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3 March 2010

N-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine

and
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah 21413, Saudi Arabia
2
The Center of Excellence for Advanced Materials, King Abdul Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank2010, 2010(1), M659;https://doi.org/10.3390/M659
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Abstract

The title compound, N-[1-(2,5-dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine has been synthesized by condensation of 2-aminobenzothiazole and 3-acetyl-2,5-dimethylthiophene in ethanol. The structure of this new compound was confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-MS spectral analysis.
Heterocyclic compounds containing nitrogen and sulphur exhibit a wide variety of biological activities such as antibacterial [1], antifungal [2], antitumor [3], or anti-HIV activity [4]. The thiazole ring dramatically increases the diversity of certain biological properties such as antibacterial [5], antiviral [6], and antitubercular [7] activities. In this paper, we report the synthesis of a novel compound by condensation of 2-aminobenzothiazole and 3-acetyl-2,5-dimethyl thiophene.
Molbank 2010 m659 i001
A mixture of 2-aminobenzothiazole (0.50 g, 0.0033 mol) and 3-acetyl-2,5-dimethylthiophene (0.475 mL, 0.0033 mol) in methanol (15 mL) was refluxed for 5 h with stirring to give a yellow precipitate. This material was filtered and recrystallized from a mixture of methanol and chloroform to give the pure compound 3.
Yield: 72%; m.p. 86 °C.
EI-MS m/z (rel. int. %): [M+1]+ 287 (68).
IR (KBr) vmax cm–1: 3271 (C-H), 3054 (C-H aromatic), 1637 (C=N), 1104 (C-N).
1H-NMR (600 MHz, CDCl3) δ: 7.59 (CH, dd, J = 7.2 Hz), 7.54 (CH, dd, J = 4.2 Hz), 7.32 (CH, d, J = 3.6 Hz), 7.12 (CH, d, J = 4.2 Hz), 6.98 (thienyl-4H, s), 2.66 (CH3, s), 2.55 (CH3, s), 2.44 (CH3, s).
13C-NMR (150 MHz, CDCl3) δ: 194.26, 166.04, 151.98, 147.31, 135.78, 135.01, 131.51, 126.61, 125.97, 122.26, 120.91, 119.12, 29.86, 16.07, 14.55.
Anal. calc. for C15H14N2S2: C, 62.97, H, 4.89, N, 9.79. Found: C, 62.95, H, 4.85, N, 9.75.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities.

References and Notes

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