N-对甲基苄基苯甲酰胺的固相合成及其晶体结构分析

Solid Phase Synthesis of N-p-Methylbenzyl Benzamide and Its Crystal Structure

标题化合物采用固相法合成: 聚苯乙烯磺酰氯树脂1与对甲基苄胺反应得到N-对甲基苄基磺酰胺树脂2, 用苯甲酰氯酰化得到N-对甲基苄基-N-苯甲酰基磺酰胺树脂3。用TiCl4/Zn/THF处理从树脂3上经自由基解脱的方法得到N-对甲基苄基苯甲酰胺4, 产率为76%。晶体结构在Bruker SMART 1000 CCD X-射线衍射仪上, 用石墨单色器单色化的MoK嵘湎?l = 0.071073 nm)测定。非氢原子坐标用直接法解出, 用最小二乘法对非氢原子进行各向异性温度因子修正。N-对甲基苄基-苯甲酰胺: 化学计量式为: C15H15NO, Mr = 225.28, 晶体属于正交晶系, Pna21空间群。晶胞参数: a = 0.9549(6), b = 1.1169(7), c = 1.1774(7) nm, V = 1.2557(13) nm3, Z = 4, Dc = 1.192 g/cm3, m = 0.075 mm-1, F(000) = 480;最终结构偏离因子R = 0.0478, wR = 0.1013, S = 0.912。化合物4的晶体结构中有分子间氢键相互作用。

N-p-Methylbenzyl benzamide 4 was synthesized by means of solid phase synthesis technique. Polystyryl-sulfonyl chloride resin I was treated with p-methylbenzyl an-fine in the presence. of pyridine to yield polymer-supported N-p-methylbenzyl sulfonamide 2. After acylation of resin 2 with benzoyl chloride, N-p-methyl-benzyl-N-benzoyl sulfonamide resin 3 was obtained. Resin 3 was cleaved with TiCl4/Zn/THF in radical way to offer 4 in 76% yield. The crystal structure of 4 was determined by single-crystal X-ray diffraction with the following data: orthorhombic, space group Pna2(1), a = 0.9549(6), b = 1.1169(7), c = 1.1774(7) nm, C15H15ON, M-r = 225.28, V = 1.2557(13) nm(3), Z = 4, D-c = 1.192 g/cm(3), mu = 0.075 mm(-1), F(000) = 480, S = 0.912, the final R = 0.0478 and wR = 0.1013. There exist intermolecular. hydrogen bonds in the N-p-methylbenzyl benzamide crystal.