N-Acetylsulfanilyl chloride → HCID 86746051, compound

HRID 846573Notes

Reaction equation

HRID 846573 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 8 N 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 1 N HCl and heated at reflux for 6 h. to produce the poly(allylamine sulfanilamide).

Workup

  1. custom[98 JACS 5996 (1970)] for 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 1 N HCl
  11. temperatureheated
  12. temperatureat reflux for 6 h.

Sources & evidence

ORD record
ord-4441c57e71c449e8b393f92b0e06d5fd
Source dataset
uspto-grants-1992_08
Patent number
US05137833

Reaction notes

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