Potassium Carbonate → 6-(5-Isoquinolylsulfanyl)quinoxaline

HRID 619743

Reaktionsgleichung

Reaktionsgleichung von HRID 619743
[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.O.S(=O)(O)[O-].[Na+].[CH:26]([CH:28]=O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[CH:13]=[C:14]4[C:15](=[CH:16][CH:17]=3)[N:18]=[CH:28][CH:26]=[N:19]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 154356894-(5-Isoquinolylsulfanyl)-1,2-benzenediamineHCID 23685989Glyoxal-sodium bisulfite hydrate

Produkt 1

HCID 218469576-(5-Isoquinolylsulfanyl)quinoxalineAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(5-Isoquinolylsulfanyl)-1,2-benzenediamine 200 mg (0.7 mmol) was dissolved in water 10 ml, a water solution 6 ml of glyoxal-sodium bisulfite hydrate 580 mg (2.3 mmol) was added, and the mixture was stirred for 1 hour at 80° C. Potassium carbonate was added to the reaction solution to alkalize the solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:acetone=1:10), and 6-(5-isoquinolylsulfanyl)quinoxaline 90 mg (41.2%) was obtained.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:acetone=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-921c43ccfe6d4d018719c5f9ab54e792
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959107

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