Triethylamine → 5-[2-[2-(Hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine

HRID 1081726

Reaktionsgleichung

Reaktionsgleichung von HRID 1081726
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.C([C:24]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:25]1[C:26](Cl)=[O:27])(=O)C>C(Cl)Cl>[OH:33][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)=[O:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridineHCID 573615642-Acetylsalicyloyl chloride

Produkt 1

HCID 233629775-[2-[2-(Hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (3.87 g, 20 mmoles) and triethylamine (5.58 ml, mmoles) in methylene chloride (200 ml) was added o-acetylsalicyloyl chloride (4.77 g, 24 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. After the solvent was distilled off, ethanol (60 ml) and 1N NaOH (40 ml) were added to the residue, followed by strirring for 1 hour. 1N HCl (40 ml) was added and ethanol was distilled off, and then the residue was extracted with chloroform and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1) to obtain 3.51 g of the desired product (56.0%, colorless solid).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationAfter the solvent was distilled off
  4. additionethanol (60 ml) and 1N NaOH (40 ml) were added to the residue
  5. addition1N HCl (40 ml) was added
  6. distillationethanol was distilled off
  7. extractionthe residue was extracted with chloroform
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-1c05986e8943460fbfcf26be8e32b5fa
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

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