Phenol → 2-chloro-4,6-diphenoxy-1,3,5-triazine

HRID 1066445Notes

Reaction equation

HRID 1066445 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[C:10](=[O:13])(O)[O-].[Na+].[C:15]1(C)[CH:20]=[CH:19]C=[CH:17][CH:16]=1.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C.O>[Cl:3][C:2]1[N:4]=[C:5]([O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=[C:8]([O:13][C:10]2[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=2)[N:1]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 7954Cyanuric chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 180882-chloro-4,6-diphenoxy-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2-liter reaction flask equipped with a magnetic stirrer and a condenser is charged with 92.2 g (0.50 mol) of cyan uric chloride, 84 g (1.0 mol) of sodium bicarbonate and 400 mL of toluene. The suspension is brought to 50° C. and 94 g (1.0 mol) of phenol are added in small portions. The mixture is refluxed for ten hours and then allowed to cool to room temperature. Portions of water and ethyl acetate (300 mL each) are added and the mixture is then filtered. The phases are separated and the organic phase is dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure to afford 150 g of crude product. The crude product is twice recrystallized from toluene to yield 48.7 g of the title compound as a white powder melting at 117-121° C.

Workup

  1. customA 2-liter reaction flask
  2. customequipped with a magnetic stirrer and a condenser
  3. customis brought to 50° C.
  4. temperatureThe mixture is refluxed for ten hours
  5. filtrationthe mixture is then filtered
  6. customThe phases are separated
  7. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  8. customThe solvent is removed under reduced pressure
  9. customto afford 150 g of crude product
  10. customThe crude product is twice recrystallized from toluene

Sources & evidence

ORD record
ord-9c6dd437f70e4cac82d080d47971ec22
Source dataset
uspto-grants-2001_06
Patent number
US06242598B1

Reaction notes

Loading…