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

Temperature

70 °C

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%).

1. temperatureThe mixture was cooled to room temperature
2. customthe produced solid was collected
3. customby removing an aqueous layer by decantation
4. washSubsequently, the obtained solid was washed with water (50 mL)
5. customto obtain a crude product
6. temperaturewas cooled to 0° C.
7. temperatureSubsequently, the temperature of the mixture was raised to room temperature
8. stirringthe mixture was stirred for 2 hours
9. concentrationThe reaction mixture was concentrated
10. additionwater (100 mL) was added to the obtained solid, and filtration
11. customto give a crude product
12. additionwas added at room temperature
13. temperaturethe mixture was heated
14. temperatureunder reflux
15. stirringstirred for 3 hours
16. concentrationThe reaction mixture was concentrated
17. additionmethylene chloride (200 mL) was added to the obtained solid, and filtration

ORD record

ord-8a0cf35199234b55bccbb6e5887e3415

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642640B2