Mechanistic, Model Compound, Copolymerization And Modification Reaction Studies of the 4-Substituted-1,2,4-Triazoline-3,5-Dione Ring System
Mechanistic, Model Compound, Copolymerization And Modification Reaction Studies of the 4-Substituted-1,2,4-Triazoline-3,5-Dione Ring System
Williams, Arthur Grady
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The reaction was complete in approximately 15 minutes. During rotoevaporation , crystals fell out of the warm solution. These were dried and gave a melting point of 150-5 C. Further drying in pistol at 0.03 mm Hg. and 136 C resulted in decomposition of the solid. A second set of crystals (0.42 g, 97 24%) fell from the original solution. These were dried at 35 in a vacuum oven and gave a melting point of 152-4° (32) . Infrared absorbances were found at (KBr) 3100 (b), 2850 (sh), 1780 (s), 1700 (...s), 1660 (s), 1610 (s), 1500 (s), 1400 (s), 1320 (s), 1260 (w), 1220 (s), 1185 (s), 1140 (w) , 1085 (w) , 1060 (s), 1000 (w), 800 (b), 770 (w) , 700 (b) and 630 (w) cm" 1 , NMR signals were found at (Acetone-dg) 1.256 (T), 1.36 (T), 2.16(s), 2.456 (s), 4.256 (Q), 4.306 (Q), 5-66 (s), 7-456 (s), 12.36 (s, broad, existed as 75% enolized tautomer In this solvent). Molecular ion: 302 m/e . Anal. Calcd. for C^H^N-0 : C, 55-08; H, 4.92; N, 13-77- Pound: C, 55-06; H, 4.94; N, 13-82. E thy 1-1 , 2-(bis-2-hydro-4-phenyl-l ,2,4-triazoline-3, 5-dionyl )- 3-one-butyrate , 33 .
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