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将2-巯基-△~2-噻唑啉(Ⅰ,R=H)(即四氢噻唑-2-硫酮)和环氧乙烷在二氧六环溶液中作用,希望得到2-β-羟乙基硫化-△~2-噻唑啉(Ⅱ,R=H)。但实际生成四氢噻唑-2-酮(Ⅲ,R=H)和环硫乙烷,与按Crawhall等方法制得的样品,各种物理性质完全相同,混合熔点不降。改将2-巯基-△~2-噻唑啉在碱性溶液中与氯乙醇反应,仍然得到四氢噻唑-2-酮。在同样条件下,5-甲基-四氢噻唑-2-硫酮(Ⅰ,R=CH_3)和环氧乙烷作用,生成5-甲基-四氢噻唑-2-酮(Ⅲ,R=CH_3),与按Niederl等方法所得相同,混合熔点不降。参考有关文献中类似化合物的反应,我们提出下列反应机理:
The role of 2-mercapto-Δ 2 -thiazoline (Ⅰ, R = H) (ie, tetrahydrothiazole-2-thione) and ethylene oxide in dioxane solution is expected to give 2-β- Ethyl sulfide - △ ~ 2 - thiazoline (Ⅱ, R = H). But the actual formation of tetrahydrothiazol-2-one (Ⅲ, R = H) and ethylene sulfide, with the Crawhall and other samples prepared by the method, the physical properties of the same, mixing melting point does not fall. Instead of 2 - mercapto - △ ~ 2 - thiazoline in alkaline solution with chloroethanol reaction, still get tetrahydrothiazol-2-one. Under the same conditions, 5-methyl-tetrahydrothiazole-2-thione (Ⅰ, R = CH_3) CH_3), and according to the method of Niederl obtained the same, mixing melting point does not fall. With reference to the reaction of similar compounds in the literature, we propose the following reaction mechanism: