Aniline → 6-iodo-N-phenylquinazolin-4-amine

Participants

Reaction Steps

In a 20 mL-volume glass vessel equipped with a stirrer, a thermometer and a reflux condenser were placed 2.00 g (7.35 mmol) of 6-iodoquinazolin-4-one, 1.35 g (8.8 mmol) of phosphorus oxychloride, and 6 mL of toluene in a nitrogen atmosphere. While the mixture was stirred at room temperature, 0.89 g (8.8 mmol) of triethylamine was slowly added. The resulting mixture was heated to 75° C., and then reaction was carried out for 2 hours. Subsequently, the mixture was cooled to room temperature, and 3 mL of acetone and 821 mg (8.8 mmol) of aniline were added. The resulting mixture was again heated to 75° C., and then reaction was carried out under stirring for one hour. After the reaction was complete, the reaction mixture was cooled to room temperature, and thus precipitated crystalline product was collected by filtration. Subsequently, the crystalline product was placed in 30 mL of aqueous sodium hydroxide (1 mol/L), and the aqueous mixture was stirred for 30 minutes at room temperature. The crystalline product was collected by filtration, washed with 30 mL of water, and dried under reduced pressure, to give 1.91 g (isolated yield: 73%, purity 97% in terms of area percentage determined by high performance liquid chromatography) of 6-iodo-4-anilinoquinazoline as a yellowish crystalline product.

Provenance & Evidence