Cyanuric chloride → HCID 131711397, compound

HRID 2052261Notes

Reaction equation

HRID 2052261 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:14](=[O:17])([OH:16])[O-].[Na+:18].[N:19]1[C:26](Cl)=[N:25][C:23](Cl)=[N:22][C:20]=1[Cl:21]>O.[OH-].[Na+].CC(C)=O>[Na+:18].[Na+:18].[Na+:18].[Na+:18].[Cl:21][C:20]1[N:19]=[C:26]([NH:1][C:2]2[CH:3]=[C:4]([C:11]([O-:13])=[O:12])[CH:5]=[C:6]([CH:10]=2)[C:7]([O-:9])=[O:8])[N:25]=[C:23]([NH:1][C:2]2[CH:10]=[C:6]([C:7]([O-:9])=[O:8])[CH:5]=[C:4]([CH:3]=2)[C:14]([O-:16])=[O:17])[N:22]=1

Participants

7

Reactant 3

HCID 7954Cyanuric chlorideHCID 668335-Aminoisophthalic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 131711397HCID 131711397, compoundYield 49.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 18.1 g of 5 -aminoisophthalic acid in 200 ml of water plus 38.2 ml of 5 N sodium hydroxide is added 9.2 g of sodium bicarbonate. The solution is cooled to 10° C. in an ice bath, then a solution of 9.2 g of cyanuric chloride in 50 ml of acetone is added. The mixture is stirred at room temperature for 10 minutes, then at 40°-45° C. for 31/2 hours. The solution is allowed to stand at room temperature for 16 hours and is filtered. The filtrate is concentrated to 150 ml and diluted with 300 ml of absolute ethanol to give a colorless precipitate. The product is collected by filtration, washed with 75% aqueous ethanol, ethanol and ether and dried by conventional means to give 25.9 g of crude product. An 8.9 g portion of this material is dissolved in 50 ml of water, allowed to stand at room temperature for 2 hours, then filtered through diatomaceous earth. The filter is washed with 10 ml of water. The filtrate is diluted with 100 ml of absolute ethanol to give a thick precipitate. The mixture is filtered and the product is washed with (1:2) aqueous ethanol, ethanol and ether. The material is dried by conventional means to yield 7.64 g of a colorless powder as the product of the example.

Workup

  1. customat 40°-45° C.
  2. custom2 hours
  3. waitto stand at room temperature for 16 hours
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated to 150 ml
  6. additiondiluted with 300 ml of absolute ethanol
  7. customto give a colorless precipitate
  8. filtrationThe product is collected by filtration
  9. washwashed with 75% aqueous ethanol, ethanol and ether
  10. customdried by conventional means
  11. customto give 25.9 g of crude product
  12. waitto stand at room temperature for 2 hours
  13. filtrationfiltered through diatomaceous earth
  14. washThe filter is washed with 10 ml of water
  15. additionThe filtrate is diluted with 100 ml of absolute ethanol
  16. customto give a thick precipitate
  17. filtrationThe mixture is filtered
  18. washthe product is washed with (1:2) aqueous ethanol, ethanol and ether
  19. customThe material is dried by conventional means

Sources & evidence

ORD record
ord-4a78a7d93b2e4da387cddca48752c364
Source dataset
uspto-grants-1980_01
Patent number
US04183929

Reaction notes

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