N-Acetylsulfanilyl chloride → N-[4-(2-dimethylaminoethylsulfamoyl)phenyl]acetamide

HRID 2185175Notes

Reaction equation

HRID 2185175 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][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19]>ClCCl>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH:19][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

4

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 3462536N-[4-(2-dimethylaminoethylsulfamoyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Acetylaminobenzenesulfonyl chloride is introduced into dichloromethane and treated at room temperature with two equivalents of N,N-dimethylethylenediamine and stirred at room temperature until complete conversion can be determined (LCMS). For work-up, the solvent is distilled off, the oily residue is taken up in dichloromethane or ethyl acetate and the mixture is washed with NaHCO3 solution. The phases are separated and the aqueous phase is extracted once more with dichloromethane or ethyl acetate. The organic phases are dried using Na2SO4 and concentrated. The crude product thus obtained is reacted further without further purification. (MS-CI+: 286.0; LCMS Rt=2.542 min)

Workup

  1. distillationFor work-up, the solvent is distilled off
  2. washethyl acetate and the mixture is washed with NaHCO3 solution
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted once more with dichloromethane or ethyl acetate
  5. customThe organic phases are dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-070247a3a76b4c02843ef4a41d25cada
Source dataset
uspto-grants-2002_06
Patent number
US06399824B1

Reaction notes

Loading…