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One-Pot Preparation of 4-(2-Nitrophenyl)-1,2,4-triazolidine-3,5-dione (
3d): 2-Nitrophenyl aniline (0.100 g, 0.0724 mmol) in acetone (5 mL) was cooled to 0 °C and Et3N (0.07 mL, 0.0724 mmol) in acetone (1 mL) was added. The reaction mixture was stirred for a further 1 h and then a solution of ethyl chloroformate (0.078 g, 0.0724 mmol) in acetone (2 mL) was added at 0 °C. The resulting reaction mixture was stirred for 1 h at the same temperature and then a solution ethyl carbazate (0.075 g, 0.0724 mmol) in acetone (2 mL) was added dropwise. Finally the reaction mixture was refluxed for 10 h. The solid was collected by filtration and recrystallized from distilled H2O. IR (KBr): 3200 (s, NH), 1780 (m, C=O), 1700 (s, C=O), 1500 (s, NO2), 1350 (s, NO2) cm-1. MS: m/z = 222 [M+]. 1H NMR (500 MHz, DMSO-d
6): δ = 7.86-7.88 (m, 2 H, ArH), 8.32-8.34 (m, 2 H, ArH), 10.72 (s, 2 H, NH).
19
4-(3-Nitrophenyl)-1,2,4-triazolidine-3,5-dione (
3e): IR (KBr): 3200 (s, NH), 1770 (m, C=O), 1679 (s, C=O), 1500 (s, NO2), 1350 (s, NO2) cm-1. MS: m/z = 222 [M+]. 1H NMR (500 MHz, DMSO-d
6): δ = 7.68-7.72 (m, 2 H, ArH), 7.86-7.90 (m, 1 H, ArH), 8.13-8.15 (dd, J
1 = 8.08 Hz, J
2 = 1.18 Hz, 1 H, ArH), 10.83 (s, 2 H, NH).
4-(2-Chloro-4-nitrophenyl)-1,2,4-triazolidine-3,5-dione (
3g): IR (KBr): 3230 (s, NH), 1780 (m, C=O), 1690 (s, C=O), 1500 (s, NO2), 1340 (s, NO2), 780 (s, CCl) cm-1. MS: m/z = 257 [M+]. 1H NMR (500 MHz, DMSO-d
6): δ = 7.95-7.98 (m, 1 H, ArH), 8.18-8.21 (m, 1 H, ArH), 8.29-8.30 (m, 1 H, ArH), 10.84 (s, 2 H, NH).
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