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

HRID 365711Notes

Reaction equation

HRID 365711 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

Procedure

To a solution of 18.5 g (0.1 mol) of cyanuric chloride in 150 mL of acetonitrile cooled to 0° C. was dropwise added a solution of 14.6 g (0.2 mol) of butylamine in 20 mL of water over 1 hour with stirring by keeping the reaction temperature not to exceed 5° C. Further, while continuing the stirring, a solution of 20.0 g (0.2 mol) of potassium hydrogen carbonate in 100 mL of water was dropwise added at the same temperature. Thereafter, the reaction temperature was gradually elevated and the stirring was continued at 45° C. for 8 hours. After confirming the completion of conversion to 2,4-bis(butylamino)-6-chloro-1,3,5-triazine by high performance liquid chromatography, the reaction mixture was cooled and the product was separated by filtration. The filtration cake was washed well with a large amount of water and this 2,4-bis(butylamino)-6-chloro-1,3,5-triazine was suspended in 100 mL of water. To the suspension was added 29.2 g (0.4 mol) of butylamine and allowed to react by heating under reflux for 6 hours. After cooling, 200 mL of toluene was added and the mixture was stirred vigorously, followed by separation of the aqueous layer. Further, the toluene layer was washed three times with 150 mL of water. Subsequently, toluene in the organic layer was distilled off by heating under reduced pressure to obtain 28.2 g (yield 96%) of the titled compound. Propery: oily product

Workup

  1. customto exceed 5° C
  2. temperaturethe reaction mixture was cooled
  3. customthe product was separated by filtration
  4. washThe filtration cake was washed well with a large amount of water
  5. customto react
  6. temperatureby heating
  7. temperatureunder reflux for 6 hours
  8. temperatureAfter cooling
  9. stirringthe mixture was stirred vigorously
  10. customfollowed by separation of the aqueous layer
  11. washFurther, the toluene layer was washed three times with 150 mL of water
  12. distillationSubsequently, toluene in the organic layer was distilled off
  13. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-a94a0225d1744fb4bed4d81fc4ee6991
Source dataset
uspto-grants-2000_10
Patent number
US06127538

Reaction notes

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