Our previous research has shown that (benzamidomethyl)triethylammonium chloride (1) is a good benzamidomethylating agent for different types of compounds in non-aqueous media [1,2].
In the course of this work, we have also carried out reaction of 1 (in dioxane) with in water insoluble hydrazide of benzilic acid (2).
To a suspension of 1 (0.271 g, 1.00 mmol) in dioxane (15 mL) was added 2 (0.368 g, 1.52 mmol) and triethylamine (TEA) (0.2-0.4 mL). The mixture was stirred and heated at 50 oC for 1 h. After cooling water was added to the mixture until white precipitate appears. Colorless crystals were filtered and first purification was performed by dissolving the product in dioxane and precipitated with water.
Yield: 85 %
Melting Point: 188 oC (toluene)
IR (KBr; cm-1): ν(N-H) and ν(O-H) 3421, 3313 and 3237; Amide I 1656 and 1636; Amide II 1514.
1H-NMR (DMSO--d6; 400 MHz); δ/ppm = 9.68 (d, 1H, N-NHCO); 8.78 (t, 1H, CONH-C); 7.82-7.18 (m, 15H, Ar); 6.60 (s, 1H, OH); 5.65 (d(q), 1H, C-NH-N) and 4.31 (s(t), 2H, CH2).
13C-NMR (DMSO--d6; 100` MHz); δ/ppm = 170.61 C=O; 166.69 C=O; 80.01 C-OH; 56.3 CH2, Ar: 143.88; 134.15; 131.14; 128.13; 127.40; 127.30; 127.17 and 127.01.
Elemental Analysis: Calculated (%) for C22H21N3O3: C 70.4, H 5.6, N 11.2. Found: C 70.5, H 5.7, N 10.9.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References and Notes
- 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]
- 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]
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