Hydrochloric Acid → 5-Amino-1,3,4-thiadiazole-2-sulfonamide

HRID 4986

Reaktionsgleichung

Reaktionsgleichung von HRID 4986
C([NH:4][C:5]1[S:6][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:8][N:9]=1)(=O)C.C(N)(=O)C.CC(NC1SC(S(N)(=O)=O)=NN=1)=O.Cl>CO>[NH2:4][C:5]1[S:6][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:8][N:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 1986AcetazolamideHCID 67839732Acetamide 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide

Produkt 1

HCID 847245-Amino-1,3,4-thiadiazole-2-sulfonamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

This is prepared by hydrolysis of the acetamide 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide (acetazolamide). A slurry of 0.2 mol of acetazolamide in 600 mL of methanol is treated with 60 mL 12N HCl. This mixture is heated with stirring to reflux for 6 hours. Reaction progress is monitored using liquid chromatography. If reaction is not completed after 6 hours, another 30 mL of 12N HCl is added, and the mixture held at reflux for 2 hours. Methanol is then removed under reduced pressure. Product is recovered after raising the pH of the suspension to 7 by addition of NaOH at 0.4° , followed by filtration. Yield is between 85 and 98% of theoretical with 99% purity. KI =40 nM.

Aufarbeitung

  1. temperatureThis mixture is heated
  2. temperatureto reflux for 6 hours
  3. customReaction progress
  4. customIf reaction
  5. temperatureat reflux for 2 hours
  6. customMethanol is then removed under reduced pressure
  7. customProduct is recovered
  8. temperatureafter raising the pH of the suspension to 7
  9. additionby addition of NaOH at 0.4°
  10. filtrationfollowed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-546e985c373d49ba8a1bca6b63eaccc9
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242937

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