4-Aminophenol → N-(4-hydroxyphenyl)methanesulfonamide

HRID 1776638Notes

Reaction equation

HRID 1776638 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11]>CO>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:10]([CH3:9])(=[O:12])=[O:11])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 31297Methanesulfonyl chloride

Product 1

HCID 4483147N-(4-hydroxyphenyl)methanesulfonamideYield 28.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold suspension of 4-aminophenol (5.45 g, 49.9 mmol) in MeOH (62 ml), methanesulfonyl chloride (1.95 ml, 25.2 mmol) was added under stirring maintaining the temperature between 10 and 15° C. The resulting solution was allowed to warm to RT and stirred for 2 hours. The solvent was removed under vacuum, and the residue was suspended in HCl 1N (62 ml); the insoluble was collected by filtration, washed with water, dried and purified by filtration through a silica gel pad (DCM:MeOH=100:15) affording N-(4-hydroxyphenyl)methanesulfonamide as a brown solid (1.35 g, 7.21 mmol, 28.6% yield).

Workup

  1. additionwas added
  2. temperaturemaintaining the temperature between 10 and 15° C
  3. stirringstirred for 2 hours
  4. customThe solvent was removed under vacuum
  5. filtrationthe insoluble was collected by filtration
  6. washwashed with water
  7. customdried
  8. filtrationpurified by filtration through a silica gel pad (DCM:MeOH=100:15)

Sources & evidence

ORD record
ord-d157e3dc57034c38aada98438f51b039
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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