N-Acetylsulfanilyl chloride → Acetamide, N-(4-((methylamino)sulfonyl)phenyl)-

HRID 1591012Notes

Reaction equation

HRID 1591012 reaction equation
Cl.[CH3:2][NH2:3].[C:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1)(=[O:6])[CH3:5]>N1C=CC=CC=1.C(Cl)Cl>[CH3:2][NH:3][S:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:4](=[O:6])[CH3:5])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 145971Acetamide, N-(4-((methylamino)sulfonyl)phenyl)-Yield 71.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methylamine hydrochloride (1.4 g) in pyridine (5 ml) was added 4-acetamidobenzenesulfonyl chloride (2.3 g), and the mixture was stirred at 50° C. for 2 hours. The residue obtained by an evaporation of pyridine under a reduced pressure was dissolved in methylene chloride (50 ml), washed with water, 1 N hydrochloric acid, and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Evaporation of the solvent under a reduced pressure gave N-methyl-4-(acetamido)benzenesulfonamide (1.6 g).

Workup

  1. washwashed with water, 1 N hydrochloric acid, and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customEvaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-1712924ee6d44809b7fd1b943a0a8df3
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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