Formic Acid → HCID 86649142, compound

Participants

Reaction Steps

Acetic anhydride (19.47 ml, 20.6 mmol) was added to formic acid (100 ml) under ice cooling keeping the temperature below 5° C. After complete addition the cooling-bath was removed and the temperature was allowed to reach 10° C. The ice cooling was continued and 2-(3-(2-acetoxyethylcarbamoyl)-5-amino-2,4,6-triiodobenzamido)propane-1,3-diyldiacetate (33 g, 41.2 mmol) was then added in portions over 3 minutes. The mixture was left to stir overnight and then evaporated in vacuo to afford a white foam to which methanol (100 ml) and water (100 ml) was added. While stirring, 10N NaOH was added drop wise until a clear solution was obtained. Drop wise addition of 10N NaOH was continued until pH stabilized at 11.60. Methanol was removed from the mixture by evaporation in vacuo and the solution was acidified to pH 2.7 with 18.6% HCl. The mixture was placed in a refrigerator overnight and the product, precipitated from the solution was collected, washed with water and dried at 60° C. to afford 24 g of N1-(1,3-dihydroxypropan-2-yl)-5-formamido-N3-(2-hydroxyethyl)-2,4,6-triiodoisophthalamide (82.9% yield).

Provenance & Evidence