Acetoxyacetyl chloride → Acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester

HRID 2188501Notes

Reaction equation

HRID 2188501 reaction equation
[I:1][C:2]1[C:10]([C:11]([Cl:13])=[O:12])=[C:9]([I:14])[C:8]([NH:15][CH3:16])=[C:7]([I:17])[C:3]=1[C:4]([Cl:6])=[O:5].[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19]>CC(N(C)C)=O.C(OCC)(=O)C>[Cl:13][C:11]([C:10]1[C:9]([I:14])=[C:8]([N:15]([CH3:16])[C:23]([CH2:22][O:21][C:18](=[O:20])[CH3:19])=[O:24])[C:7]([I:17])=[C:3]([C:4]([Cl:6])=[O:5])[C:2]=1[I:1])=[O:12]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 214667042,4,6-Triiodo-5-(methylamino)-1,3-benzenedicarbonyl dichloride

Product 1

HCID 53903191Acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl esterYield 69.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

2,4,6-Triiodo-5-methylamino-isophthaloyl dichloride (20 g, 32.8 mmol) was dissolved in DMA (60 ml) and acetoxyacetyl chloride (15.32 ml, 142 mmol) was added. The reaction was stirred overnight at room temperature with nitrogen bubbling through the reaction mixture. The reaction mixture was poured slowly onto ice-water (300 ml) and a white solid was isolated by filtration. The solid was dissolved in ethyl acetate and washed with water. The ethyl acetate was collected, dried over MgSO4, filtered and evaporated to give a white solid. This was purified by silica column chromatography eluting with petrol:ethyl acetate to give acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester (16.25 g, 22.9 mmol).

Workup

  1. additionThe reaction mixture was poured slowly onto ice-water (300 ml)
  2. customa white solid was isolated by filtration
  3. washwashed with water
  4. customThe ethyl acetate was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a white solid
  9. customThis was purified by silica column chromatography
  10. washeluting with petrol

Sources & evidence

ORD record
ord-698cbab603854742b1347453baeb6691
Source dataset
uspto-grants-2012_12
Patent number
US08323619B2

Reaction notes

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