Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure

N-p-Methylbenzyl benzamide 4 was synthesized by means of solid phase synthesis technique. Polystyryl-sulfonyl chloride resin 1 was treated with p-methylbenzyl amine in the presence of pyridine to yield polymer-supported N-p-methylbenzyl sulfonamide 2. After acylation of resin 2 with benzoyl chloride, N-p-methylbenzyl-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 Pna2₁, a = 0.9549(6), b = 1.1169(7), c = 1.1774(7) nm, C₁₅H₁₅ON, M_r = 225.28, V = 1.2557(13) nm³, Z = 4, D_c = 1.192 g/cm³, μ = 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.