4-Aminophenol → p,p',p''-(1,3,5-Triazine-2,4,6-triyltriimino)trisphenol

HRID 720692Notes

Reaction equation

HRID 720692 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[CH:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([OH:17])[CH:11]=1.[C:18]([O-:21])(=O)[CH3:19].[Na+]>C(C(C)=O)C>[OH:17][C:12]1[CH:13]=[CH:14][C:15]([NH:16][C:2]2[N:4]=[C:5]([NH:16][C:15]3[CH:14]=[CH:13][C:12]([OH:17])=[CH:11][CH:10]=3)[N:7]=[C:8]([NH:16][C:15]3[CH:10]=[CH:19][C:18]([OH:21])=[CH:13][CH:14]=3)[N:1]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 7954Cyanuric chlorideHCID 517045Sodium Acetate

Product 1

HCID 9909071p,p',p''-(1,3,5-Triazine-2,4,6-triyltriimino)trisphenolYield 95%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a 300 ml three-neck flask equipped with a stirrer, a thermometer and a dropping funnel, 3.68 g (0.02 mol) of cyanuric chloride was dissolved in 60 ml of methyl ethyl ketone. Subsequently, 6.55 g (0.06 mol) of p-aminophenol was added slowly to the solution at an inner temperature not higher than 5° C. After the addition, the solution was stirred for 30 minute, and 30 ml of an aqueous solution of 4.92 g (0.06 mol) sodium acetate was added dropwise to the solution with keeping an inner temperature of 10° C. After the dropwise addition, the solution was stirred for 30 minutes at room temperature and was reacted with refluxing for 3 hours. During the reaction, the mixed solvent of methyl ethyl ketone and water was separated into two phases. When the reaction was complete, the reaction solution was poured into 500 ml of ice water to be crystallized. After the filtration, the obtained crystal was washed once with a weakly alkaline solution and twice with 500 ml of water, and dried, to give 7.6 g of a target compound in a 95% yield.

Workup

  1. customIn a 300 ml three-neck flask equipped with a stirrer
  2. additionAfter the addition
  3. customan inner temperature of 10° C
  4. additionAfter the dropwise addition
  5. stirringthe solution was stirred for 30 minutes at room temperature
  6. customwas reacted
  7. temperaturewith refluxing for 3 hours
  8. customDuring the reaction
  9. customthe mixed solvent of methyl ethyl ketone and water was separated into two phases
  10. additionthe reaction solution was poured into 500 ml of ice water
  11. customto be crystallized
  12. filtrationAfter the filtration
  13. washthe obtained crystal was washed once with a weakly alkaline solution and twice with 500 ml of water
  14. customdried

Sources & evidence

ORD record
ord-f847178f886b43fcb0ad27f12d8062e4
Source dataset
uspto-grants-2006_11
Patent number
US07135567B2

Reaction notes

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