Acetoxyacetyl chloride → HCID 59824355, compound

HRID 1645489Notes

Reaction equation

HRID 1645489 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[C:8]([I:19])=[C:9]([C:13]([I:18])=[C:14]([NH2:17])[C:15]=1[I:16])[C:10]([Cl:12])=[O:11])=[O:6])[CH:2]=[CH2:3].[C:20]([O:23][CH2:24][C:25](Cl)=[O:26])(=[O:22])[CH3:21]>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:1]([NH:4][C:5]([C:7]1[C:15]([I:16])=[C:14]([NH:17][C:25]([CH2:24][O:23][C:20](=[O:22])[CH3:21])=[O:26])[C:13]([I:18])=[C:9]([C:10]([Cl:12])=[O:11])[C:8]=1[I:19])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 59309441HCID 59309441, compound

Product 1

HCID 59824355HCID 59824355, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

3-Allylcarbamoyl-5-amino-2,4,6-triiodo-benzoyl chloride (6) (5 g, 8.11 mmol) was dissolved in dry DMA (5 mL) and acetoxyacetylchloride (1.73 mL, 16.2 mmol) was added. The reaction was stirred overnight at room temperature with nitrogen bubbling through. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with ice-water (5×20 mL). The organics were collected, dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The residue was washed with acetonitrile, filtered and dried under vacuum to give acetic acid (3-allylcarbamoyl-5-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-methyl ester as a white solid. (4.47 g, 77%). The structure was confirmed by 1H and 13C NMR, and purity by LCMS.

Workup

  1. washwashed with ice-water (5×20 mL)
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. washThe residue was washed with acetonitrile
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7055329a767449d489791ce9814eae4d
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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