Sulfanilamide → N-(p-aminosulfonylphenyl)methacrylamide

HRID 847350Notes

Reaction equation

HRID 847350 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O1CCCC1.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19]>O>[NH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])=[CH:3][CH:4]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 8028TetrahydrofuranHCID 13528Methacryloyl chloride

Product 1

HCID 350062N-(p-aminosulfonylphenyl)methacrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

170.2 g (1.0 mole) of p-aminobenzenesulfonamide and 700 ml of tetrahydrofuran were placed in one liter three-necked flask equipped with a stirrer, a cooling coil and a dropping funnel and stirred in an ice-water bath. 52.3 g (0.5 mole) of methacrylic acid chloride was added dropwise from the dropping funnel to the mixture over a period of about one hour. After the completion of dropping, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes and then stirred further for one hour while heating it in an oil bath at 60° C. After the completion of the reaction, the reaction mixture was introduced into 3 l of water with stirring, stirred for 30 minutes and filtered to obtain N-(p-aminosulfonylphenyl)methacrylamide as a white solid. The white solid was purified by recrystallizing it from a mixed solvent of water-acetone (yield: 39.3 g).

Workup

  1. customequipped with a stirrer
  2. customthe ice-water bath was removed
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. stirringstirred further for one hour
  5. customAfter the completion of the reaction
  6. stirringwith stirring
  7. stirringstirred for 30 minutes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-202165aabb7b46f6ac1e3cb7d1e0bea5
Source dataset
uspto-grants-1992_08
Patent number
US05141838

Reaction notes

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