1-Pentanethiol → HCID 178447693, Verbindung

HRID 373220

Reaktionsgleichung

Reaktionsgleichung von HRID 373220
Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1.[CH2:50]([SH:55])[CH2:51][CH2:52][CH2:53][CH3:54].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:50]([S:55][C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:22][N:23]=[N:24][N:25]=3)=[CH:13][CH:14]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1)[CH2:51][CH2:52][CH2:53][CH3:54]

Komponenten

5

Edukt 3

HCID 80671-PentanethiolHCID 11430Potassium CarbonateHCID 19811527HCID 19811527, Verbindung

Produkt 1

HCID 178447693HCID 178447693, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.5 g), pentylmercaptan (0.12 ml) and potassium carbonate (0.13 g) in acetonitrile (10 ml) was heated under reflux for 4 hours with stirring. The reaction mixture was allowed to cool and the precipitate was removed by filtration. The filtrate was concentrated to dryness. The resulting residue was dissolved in methanol (15 ml) and then 1N hydrochloric acid (1.5 ml) was added to the solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated to dryness and then the residue was extracted with methylene chloride-water. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give colorless amorphous powders (0.16 g, 43%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  7. addition1N hydrochloric acid (1.5 ml) was added to the solution
  8. stirringby stirring at room temperature for 2 hours
  9. concentrationThe reaction mixture was concentrated to dryness
  10. extractionthe residue was extracted with methylene chloride-water
  11. washThe organic layer was washed with water
  12. customdried
  13. customevaporated to dryness
  14. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-93b5db0e8e77449498028c7166f52955
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162326

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