Water → 5-[2-(Acetylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 1608599

Reaktionsgleichung

Reaktionsgleichung von HRID 1608599
Cl.Cl.[NH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24].O>CN(C)C=O>[C:23]([NH:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)(=[O:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 233628335-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine dihydrochloride

Produkt 1

HCID 233628825-[2-(Acetylamino)ethylthio]imidazo[1,2-a]pyridineAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine dihydrochloride (2.66 g, 10 mmoles) and triethylamine (4.32 ml, 31 mmoles) in N,N-dimethylformamide (24 ml) was added acetyl chloride (0.71 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:3) to obtain 1.57 g of the desired product (66.8%, colorless crystals).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:3)

Quellen und Nachweise

ORD-Eintrag
ord-337cd8ee53ef4162a459ee877df5eed2
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395839

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