Dimethyl Sulfoxide → 5-[3-(Amino)propylthio]imidazo[1,2-a]pyridine

HRID 1608637

Reaktionsgleichung

Reaktionsgleichung von HRID 1608637
[OH-].[K+].CS(C)=O.Br.Br.[NH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14](=[NH:16])N.ClC1[N:23]2[CH:24]=[CH:25]N=[C:22]2[CH:21]=[CH:20][CH:19]=1>O>[NH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14]1[N:16]2[CH:25]=[CH:24][N:23]=[C:22]2[CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 145992Pseudourea, 2-(3-aminopropyl)-2-thio-, dihydrobromideHCID 109537225-Chloroimidazo[1,2-A]pyridine

Produkt 1

HCID 233628495-[3-(Amino)propylthio]imidazo[1,2-a]pyridineAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixed solution of 10% (w/w) potassium hydroxide (69.3 g, 105 mmoles) and dimethylsulfoxide (50 ml) was added S-(3-aminopropyl)isothiourea dihydrobromide (8.85 g, 39 mmoles) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added 5-chloroimidazo[1,2-a]pyridine (3.05 g, 20 mmoles), followed by stirring at room temperature and additionally at 65° C. for 20 hours. Water was added to the reaction mixture, which was extracted with chloroform, washed with 1N sodium hydroxide several times and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off to obtain 2.66 g of the desired product (64.3%, pale yellow oily product).

Aufarbeitung

  1. stirringby stirring at room temperature and additionally at 65° C. for 20 hours
  2. extractionwas extracted with chloroform
  3. washwashed with 1N sodium hydroxide several times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-92329c83edc346c9b76926721c806c76
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395839

Verknüpfte Notizen

Wird geladen…