Reacción #2275683

Ecuación de reacción

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

Rendimiento 69.8%

Disolventes

ethyl acetate

DMA

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was poured slowly onto ice-water (300 ml)
2. 2
   Otroa white solid was isolated by filtration
3. 3
   Lavadowashed with water
4. 4
   OtroThe ethyl acetate was collected
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   Otroto give a white solid
9. 9
   OtroThis was purified by silica column chromatography
10. 10
    Lavadoeluting with petrol

Procedimiento

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).

Fuente