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

HRID 5450

Reaktionsgleichung

Reaktionsgleichung von HRID 5450
[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][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(N(CC)CC)C>C(O)C>[C:15]1(=[O:24])[N: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:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 178418687HCID 178418687, Verbindung

Produkt 1

HCID 233629915-[2-(Phthalimido)ethylthio]imidazo[1,2-a]pyridineAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[2-(bromo)ethyl]phthalimide (5.59 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 3 hours and heated at reflux for 4 hours. After the solvent was distilled off, chloroform was added to the residue, which was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 3.95 g of the desired product (61.1%, yellow crystals).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. distillationAfter the solvent was distilled off
  4. additionchloroform was added to the residue, which
  5. washwas washed with water
  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-4e1bc24fc8084853ba0216a3bf0feced
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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