Dimethylformamide → 1-(4-Iodophenyl)-3-phenyl-1H-pyrazole-4-carbaldehyde

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Reaction Conditions

Reaction Steps

At 0° C., 1.08 ml (11.58 mmol) of phosphoryl chloride (POCl3) are slowly added dropwise to 10 ml of anhydrous N,N-dimethylformamide. After 30 minutes at 0° C., a solution of 1.95 g (5.792 mmol) of the product from Example 1A in 10 ml of N,N-dimethylformamide is added dropwise, and the reaction mixture is stirred at 0° C. for a further hour. The mixture is then allowed to warm to room temperature, stirred for a further hour and then warmed to 60° C. The reaction mixture is stirred at this temperature for 15 hours. The mixture is then allowed to cool to room temperature, 80 ml of saturated sodium bicarbonate solution are added and the mixture is extracted with ethyl acetate. The organic extract is washed successively with water and saturated sodium chloride solution. The mixture is dried over anhydrous sodium sulphate, and the solvent is then removed on a rotary evaporator. The residue obtained is triturated with diisopropyl ether. The solid is filtered off with suction, washed with diisopropyl ether and dried under high vacuum. This gives 1.34 g (62% of theory) of the title compound.

Provenance & Evidence