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Short Note

3-Cyano-2-(2,5-dimethoxybenzalamino)-4-5-tetramethylenethiophene

by
Abdullah Mohamed Asiri
Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
Molecules 2001, 6(6), M212; https://doi.org/10.3390/M212
Submission received: 18 December 2000 / Accepted: 15 May 2001 / Published: 25 May 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 06 m212 i001
3-Cyano-2-(2,5-dimethoxybenzalamino)-4-5-tetramethylenethiophene was prepared by condensation of 2-amino-3-cyano-4,5-tetramethylenethiophene 1 and 2,5-dimethoxybenzaldehyde 2 [1,2]. A mixture of 2-amino-3-cyano-4,5-tetramethylenethiophene 1 (1.0 g, 5.62 mmol) and 2,5-dimethoxybenzaldehyde 2 (0.93 g, 5.62 mmol) in ethanol (20 mL) was heated under reflux for four hours. The reaction mixture was left to cool to room temperature and orang crystals was separated, filtered and washed with ethanol. Rerecrystallization from ethanol gave 3 as orange crystals (1.74 g, 95%).
Mp. 140-142 oC (EtOH, uncorrected).
UV lmax (nm; Acetone)/e (dm3.mol-1.cm-1): 408/11410.
IR (KBr) 2220 (CN), 1600 (C=N).
1H-NMR (400 MHz; CDCl3; Me4Si): 1.85 (4H, d, 2xCH2-5,6), 2.67 (4H, dd, 42xCH2-4,7), 3.84, 3.85 (6H, s, CH3O), 6.85 (1H, d, J = 9.0 Hz), 7.01 (1H, dd, J46 = 3.1 Hz, J 43 = 9.0 Hz, H-4), 7.72 (1H, d, J64 = 3.1 Hz, H-6), 8.82 (1H, s, CH=N-).
13C-NMR: 22.0, 23.1, 24.3, 25.2, 55.8, 56.1 (2xCH3O), 106.4 (CN), 110.5, 112.6, 114.6, 121.3, 123.9, 132.1, 134.9, 153.7, 154.7, 154.8 (CH=N), 160.9.
Anal.Calc. for C18H18N2O2S (326.420): C 66.23, H 5.56, N 8.58; found : C 66.41, H 5.35 , N 8.39.

Supplementary Materials

References

  1. Asiri, A. M. Pak. J. Sci. Ind. Res. 1998, 41, 242.
  2. Chalkley, L. Chem. Rev. 1929, 6, 217.
Sample availability: available from the authors and MDPI.

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MDPI and ACS Style

Asiri, A.M. 3-Cyano-2-(2,5-dimethoxybenzalamino)-4-5-tetramethylenethiophene. Molecules 2001, 6, M212. https://doi.org/10.3390/M212

AMA Style

Asiri AM. 3-Cyano-2-(2,5-dimethoxybenzalamino)-4-5-tetramethylenethiophene. Molecules. 2001; 6(6):M212. https://doi.org/10.3390/M212

Chicago/Turabian Style

Asiri, Abdullah Mohamed. 2001. "3-Cyano-2-(2,5-dimethoxybenzalamino)-4-5-tetramethylenethiophene" Molecules 6, no. 6: M212. https://doi.org/10.3390/M212

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