Dimethylacetamide → 3-[N-(2,3-dihydroxypropyl)carbamoyl]-5-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-2,4,6-triiodobenzonitrile

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Reaction Steps

6.6 g of 5-cyano-3-[N-(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodobenzoic acid chloride is dissolved in 40 ml of dimethylacetamide and combined with 2.3 g of N-methylamino-2,3-propanediol. The mixture is stirred for one hour at room temperature and then concentrated under vacuum. The thus-obtained crude product can be used directly for nitrile saponification. To isolate the pure product the dilute aqueous solution of the crude product is treated with a cation exchange resin and an anion exchange resin, and the filtered solution is concentrated under vacuum to dryness, thus obtaining 5.9 g (81% of theory) of 3-[N-(2,3-dihydroxypropyl)carbamoyl]-5-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-2,4,6-triiodobenzonitrile; mp 215° C.

Provenance & Evidence