Water → 2-(2-Methylpropyl)thiazolo[4,5-c]quinoline

HRID 430546

Reaktionsgleichung

Reaktionsgleichung von HRID 430546
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](O)(=O)[CH2:14][CH:15]([CH3:17])[CH3:16].O>ClCCl>[CH3:16][CH:15]([CH3:17])[CH2:14][C:13]1[S:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 10430Isovaleric AcidHCID 1785079903-Aminoquinoline-4-thiol

Produkt 1

HCID 226482712-(2-Methylpropyl)thiazolo[4,5-c]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3-Aminoquinoline-4-thiol (4.6 g) was added to polyphosphoric acid (80 g). Isovaleric acid (3.5 mL) was added and the reaction mixture was heated at 140° C. for 2 hours. The reaction mixture was poured into a mixture of ice and water (300 mL). The mixture was filtered through a layer of Celite® filter aid to remove some insoluble material. The filtrate was made alkaline with 50% sodium hydroxide while cooling with ice and then extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide an oil. The oil was dissolved in dichloromethane and then placed on a layer of silica gel and eluted with 1:1 ethyl acetate:hexanes. The eluant was concentrated under vacuum to provide 2-(2-methylpropyl)thiazolo[4,5-c]quinoline.

Aufarbeitung

  1. filtrationThe mixture was filtered through a layer of Celite®
  2. filtrationfilter aid
  3. customto remove some insoluble material
  4. temperaturewhile cooling with ice
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto provide an oil
  10. washeluted with 1:1 ethyl acetate
  11. concentrationThe eluant was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0eddf79f18854f6cb77d6942cf8c45d2
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323200B1

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