Methylamine → Acetamide, N-(4-((methylamino)sulfonyl)phenyl)-

HRID 2185178Notes

Reaction equation

HRID 2185178 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:15][NH2:16]>>[CH3:15][NH:16][S:11]([C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 8481N-Acetylsulfanilyl chloride

Product 1

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

Procedure

10.5 g (45 mmol) of 4-acetylaminobenzenesulfonyl chloride are stirred at 50° C. for 3 hours in 100 ml of 40% strength methylamine solution. The solution is then extracted three times with ethyl acetate. The organic phases are dried using Na2SO4 and concentrated. The residue is stirred with dichloromethane and the insoluble constituents are filtered off. Concentration of the filtrate gives the desired sulfonamide in adequate purity and almost quantitative yield. (MS-CI+: 229.1; LCMS Rt=3.249 min)

Workup

  1. extractionThe solution is then extracted three times with ethyl acetate
  2. customThe organic phases are dried
  3. concentrationconcentrated
  4. filtrationthe insoluble constituents are filtered off

Sources & evidence

ORD record
ord-35c085e3d4c14db29cd37a7023702cfa
Source dataset
uspto-grants-2002_06
Patent number
US06399824B1

Reaction notes

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