Journal of Sulfur Chemistry 317
4
4
.
Experimental
.1. Chemicals and apparatus
All reagents were obtained from Merck (Germany) and Fluka (Switzerland) and were used without
further purification. IR spectra were recorded on a Shimadzu IR-460 spectrometer. Melting points
were measured on an Electrothermal 9100 apparatus.
4
.2. General procedure for synthesis of rhodanine derivatives
The amine derivative (1.2 mmol) and carbon disulfide (1.5 mmol) were added to a solution of
CTAB (15 mol%) in H2O (4 ml) and the mixture stirred at room temperature for 1 min, and then
1
mmol of activated acetylene was added to the mixture during 1 min. After completion (Table 2,
TLC), the reaction mixture was extracted with CH2Cl2 (4 × 10 ml) and dried over anhydrous
MgSO , and evaporated to give the rhodanine. All the products were previously reported (16, 22)
4
and were characterized by direct comparison of their IR and physical data.
4
.2.1. Ethyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-yliden]
ethanoate (3b)
◦
−1
Orange powder, m.p. 115–117 C. IR (KBr) (νmax, cm ): 1728 (C=O), 1649 (C=C), 1310 and
1
1
177 (C=S). H NMR (500.1 MHz, CDCl3): δH = 3.87 (3H, s, OMe), 5.24 (2H, s, CH2Ph), 6.84
3
3
(
1H, s, C=CH), 7.28 (2H, d, JHH = 8.4 Hz, 2CH of Ar), 7.37 (2H, d, JHH = 8.4 Hz, 2CH of
Ar) ppm. C NMR (125.7 MHz, CDCl3): δC = 46.62 (OMe), 52.89 (CH2Ph), 117.16 (C=CH),
28. 86 (2CH of Ar), 130.49 (2CH of Ar), 132.79 (Cipso of Cl), 134.36 (Cipso of NCH2), 141.82
C=CH), 165.45 (CON), 166.46 (CO2Me), 195.43 (C=S) ppm.
1
3
1
(
Acknowledgements
We are grateful to the University of Maragheh for the financial support. The authors thank the editorial office and referees
for their valuable comments.
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