Benzoyl chloride → 5-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridine

HRID 1081733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081733
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:22]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 233629675-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridineAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added benzoyl chloride (1.10 ml, 11.6 moles) with stirring at room temperature and the mixture was further stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 1.32 g of the desired product (88.1%, white solid).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. washThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

Quellen und Nachweise

ORD-Eintrag
ord-17bc351322f544d48809a5a3bbe6481a
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

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