Methyl chloroformate → 5-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 5448

Reaktionsgleichung

Reaktionsgleichung von HRID 5448
[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.Cl[C:22]([O:24][CH3:25])=[O:23]>C(Cl)Cl>[CH3:25][O:24][C:22]([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:23]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 98164115-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridineAusbeute 66,9 %

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 (30 ml) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was washed in turn with an aqueous sodium bicarborate solution and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to obtain 1.68 g of the desired product (66.9%, colorless crystals).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. washThe reaction mixture was washed in turn with an aqueous sodium bicarborate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-a1682d3d63114f3888105607aebf2126
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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