Electric Literature of 22047-25-2, A common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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.
In a 250cm3 round-bottom flask equipped with a magnetic stirrer, 2-acetylpyrazine (2.44g, 20.0mmol) was added to a solution of 4 -hexyloxybenzaldehyde (2.06g, 10.0mmol) in EtOH (50cm3). KOH pellets (0.56g, 10mmol) were then added, followed by aqueous NH3 (28%, 40cm3). The resulting orange solution was stirred at room temperature overnight, during which time a suspension had formed. White solid was collected by filtration, washed with H2O and EtOH, and dried in vacuo over P2O5. Yield: 2.28g (55%). Crystals of polymorph 1a was grown by slow evaporation of a solution of 1 in DCM-MeOH over one week. Crystals of polymorph 1b was obtained by slow evaporation of a DCM-MeCN solution containing 1 and AgPF6 (2.0equiv.). 1H NMR (500MHz, CDCl3) delta 9.39(d, J=2.0Hz, 2 H), 8.72 (dd, J=4.5, 1.5Hz, 2 H), 8.54 (dt, J=8.0, 2.0Hz, 2 H), 7.95 (s, 2 H), 7.73 (dd, J=7.0, 2.0Hz, 2 H), 7.49 (dd, J=13.0, 5.0Hz, 2 H), 7.08 (d, J=8.5Hz, 2 H), 4.07 (t, J=6.5Hz, 2 H), 1.86 (m, 2 H), 1.52 (m, 2 H), 1.39 (m, 4 H), 0.95 (t, J=7.0Hz, 3 H) ppm. 13C NMR (125MHz, CDCl3) delta 160.48, 155.21, 150.45, 149.97, 148.25, 134.89, 134.73, 130.04, 128.33, 123.71, 117.23, 115.26, 68.26, 31.60, 29.19, 25.74, 22.64, 14.09ppm. FT-IR (solid, cm-1): 1600m, 1515s, 1376m, 1260s, 1182s, 1110m, 1033s, 1016s, 850w, 826s, 607m. HR-MS: m/z 434.1943 [M+ Na]+ (calc. 434.1957), 412.2132 [M+ H]+ (base peak, calc. 412.2137).
The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Li, Li; Zhang, Yuan Zhuo; Yang, Chengxiong; Liu; Fettinger, James C.; Zhang, Guoqi; Journal of Molecular Structure; vol. 1110; (2016); p. 19 – 23;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem