N,N-Dimethylaniline → Methyl 7-chloro-5-(propan-2-yl)-(1,2,4)triazolo(1,5-a)pyrimidine-2-carboxylate
Reaktionsgleichung
O[C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1Komponenten
4
Versuchsvorschrift
To a suspension of the product obtained in Step 1 (50 g) in 700 ml of phosphorus oxychloride 31 g of N,N-dimethylaniline was dropwise added at room temperature over a period of 20 minutes. The mixture was refluxed for one hour, excess phosphorus oxychloride was removed by distillation under normal pressure, and the reddish brown residue was dissolved in 2 liters of chloroform. This solution was slowly poured into 1.5 liters of ice-cooled saturated sodium bicarbonate solution, the chloroform layer was collected after shaking, and the aqueous layer was again extracted with fresh chloroform. The organic layers were joined together, washed with 800 ml of saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The dried solution was concentrated under reduced pressure to about 100 ml, and 200 ml n-hexane was added to this concentrate, giving 47 g of the objective compound as colorless crystals.