The Synthesis Of Tetraiodoterephthalamide Derivatives As Non-ionic X-ray Contrast Agents

The design and synthesis of tetraiodoterephthalamide derivatives as non-ionic X-ray contrast agents were described in this thesis. All the compounds have not been reported in literature.The compound 1,2,4-trihydroxy-2-aminobutane was synthesized from 2-butene-1, 4-diol, via esterification, epoxidation and amination.Tetraiodoterephthalic acid was synthesized from terephthalic acid by iodination, the yield was 36.3% under the optimal reaction conditions (terephthalic acid: iodine=1:5, at 170℃for 3 hours). The structure was identified by IR, EIMS, elementary analysis and the test of iodine content.Five compounds were synthesized from tetraiodophthalic acid, via acyl chloride and amdiation. They were N,N'– bis [ ( 2 , 3 - dihydroxypropyl ) ]– 2 , 3 , 5 , 6– tetraiodoterephthalamide(1a),N,N'-bis[1,3-dihydroxypropyl]-2,3,5,6-tetraiodoterephth-alamide (1b), N,N'– bismethyl - N,N' - bis ( 2 , 3 - dihydroxypropyl )- 2, 3 ,5, 6 - tetraiodoterephthalamide(1c),N,N'-bismethyl-N,N'-bis[(2,3,4,5,6-pentahydroxyhexyl)-2 , 3 , 5 , 6 - tetraiodoterephthalamide (1d) and N,N'– Bismethyl - N,N' - bis(1-hydroxymrthyl-2,3-dihydroxypropyl)-2,3,5,6-tetraiodoterephthalamide(1e) All the compounds were identified by IR, 1HNMR, MS and elementary analysis. The reaction condition of 1d was optimized via uniform design, the yield was 71.5% under the optimal reaction conditions (triethylamine: Tetraiodoisophthalic acid dichloride: N-methylglucamine=2.1:1:2.4, at 40℃for 12hours).