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Short Note

2-[N-(O-ethylaminophenyl) phenyl imidoyl methylylidene]-3,5-diphenyl-1,3,4-thiadiazole

Laboratoire de Chimie Organique Hétérocyclique, Faculté des Sciences, Avenue Ibn Batouta, BP-1014- Rabat-Maroc
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Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M487; https://doi.org/10.3390/M487
Submission received: 18 July 2006 / Accepted: 20 July 2006 / Published: 1 September 2006
4-phenyl-1,5-benzodiazepine-2-thione are used as starting materials in the synthesis of several heterocyclic compounds for potential biological actvities.1-3 The synthesis of a new 1,3,4-thiadiazole derivative is reported.
To a solution of 0.01mol of 1-ethyl-4-phenyl-1,5-benzodiazepine-2-thione 1 [1] in 60 ml of tetrahydrofuran, 0,02 mol of hydrazonoyl chloride and 0.04 mol of triethylamine were added. Then, the mixture was refluxed for 12 hours. After cooling, salts are removed by filtration and solvent was evaporated under reduced pressure. The residue isolated was recrystallized from ethanol. The 1,3,4-thiadiazole derivative 2 was obtained in 60 % yield.
Melting point: 165 °C
1H-NMR (CDCl3, 250 MHz ): δ= 1,34 (t, J = 7,12 Hz, 3H), 3,36 (q, J = 7,12 Hz, 2H), 7,24 (s, 1H), 6,05-7,92 (m, 19H).
13C-NMR (CDCl3, 67.5 MHz ): δ= 15,24 (CH3), 38,94 (CH2), 90,19 (CH=), 110,00-130,26 (CHar), 130,53-142,35 (Car), 151,53 (C=N), 162,98 (C=N).
MS (EI): 474 [M]+
Elemental analysis: Calculated for C30H26N4S : C, 75.92%; H, 5.52%; N, 11.80%. Found: C, 75.97%; H, 5.46%; N, 11.84%;

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References:

  1. Essassi, E. M.; Salem, M. Bull. Soc. Chim. Belg. 1988, 97, 387.
  2. Essassi, E. M. Bull. Soc. Chim. Belg. 1994, 103, 679.
  3. Ghomsi, J.N.T; Ahabchane, N.H.; Essassi, E.M. Phosphorus Sulfur and Silicon 2004, 179, 353.
Scheme 1.
Scheme 1.
Molbank 2006 m487 sch001

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MDPI and ACS Style

Ghomsi, J.N.; Doumbia, M.L.; Ahabchane, N.H.; Essassi, E.M. 2-[N-(O-ethylaminophenyl) phenyl imidoyl methylylidene]-3,5-diphenyl-1,3,4-thiadiazole. Molbank 2006, 2006, M487. https://doi.org/10.3390/M487

AMA Style

Ghomsi JN, Doumbia ML, Ahabchane NH, Essassi EM. 2-[N-(O-ethylaminophenyl) phenyl imidoyl methylylidene]-3,5-diphenyl-1,3,4-thiadiazole. Molbank. 2006; 2006(5):M487. https://doi.org/10.3390/M487

Chicago/Turabian Style

Ghomsi, J. Nathantene, M. Lamine Doumbia, Noureddine Hamou Ahabchane, and El Mokhtar Essassi. 2006. "2-[N-(O-ethylaminophenyl) phenyl imidoyl methylylidene]-3,5-diphenyl-1,3,4-thiadiazole" Molbank 2006, no. 5: M487. https://doi.org/10.3390/M487

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