Cyanuric chloride → 2,4,6-tris(butylamino)-1,3,5-triazine

Participants

Reaction Conditions

Reaction Steps

To a solution of 18.5 g (0.1 mol) of cyanuric chloride dissolved in 150 ml of acetonitrile and cooled to 0° C., a solution of 14.6 g (0.2 mol) of butylamine in 20 ml of water was added at dropwise over 1 hour with stirring such that the reaction temperature did not exceed 5° C. While continuing the stirring, a solution of 20.0 g (0.2 mol) of potassium hydrogen carbonate in 100 ml of water was added at dropwise at the same temperature. Thereafter, the reaction temperature was gradually elevated to 45° C., at which temperature the reaction was continued for additional 8 hours. After confirming completion of the conversion to 2,4-bis(butylamino)-6-chloro-1,3,5-triazine by high performance liquid chromatography, the product was cooled and filtered off. The filtrate cake waswashed sufficiently with a large amount of water and then the obtained 2,4-bis(butylamino)-6-chloro-1,3,5-triazine was suspended in 100 ml of water, 29.2 g (0.4 mol) of butylamine was added thereto, and the mixture was further allowed to react for 6 hours under heating at reflux. After cooling, 200 ml of toluene was added and the mixture was vigorously stirred. Then, the water layer was separated. Further, the toluene layer was washed 3 times with 150 ml of water and then toluene was distilled off from the organic layer by heating under reduced pressure to obtain 28.2 g (yield: 96%) of the titled compound. Property: oily substance.

Provenance & Evidence