Acetoxyacetyl chloride → 5-Acetoxyacetamido-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide

HRID 1280151Notes

Reaction equation

HRID 1280151 reaction equation
[NH2:1][C:2]1[C:3]([I:29])=[C:4]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:5]([I:23])=[C:6]([C:21]=1[I:22])[C:7]([NH:9][CH2:10][CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:8].[C:30]([O:33][CH2:34][C:35](Cl)=[O:36])(=[O:32])[CH3:31].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[C:30]([O:33][CH2:34][C:35]([NH:1][C:2]1[C:3]([I:29])=[C:4]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:5]([I:23])=[C:6]([C:21]=1[I:22])[C:7]([NH:9][CH2:10][CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:8])=[O:36])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 184291303-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

Product 1

HCID 184291395-Acetoxyacetamido-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamideYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-Amino-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide (3.0 g, 4.03 mmol) was dissolved in dry N,N-dimethylacetamide (8 ml) at ambient temperature. With efficient stirring acetoxyacetyl chloride (4.39 ml, 40.3 mmol) was added dropwise, and the mixture was stirred overnight. The mixture was then added slowly with stirring into a saturated solution of sodium hydrogen carbonate (80 ml). The precepitate formed was filtered off and dissolved in chloroform (80 ml). The organic solution was washed with an aqueous saturated solution of NaHCO3 (25 ml), and then evaporated to dryness. The solid residue was dissolved in acetone and filtered through a pad of alumina with acetone as eluent. Evaporation of the solvent gave 3.38 g (100%) of a white crystalline product.

Workup

  1. additionwas added dropwise
  2. additionThe mixture was then added slowly
  3. customThe precepitate formed
  4. filtrationwas filtered off
  5. dissolutiondissolved in chloroform (80 ml)
  6. washThe organic solution was washed with an aqueous saturated solution of NaHCO3 (25 ml)
  7. customevaporated to dryness
  8. dissolutionThe solid residue was dissolved in acetone
  9. filtrationfiltered through a pad of alumina with acetone as eluent
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d186b94760d84370b0bdff4adda95a15
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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