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

HRID 5440

Reaktionsgleichung

Reaktionsgleichung von HRID 5440
[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.[CH2:21]([S:23](Cl)(=[O:25])=[O:24])[CH3:22]>C(Cl)Cl>[CH2:21]([S:23]([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:25])=[O:24])[CH3:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 152293645-[2-(Ethylsulfonylamino)ethylthio]imidazo[1,2-a]pyridineAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (100 ml) was added ethanesulfonyl chloride (0.95 ml, 10 mmoles) at room temperature with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5) to obtain 2.23 g of the desired product (78.2%, colorless crystals).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. washThe reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-b37486258c7548529fd7103f125f8261
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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