N-(3-Methylphenyl)acetamide → 5-Aminotoluene-2-sulphonamide

Participants

Reaction Conditions

Reaction Steps

To chlorosulfuric acid (20 mL, 302 mmol), m-acetotoluidine (10 g, 67 mmol) was added at room temperature over 20 minutes, and subsequently, the mixture was heated to 70° C. and stirred for 8 hours. The mixture was cooled to room temperature, ice (50 g) was added to the reaction mixture, and the produced solid was collected by removing an aqueous layer by decantation. Subsequently, the obtained solid was washed with water (50 mL) to obtain a crude product. A solution of the obtained crude product in THF (50 mL) was cooled to 0° C., and concentrated ammonia water (20 mL) was added. Subsequently, the temperature of the mixture was raised to room temperature and the mixture was stirred for 2 hours. The reaction mixture was concentrated, water (100 mL) was added to the obtained solid, and filtration was carried out to give a crude product. To a solution of the obtained crude product in ethanol (200 mL), 6N hydrochloric acid (200 mL) was added at room temperature, and the mixture was heated under reflux and stirred for 3 hours. The reaction mixture was concentrated, methylene chloride (200 mL) was added to the obtained solid, and filtration was carried out to give the title compound (7.1 g, yield: 48%).

Provenance & Evidence