N-Acetylsulfanilyl chloride → HCID 86746051, compound

HRID 1721547Notes

Reaction equation

HRID 1721547 reaction equation
C([NH:4][C:5]1C=CC=[CH:7][C:6]=1S(Cl)(=O)=O)(=O)C.[OH-].[Na+].S(Cl)(Cl)(=O)=O.C([NH:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)(=O)C>O.O1CCCC1>[S:32]([NH2:4])(=[O:34])([C:29]1[CH:30]=[CH:31][C:26]([NH2:25])=[CH:27][CH:28]=1)=[O:33].[CH2:5]([NH2:4])[CH:6]=[CH2:7]

Participants

7

Reactant 4

HCID 8481N-Acetylsulfanilyl chloride2×HCID 14798Sodium Hydroxide2×HCID 24648Sulfuryl chlorideHCID 125069442-Acetamidobenzene-1-sulfonyl chloride

Product 1

HCID 86746051HCID 86746051, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Poly(allylamine sulfanilamide) is synthesized from poly(allylamine) and acetamidobenzenesulfonyl chloride by a variation of a method developed by Dawson, Gless & Wingard, Jr. 98 JACS 5996 (1970)! for the synthesis of polysulfanilamide. 1.66 g of poly(allylamine) which contained 17.6 mmol of amine groups were dissolved in 14 ml of water. 1.5 ml of 8 N NaOH were added to bring the pH to 10. 7 ml of tetrahydrofuran (THF) were added to promote co-solubility of the polymer and sulfonyl chloride during reaction. 1.51 g of p-acetamidobenzenesulfonyl chloride was added to the stirred solution, and 8N NaOH was added as required to maintain the pH between 9 and 10. After 5 min. a further 1.51 g of the p-acetamidobenzenesulfonyl chloride was added, along with 7 ml of THF. This procedure was repeated a third time. The solution separated into two phases, a lower water-rich phase, and an upper THF-rich phase containing poly(p-acetamido-N-propylbenzene-sulfonamide). The polymer was precipitated from the THF with ethanol, washed with ethanol, and dried. Recovery was 73% of the theoretical weight of the polymer. The polymer was dissolved in 30 ml of 1N HCl and heated at reflux for 6 h. to produce the poly(allylamine sulfanilamide).

Workup

  1. customfor the synthesis of polysulfanilamide
  2. customduring reaction
  3. additionwas added
  4. temperatureto maintain the pH between 9 and 10
  5. customThe solution separated into two phases
  6. additiona lower water-rich phase, and an upper THF-rich phase containing poly(p-acetamido-N-propylbenzene-sulfonamide)
  7. customThe polymer was precipitated from the THF with ethanol
  8. washwashed with ethanol
  9. customdried
  10. dissolutionThe polymer was dissolved in 30 ml of 1N HCl
  11. temperatureheated
  12. temperatureat reflux for 6 h.

Sources & evidence

ORD record
ord-5621a7139b2840f8aaec490ed5b884c8
Source dataset
uspto-grants-1996_04
Patent number
US05512246

Reaction notes

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