Application of 55557-52-3, A common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, its 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.
To a solution of 1.50 g (10.75 mmol, 1 equiv) of 2 chloro-3-cyanopyrazine 15 in propanenitrile (10 mL) was added 3.30 g (21.50 mmol, 2 equiv) of bromotrimethylsilane dropwise, and the resulting mixture was stirred for 16 h at room temperature. Subsequently, the reaction mixture was cooled to 0 C and quenched with an aqueous solution of 2 M NaOH (10 mL). Afterward, the aqueous phase was extracted with EtOAc (3¡Á10 mL), and the combined organic phases were washed with brine (2¡Á10 mL). After drying (MgSO4) and evaporation of the solvents in vacuo, the product was recrystallized from Et2O to afford 1.56 g (8.49 mmol, 79% yield) of 3-bromo-2-cyanopyrazine 16 as white crystals (mp=43.5 C). 1H NMR (CDCl3): delta 8.61 (1H, d, J=2.2 Hz, CH); 8.71 (1H, d, J=2.2 Hz, CH). 13C NMR (CDCl3): delta 114.7 (CN); 133.3 (CCN); 143.3 (CBr); 143.4 (CH); 147.0 (CH). IR (ATR, cm-1): nu=3101; 2243 (CN); 1958; 1538; 1515; 1425; 1364; 1336; 1249; 1184; 1161; 1071; 1048; 945; 870; 839; 824; 668; 653. GC-MS (EI) m/z (%): 183/185 (M+, 58); 129/131 (13); 104 (M+-Br, 100); 77 (23); 52 (28). Anal. Calcd for C5H2BrN3: C, 32.64; H, 1.10; N, 22.84. Found: C, 32.78; H, 1.15; N, 22.67.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Piron, Karel; Kenis, Sara; Verniest, Guido; Surmont, Riccardo; Thuring, Jan Willem; Ten Holte, Peter; Deroose, Frederik; De Kimpe, Norbert; Tetrahedron; vol. 68; 34; (2012); p. 6941 – 6947;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem