Methoxyacetyl chloride → 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-diacetoxypropyl)amide chloride

HRID 233423Notes

Reaction equation

HRID 233423 reaction equation
[CH3:1][O:2][CH2:3][C:4]([Cl:6])=[O:5].[Cl-].[C:8]([O:11][CH:12]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[CH2:13][NH:14][C:15](=[O:29])[C:16]1[C:24]([I:25])=[C:23]([NH2:26])[C:22]([I:27])=[C:18]([C:19]([OH:21])=[O:20])[C:17]=1[I:28])(=[O:10])[CH3:9]>O1CCOCC1>[Cl-:6].[C:8]([O:11][CH:12]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[CH2:13][NH:14][C:15](=[O:29])[C:16]1[C:24]([I:25])=[C:23]([NH:26][C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:22]([I:27])=[C:18]([C:19]([OH:21])=[O:20])[C:17]=1[I:28])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 867501615-amino-2,4,6-triiodisophthalic acid-N-(2,3-diacetoxypropyl)-amide-chloride

Product 1

HCID 866509095-Methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-diacetoxypropyl)amide chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

24.7 g (150 mmol) of methoxyacetyl chloride is added to a suspension of 73.4 g (100 mmol) of 5-amino-2,4,6-triiodoisophthalic acid-N-(2,3-diacetoxypropyl)-amide-chloride (EP 0308364) in 500 ml of anhydrous dioxane, stirred with exclusion of moisture, at room temperature. The batch is refluxed for several hours, until, according to thin-layer chromatography, feedstock is no longer detectable, then it is concentrated by evaporation, the residue is taken up in dichloromethane and shaken out with saturated aqueous sodium bicarbonate solution. After drying on anhydrous magnesium sulfate, the organic phase is concentrated by evaporation, and the residue is recrystallized from ethyl acetate/tert-butyl methyl ether.

Workup

  1. temperatureThe batch is refluxed for several hours
  2. concentrationit is concentrated by evaporation
  3. stirringshaken out with saturated aqueous sodium bicarbonate solution
  4. dry with materialAfter drying on anhydrous magnesium sulfate
  5. concentrationthe organic phase is concentrated by evaporation
  6. customthe residue is recrystallized from ethyl acetate/tert-butyl methyl ether

Sources & evidence

ORD record
ord-a724e2f10f6f4f04b0abe90a3d63279d
Source dataset
uspto-grants-1997_01
Patent number
US05593660

Reaction notes

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