Application of 98873-55-3,Some common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, molecular formula is C5H5N3, 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.
A mixture of potassium hydroxide (0.25 g, 4.5 mmol) in 3 ml of dimethylsulfoxide was purged with argon and cooled to 10C. A solution of 2-imidazol-1-ylacetonitrile (13, 0.23 g, 2.2 mmol) and carbon disulfide (0.32 g, 4.3mmol) in 2 ml of dimethylsulfoxide was then slowly added. The cooling bath was removed and the resulting orange mixture was stirred for 15 min at room temperature. A solution of [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl]methanesulfonate (25, 0.54 g, 1.4 mmol) in 2 ml of dimethylsulfoxide was then added dropwise. The reaction mixture was stirred for 1 h at room temperature and then poured on water. The phases were separated, the aqueous phase was extracted with dichloromethane, the combined organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure.The remainder was purified by chromatography on silica gel, using ethyl acetate/ heptane 1 : 1 as eluent system to deliver 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-yl-acetonitrile (26, 0.49 g, 1.3 mmol, 92 %) as an inseparable 1 : 1 mixture of the E- and Z-isomer. 1H-NMR (400 MHz, CDCl3): delta= 3.12 (dd, 1H, J = 7.1, 14.1 Hz), 3.18 (dd, 1H, J = 6.8, 14.1 Hz), 3.31 (dd, 1H, J= 6.8, 14.1 Hz), 3.49 (dd, 1H, J = 7.1, 14.1 Hz), 4.10 (q, 1H, J = 7.1 Hz), 7.02 (t,1H, J = 1.3 Hz), 7.17 (s, 1H), 7.29 (dd, 1H, J = 2.2, 8.4 Hz), 7.44 (d, 1H, J = 2.2Hz), 7.48 (d, 1H, J = 8.4 Hz), 7.59 (s, 1H). LC-MS: Rt = 0.97 min; MS: m/z = 368[M+1]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-1-yl)acetonitrile, its application will become more common.
Reference:
Article; Gagnepain, Julien; Jeanmart, Stephane; Bonvalot, Damien; Jacob, Olivier; Lamberth, Clemens; Synlett; vol. 30; 1; (2019); p. 59 – 62;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem