1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Asiri, Abdullah Mohamed; Alamry, Khaled Ahmed; Jalbout, Abraham F.; Zhang, Suhong

doi:10.3390/M359

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1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

by

Abdullah Mohamed Asiri

^1,*,

Khaled Ahmed Alamry

¹,

Abraham F. Jalbout

^2,3 and

Suhong Zhang

²

¹

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21413, P.O. Box 9028, Saudi Arabia

²

Department of Physics, Dillard University, New Orleans, LA 70112, USA

³

EJMAPS Organization, 1107 Carrolton Ave., Metairie, LA 70005, USA

^*

Author to whom correspondence should be addressed.

Molbank 2004, 2004(1), M359; https://doi.org/10.3390/M359

Submission received: 13 September 2003 / Accepted: 24 October 2003 / Published: 24 February 2004

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1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 3 was prepared by Knoevenagel condensation of 2-methoxybenzaldehyde 1 and N,N-diethylthiobarbituric acid 2 in ethanol using piperidine as a base [1,2].

N,N-Diethylthiobarbituric acid 2 ( 1.50 g, 7.5 mmol) and 2-methoxybenzaldehyde 1 (1.02 g, 0.02 mol) in ethanol ( 30 mL) were heated under reflux for five minutes. Piperidine (0.5 mL) was added in one portion and the reflux was continued for two hours. The reaction mixture was cooled to room temperature and the solid formed was filtered, washed with cold ethanol ( 2x 20 mL) and dried. 1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 3 was recrystallized from ethanol as deep yellow crystals (2.03 g, 85%).

M.p. 108 °C (recrystallized from EtOH, uncorrected).

UV l_max (nm; CHCl₃)/e (dm³.mol^-1.cm^-1) 406/16000 and 253/ 6060.

IR nmax ( KBr) cm^-1 2980, 1674 (C=O), 1632 (C=C), 1391 (CS).

Theoretical (cm^-1, AM1)= 1675.4, 1391.4, 1599.8

¹H-NMR (400 MHz; CDCL₃; Me₄Si) d 8.90 (1H, s, CH=C), 8.10 (1H, d, J = 7.84 Hz ), 7.5 (1H, d, J = 7.24 Hz, J = 7.14 Hz ), 7.02 (1H, t(dd), J= 7.6 Hz), 6.94 (1H, d, J = 8.42 Hz ), 4.51, 4.50 ( 4H, t, CH₂),3.99 ( 3H, s, CH₃O), 1.33, 1.28 ( 6H, q, CH₃).

¹³C-NMR (100 MHz, CDCL₃; Me₄Si) d 179 (C=S), 157.04, 155.6 (2xC=O), 148.16 (CH oliefinc), 134.4, 132.1, 122.5, 120.8, 119.2, 109.9, 43.7, 43.73 (CH₂), 13.3, 13.1 (CH₃).

Anal.Calc. for C₁₆H₁₈N₂O₃S ( 318.392): C 60.36, H 5.70 , N 10.07; found : C 60.21, H 5.82, N 10.16.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

Jones, G. Org. React. 1967, 15, 204–599.
Tanaka, K.; Chen, X.; Yoneda, F. Tetrahedron 1988, 44, 3241–3249.

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MDPI and ACS Style

Asiri, A.M.; Alamry, K.A.; Jalbout, A.F.; Zhang, S. 1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione. Molbank 2004, 2004, M359. https://doi.org/10.3390/M359

AMA Style

Asiri AM, Alamry KA, Jalbout AF, Zhang S. 1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione. Molbank. 2004; 2004(1):M359. https://doi.org/10.3390/M359

Chicago/Turabian Style

Asiri, Abdullah Mohamed, Khaled Ahmed Alamry, Abraham F. Jalbout, and Suhong Zhang. 2004. "1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione" Molbank 2004, no. 1: M359. https://doi.org/10.3390/M359

APA Style

Asiri, A. M., Alamry, K. A., Jalbout, A. F., & Zhang, S. (2004). 1,3-Diethyl-5-(2-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione. Molbank, 2004(1), M359. https://doi.org/10.3390/M359

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