Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. 624-75-9
To a solution of iodoacetonitrile 11 (0.16?mL, 2.10?mmol) and N-Boc piperidinone 9 (398?mg, 2.0?mmol) in THF was added i-PrMgBr (3.0?N in THF, 0.7?mL, 2.10?mmol) at -78?C under an Argon atmosphere. After being stirred for 2?h, the reaction was quenched with saturated aqueous NH4Cl solution (5.0?mL) and extracted with ethyl acetate (3?*?5.0?mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel (eluent: EtOAc/n-hexane?=?1:2) to give the ketoamide 12 in 88% yield as a light yellow wax. IR (film) numax: 3362, 2977, 2921, 2260, 1729, 1698, 1519, 1454, 1392, 1366, 1273, 1251, 1170, 1058, 1009?cm-1; 1H NMR (400?MHz, CDCl3) delta 1.44 (s, 9H), 1.47-1.57 (m, 2H), 1.57-1.73 (m, 2H), 2.65 (t, J?=?7.1?Hz, 2H), 3.02-3.21 (m, 2H), 3.49 (s, 2H), 4.63 (s br, 1H); 13C NMR (100?MHz, CDCl3) delta 20.2, 28.3, 29.2, 31.9, 39.8, 41.5, 79.2, 113.7, 156.0, 197.3; HRMS calcd for [C12H20N2NaO3]+ (M + Na+): 263.1366; found: 263.1365.
The chemical industry reduces the impact on the environment during synthesis 2-Iodoacetonitrile. I believe this compound will play a more active role in future production and life.
Reference:
Article; Cheng, Jiang-Tao; Zheng, Xiao; Huang, Pei-Qiang; Tetrahedron; vol. 75; 12; (2019); p. 1612 – 1623;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com