Sodium Carbonate → 4,4'-[5-Carboxy-1,3-phenylenebis(carbonylimino)]-diphthalic acid pentasodium salt

HRID 372224

Reaction equation

HRID 372224 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[OH-:14].[Na+:15].[C:16](=[O:19])([O-:18])[O-].[Na+].[Na+].[C:22]1([C:34](Cl)=[O:35])[CH:27]=[C:26]([C:28](Cl)=[O:29])[CH:25]=[C:24]([C:31](Cl)=[O:32])[CH:23]=1>O>[Na+:15].[Na+:15].[Na+:15].[Na+:15].[Na+:15].[C:34]([C:22]1[CH:27]=[C:26]([C:28]([NH:1][C:2]2[CH:3]=[C:4]([C:11]([O-:13])=[O:12])[C:5](=[CH:9][CH:10]=2)[C:16]([O-:18])=[O:19])=[O:29])[CH:25]=[C:24]([C:31]([NH:1][C:2]2[CH:3]=[C:4]([C:11]([O-:13])=[O:12])[C:5](=[CH:9][CH:10]=2)[C:6]([O-:8])=[O:7])=[O:32])[CH:23]=1)([OH:35])=[O:14]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 729124-Aminophthalic acidHCID 78138Trimesoyl chloride

Product 1

HCID 1371959144,4'-[5-Carboxy-1,3-phenylenebis(carbonylimino)]-diphthalic acid pentasodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2.5 g portion of 4-amino phthalic acid stirred in 100 ml of water is neutralized to pH 7.2 with sodium hydroxide then 1.47 g of sodium carbonate is added. To this solution is added dropwise 1.21 g of 1,3,5-benzenetricarboxylic acid chloride with vigorous stirring. Stirring is continued for 18 hours, then the reaction mixture is concentrated, dissolved in 60 ml of water and acidified with hydrochloric acid. The precipitate is filtered and washed with ethanol and ether to yield 2.8 g of product. This product is dissolved in 50 ml of water, is neutralized and fractionally precipitated with ethanol 6 times. The final crop, 523 mg, is identified as the product of the Example.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutiondissolved in 60 ml of water
  3. filtrationThe precipitate is filtered
  4. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-6ecf7df2ed454e33b4ecfae66281349c
Source dataset
uspto-grants-1978_05
Patent number
US04089974

Linked notes

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