Cyanuric chloride → 2,4-Dichloro-6-(N,N-diallylamino)-1,3,5-triazine

HRID 877851Notes

Reaction equation

HRID 877851 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[C:14]([Cl:15])=[N:13][C:11](Cl)=[N:10][C:8]=1[Cl:9].[CH2:16]([NH:19][CH2:20][CH:21]=[CH2:22])[CH:17]=[CH2:18].[OH-].[Na+]>O1CCOCC1>[Cl:15][C:14]1[N:7]=[C:8]([Cl:9])[N:10]=[C:11]([N:19]([CH2:20][CH:21]=[CH2:22])[CH2:16][CH:17]=[CH2:18])[N:13]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 31279Diallylamine

Product 1

HCID 971902,4-Dichloro-6-(N,N-diallylamino)-1,3,5-triazineYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

After 10.6 g (0.10 mol) of sodium carbonate and 20.0 g (0.10 mol) of cyanuric chloride were added and dissolved into 140 g of 1,4-dioxane, 9.9 g (0.10 mol) of diallylamine was gradually added thereinto and further, 4.2 g (0.10 mol) of caustic soda was added thereinto. By generating the heat of reaction, the temperature of reaction solution was raised to about 60° C. and the reaction was continued at the temperature for 3 hours. Thereafter, the reaction mixture was cooled and filtered to remove the sodium chloride generated as the byproduct. The obtained filtrate was distilled under reduced pressure to recover the solvent. Therefore, 18.3 g (0.05 mol) of 4,6-dichloro-2-diallylamino-1,3,5-triazine was obtained.

Workup

  1. additionwas gradually added
  2. temperatureheat of reaction
  3. customthe temperature of reaction solution
  4. temperatureThereafter, the reaction mixture was cooled
  5. filtrationfiltered
  6. customto remove the sodium chloride
  7. distillationThe obtained filtrate was distilled under reduced pressure
  8. customto recover the solvent

Sources & evidence

ORD record
ord-bbc83a6bb85443e6b498aad817eabb89
Source dataset
uspto-grants-2015_03
Patent number
US08987383B2

Reaction notes

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