Synthesis of N-(N’-benzoylhydrazinomethyl)benzamide

Our previous research has shown that (benzamidomethyl)triethylammonium chloride (1) is an excellent benzamidomethylating agent for different types of compounds in aqueous media because of the mild reaction conditions, high yields and simple isolation of products [1,2,3].

In the course of this work, we have also carried out reaction of 1 with benzhydrazide (2) in aqueous media.

A solution of (benzamidomethyl)triethylammonium chloride (1) (0.273 g; 1.01 mmol) in water (10 mL) was added in small portions to a solution of benzhydrazide (2) (0.204 g; 1.50 mmol) in water (20 mL). In the same time, triethylamine (TEA) (0,2-0,4 mL; pH >9), drop by drop was added to the mixture. The mixture was stired for 4-5 h at room temperature, afterward, 30 min. in ice bath. Colorless crystals were collected by filtration and purification was performed by recrystallization from dioxane.

Yield: 86 %

Melting Point: 144 ^oC (dioxane)

IR (KBr; cm^-1): ν(N-H) 3329 and 3302; Amide I 1651 and 1638; Amide II 1543.

¹H-NMR (DMSO-_-d6; 250 MHz); δ/ppm = 10.03 (d, 1H, N-NHCO); 8.85 (t, 1H, CONH-C); 7.83-7.40 (m, 10H, Ar); 5.67 (q, 1H, C-NH-N) and 4.34 (t, 2H, CH₂).

¹³C-NMR (DMSO-_-d₆; 63 MHz); δ/ppm = 167.0 C=O; 165.6 C=O; 56.3 CH₂, Ar: 134.6; 133.4; 131.3; 128.3; 127.3 and 127.2.

Elemental Analysis: Calculated (%) for C₁₅H₁₅N₃O₂: C 66.9, H 5.6, N 15.6. Found: C 66.7, H 5.7, N 15.3.