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31 May 2007

Synthesis of N-(N’-benzoylhydrazinomethyl)benzamide

Institute of Chemistry, Faculty of Natural Sciences & Mathematics, Sts. Cyril and Methodius University, Arhimedova 5, PO Box 162, 1000 Skopje, Macedonia
Molbank2007, 2007(2), M525;https://doi.org/10.3390/M525
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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.
Molbank 2007 m525 i001
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.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Popovski, E.; Klisarova, L.; Vikic-Topic, D. Simple Method for Benzamidomethylation of Phenols in Water Solution. Synth. Commun. 1999, 29, 3451–3458. [Google Scholar] [CrossRef]
  2. Popovski, E.; Klisarova, L.; Vikic-Topic, D. Benzamidomethylation with (Benzamidomethyl)-triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic acids. Molecules 2000, 5, 927–936. [Google Scholar] [CrossRef]
  3. Popovski, E.; Bogdanov, J.; Najdoski, M.; Hey-Hawkins, E. Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media. Molecules 2006, 11, 279–285. [Google Scholar] [CrossRef] [PubMed]

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