Electric Literature of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.
Compound 9 (5.534 g, 12.73 mmol) was dissolved inCH2CI2 (14 ml_) in a flamed dried round bottom flask. To this stirring solution was added DMAP (0.1555 g, 1.273 mmol) and TCDI (3.402 g, 19.09 mmol) which dissolved into solution after several hours of stirring. The reaction vessel was sealed with a rubber septum and flushed with argon, and the reaction mixture stirred at room temperature for 3 days. The reaction mixture was then concentrated to provide the crude product as a dark orange viscous oil, which was directly loaded on the silica gel. Compound 10 was isolated as a pale yellow viscous oil via FCC (gradient 30% to 50% EtOAc in hexanes) in 92% yield (6.401 g, 1 1 .75 mmol). Rf = 0.20 (30% EtOAc in hexanes); 1H NMR (300 MHz, CDCI3) delta 8.28 (1 H, s), 7.54 (1 H, s), 6.95 (1 H, s), 5.43 (1 H, dd, J = 8.5, 3.0 Hz), 4.61 -4.54 (2H, m), 4.50-4.41 (1 H, m), 3.70 (3H, s), 2.27- 2.13 (2H, m), 2.04-1.92 (2H, m), 0.82 (9H, s), 0.70 (9H, s), 0.01 (3H, s), 0.00 (3H, s), -0.05 (3H, s), -0.17 (3H, s); 13C NMR (75 MHz, CDCb) delta 183.6, 173.2, 137.0, 130 7, 1 17.7, 86.0, 75.1 , 68.3, 65.4, 52.7, 43.0, 38.0, 25.8, 25.7 (2C), 25.5 (2C), 25.4, 17.8, 17.7, -4.2, -4.7, -4.9, -5.6.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Thiocarbonyldiimidazole, its application will become more common.
Reference:
Patent; McGILL UNIVERSITY; WO2007/131364; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem