Dimethylformamide → N-Methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid-N,N-bis-(ethoxycarbonylmethyl)-amide-chloride

HRID 233424Notes

Reaction equation

HRID 233424 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]([CH3:22])[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.[CH2:24]([O:26][C:27](=[O:36])[CH2:28][NH:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:25].C(N(CC)CC)C.CN(C)C=[O:47]>>[Cl-:14].[CH2:24]([O:26][C:27]([CH2:28][N:29]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:18](=[O:19])[C:9]1[C:8]([I:21])=[C:7]([N:6]([CH3:22])[C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:15]([I:16])=[C:11]([C:12]([OH:47])=[O:13])[C:10]=1[I:17])=[O:36])[CH3:25]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 12365601Ethyl 2-[(2-ethoxy-2-oxoethyl)amino]acetate hydrochlorideHCID 17887369N-methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid dichloride

Product 1

HCID 131719780N-Methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid-N,N-bis-(ethoxycarbonylmethyl)-amide-chloride

Procedure

A solution of 68.2 g (100 mmol) of N-methoxyacetyl-5-methylamino-2,4,6-triiodoisophthalic acid dichloride (EP 0015867) in 500 ml of N,N-dimethylformamide is mixed with 22.6 g (100 mmol) of iminodiacetic acid diethyl ester hydrochloride (production according to Jongkees, Recl. Trav. Chimys-Bas, 27, 296 (1908)) and 10.1 g (100 mmol) of triethylamine. A suspension results, which is stirred overnight under argon at room temperature. Then, it is concentrated by evaporation and the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/ethyl acetate. After concentration by evaporation of the product fractions, a colorless solid is obtained, which is dried in a vacuum.

Workup

  1. customA suspension results
  2. concentrationThen, it is concentrated by evaporation
  3. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/ethyl acetate
  4. concentrationAfter concentration
  5. customby evaporation of the product fractions
  6. customa colorless solid is obtained
  7. customwhich is dried in a vacuum

Sources & evidence

ORD record
ord-3442cf223f44422e9e3d4bf2eb72f503
Source dataset
uspto-grants-1997_01
Patent number
US05593660

Reaction notes

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