Dimethylformamide → HCID 18983806, Verbindung

Reaktionsgleichung

Br.[C:2]1([C:8]2[N:9]=[C:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]3[CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN([CH:32]=[O:33])C>>[CH:32]([C:21]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2=[N:9][C:8]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:33]

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 67768891Ethyl 2-phenyl-imidazo[1,2-a]pyridine-8-carboxylate hydrogen bromide

Produkt 1

HCID 18983806HCID 18983806, VerbindungAusbeute 85,5 %

Versuchsvorschrift

To a solution of ethyl 2-phenyl-imidazo[1,2-a]-pyridine-8-carboxylate hydrogen bromide (14.7 g, 4 m mol) in DMF (8 ml) was dropwise added phosphorus oxychloride (2 ml) keeping the inner temperature to below 15° C. Then, the mixture was allowed to react at room temperature for 30 minutes and at 70° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled, poured into ice water and adjusted to pH 7 by adding 20% sodium hydroxide. The precipitated crystals were collected by filtration and recrystallized from ethanol to obtain the object compound (1.0 g, yield 85.5%) as colorless crystals. m.p. 139° C.