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

HRID 1110671Notes

Reaction equation

HRID 1110671 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 4N 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 1N 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 1N 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-543d73234fb34527b601c5aeef653542
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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