Dimethylamine → HCID 13078516, compound

HRID 2164635Notes

Reaction equation

HRID 2164635 reaction equation
Cl[S:2]([OH:5])(=[O:4])=O.[CH3:6][S:7]([C:10]1[CH:22]=[CH:21][C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH3:23][NH:24][CH3:25]>O>[CH3:23][N:24]([CH3:25])[S:2]([C:18]1[CH:19]=[CH:20][C:15]([O:14][C:13]2[CH:21]=[CH:22][C:10]([S:7]([CH3:6])(=[O:8])=[O:9])=[CH:11][CH:12]=2)=[CH:16][CH:17]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 24638Chlorosulfonic acidHCID 130785151-(Methanesulfonyl)-4-phenoxybenzene

Product 1

HCID 13078516HCID 13078516, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15 ml (0.227 mole) of chlorosulfonic acid was added 10.0 g (0.0403 mole) of 1-(4-(methylsulfonyl)phenoxy)benzene in small portions keeping the temperature below 55° C. After the addition was complete and the mixture had stirred at ambient temperature for 10 minutes, the mixture was slowly poured over ice and water. The crystalline 4-(4-(methylsulfonyl)phenoxy)benzenesulfonyl chloride was collected by filtration, washed with water and dried. The material was dissolved in 350 ml of CH2Cl2 and 26.6 g (0.177 mole) of 30% aqueous dimethylamine was added dropwise. The reaction mixture was heated at reflux temperature for 1.5 hrs and cooled. The mixture was extracted with 3N aqueous hydrogen chloride, dried (Na2SO4) and solvent removed in vacuo, which gave 13.4 g (93.7% yield) of product. Recrystallization from ethanol, followed by purification using column chromatography with silica gel as the support and chloroform as the eluent gave purified N,N-dimethyl-4-(4-(methylsulfonyl)phenoxy)benzenesulfonamide, mp 127.5°-130° C.

Workup

  1. customthe temperature below 55° C
  2. additionAfter the addition
  3. filtrationThe crystalline 4-(4-(methylsulfonyl)phenoxy)benzenesulfonyl chloride was collected by filtration
  4. washwashed with water
  5. customdried
  6. dissolutionThe material was dissolved in 350 ml of CH2Cl2
  7. temperatureThe reaction mixture was heated
  8. temperatureat reflux temperature for 1.5 hrs
  9. temperaturecooled
  10. extractionThe mixture was extracted with 3N aqueous hydrogen chloride
  11. dry with materialdried (Na2SO4) and solvent
  12. customremoved in vacuo, which

Sources & evidence

ORD record
ord-b86b071471e8475782948bbf398dd5cc
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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