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

HRID 233422Notes

Reaction equation

HRID 233422 reaction equation
COCC([C:6]1[C:7]([I:21])=[C:8](C(Cl)=O)[C:9]([I:17])=[C:10]([C:15]=1[I:16])[C:11]([ClH:13]N)=[O:12])=O.Cl.[CH3:23][O:24][C:25](=[O:33])[CH2:26][NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].[CH2:34]([N:36](CC)CC)[CH3:35].C(O)(=O)C[C:43](CC(O)=O)(C(O)=O)[OH:44].[C:54](=[O:57])(O)[O-:55].[Na+].CN(C)C=[O:62]>ClCCl.O>[Cl-:13].[CH3:32][O:31][C:29]([CH2:28][N:27]([CH2:26][C:25]([O:24][CH3:23])=[O:33])[C:11](=[O:12])[C:10]1[C:15]([I:16])=[C:6]([NH:36][C:34](=[O:62])[CH2:35][O:44][CH3:43])[C:7]([I:21])=[C:8]([C:54]([OH:55])=[O:57])[C:9]=1[I:17])=[O:30]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2727727Dimethyl Iminodiacetate Hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 66.8 g (100 mmol) of 5-methoxyacetyl-amino-2,4,6-triiodoisophthalic acid dichloride (EP 0 015 867) 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 instilling tert-butyl ether in the concentrated solution, the title compound can precipitate 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. customthe title compound can precipitate as crystalline solid, which
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-09390b4a2fba4c1da8a2cce57493961f
Source dataset
uspto-grants-1997_01
Patent number
US05593660

Reaction notes

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