Citric Acid → 5-Methoxyacetylamino-2,4,6-triiodisophthalic acid-N,N-bis-(methoxycarbonylmethyl)-amide-chloride

HRID 1291971Notes

Reaction equation

HRID 1291971 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:8]([I:21])=[C:9]([C:18](Cl)=[O:19])[C:10]([I:17])=[C:11]([C:15]=1[I:16])[C:12]([Cl:14])=[O:13])=[O:5].Cl.[CH3:23][O:24][C:25](=[O:33])[CH2:26][NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:44].C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl.O>[Cl-:14].[CH3:32][O:31][C:29]([CH2:28][N:27]([CH2:26][C:25]([O:24][CH3:23])=[O:33])[C:18](=[O:19])[C:9]1[C:8]([I:21])=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:15]([I:16])=[C:11]([C:12]([OH:44])=[O:13])[C:10]=1[I:17])=[O:30]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2727727Dimethyl Iminodiacetate HydrochlorideHCID 135899615-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride

Product 1

HCID 867501575-Methoxyacetylamino-2,4,6-triiodisophthalic acid-N,N-bis-(methoxycarbonylmethyl)-amide-chloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 66.8 g (100 mmol) of 5-methoxyacetylamino-2,4,6-triiodisophthalic acid dichloride (EP 0015867) in 300 ml of anhydrous N,N-dimethylformamide is mixed with 21.75 g (110 mmol) of iminodiacetic acid dimethyl ester-hydrochloride (synthesis according to Dubsky, Graenacher, Chem. Ber. 50, 1693 (1917)) and 30.5 ml (220 mmol) of triethylamine. A suspension results, which is stirred for 14 hours at room temperature under argon. The batch is taken up in dichloromethane, shaken out once with water, twice with 2n aqueous citric acid and once with aqueous sodium bicarbonate solution. The organic phase is dried on anhydrous magnesium sulfate and concentrated by evaporation in a vacuum. By instillation of tert-butyl ether in the concentrated solution, the title compound can be precipitated as crystalline solid, which is suctioned off and dried in a vacuum.

Workup

  1. customA suspension results
  2. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customBy instillation of tert-butyl ether in the concentrated solution, the title compound can be precipitated as crystalline solid, which
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-00d55bd08aaa4746bdd3ccdcc710804b
Source dataset
uspto-grants-1998_05
Patent number
US05756066

Reaction notes

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