Studies on Syntheses of Thiohydantoin Related Compounds. XVII. Synthesis of 1,3-Diphenyl-5-butylhydantoin

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概要

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• 1,3-Diphenyl-5-butylhydantoin (I) was synthesized by two methods, indirect and direct, with the object of the development of a new analgesic agent. In the course of the indirect method, treatment of 1,3-diphenyl-2-thiohydantoin (IV) with n-butylaldehyde gave 1,3-diphenyl-5-butylidene-2-thiohydantoin (V) as two kinds of crystals, which were confirmed to be geometrical isomers with each other. The configurations of them were determined from the NMR spectral data. Two by-products obtained in this reaction was also geometrical isomers with each other, and they were deduced to be dimers of 1,3-diphenyl-5-butylidene-2-thiohydantoin, 1,3-diphenyl-5-{β-ethyl-γ-(1,3-diphenyl-2-thiohydantoinyl)} hexylidene-2-thiohydantoin (Xa and Xb) from some physical data. In the direct method, 1,3-diphenyl-5-butylhydantoin was obtained in 40% yield by refluxing 2-anilinohexanoic acid (IX) and phenyl isocyanate in xylene.

• 公益社団法人日本薬学会の論文
• 1969-12-25

著者

• 八代 有

  Faculty of Pharmaceutical Sciences Nagoya City University

• 三輪 一智

  Laboratories For Biochemical Research Howard Hughes Medical Institute And Departments Of Biochemistr

• 白井 秀明

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 三輪 一智

  Faculty of Pharmaceutical Science, Meijo University

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