Sulfuric Acid → 1-[4-(Imidazo[1,2-a]pyridin-2-yl)phenyl]ethan-1-one

HRID 1284102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1284102
[CH3:1][Mg]I.[N:4]1[C:5]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#N)=[CH:15][CH:14]=2)=[CH:6][N:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12.S(=O)(=O)(O)O.[OH-:26].[Na+]>CCOCC.O.O1CCCC1>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([C:5]2[N:4]=[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][N:7]3[CH:6]=2)=[CH:14][CH:15]=1)(=[O:26])[CH3:1]

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 8211074-imidazo[1,2-a]pyridin-2-ylbenzonitrileHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 215155611-[4-(Imidazo[1,2-a]pyridin-2-yl)phenyl]ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methylmagnesium iodide (prepared from 3.6 g of magnesium and 22 g of methyl iodide) in 40 ml of ether is added dropwise to a mixture of 6.5 g of 4-(imidazo[1,2-a]pyridin-2-yl)benzonitrile and 50 ml of tetrahydrofuran with stirring on an ice bath. The mixture is heated under reflux for 3 hours, and the reaction mixture is cooled with salt and ice. 100 ml of 50% sulfuric acid is added dropwise to the reaction mixture, water is added, and the whole mixture is adjusted to pH 8 by addition of 20% sodium hydroxide. The crystalline precipitate is filtered off, washed with water and recrystallized from dimethylformamide to give 4.2 g of 2-(4-acetylphenyl)-imidazo[1,2-a]pyridine as colorless crystals melting at 209°-210°C. 2.2 g of the thus-obtained 2-(4-acetylphenyl)-imidazo[1,2-a]pyridine is heated with 0.45 g of sulfur and 10 ml of morpholine under reflux for 6 hours. The reaction mixture is cooled, and ethanol is added. The crystalline precipitate is filtered off and washed with ethanol to give 1.4 g of 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetothiomorpholide as yellowish brown crystals melting at 204°-206°C.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe reaction mixture is cooled with salt and ice
  4. additionis added
  5. filtrationThe crystalline precipitate is filtered off
  6. washwashed with water
  7. customrecrystallized from dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-15ce9d84be9546278c8b765da23a2fe7
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03978071

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