Methacrylic Acid → N-(p-aminosulfonylphenyl)methacrylamide

Temperature

70 °C

To a 500 ml volume three-necked flask equipped with a stirring machine, a cooling tube and a dropping funnel, there were added 31.0 g (0.36 mole) of methacrylic acid, 39.1 g (0.36 mole) of ethyl chloroformate and 200 ml of acetonitrile and then the resulting mixture was stirred while cooling it in an ice-water bath. To this mixture, there was dropwise added 36.4 g (0.36 mole) of triethylamine through the dropping funnel over about one hour. After the completion of the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture, there was added 51.7 g (0.30 mole) of p-aminobenzene sulfonamide and the resulting mixture was stirred over one hour while warming the mixture at 70° C. in an oil bath. After the completion of the reaction, the mixture was introduced into 1 L of water while stirring the water and the resulting mixture was stirred for 30 minutes. This mixture was filtered to recover the precipitates, followed by addition of 500 ml of water to the precipitates to give a slurry, filtration of the slurry and drying the resulting solid to give N-(p-aminosulfonylphenyl) methacrylamide as a white solid (yield 46.9 g).

1. customTo a 500 ml volume three-necked flask equipped with a stirring machine, a cooling tube and a dropping funnel, there
2. temperaturewhile cooling it in an ice-water bath
3. customover about one hour
4. additionAfter the completion of the dropwise addition
5. customthe ice-water bath was removed
6. stirringthe mixture was stirred at room temperature for 30 minutes
7. stirringthe resulting mixture was stirred over one hour
8. customAfter the completion of the reaction
9. stirringthe resulting mixture was stirred for 30 minutes
10. filtrationThis mixture was filtered
11. customto recover the precipitates
12. additionfollowed by addition of 500 ml of water to the
13. customprecipitates
14. customto give
15. filtrationa slurry, filtration of the slurry
16. customdrying the resulting solid

ORD record

ord-3afd0984f64d4c40a17b36224f4a037c

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06919166B2