N-Methylaniline → 4,6-dichloro-N-methyl-N-phenyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

Cyanuric chloride (7.30 g, 39.6 mmol) was dissolved in toluene (100 ml), cooled to -15° C., added with anhydrous sodium carbonate (4.19 g, 39.6 mmol), stirred for 10 minutes and gradually added dropwise with N-methylaniline (4.24 g, 39.2 mmol) dissolved in toluene (50 ml). This reaction mixture was stirred at the same temperature for 30 minutes and then stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The residue was added with dichloromethane and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography, using n-hexane and ethyl acetate (4: 1) as eluant, to obtain 6.13 g (yield: 60.6%) of 2,4-dichloro-6-(N-methyl-N-phenylamino)-1,3,5-triazine as colorless crystals having melting point of 131.5° C.-132.5° C.

Provenance & Evidence