Carbonate Ion → 3-[2-(4-(4-Methylphenylsulfonyl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine

HRID 476909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476909
C(=O)([O-])[O-].[SH:5][C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][N:7]=1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:20][CH2:19]1>C(O)C>[CH3:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][S:5][C:6]3[N:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]4=[N:8][N:7]=3)[CH2:23][CH2:22]2)(=[O:26])=[O:25])=[CH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 19660Carbonate IonHCID 47419321-Chloro-2-[4-(4-methylphenylsulfonyl)piperazin-1-yl]ethaneHCID 178527925HCID 178527925, Verbindung

Produkt 1

HCID 198371133-[2-(4-(4-Methylphenylsulfonyl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridineAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

30 g of postassium carbonate are added to a solution of 32.7 g of 3-mercapto-1,2,4-triazolo(4,3-a)pyridine in 300 ml of ethanol and the mixture is heated to the reflux temperature. After 15 minutes, a solution of 65.5 g of 1-chloro-2-[4-(4-methylphenylsulfonyl)piperazin-1-yl]ethane in 100 ml of ethanol is added and refluxing is continued for 3 hours. The reaction mixture is then cooled, the mineral substances are filtered off and the filtrate is concentrated in vacuo. The residue is taken up with chloroform, which is washed with water, and the chloroform phase is then extracted with a 0.5N solution of hydrochloric acid. The acidic aqueous phase is then rendered basic in the cold with a 0.5N aqueous solution of sodium hydroxide and then extracted with chloroform. The chloroform phase is washed with water, dried over sodium sulfate and then concentrated in vacuo to give 73 g of 3-[2-(4-(4-methylphenylsulfonyl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine in the form of a thick oil, which is used in the crude state for the next step.

Aufarbeitung

  1. temperaturethe mixture is heated to the reflux temperature
  2. temperaturerefluxing
  3. waitis continued for 3 hours
  4. temperatureThe reaction mixture is then cooled
  5. filtrationthe mineral substances are filtered off
  6. concentrationthe filtrate is concentrated in vacuo
  7. washis washed with water
  8. extractionthe chloroform phase is then extracted with a 0.5N solution of hydrochloric acid
  9. extractionextracted with chloroform
  10. washThe chloroform phase is washed with water
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4097b6d1d2e44128b0f7ef9648b43565
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886805

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