Electric Literature of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
2-[(Benzen-1-yl)methyleneamino]-3-aminomaleonitrile(L) was prepared by a modification of the method described in the literature [18]. To a solution of benzaldehyde (0.500 g,4.71 mmol) in methanol (10 ml), a solution of 2,3-diaminomaleonitrile(0.509 g, 4.71 mmol) in methanol(10 ml) was added dropwise with constant stirring. Theresulting mixture was refluxed at about 80 C for 5 h until completion of the reaction (checked by TLC). The product2-[(benzen-1-yl)methyleneamino]-3-aminomaleonitrile obtained was filtered off and purified by column chromatography(ether:dichloromethane) to afford a yellowish-brown solid.Yield: 0.847 g (84percent); Elemental analyses (C, H and N,wtpercent) Anal. Calc. for C11H8N4: C, 67.3; H, 4.1, N, 28.5;found: C, 67.3; H, 4.09; N, 28.5percent; IR (KBr, m/cm-1): 3404 s,3298w, 2237w, 2204 s, 1605 s; 1HNMR(CDCl3; 300 MHz):d 8.46 (s, 1H, HC=N), d 7.46?7.96 (m, 5H, phenyl), d 7.45 (s,2H,NH2); 13CNMR(CDCl3; 300 MHz): d 156.61(HC=N), d128.99?128.88 (phenyl-C), d 115.84 (CN), d 114.85 (CN), d113.61 (HCNC=C), d 104.65 (CNC=C).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diaminomaleonitrile, its application will become more common.
Reference:
Article; Devkule; Chavan; Transition Metal Chemistry; vol. 42; 4; (2017); p. 347 – 356;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts