Ammonium → HCID 11806705, compound

HRID 366847Notes

Reaction equation

HRID 366847 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].C(=O)([O-])O.[K+].[NH4+:20]>C(#N)C.O.C1(C)C=CC=CC=1>[NH2:20][C:2]1[N:4]=[C:5]([NH:14][CH2:10][CH2:11][CH2:12][CH3:13])[N:7]=[C:8]([NH:14][CH2:10][CH2:11][CH2:12][CH3:13])[N:1]=1

Participants

8

Reactant 4

HCID 223AmmoniumHCID 7954Cyanuric chlorideHCID 8007Butylamine2×HCID 516893Potassium Bicarbonate

Product 1

HCID 11806705HCID 11806705, compoundYield 185.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

18.5 g (0.1 mol.) of cyanuric chloride was dissolved in 150 mL of acetonitrile. The solution was cooled to 0° C. and the cooled solution was dropwise added, while stirring, with a solution of 7.3 g (0.1 mol.) of butylamine in 20 mL of water over one hour in such a manner that the reaction temperature did not raise over 5° C. While further continuing the stirring, a solution of 10.0 g (0.1 mol.) of potassium hydrogencarbonate in 100 mL of water was dropwise added to the mixture at the same temperature and stirred for three hours. After the completion of the conversion of the resulting product into 2-butylamino-4,6-dichloro-1,3,5-tirazine was recognized by a high-performance liquid chromatography, 24.3 g (0.4 mol.) of an aqueous 28-% ammonium solution were added. The temperature was raised to 50° C. and the reaction was carried out for five hours. After the cooling, an obtained product was separated through filtration and washed fully with a large amount of water. An obtained crude product was suspended in 100 mL of water and added with 29.2 g (0.4 mol.) of butylamine and reacted for six hours under heating and refluxing. After the completion of the cooling, the resulting product was added with 200 mL of toluene and vigorously stirred and then, the aqueous layer was separated. Further, after the toluene layer was thrice washed with each 150 mL of water, toluene was distilled off from the organic layer under heating and reduced pressure to obtain 22.1 g of 2-amino-4,6-bis-(n-butylamino)-1,3,5-triazine (yield: 93%).

Workup

  1. additionthe cooled solution was dropwise added
  2. temperaturedid not raise over 5° C
  3. additionwere added
  4. temperatureThe temperature was raised to 50° C.
  5. waitthe reaction was carried out for five hours
  6. customAfter the cooling, an obtained product was separated through filtration
  7. washwashed fully with a large amount of water
  8. customAn obtained crude product
  9. customreacted for six hours
  10. temperatureunder heating
  11. temperaturerefluxing
  12. stirringvigorously stirred
  13. customthe aqueous layer was separated
  14. washFurther, after the toluene layer was thrice washed with each 150 mL of water, toluene
  15. distillationwas distilled off from the organic layer
  16. temperatureunder heating

Sources & evidence

ORD record
ord-abcaa483dd8d4c219dd7092c23b76ae4
Source dataset
uspto-grants-2000_10
Patent number
US06130332

Reaction notes

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