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Short Note

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

by
Abdullah Mohamed Asiri
1,2,* and
Salman A. Khan
1
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.
Molbank 2010, 2010(1), M659; https://doi.org/10.3390/M659
Submission received: 10 January 2010 / Accepted: 22 February 2010 / Published: 3 March 2010
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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.

Graphical Abstract

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

  1. Przybylski, P.; Pyta, K.; Stefanska, J.; Ratajczak-Sitarz, M.; Katrusiak, A.; Huczynski, A.; Brzezinski, B. Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant–gossypol. Eur. J. Med. Chem. 2009, 44, 4393–4403. [Google Scholar] [CrossRef] [PubMed]
  2. Ramesh, R.; Maheswaran, S. Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes. J. Inorg. Biochem. 2003, 96, 457–462. [Google Scholar] [CrossRef]
  3. Silveira, V.C.; Luz, J.S.; Oliveira, C.C.; Graziani, I.; Ciriolo, M.R.; Ferreira, A.M.C. Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity. J. Inorg. Biochem. 2008, 102, 1090–1103. [Google Scholar] [CrossRef] [PubMed]
  4. Pandeya, S.N.; Sriram, D.; Nath, G.; Clercq, E. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl]thiosemicarbazide. Eur. J. Pharma. Scie. 1999, 9, 25–31. [Google Scholar] [CrossRef]
  5. Holla, B.S.; Malini, K.V.; Rao, V.S.; Sarojini, B.K.; Kumari, N.S. Synthesis of some new 2,4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents. Eur. J. Med. Chem. 2003, 38, 313–318. [Google Scholar] [CrossRef]
  6. El-Sabbagh, O.I.; Baraka, M.M.; Ibrahim, S.M.; Pannecouque, C.; Graciela, Andrei; Snoeck, R.; Balzarini, J.; Rashad, A.A. Synthesis and antiviral activity of new pyrazole and thiazole derivatives. Eur. J. Med. Chem. 2009, 44, 3746–3753. [Google Scholar] [CrossRef] [PubMed]
  7. Mallikarjuna, B.P.; Sastry, B.S.; Kumar, G.V.S.; Rajendraprasad, Y.; Chandrashekar, S.M.; Sathisha, K. Synthesis of new 4-isopropylthiazole hydrazide analogs and some derived clubbed triazole, oxadiazole ring systems–A novel class of potential antibacterial, antifungal and antitubercular agents. Eur. J. Med. Chem. 2009, 44, 4739–4746. [Google Scholar] [CrossRef] [PubMed]

Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. N-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine. Molbank 2010, 2010, M659. https://doi.org/10.3390/M659

AMA Style

Asiri AM, Khan SA. N-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine. Molbank. 2010; 2010(1):M659. https://doi.org/10.3390/M659

Chicago/Turabian Style

Asiri, Abdullah Mohamed, and Salman A. Khan. 2010. "N-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine" Molbank 2010, no. 1: M659. https://doi.org/10.3390/M659

APA Style

Asiri, A. M., & Khan, S. A. (2010). N-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-1,3-benzothiazol-2-amine. Molbank, 2010(1), M659. https://doi.org/10.3390/M659

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