Potassium Carbonate → N,N-Diethyl-4-(4-((trifluoromethyl)sulfonyl)phenoxy)benzenesulfonamide

HRID 2164646Notes

Reaction equation

HRID 2164646 reaction equation
[F:1][C:2]([S:5]([C:8]1[CH:13]=[CH:12][C:11](Cl)=[CH:10][CH:9]=1)(=[O:7])=[O:6])([F:4])[F:3].[CH2:15]([N:17]([CH2:28][CH3:29])[S:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:16].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CS(C)=O>[CH2:28]([N:17]([CH2:15][CH3:16])[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:11]2[CH:12]=[CH:13][C:8]([S:5]([C:2]([F:4])([F:3])[F:1])(=[O:7])=[O:6])=[CH:9][CH:10]=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:29]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 7033241-Chloro-4-(trifluoromethylsulfonyl)benzeneHCID 2318424N,N-diethyl-4-hydroxybenzenesulfonamide

Product 1

HCID 13078532N,N-Diethyl-4-(4-((trifluoromethyl)sulfonyl)phenoxy)benzenesulfonamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4.6 g (0.0188 mole) of 4-chlorophenyl trifluoromethyl sulfone and 4.8 g (0.0210 mole) of N,N-diethyl-4-hydroxybenzenesulfonamide in 80 ml of DMSO was added 2.9 g (0.0210 mole) of K2CO3. The mixture was heated at 100° C. for 3.25 hrs and cooled. The mixture was poured into aqueous NaOH and the crystalline product collected by filtration, washed well with water and dried, which gave 7.25 g (88.2% yield) of product. Recrystallization from 2-propanol afforded purified N,N-diethyl-4-(4-((trifluoromethyl)sulfonyl)phenoxy)benzenesulfonamide, mp 83°-84° C.

Workup

  1. temperaturecooled
  2. filtrationthe crystalline product collected by filtration
  3. washwashed well with water
  4. customdried

Sources & evidence

ORD record
ord-e498d9aaac984dac99c72cf90fface3e
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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