These common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, 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. Application In Synthesis of 2-(1H-Imidazol-1-yl)acetonitrile
A 25 mL flask is charged with powdered KOH (239 mg, 4.26 mmol), DMSO (5 mL), purged with Argon and is cooled at 10C with a water bath. A solution of 2-imidazol-1-ylacetonitrile (228 mg, 2.13 mmol) and CS2 (257 mu, 4.26 mmol) in DMSO (2 mL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 15 minutes. A solution of [2-chloro-1-[2-chloro-4-[(6-methoxy-3-pyridyl)oxy]phenyl]ethyl] methanesulfonate (620 mg, 1.59 mmol) in DMSO (2 mL) is then added dropwise. After 4 hours, the reaction mixture is poured into H20 (15 mL). The aqueous phase is extracted with dichloromethane, the combined organic phases are washed with brine, dried with Na2S04, filtered and are evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes / EtOAc, 1 :1?1 :3?1 :4) afford (2E)-2- [4-[2-chloro-4-[(6-methoxy-3-pyridyl)oxy]phenyl]-1 ,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile (compound l.bj.25) as a white foam. Mp = 88-91 C. H-NMR (400 MHz, CDCI3): delta = 7.96 (d, J = 3.0 Hz, 1 H), 7.63 (s, 1 H), 7.50 (d, J = 8.9 Hz, 1 H), 7.31 (dd, J = 3.0, 8.9 Hz, 1 H), 7.16 (s, 1 H), 7.05 (t, J = 1.3 Hz, 1 H), 6.97 (d, J = 2.7 Hz, 1 H), 6.88 (dd, J = 2.7, 8.5 Hz, 1 H), 6.79 (d, J = 8.5 Hz, 1 H), 5.65 (dd, J = 5.1 , 8.3 Hz, 1 H), 3.95 (s, 3H), 3.92 (dd, J = 5.1 , 12.0 Hz, 1 H), 3.74 (dd, J = 8.3, 12.0 Hz, 1 H). MS (ESI): m/z = 443, 445 (M+1 ).
The synthetic route of 2-(1H-Imidazol-1-yl)acetonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien Daniel Henri; MAITY, Pulakesh; RAJAN, Ramya; JEANMART, Stephane Andre Marie; LAMBERTH, Clemens; WO2015/162271; (2015); A1;,
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