1，4-二苯基-6-苯基氨基-1，3，5-三嗪-2（1H）-硫酮的合成与晶体结构

Synthesis and crystal structure of 1,4 - diphenyl -6 - phenylamino - 1,3,5 - triazine -2 （1H） - thione

目的研究1，4-二苯基-6-苯基氨基-1，3，5-三嗪-2（1H）-硫酮（分子式C2，H16N4S，相对分子质量356．44）的合成方法和其单晶结构。方法先将一定量的苄脒、氢氧化钠和N，N-二甲基甲酰胺（DMF）混合放入10ml反应器中搅拌10min，然后将一定量的苯基异硫氰酸酯加入反应器中，预搅拌20S后，在110℃温度下微波辐射（MWI）15min，高产率得到目标化合物。化合物的结构通过核磁共振氢谱（^1HNMR）、红外光谱（IR）和高分辨率气相色谱质谱（HRMS）验证，并通过X—ray单晶衍射进一步确定了产物的结构。结果合成的标题化合物C21H16N4S结构通过单晶X射线衍射分析确定，单斜晶系，空间群C2／c，a=22．94（2），b=9．5092（15），c=22．027（2）A，d=90°，D=110．473（2）°，^γ=90°，R=0．0465andwR：0．0758。分子中新形成的1，3，5-三嗪-2（1H）-硫酮环是个平面结构；它与相邻的苯环接近于共平面，二者的二面角为7．36（0．17）；而它与相邻的N一取代苯环近似于垂直，二者的二面角为85．31（0．13）。结论提供了一种1，3，5-三嗪衍生物的绿色合成方法，并经过单晶衍生确定了其分子结构及分子结构中各个六员环之间的关系。

Objective The authors proposed a new method for the synthesis of the title compound, 1,4 - diphenyl - 6 - phenylamino - 1,3,5 - triazine - 2 （ 1 H） - thione （ C21H16 N4 S, Mr = 356.44）. The structure of the title compound was investigated by X - ray analysis. Methods A certain amount of benzamidine, sodium hydroxide and DMF were mixed and then stirred for 10 rain. Subsequently, the certain amount of phenylisothiocyanate was added to the reaction mixture, and pre -stirring for 20 seconds. The mixture was subjected to microwave irradiation （time： 15 min, tempera- ture ： 110 ~C ） the corresponding product 1,3,5 - triazine - 2 （1H） - thione. Results The crystal of the title compound belongs to monoclinic, space group C2/c with a = 22.94 （ 2 ） , b = 9. 5092 （ 15 ） , c = 22. 027 （ 2 ） A, R = 0.0465 and wR = 0. 0758. X -ray analysis revealed that the newly formed 1,3,5 -triazine -2 （1H） -thione ring in the crystal struc- ture was a coplanar structure. It was nearly coplanar with the adjacent benzene ring （C3） of 7.36 （0.17） ° and perpen- dicular to the N - substituted benzene ring of 85.31 （0.13） °. Conclusion This paper reports a multicomponent domino reaction （MDR） to synthesize N - aryl amino substituted 1,3,5 - triazine derivative with 84% yield. The structure of the product was confirmed by 1 H NMR, IR, HRMS and single X - ray diffraction and the conformation of the six member rings in the molecular were also studied.