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

HRID 366848Notes

Reaction equation

HRID 366848 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].[K].[CH2:16]([NH:20][C:21]1[N:26]=[C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:24]=[C:23](Cl)[N:22]=1)[CH2:17][CH2:18][CH3:19]>C(#N)C.O.C1(C)C=CC=CC=1>[CH2:10]([NH:14][C:23]1[N:24]=[C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:26]=[C:21]([NH:20][CH2:16][CH2:17][CH2:18][CH3:19])[N:22]=1)[CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 7954Cyanuric chlorideHCID 8007Butylamine2×HCID 5462222PotassiumHCID 14045984N~2~,N~4~-Dibutyl-6-chloro-1,3,5-triazine-2,4-diamine

Product 1

HCID 108917352,4,6-tris(butylamino)-1,3,5-triazineYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

18.5 g (0.1 mol.) of cyanuric chloride were dissolved in 150 mL of acetonitrile. The mixture solution was cooled to 0° C. The cooled solution was dropwise added with a solution of 14.6 g (0.2 mol.) of butylamine in 20 mL of water over one hour while stirring in such a manner that the temperature did not raise over 5° C. While further continuing the stirring, a solution of 20.0 g (0.2 mol.) of potassium hydrogenecarbonate in 100 mL of water was dropwise added to the solution at the same temperature. Thereafter, the reaction temperature was gradually raised and the stirring was continued at 45° C. for eight hours. After the completion of the conversion of the resulting product into 2,4-bis(butylamino)-6-chloro-1,3,5-triazine was recognized by a high-performance liquid chromatography, the obtained produt was cooled and separated through filtration. After the filtrated cake was fully wahsed with a large amount of water, the obtained 2,4-bis(butylamino)-6-chloro-1,3,5-triazine was suspended in 100 mL of water and added with 29.2 g (0.4 mol.) of butylamine and further reacted for six hours under heat-reflux. After cooling, the resulting product was added with 200 mL of toluene and vigorously stirred. Thereafter, the aqueous layer was separated. After the toluene layer was further washed thrice with each 150 mL of water, toluene was distilled off from the organic layer under heating and reduced pressure to obtain 28.2 g of 2,4,6-tris(n-butylamino)-1,3,5-triazine (yield: 96%).

Workup

  1. temperaturedid not raise over 5° C
  2. temperatureThereafter, the reaction temperature was gradually raised
  3. temperaturethe obtained produt was cooled
  4. customseparated through filtration
  5. customfurther reacted for six hours
  6. temperatureunder heat-reflux
  7. temperatureAfter cooling
  8. stirringvigorously stirred
  9. customThereafter, the aqueous layer was separated
  10. distillationwas distilled off from the organic layer
  11. temperatureunder heating

Sources & evidence

ORD record
ord-44f20a075ec0439da7a537a2d658ff1c
Source dataset
uspto-grants-2000_10
Patent number
US06130332

Reaction notes

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