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化学学报
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化学学报 ›› 1963, Vol. 29 ›› Issue (5): 336-343. 上一篇    下一篇

论文

1, 2, 4-三嗪类化合物的研究——Ⅱ. 3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪的不正常甲苯磺酰化反应

李鈞, 張礼和, 董振环, 倪沛洲, 王序   

  1. 北京医学院药学系
  • 投稿日期:1962-10-31 发布日期:2013-06-03

CHEMISTRY OF 1, 2, 4-TRIAZINES Ⅱ. AN ANOMALOUS TOSYLATION OF 3-METHYLMERCAPTO-5-HYDROXY-6-METHYL-1, 2, 4-TRIAZINE

LI CHUN, CHANG LI-Ho, TUNG CHEN-HUAN, NI PEI-CHOU, WANG HSIU   

  1. Department of Pharmacy, Peking Medical College
  • Received:1962-10-31 Published:2013-06-03

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3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪(Ⅱ)在无水吡啶中与对甲苯磺酰氯作用, 得氯化N-[5-(3-甲硫基-6-甲基)-1, 2, 4-三嗪基]-吡啶鎓盐(Ⅷ).它在含微量呲啶的水溶液中回餾得結构可能是O-[5'-(3'-甲硫基-6'-甲基)-1', 2', 4'-三嗪基]-3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪(Va)的化合物.此化合物与二乙胺作用得3-甲硫基-5-二乙氨基-6-甲基-1, 2, 4-三嗪(Ⅶ), 后者水解得高熔点的物貭.O-[5'-(3'-甲硫基-6'-甲基)-1', 2', 4'-三嗪基]-3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪(Va)的結构是借其水解反应及胺解反应等加以推論.对于这类化合物的紅外吸收光譜也进行討論.作者对于3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪在吡啶中与对甲苯磺酰氯作用生成O-[5'-(3'-甲硫基-6'-甲基)-1', 2', 4'-三嗪基]-3-甲硫基-5-羥基-6-甲基-1, 2, 4-三嗪(Va)的反应历程提出建議.

3-Methylmercapto-5-hydroxy-G-methyl-1, 2, 4-triazine(Ⅱ) reacted with p-toluenesulfonyl chloride in anhydrous pyridine to give N-[5-(3-methylmercapto-6-methyl)-1, 2, 4-triazinyl]-pyridinium chloride(Ⅷ), the latter compound gave O-[5'-(3'-methylmercapto-6'-methyl)-1', 2', 4'-triazinyl]-3-methylmercapto-5-hydroxy-6-methyl-1, 2, 4-triazine(Ⅴa) fluxing with water containing small amount of pyridine.