The purpose of the current study was to synthesize a methacrylate monomer with a thiohydantoin structure. In a flask, (2-thiohydantoin-4-yl) propionic acid, 10-hyroxydecyl methacrylate, 4-dimethylaminopyridine, and tetrahydrofuran (THF) were placed in a nitrogen atmosphere. A THF solution of N,N’-dicyclohexylcarbodiimide was added and stirred at room temperature. Ethyl acetate and n-hexane were then added to the reaction mixture. The reacted slurry was purified by chromatography with silica gel and hexane-ethyl acetate gradient elution solvent. The structure of the compound was assigned with proton nuclear magnetic resonance spectrum analysis, infrared spectroscopy, and high-resolution mass spectral analysis. The colorless viscous liquid obtained in yield of 49% was characterized as 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl)propionate (MDTHP) or 10-((3-(5-oxo-2-thioxysoimidazolidin-4-yl)propanoyl)oxy)decyl methacrylate (2-THPDM). The MDTHP was soluble to acetone, isopropanol, and methyl methacrylate up to 2.6% or more. This compound could be potentially applicable as a functional monomer for bonding metals and alloys.

本研究的目的是合成具有巯基乙内酰脲结构的甲基丙烯酸酯单体。在烧瓶中，将（2-硫代乙内酰脲-4-基）丙酸，甲基丙烯酸10-羟癸基酯，4-二甲基氨基吡啶和四氢呋喃（THF）置于氮气气氛中。加入N，N′-二环己基碳二亚胺的THF溶液，并在室温下搅拌。乙酸乙酯和正己烷然后将-己烷加入到反应混合物中。通过硅胶色谱法和己烷-乙酸乙酯梯度洗脱溶剂纯化反应的浆液。对该化合物的结构进行了质子核磁共振光谱分析，红外光谱和高分辨率质谱分析。以49％的收率获得的无色粘性液体被表征为10-甲基丙烯酰氧基癸基-（2-硫代乙内酰脲-4-基）丙酸酯（MDTHP）或10-（（3-（5-氧代-2-硫代氧杂嘧啶并咪唑啉-4-基））。甲基丙烯酸丙酰基）氧基）癸基酯（2-THPDM）。MDTHP最多可溶于2.6％或更高的丙酮，异丙醇和甲基丙烯酸甲酯。该化合物可能潜在地用作结合金属和合金的功能单体。