Application of 15813-09-9, A common heterocyclic compound, 15813-09-9, name is 4,5-Diiodo-1H-imidazole, molecular formula is C3H2I2N2, 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.
To a solution of 4,5-diiodoimidazole (35.5 g, 111.2 mmol) in anhydrous CH3CN (200 mL) at 0 C was added NaH (95%, 2.8 g, 111.2 mmol) portion wise. After the mixture was stirred for 30 min at rt, 10 (32 g, 101.1 mmol) was added portion wise at rt over a period of 1 h. After stirring at the same temperature for 18 h the reaction mixture was filtered over celite and washed with EtOAc (3 ¡Á 150 mL). The organic layer was concentrated under reduced pressure. The product was isolated by flash chromatography on silica gel using hexane/EtOAc (3:1) to give 11 as a pale yellow syrup. Yield: 57 g, 84%. 1H NMR (CDCl3, 400 MHz): delta 2.39 (s, 3H), 2.42 (s, 3H), 2.54 (ddd, 6.40 Hz, 7.80 Hz, 14.20 Hz, 1H), 2.80 (ddd, 2.32 Hz, 5.96 Hz, 14.24 Hz, 1H), 4.60 (m, 1H), 4.64 (d, 3.64 Hz, 2H), 5.63 (dt, 2.76 Hz, 6.4 Hz, 1H), 6.06 (dd, 5.48 Hz, 7.76 Hz, 1H), 7.22 (d, 8.24 Hz, 2H), 7.27 (d, 8.24 Hz, 2H), 7.84 (d, 8.24 Hz, 2H), 7.85 (s, 1H), 7.93 (d, 8.24 Hz, 2H);13C NMR (CDCl3, 100 MHz) delta 21.81, 21.87, 39.8, 63.8, 74.6, 79.8, 83.2, 89.5, 97.2, 126.3, 126.5, 129.4, 129.5, 129.6, 129.9, 138.9, 144.4, 144.7, 165.9, 166.2. HRMS (ESI): calcd for C24H23I2N2O5 (M+H)+ 672.9696, found 672.9693.
The synthetic route of 15813-09-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Wauchope, Orrette R.; Johnson, Cameron; Krishnamoorthy, Pasupathy; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Seley-Radtke, Katherine L.; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3009 – 3015;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem