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

HRID 1081755

Reaktionsgleichung

Reaktionsgleichung von HRID 1081755
[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-b3fe52b2030344dc869ec66da096ec53
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

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