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

HRID 381656Notes

Reaction equation

HRID 381656 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].C(=O)([O-])O.[K+].[CH2:20]([NH:24][C:25]1[N:30]=[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:28]=[C:27](Cl)[N:26]=1)[CH2:21][CH2:22][CH3:23]>C(#N)C.O.C1(C)C=CC=CC=1>[CH2:10]([NH:14][C:27]1[N:28]=[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:30]=[C:25]([NH:24][CH2:20][CH2:21][CH2:22][CH3:23])[N:26]=1)[CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 7954Cyanuric chlorideHCID 8007Butylamine2×HCID 516893Potassium BicarbonateHCID 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

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.

Workup

  1. customdid not exceed 5° C
  2. customwas gradually elevated to 45° C., at which temperature
  3. temperaturethe product was cooled
  4. filtrationfiltered off
  5. customto react for 6 hours
  6. temperatureunder heating
  7. temperatureat reflux
  8. temperatureAfter cooling
  9. stirringthe mixture was vigorously stirred
  10. customThen, the water layer was separated
  11. washFurther, the toluene layer was washed 3 times with 150 ml of water
  12. distillationtoluene was distilled off from the organic layer
  13. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-0439f82998de4cd6a62a941c7dca7925
Source dataset
uspto-grants-2001_10
Patent number
US06307046B1

Reaction notes

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