Réaction #2275683

Équation de réaction

2,4,6-Triiodo-5-methylamino-isophthaloyl dichloride

acetoxyacetyl chloride

→

acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester

Rendement 69.8%

Solvants

ethyl acetate

DMA

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe reaction mixture was poured slowly onto ice-water (300 ml)
2. 2
   Autrea white solid was isolated by filtration
3. 3
   Lavagewashed with water
4. 4
   AutreThe ethyl acetate was collected
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   Autreto give a white solid
9. 9
   AutreThis was purified by silica column chromatography
10. 10
    Lavageeluting with petrol

Mode opératoire

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).

Source