Hydrochloric Acid → 4-amino-N-methylbenzene-1-sulfonamide

HRID 1591013Notes

Reaction equation

HRID 1591013 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl>CO>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 145971Acetamide, N-(4-((methylamino)sulfonyl)phenyl)-

Product 1

HCID 743684-amino-N-methylbenzene-1-sulfonamideYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The acetamide (1.6 g) was dissolved in methanol (5 ml) and refluxed, with an addition of 4 N hydrochloric acid (7 ml), for 1 hour. After an evaporation of methanol under a reduced pressure, the residue was made basic with an addition of 1 N sodium hydroxide, and extracted with ethyl acetate (30 ml), followed by drying over anhydrous sodium sulfate. Evaporation of the solvent under a reduced pressure gave N-methyl-4-(amino)benzenesulfonamide (1.2 g) (m.p. 110.9° C.-112° C.).

Workup

  1. customAfter an evaporation of methanol under a reduced pressure
  2. additionthe residue was made basic with an addition of 1 N sodium hydroxide
  3. extractionextracted with ethyl acetate (30 ml)
  4. dry with materialby drying over anhydrous sodium sulfate
  5. customEvaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-8a32837b47194d97a289b849b73517f7
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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