Triethylamine → 5-[4-(Phthalimido)butylthio]imidazo[1,2-a]pyridine

HRID 5452

Reaktionsgleichung

Reaktionsgleichung von HRID 5452
[SH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(N(CC)CC)C>C(O)C>[C:17]1(=[O:26])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][S:1][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 178418687HCID 178418687, Verbindung

Produkt 1

HCID 233628715-[4-(Phthalimido)butylthio]imidazo[1,2-a]pyridineAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[4-(bromo)butyl]phthalimide (6.21 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour and heated at reflux for 45 minutes. After the solvent was distilled off, chloroform was added to the residue, which was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 4.50 g of the desired product (64.1%, pale yellow crystals).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. distillationAfter the solvent was distilled off
  4. additionchloroform was added to the residue, which
  5. washwas washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThen, the residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-50be1fc82c544b38bf6a4a6ff7e52623
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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