Ammonia → 1,3,5-Triazine-2,4-diamine, N-butyl-6-chloro-

Temperature

5 °C

To a mixture of 18.5 g (0.1 mol) of cyanuric chloride and 150 mL of acetonitrile was added a mixed solution of 7.3 g (0.1 mol) of n-butylamine and 20 mL of water over 2 hours by keeping the reaction temperature not to exceed 5° C. Thereafter, while maintaining the temperature at 5° C. or lower, a solution of 10.0 g (0.1 mol) of potassium hydrogen carbonate in 40 mL of water was dropwise added over 1 hour, and stirring was continued for additional 2 hours. Subsequently, 15.2 g (0.25 mol) of an aqueous 28% ammonia solution was dropwise added at the same temperature, followed by gradually elevating the temperature and stirring the mixture at 50° C. for 4 hours. Crystals were collected by filtration from the slurry solution thus obtained, washed well with water, and dried to obtain 2-amino-4-n-butylamino-6-chloro-1,3,5-triazine, as intermediate. The total amount of the crystals obtained was suspended in 100 mL of water, to which was added 8.1 g (0.11 mol) of n-butylamine, and allowed to react at a reflux temperature for 2 hours. Thereafter, a solution of 4.0 g (0.1 mol) of sodium hydroxide in 20 mL of water was dropwise added over 1 hour, and allowed to react at a reflux temperature for 2 hours. The reaction mixture was cooled and 100 mL of toluene was added thereto to extract the product, which was then washed 5 times with 80 mL of water. The solvent was distilled off from the organic layer thus obtained under reduced pressure to obtain 27.0 g (yield 92%) of the titled compound. Melting point: 73° C.

1. customto exceed 5° C
2. stirringstirring the mixture at 50° C. for 4 hours
3. filtrationCrystals were collected by filtration from the slurry solution
4. customthus obtained
5. washwashed well with water
6. customdried

ORD record

ord-796fecc6d347427d8973b78a9f76ab4a

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127538