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

HRID 5483

Reaktionsgleichung

Reaktionsgleichung von HRID 5483
[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 aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethanol/etyl 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 aqueous sodium bicarbonate and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography [eluent: ethanol/etyl acetate (1:10)]

Quellen und Nachweise

ORD-Eintrag
ord-153f77bc2a644cc5babb03217d5b3d48
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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