Methylamine → 4-acetyl-N-methylbenzene-1-sulfonamide

HRID 866971Notes

Reaction equation

HRID 866971 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1C=CC(S([O-])(=O)=O)=CC=1)(=O)C.[Na+].[CH3:28][NH2:29]>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:29][CH3:28])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 23668814Sodium 4-acetylbenzenesulphonate

Product 1

HCID 20640424-acetyl-N-methylbenzene-1-sulfonamide

Procedure

The damp 4-acetylbenzenesulfonyl chloride from 50 g. of sodium 4-acetylbenzenesulfonate is added in portions, with stirring, to 500 ml. of cold 40% aqueous methylamine. The mixture is stirred at room temperature for 16 hours, then cooled and the precipitate collected by filtration. The solid (which proved to be the N-methylimine derivative of the ketosulfonamide) is dissolved in 300 ml. of 6% hydrochloric acid and the solution is heated at 80°-90° C. for 30 minutes, then cooled. The resulting precipitate of 4-acetyl-N-methylbenzenesulfonamide is collected by filtration and crystallized from aqueous ethanol; m.p. 107°-109° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. temperaturecooled
  3. filtrationthe precipitate collected by filtration
  4. dissolutionis dissolved in 300 ml
  5. temperatureof 6% hydrochloric acid and the solution is heated at 80°-90° C. for 30 minutes
  6. temperaturecooled
  7. filtrationThe resulting precipitate of 4-acetyl-N-methylbenzenesulfonamide is collected by filtration
  8. customcrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-b2c0030f9aee4179b95f0671114f45be
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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