Benzalkonium → Benzalkonium Sulfathiazole

HRID 1517231

Reaktionsgleichung

Reaktionsgleichung von HRID 1517231
[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-].[CH:25]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]([S:32]([N-:35][C:36]2[S:40][CH:39]=[CH:38][N:37]=2)(=[O:34])=[O:33])[CH:26]=1.[Na+].C(Cl)(Cl)Cl.CCCCCCCCCCCCC[N+](CC1C=CC=CC=1)(C)C>O.CS(C)=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].[CH:29]1[C:30]([NH2:31])=[CH:25][CH:26]=[C:27]([S:32]([NH:35][C:36]2[S:40][CH:39]=[CH:38][N:37]=2)(=[O:34])=[O:33])[CH:28]=1

Komponenten

7

Edukt 4

HCID 2330BenzalkoniumHCID 6212ChloroformHCID 3014024Benzalkonium ChlorideHCID 12285822Sodium sulfathiazole

Produkt 1

HCID 86612079Benzalkonium SulfathiazoleAusbeute 50,04 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Benzalkonium chloride (0.003 mol) was dissolved in 100 mL of distilled water by gentle stirring and heating. Sulfathiazole sodium (0.003 mol) was dissolved in 60 mL of distilled water by gentle stirring and heating. The two solutions were combined and the reaction mixture was stirred and heated for 1 h. The reaction mixture was cooled to room temperature and 60 mL of chloroform was added to the reaction mixture. 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 ions was monitored by silver nitrate test. A rotary evaporator removed the chloroform and an orange wax was obtained in a 50.04% yield. 1H and 13C NMR (DMSO) were obtained. Melting point (hot plate apparatus)=40-50° C. Thermal data was determined by thermalgravimetric analysis: Tonset5%=156° C. and Tonset=173° C. The benzalkonium ion is a known antibacterial and the other ion is used to treat, for example, gonorrhea and other bacterial infections.

Aufarbeitung

  1. temperatureheating
  2. stirringby gentle stirring
  3. temperatureheating
  4. stirringthe reaction mixture was stirred
  5. temperatureheated for 1 h
  6. customThe two phases were separated
  7. washthe chloroform phase was washed several times
  8. temperaturewith cool
  9. distillationdistilled water
  10. customto remove any inorganic salt
  11. customA rotary evaporator
  12. customremoved the chloroform
  13. customan orange wax was obtained in a 50.04% yield
  14. customMelting point (hot plate apparatus)=40-50° C
  15. customTonset5%=156° C. and Tonset=173° C

Quellen und Nachweise

ORD-Eintrag
ord-2282d565785b48b88781208c63e74018
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232265B2

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