum afforded a bright yellow solid. Column chromatography on silica gel using 1:1 chloroform/hexane as the mobile phase afforded 3-amino-4-chlorobenzene thiol as a white solid (0.632 g, 60%).

Provenance & Evidence