5-Aminoisophthalic acid → 5,5',5"-(s-Triazine-2,4,6-triyltriimino)triisophthalic acid hexasodium salt

HRID 2052262Notes

Reaction equation

HRID 2052262 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(=O)(O)[O-].[Na+:18].[Na+].[Na+].[Na+].[Na+].Cl[C:24]1[N:29]=[C:28]([NH:30][C:31]2[CH:32]=[C:33]([C:40]([O-:42])=[O:41])[CH:34]=[C:35]([CH:39]=2)[C:36]([O-:38])=[O:37])[N:27]=[C:26]([NH:43][C:44]2[CH:45]=[C:46]([C:53]([O-:55])=[O:54])[CH:47]=[C:48]([CH:52]=2)[C:49]([O-:51])=[O:50])[N:25]=1>O.[OH-].[Na+]>[Na+:18].[Na+:18].[Na+:18].[Na+:18].[Na+:18].[Na+:18].[N:25]1[C:24]([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:29][C:28]([NH:30][C:31]2[CH:32]=[C:33]([C:40]([O-:42])=[O:41])[CH:34]=[C:35]([CH:39]=2)[C:36]([O-:38])=[O:37])=[N:27][C:26]=1[NH:43][C:44]1[CH:52]=[C:48]([C:49]([O-:51])=[O:50])[CH:47]=[C:46]([CH:45]=1)[C:53]([O-:55])=[O:54]

Participants

6

Reactant 3

HCID 668335-Aminoisophthalic acidHCID 516892Sodium BicarbonateHCID 131711397HCID 131711397, compound

Product 1

HCID 1317113985,5',5"-(s-Triazine-2,4,6-triyltriimino)triisophthalic acid hexasodium salt

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent2×

Procedure

To a stirred solution of 3.62 g of 5-aminoisophthalic acid and 1.85 g of sodium bicarbonate in 80 ml of water plus 7.8 ml of 5 N sodium hydroxide is added 11.24 g of crude 5,5'-[6-chloro-s-triazine-2,4-diyl)diimino]diisophthalic acid tetrasodium salt (prepared as described in Example 2). The reaction mixture is refluxed for 15 hours, then is filtered. The filtrate is diluted with 100 ml of absolute ethanol to give a precipitate. The precipitate is collected by filtration and is washed with (8:10) aqueous ethanol, 75% aqueous ethanol, ethanol and ether to give 14.2 g of crude product. The product is warmed with 80 ml of water and 0.1 ml of 5 N sodium hydroxide is added to achieve pH 9. The mixture is filtered through diatomaceous earth and the filtrate is diluted with 100 ml of absolute ethanol with formation of a thick paste on stirring. The paste is filtered, stirred in absolute ethanol and filtered again, then is washed with ether and dried by conventional means to give 9.9 g of a colorless powder as the product of the example.

Workup

  1. temperatureThe reaction mixture is refluxed for 15 hours
  2. filtrationis filtered
  3. additionThe filtrate is diluted with 100 ml of absolute ethanol
  4. customto give a precipitate
  5. filtrationThe precipitate is collected by filtration
  6. washis washed with (8:10) aqueous ethanol, 75% aqueous ethanol, ethanol and ether
  7. customto give 14.2 g of crude product
  8. additionis added
  9. filtrationThe mixture is filtered through diatomaceous earth
  10. additionthe filtrate is diluted with 100 ml of absolute ethanol with formation of a thick paste
  11. filtrationThe paste is filtered
  12. stirringstirred in absolute ethanol
  13. filtrationfiltered again
  14. washis washed with ether
  15. customdried by conventional means

Sources & evidence

ORD record
ord-7a19af239fb3440d969c9c442a098f35
Source dataset
uspto-grants-1980_01
Patent number
US04183929

Reaction notes

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