Cyanuric chloride → 2,4-Bis(2-methoxyethoxy)-1,3,5-triazine

HRID 1613862Notes

Reaction equation

HRID 1613862 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[N:6]1[C:13](Cl)=[N:12][C:10](Cl)=[N:9][C:7]=1Cl>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:7]1[N:9]=[CH:10][N:12]=[C:13]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:6]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 80192-Methoxyethanol

Product 1

HCID 1263052,4-Bis(2-methoxyethoxy)-1,3,5-triazineYield 1,608.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
110 °C

Procedure

In 100 ml of dry toluene containing 10 g of anhydrous sodium carbonate was dissolved 20 g of monomethoxypolyethylene glycol having an average molecular weight of 4000 (Nippon Oil and Fats) and the solution was heated at 110° C. for 30 minutes. Then, 500 mg of cyanuric chloride was added and the mixture was heated at 110° C. for 24 hours. The reaction residue was filtered off, followed by addition of 300 ml of petroleum ether to cause precipitation. The precipitate was washed with several portions of petroleum ether to recover 10 g of 2,4-bis(O-methoxypolyethylene glycol)-6-chloro-s-triazine (yield 50%).

Workup

  1. temperaturethe mixture was heated at 110° C. for 24 hours
  2. filtrationThe reaction residue was filtered off
  3. additionfollowed by addition of 300 ml of petroleum ether
  4. customprecipitation
  5. washThe precipitate was washed with several portions of petroleum ether

Sources & evidence

ORD record
ord-e719641f24ad4aa788d46b3b90b41b2a
Source dataset
uspto-grants-1993_03
Patent number
US05194592

Reaction notes

Loading…