Water → HCID 13502333, compound

HRID 1702818Notes

Reaction equation

HRID 1702818 reaction equation
[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[OH-].[Na+].[C:16]1([S:22]([C:25]2[CH:30]=[CH:29][C:28](F)=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CS(C)=O>[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:19]2[CH:18]=[CH:17][C:16]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:21][CH:20]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 675561-Fluoro-4-(phenylsulphonyl)benzeneHCID 84760Benzenesulfonamide, 4-hydroxy-N,N-dimethyl-

Product 1

HCID 13502333HCID 13502333, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.60 g (0.0330 mole) of N,N-dimethyl-4-hydroxybenzenesulfonamide dissolved in 150 ml of DMSO was added 1.32 g (0.0330 mole) of NaOH. The mixture was heated at 60° C. for 10 minutes and 7.1 g (0.030 mole) of 4-fluorophenyl phenyl sulfone was added. The reaction mixture was heated at 100° C. for 3 hrs and at 125° C. for 3 hrs and cooled. The mixture was poured into a solution of 200 ml of 20% aqueous NaOH and 500 ml of water. The crystalline product was collected, washed well with water and dried, which gave 11.5 g (92% yield) of product. Recrystallization from aqueous DMSO followed by recrystallization from ethanol afforded purified N,N-dimethyl-4-(4-(phenylsulfonyl)phenoxy)benzenesulfonamide, mp 99°-100° C.

Workup

  1. temperatureThe reaction mixture was heated at 100° C. for 3 hrs and at 125° C. for 3 hrs
  2. temperaturecooled
  3. customThe crystalline product was collected
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-450bae7fe53b4a919a93ac47188ad23c
Source dataset
uspto-grants-1982_09
Patent number
US04349568

Reaction notes

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