Water → 2,4,6-Trimethylmelamine

HRID 1815596Notes

Reaction equation

HRID 1815596 reaction equation
[N:1]1C(Cl)=NC(Cl)=N[C:2]=1Cl.CN.O.C(=O)([O-])O.[K+].[CH3:18][NH:19][C:20]1[N:25]=[C:24]([NH:26][CH3:27])[N:23]=[C:22](Cl)[N:21]=1>C(#N)C>[CH3:18][NH:19][C:20]1[N:25]=[C:24]([NH:26][CH3:27])[N:23]=[C:22]([NH:1][CH3:2])[N:21]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6329MethylamineHCID 7954Cyanuric chlorideHCID 17987s-Triazine, 4,6-bis(methylamino)-2-chloro-HCID 516893Potassium Bicarbonate

Product 1

HCID 178042,4,6-TrimethylmelamineYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

After 18.5 g (0.1 mol) of cyanuric chloride was dissolved into 150 ml of acetonitrile, the resulting mixture was cooled to 0° C. and 15.5 g (0.2 mol) of 40% aqueous solution of methylamine was added dropwise in 1 hour thereto under stirring in such a manner that the reaction temperature did not exceed 5° C. While further stirring, 100 ml of water including 20.0 g (0.2 mol) of potassium hydrogencarbonate was added dropwise at the same temperature. Thereafter, the reaction temperature was gradually raised, and stirred at 45° C. for 8 hours. After confirming that an inversion to 2.4-bis(methylamino)-6-chloro-1,3,5-triazine was completed, the reaction solution was cooled and products were filtered off. The filter cake was fully washed with water, and then the resulting 2,4-bis(methylamino)-6-chloro-1,3,5-triazine was suspended into 100 ml of water, and 31.1 g (0.4 mol) of 40% aqueous solution of methylamine was added, and further heated under reflux for 6 hours. After cooling, the deposited crystal was filtered, washed fully with water and dried to give 13.1 g (yield: 78%) of the titled compound. Melting point 133° C.

Workup

  1. customdid not exceed 5° C
  2. temperatureThereafter, the reaction temperature was gradually raised
  3. stirringstirred at 45° C. for 8 hours
  4. temperaturethe reaction solution was cooled
  5. filtrationproducts were filtered off
  6. washThe filter cake was fully washed with water
  7. additionwas added
  8. temperaturefurther heated
  9. temperatureunder reflux for 6 hours
  10. temperatureAfter cooling
  11. filtrationthe deposited crystal was filtered
  12. washwashed fully with water
  13. customdried

Sources & evidence

ORD record
ord-b3c50debf34447fbbf8f0bcf658de754
Source dataset
uspto-grants-2005_04
Patent number
US06878824B2

Reaction notes

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