Hydrochloric Acid → N-(4-Acetyl-2-methylphenyl)methanesulfonamide

To a solution of o-toluidine (10.7 ml, 100 mmol) and pyridine (8.49 ml, 105 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (7.74 ml, 100 mmol) dropwise over 15 minutes at 0° C. The reaction mixture was stirred at room temperature for 1 hour. After cooling to 0° C., aluminum chloride (33.3 g, 250 mmol) was added carefully to the reaction mixture. Then acetyl chloride (10.7 ml, 150 mmol) was added dropwise over 20 minutes at 5˜20° C. The reaction mixture was stirred at room temperature for 0.5 hours, the reaction was monitored by using TLC and 1H-NMR, and after completion of the reaction, the reaction mixture was diluted with toluene and poured into 2N HCl aqueous solution with stirring at 0° C. The precipitate solid was filtered, washed with H2O and heptane, and dried in vacuo to give the title compound (20.3 g, 89.3 mmol, 89% yield in 2 steps) as a light orange powder.

1. temperatureAfter cooling to 0° C.
2. stirringThe reaction mixture was stirred at room temperature for 0.5 hours
3. custom1H-NMR, and after completion of the reaction
4. stirringwith stirring at 0° C
5. filtrationThe precipitate solid was filtered
6. washwashed with H2O and heptane
7. customdried in vacuo

ORD record

ord-8fd42c6d48934c828a60d1fa0d64ff0a

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622589B2