Methacrylic Acid → N-(p-aminosulfonylphenyl)methacrylamide

HRID 2120035Notes

Reaction equation

HRID 2120035 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[CH2:3].C(OCCCl)=O.C(#N)C.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>O.C(N(CC)CC)C>[NH2:26][S:23]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])=[CH:22][CH:21]=1)(=[O:24])=[O:25]

Participants

7

Conditions

Temperature
70 °C

Procedure

31.0 g of methacrylic acid, 39.1 g of chloroethyl formate, and 200 ml of acetonitrile were put in an ice water bath, and this mixture was agitated while cooling. 36.4 g of triethylamine was dropped into the mixture by a dropping funnel over about 1 hour. After the dropping was finished, the ice water bath was taken away, the mixture was agitated for 30 minutes at room temperature. 51.7 g of p-amino benzene sulfonamide was added to the reaction mixture, and the mixture was agitated for 1 hour while being heated at 70° C. After finishing the reaction, an obtained mixture was introduced into 1,000 ml of water while agitating the water, and the obtained mixture was agitated for 30 minutes. The mixture was filtrated for taking out a precipitate. After adding 500 ml of water to the precipitate to make a slurry, the slurry was filtrated, and an obtained solid was dried so as to obtain N-(p-aminosulfonyl phenyl) methacrylamide (yield 46.9 g).

Workup

  1. temperaturewhile cooling
  2. stirringthe mixture was agitated for 30 minutes at room temperature
  3. stirringthe mixture was agitated for 1 hour
  4. customthe reaction
  5. stirringthe obtained mixture was agitated for 30 minutes
  6. filtrationThe mixture was filtrated
  7. additionAfter adding 500 ml of water to the precipitate
  8. filtrationthe slurry was filtrated
  9. customan obtained solid was dried so as

Sources & evidence

ORD record
ord-6acbcb0c29c9492eac3e6a36dedef7e4
Source dataset
uspto-grants-2004_02
Patent number
US06689534B2

Reaction notes

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