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

HRID 1110670Notes

Reaction equation

HRID 1110670 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, 1N 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, 1N 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-e444d8d5fbff4625a2cf8fc78a423fef
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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