Triethylamine → N-{4-[(4-hydroxyphenyl)(methyl)sulfamoyl]phenyl}acetamide

HRID 395597

Reaction equation

HRID 395597 reaction equation
S([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][CH:7]=1)(O)(=O)=O.[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].C(N(CC)CC)C>C(O)C>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH3:13])[S:24]([C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:14](=[O:16])[CH3:15])=[CH:23][CH:22]=2)(=[O:26])=[O:25])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 10198132p-(N-methylamino)phenol sulfate

Product 1

HCID 2998367N-{4-[(4-hydroxyphenyl)(methyl)sulfamoyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylaminophenol sulfate and equivalent 4-acetamidobenzenesulfonyl chloride and double equivalent triethylamine were reacted in ethanol at room temperature for 4 hours. After the solvent was removed in vacuo, the residue was extracted with diethyl ether. The ether layer was washed successively with 2 N hydrochloric acid, saturated aqueous NaHCO3 solution and water, then dried over anhydrous Na2SO4 The solvent was removed and the residue was recrystallized from ethanol to give N-(4-hydroxyphenyl)-N-methyl-4-acetamidobenzenesulfonamide, mp 202-203° C.

Workup

  1. customAfter the solvent was removed in vacuo
  2. extractionthe residue was extracted with diethyl ether
  3. washThe ether layer was washed successively with 2 N hydrochloric acid, saturated aqueous NaHCO3 solution and water
  4. dry with materialdried over anhydrous Na2SO4 The solvent
  5. customwas removed
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c49085fcab17466c95941101e1a3525b
Source dataset
uspto-grants-2003_08
Patent number
US06605635B1

Linked notes

Loading…