The crystal structure of N -benzyl-2-chloro- N - ( p -tolyl) acetamide, C 16 H 16 ClNO

C 16 H 16 ClNO, monoclinic, P 2 1 / n (no. 14), a = 9.2566 Å, b = 9.2270(7) Å, c = 17.2231(14) Å, β = 103.745(8) ° , V = 1428.9(2) Å 3 , Z = 4, R gt ( F ) = 0.0655, wR ref ( F 2 ) = 0.2113, T = 293 K.

To (E)-1-phenyl-N-(p-tolyl)methanimine (1 g, 5.12 mmol) in a solution in anhydrous methanol (150 ml), we slowly added sodium borohydride (0.77 g, 20.48 mmol) for 0.5 h at low temperature, then moved to room temperature for 2 h.The solvent was steamed and dried, and a small amount of dichloromethane and dilute hydrochloric acid were added to regulate pH = 1-2.The product was washed three times with dichloromethane (30 ml), the combined organic phase, dried with anhydrous magnesium sulfate, and steamed to obtain light yellow solid (0.96 g, yield 95.02 %). 4 We added triethylamine (1.06 ml, 7.60 mmol) to a solution of N-benzyl-4-methylaniline (1 g, 5.07 mmol) in dichloromethane (100 ml), and then added chloroacetyl chloride (1.03 g, 9.12 mmol) dropwise after a 0.5 h ice salt bath.After addition, we stabilize at low temperature for 1 h.Transferred to room temperature and stirred for 9 h.Then we extracted the organic layer from a saturated salt aqueous solution and merged the organic layers.We dried with anhydrous magnesium sulfate, filtered, and evaporated the filtrate to obtain a light yellow solid (1.24 g, yield 89.36 %).The compounds were dissolved in dichloromethane/methanol.The solvent was then slowly volatilized in the air at low temperatures.A few days later, the crystals of the compound were obtained.

Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment
The amide bond is undoubtedly one of the most important structural motifs in nature. 5,6Amides are not only restricted to biological systems but also undeniably present in an enormous array of molecules, along with major marketed drugs.In addition, the US FDA approved drugs like imatinib (Bcr-Abl tyrosine-kinase inhibitor), nilotinib (tyrosine-kinase inhibitor), ponatinib (multi-targeted tyrosine-kinase inhibitor), dasatinib (tyrosine-kinase inhibitor), afatinib (tyrosine kinase inhibitor), methotrexate (dihydrofolate reductase inhibitor) and carfilzomib (selective proteasome inhibitor) which are used for the treatment of different types of cancers also carry amide bond as an indispensable structural motif. 7And the acylation of amine is one of the most widely practiced reactions in the pharmaceutical industry. 8The crystal molecular packing of the title compound was formed by hydrogen bonds and van der Waals interactions.The hydrogen bond in the molecular structure of the target compound includes one intramolecular C41-H41A⋯O2 (2.750 Å) hydrogen bond.The above mentioned interactions play an important role in the stability of the crystal structure.Geometric parameters are all in the expected ranges. 9

Table  :
Data collection and handling.

Table  :
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å  ).