Water → N-(4-hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841595Notes

Reaction equation

HRID 1841595 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.[F:14][C:15]([F:27])([F:26])[C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1(C)C=CC=CC=1>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH3:13])[S:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:26])[F:27])=[CH:21][CH:20]=2)(=[O:24])=[O:23])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 10198132p-(N-methylamino)phenol sulfate

Product 1

HCID 23446603N-(4-hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamideYield 100.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.8 g (40 mmol) of 4-methylaminophenol hemisulfate (twice suspended in toluene and evaporated under reduced pressure to remove water) were suspended in 100 ml hexamethyldisilazane and refluxed for 2.5 h. The solution was evaporated under reduced pressure and dissolved in 270 ml THF. 9.79 g (40 mmol) of 4-(trifluoromethyl)benzenesulfonyl chloride were added slowly at 0° C. and the reaction mixture was stirred for 16 h at room temperature. 30 ml H2O were added and after 1 h the solvents were evaporated. The residue was extracted with water/Et2O (3×), the organic phases were washed with 10% NaCl, dried (Na2SO4) and evaporated to yield 13.3 g (100%) of N-(4-hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide, mp: 145-146° C.; MS: 331 (M).

Workup

  1. customevaporated under reduced pressure
  2. customto remove water)
  3. temperaturerefluxed for 2.5 h
  4. customThe solution was evaporated under reduced pressure
  5. dissolutiondissolved in 270 ml THF
  6. customwere evaporated
  7. extractionThe residue was extracted with water/Et2O (3×)
  8. washthe organic phases were washed with 10% NaCl
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-7371c4166a0c4115b4dddc7db14df458
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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