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有机化学 ›› 2005, Vol. 25 ›› Issue (10): 1244-1247. 上一篇    下一篇

研究论文

5-(N-2-羟乙基)羟乙酰氨基-N,N'-双(2,3-二羟丙基)-2,4,6-三碘-1,3-苯二甲酰胺的合成

邹霈1,2，刘娅灵1,2，罗世能1，谢敏浩1，何拥军1，沈永嘉*,2   

  1. (1江苏省原子医学研究所 无锡 214063)
    (2华东理工大学精细化工研究所 上海 200237)
  • 收稿日期:2005-02-01 修回日期:2005-04-22 发布日期:2005-10-08
  • 通讯作者: 沈永嘉

Synthesis of N,N'-Bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)-hydroxy-acetamido]-2,4,6-triiodoisophthalamide

ZOU Pei 1,2,LIU Ya-Ling1,2,LUO Shi-Neng1,XIE Min-Hao1
HE Yong-Jun1,SHEN Yong-Jia*,2   

  1. (1 Jiangsu Institute of Nuclear Medicine, Wuxi 214063)
    (2 Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
  • Received:2005-02-01 Revised:2005-04-22 Published:2005-10-08
  • Contact: SHEN Yong-Jia

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5-氨基-N,N'-双(2,3-二羟丙基)-2,4,6-三碘-1,3-苯二甲酰胺(2)在N,N-二甲基乙酰胺中可直接与乙酰氧基乙酰氯反应, 产物再经碱性水解得5-羟乙酰氨基-N,N'-双(2,3-二羟丙基)-2,4,6-三碘-1,3-苯二甲酰胺(3), 后者再与氯乙醇反应生成5-(N-2-羟乙基)羟乙酰胺基-N,N'-双(2,3-二羟丙基)-2,4,6-三碘-1,3-苯二甲酰胺(1), 经乙二醇甲醚/正丁醇重结晶, 纯度高于99% (HPLC), 反应总收率由39.3% (文献值)提高到55.1%.

关键词: 乙酰氧基乙酰氯, 非离子型X射线造影剂, 碘佛醇, 合成

5-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (2) was reacted with acetoxyacetyl chloride in N,N-dimethylacetamide and subsequently hydrolyzed in alkali aqueous medium to afford N,N'-bis(2,3-dihydroxypropyl)-5-hydroxyacetamido-2,4,6-triiodoisophthalamide (3). The latter was reacted further with chlorohydrin to form N,N'-bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)hydroxy- acetamido]-2,4,6-triiodo-isophthalamide (1). After recrystallization in 2-methoxyethanol/butanol twice, its purity was over 99% (HPLC) with yield of 55.1%.

Key words: non-ionic X-ray contrast agent, ioversol, synthesis, acetoxyacetyl chloride