Sulfanilamide → N-(p-aminosulfonylphenyl)methacrylamide

HRID 1195642Notes

Reaction equation

HRID 1195642 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

To a 1 l three-necked flask equipped with a stirring machine, a condenser and a dropping funnel, there were introduced 170.2 g (1.0 mole) of p-aminobenzenesulfonamide and 700 ml of tetrahydrofuran, and the mixture was stirred while cooling it in an ice-water bath. 52.3 g (0.5 mole) of methacrylic acid chloride was dropwise added to the mixture through the dropping funnel over about one hour. After the dropwise addition, the flask was removed from the ice-water bath and the content thereof was stirred at room temperature for 30 minutes and further stirred for additional one hour while heating it to 60° C. in an oil bath. After completion of the reaction, the reaction mixture was poured into 3 l of water while stirring. The stirring was continued for 30 minutes and then the mixture was filtered to give white solid of N-(p-aminosulfonylphenyl) methacrylamide. The white solid thus obtained was purified by recrystallization from ethanol-acetone mixed solvent (yield 39.3 g).

Workup

  1. customTo a 1 l three-necked flask equipped with a stirring machine, a condenser and a dropping funnel, there
  2. temperaturewhile cooling it in an ice-water bath
  3. additionAfter the dropwise addition
  4. customthe flask was removed from the ice-water bath
  5. stirringthe content thereof was stirred at room temperature for 30 minutes
  6. stirringfurther stirred for additional one hour
  7. customAfter completion of the reaction
  8. stirringwhile stirring
  9. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-b4051cbe10d340a98bd45fbb0a6cc892
Source dataset
uspto-grants-1992_05
Patent number
US05112743

Reaction notes

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