Methacrylic Acid → N-(p-aminosulfonylphenyl)methacrylamide

Temperature

70 °C

Into a 500 ml-volume three-necked flask equipped with a stirrer, a condenser tube and a dropping funnel were charged 31.0 g (0.36 mol) of methacrylic acid, 39.1 g (0.36 mol) of ethyl chloroformate and 200 ml of acetonitrile, and the resulting mixture was stirred under cooling in an ice water bath. To the mixture, 36.4 g (0.36 mol) of triethylamine was added dropwise through the dropping funnel over a period of 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 the reaction mixture was added 51.7 g (0.30 mol) of p-aminobenzenesulfonamide, and the resulting mixture was stirred for one hour while heating to 70° C. on an oil bath. After the completion of the reaction, the reaction mixture was poured into one liter of water while stirring the water, and the resulting mixture was stirred for 30 minutes. The mixture was filtered to collect deposit and the deposit was made into a slurry with 500 ml of water. The slurry was filtered and the resulting solid was dried to obtain a white solid of N-(p-aminosulfonylphenyl)methacrylamide (yield: 46.9 g).

1. customInto a 500 ml-volume three-necked flask equipped with a stirrer, a condenser tube and a dropping funnel
2. temperatureunder cooling in an ice water bath
3. additionAfter the completion of the dropwise addition
4. customthe ice water bath was removed
5. stirringthe mixture was stirred at room temperature for 30 minutes
6. stirringthe resulting mixture was stirred for one hour
7. customAfter the completion of the reaction
8. stirringthe resulting mixture was stirred for 30 minutes
9. filtrationThe mixture was filtered
10. customto collect deposit
11. filtrationThe slurry was filtered
12. customthe resulting solid was dried

ORD record

ord-fa33da9e9be24f79a4625b6ca462ac11

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07316185B2