Dimethylamine → 2,4-Dichloro-6-(dimethylamino)-1,3,5-triazine

HRID 2395608Notes

Reaction equation

HRID 2395608 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH3:10][NH:11][CH3:12].ClCCl.O>COCCOC>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:11]([CH3:12])[CH3:10])[N:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 6344DichloromethaneHCID 7954Cyanuric chloride

Product 1

HCID 169852,4-Dichloro-6-(dimethylamino)-1,3,5-triazineYield 95.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Cyanuric chloride (11.0 g, 59.6 mmol) was dissolved in ethylene glycol dimethyl ether (100 ml), cooled to -5° C. and gradually added dropwise with 50% aqueous dimethylamine solution (10.8 ml, 120 mmol). This reaction mixture was stirred at the same temperature for 2 hours and then stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The residue obtained was added with dichloromethane and water, and then was shaken for mixing. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed to obtain 11.0 g (yield: 95.4%) of 2,4-dichloro-6-dimethylamino-1,3,5-triazine as colorless crystals having melting point of 122.5° C.-123° C.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customThe residue obtained
  4. stirringwas shaken
  5. additionfor mixing
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed

Sources & evidence

ORD record
ord-c8f6fe63c51c4fa787e61a342d05bc83
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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