Dimethyl Sulfoxide → N-(4-aminophenyl)sulfonylacetamide;benzyl-dimethyl-tridecylazanium

HRID 2403113Notes

Reaction equation

HRID 2403113 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:16])[CH3:15].[Cl-].[CH3:25][C:26]([N-:28][S:29]([C:32]1[CH:33]=[CH:34][C:35]([NH2:38])=[CH:36][CH:37]=1)(=[O:31])=[O:30])=[O:27].[Na+].C(Cl)(Cl)Cl.CS(C)=O>O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:16])[CH3:15].[CH3:25][C:26]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30])=[O:27]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6212ChloroformHCID 3014024Benzalkonium ChlorideHCID 4022878Sodium Sulfacetamide

Product 1

HCID 86612071N-(4-aminophenyl)sulfonylacetamide;benzyl-dimethyl-tridecylazaniumYield 76.99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Benzalkonium chloride (0.001 mol) was dissolved in 60 mL of distilled water by gentle heating and stirring. Sodium sulfacetamide (0.001 mol) was dissolved in 60 mL of distilled water by gentle heating and stirring. The two solutions were combined and the reaction mixture was heated and stirred for 30 minutes. The reaction mixture cooled to room temperature and then 60 mL of chloroform was added. The reaction mixture was stirred for an additional 30 minutes. The two phases were separated and the chloroform phase was washed several times with cool distilled water to remove any inorganic salt. The presence of chloride anions was monitored by silver nitrate test. A rotary evaporator removed the chloroform and a yellowish gel was obtained in 76.99% yield. 1H and 13C NMR (DMSO) were obtained. Melting point (hot plate apparatus)=35-40° C. Thermal data determined by thermalgravimetric analysis (TGA): Tonset5%=164° C. and Tonset=181° C.

Workup

  1. temperatureby gentle heating
  2. temperatureby gentle heating
  3. stirringstirring
  4. temperaturethe reaction mixture was heated
  5. stirringstirred for 30 minutes
  6. stirringThe reaction mixture was stirred for an additional 30 minutes
  7. customThe two phases were separated
  8. washthe chloroform phase was washed several times
  9. temperaturewith cool
  10. distillationdistilled water
  11. customto remove any inorganic salt
  12. customA rotary evaporator
  13. customremoved the chloroform
  14. customa yellowish gel was obtained in 76.99% yield
  15. customMelting point (hot plate apparatus)=35-40° C
  16. custom=164° C. and Tonset=181° C.

Sources & evidence

ORD record
ord-e89e09349eb84de3801f374de44f22a6
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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