The origin of a common compound about 6160-65-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Thiocarbonyldiimidazole, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6160-65-2, Computed Properties of C7H6N4S

To a solution of TCDI (3.87 g, 19.55 mmol, 2.0 equiv) and DMAP (0.60 g, 4.88 mmol, 0.5 equiv) in DCM (110 mL) was added a solution of 12 (2.06 g, 9.77 mmol, 1.0 equiv) in DCM (38 mL) at 0 C. After being stirred for 10 h at rt, the resulting mixture was quenched with saturated NH4Cl solution (50 mL). The layers were separated and the aqueous layer was extracted with DCM (3×50 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc 2:1) to furnish 11 (2.06 g, 84%) as a white powder. Colorless block-shaped crystals of 11 were obtained by slow evaporation of a petroleum ether/DCM solution after several days. Mp 185-186 C; IR (thin film): numax 2966, 2924, 1707, 1565 cm-1; 1H NMR (400 MHz, CDCl3): delta 4.48 (d, J=8.8 Hz, A of AB, 1H), 4.35 (d, J=8.8 Hz, B of AB, 1H), 2.95 (dd, J=13.2, 3.2 Hz, 1H), 2.60 (d, J=14.4 Hz, A? of A?B?, 1H), 2.55 (d, J=14.4 Hz, B? of A?B?, 1H), 2.51 (dd, J=16.2, 5.0 Hz, 1H), 2.28 (ddd, J=16.5, 11.6, 8.0 Hz, 1H), 2.16-2.11 (m, 1H), 1.87-1.81 (m, 1H), 1.69 (ddd, J=8.0, 8.0, 3.6 Hz, 1H), 1.54 (dddd, J=12.6, 12.6, 12.6, 5.4 Hz, 1H), 1.02-0.95 (m, 1H), 0.76 (ddd, J=7.2, 3.6, 3.6 Hz, 1H), 0.61 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 208.8, 190.7, 94.3, 72.6, 63.1, 56.3, 39.9, 39.3, 28.2, 27.9, 19.2, 18.3, 12.5; HRMS (ESI): m/z calcd for C13H16O3SNa [M+Na]+ 275.0718, found 275.0710.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Thiocarbonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yue, Guizhou; Yang, Li; Yuan, Changchun; Du, Biao; Liu, Bo; Tetrahedron; vol. 68; 47; (2012); p. 9624 – 9637,14;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem