3-(2-Nitrophenyl)-2-(4-nitrophenyl)-4-thiazolidinone

Abdullah Mohamed Asiri

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia. Tel.(+696)-2-6952293, Fax (+696)-2-6952293, E-mail: [email protected]

Received: 18 December 2000 / Accepted: 15 May 2001 / Published: 25 May 2001

The 4-thiazolidinone 3 was prepared from the Schiff base 1 thioglycolic acid 2 [1,2]. A mixture of 4-(Nitrobenzalamino)-(2-nitrobenzen) 1 (3.0 g, 0.011 mmol) and thioglycolic acid 2 (1.02 g, 0.011 mol) was refluxed for 15 hours at 110-120 ^oC in an oil bath. Sodium bicarbonate solution was added for removal of excess thioglycolic acid. The product was isolated and recrystallized from ethanol as orange crystals (3.52 g, 92%).

Mp. 70-72 °C (EtOH, uncorrected).

UV l_max (nm; Acetone)/e (dm³.mol^-1.cm^-1) 280/3185, 401/6107.

IR (KBr) 1690 (C=O), 700 (C-S-C).

¹H-NMR (400 MHz; CDCL₃; Me₄Si) d_H3.09 (2H, CH₂), 6.07 (1H, d, S-CH), 6.71 (2H, dd, J = 7.6 Hz), 6.81 (2H, d, J = 8.3 Hz), 7.36 (2H, d, J = 7.33 Hz), 8.11 (2H, d, J = 8.5 Hz).

¹³C NMR (100 MHz; CDCl₃):: 20.0 (CH₂), 51.8 (C-S), 111.83, 116.1, 116.97, 118.75, 126.22, 135.65, 144.65, 196.24.

Anal.Calc. for C₁₅H₁₁N₃O₅S (345.339): C 52.17, H 3.21, N 12.17; found : C 52.33, H 3.11 , N 11.98.

References

1. Patoli, V. N.; Patel, P. K.; Xi, A. J. J. Indian Chem. Soc. 1994, 71, 683.
2. Ergenc, N.; Capan, G.; Guenay, N. S.; Oezkirimli, S.; Geuengoer, M.; Oezbey, S.; Kendi, E. Archi der Pharm. 1999, 332, 343.

Sample availability: available from the authors and MDPI.

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