Toluene → N-[beta-(2-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoyl]-2-ethyl-piperidine

Reaktionsgleichung

[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]([CH:10]=[CH:11]C(O)=O)[N:4]2[N:3]=1.S(Cl)(Cl)=[O:22].C(C1CCC[CH2:29][NH:28]1)C.[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:9]([C:10](=[CH2:11])[C:29]([N:28]3[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]3[CH2:33][CH3:39])=[O:22])[N:4]2[N:3]=1

Komponenten

Edukt 4

HCID 1140Toluene

HCID 24386Thionyl Chloride

HCID 942052-Ethylpiperidine

HCID 53799720beta-(2-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoic acid

Produkt 1

HCID 86739370N-[beta-(2-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoyl]-2-ethyl-piperidine

Versuchsvorschrift

143 g (0.5 mole) of β-(2-methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoic acid were suspended in 1.5 liters of absolute toluene at 60° to 70° C. 50 ml of thionyl chloride were added dropwise, a clear solution resulting. The solution was then heated under reflux for 2 hours and subsequently cooled to room temperature. 220 ml (1.5 moles) of 2-ethylpiperidine were next added dropwise and the mixture was boiled under reflux for one hour. The cooled mixture was filtered (the residue was discarded) and the filtrate was extracted twice with 300 ml of water. The toluene phase was dried over sodium sulphate and filtered and the filtrate was concentrated by distillation. The residue was recrystallised from 400 ml of ethyl acetate.