5-(β-羟基-α-萘偶氮基)-N,N’-双(2,3-二羟丙基)-2,4,6-三碘异酞酰胺的合成及应用

Synthesis of 5-(β-Hydroxyl-α-naphthalene azo)-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide and Its Application

以 5 -氨基 - N ,N’-双 ( 2 ,3-二羟丙基 ) - 2 ,4,6-三碘异酞酰胺为原料 ,经重氮化后与β-萘酚偶合反应制得产物 5 - ( β-羟基 - α-萘偶氮基 ) - N,N’-双 ( 2 ,3-二羟丙基 ) - 2 ,4,6-三碘异酞酰胺。产物经元素分析、红外光谱、核磁共振谱和质谱等测定确证结构。产物的紫外最大吸收波长为 45 0 nm,摩尔吸收系数为 1 .2× 1 0 4,吸收度与浓度在 0 .5 8× 1 0 -6mol/L～ 5 8.1× 1 0 -6mol/L范围内呈良好的线性关系 ,用于检测碘佛醇中杂质 5 -氨基 - N,N’-双 ( 2 ,3-二羟丙基 ) - 2 ,4,6-三碘异酞酰胺的含量。

5-(β-Hydroxyl α naphthalene diazo) N,N' bis(2,3 dihydroxypropyl) 2,4,6 triiodoisophthalamide was synthesized by two steps. Firstly, 5 diazo N,N' bis(2,3 dihydroxypropyl) 2,4,6 triiodoisophthalamide chloride was prepared by diazotization of 5 amino N,N' bis(2,3 dihydroxypropyl) 2,4,6 triiodoisophthalamide. Secondly, 5 diazo N,N' bis(2,3 dihydroxypropyl) 2,4,6 triiodoisophthalamide chloride reacted with β naphthol to form 5 ( β hydroxyl α naphthalene azo) N,N' bis(2,3 dihydroxypropyl) 2,4,6 triiodoisophthalic acid amide. The structure of the product was confirmed by elemental analysis, IR, 1H NMR and FAB MS. The UV spectrum of the product showed a maximum at 450nm and an ε max of 1.2×10 4. The linearity of the absorption curve was fairly good in the range of(0.58×10 -6 mol/L^58.1×10 -6 mol/L). This method can be used in determining the impurity in Ioversol.