4,5-Diiodo-1H-imidazole

A mixture of KI (29.3 g, 176.0 mmol) and I2 (22.4 g, 88.0 mmol) inwater (60 mL) was addedto a solution of 1H-imidazole (3.0 g, 44.1 mmol) in 2 M NaOH(10.6 g, 264.5 mmol). The mixture was stirred at 20 C for 3 h andthen neutralized with 6 M HCl (pH 7). The resulting solid wascollected by filtration, recrystallization from ethanol to give 2 as agrey solid (14.0 g, 99.0percent). Mp 166e168 C. 1H NMR (300 MHz, DMSO-d6) d(ppm) 12.75 (br s, 1H), 7.8 (br s, 1H). MS (EI) m/z 320.8[MH].1H-imidazole (3 g, 44.1 mmol) was dissolved in 2M NaOH (10.6 g, 265.0 mmol)KI (29.3 g, 176.0 mmol)And I2 (22.4 g, 88.0 mmol) in 100 mL of water, Reaction at room temperature for 3 hours, Dropping 6M dilute hydrochloric acid to adjust the pH of the reaction solution to neutral, Produce a lot of solid, Suction filtration, Ethanol recrystallization, Obtained as an off-white solid, Yield 99.0percentStep a: 4, 5-diiodo-lH-imidazole[0547] A mixture of KI (149.4 g, 0.91 mol) and IThis compound was prepared following a literature procedure.22 To a solution of imidazole 19 (1.11 g, 16 mmol) in NaOH (4 M, 60 mL) wasadded a solution of KI (13.3 g, 80 mmol) and I2 (8.88 g, 35 mmol) inH2O (50 mL) dropwise. The resulting mixture stirred at RT for 10 h.After completion monitored by TLC, the mixture was reduced to pH=8with acetic acid, and the resulting white precipitate was filtered andwashed with cold water. The remaining solid was air dried to afford theproduct 20 as a white creamy solid (4.1 g, 80percent). m.p. 188–190 °C; Rf(hexane/ethyl acetate 1:1): 0.15; 1H NMR (300 MHz, d6-DMSO): δ 7.77(1H, s); 13C NMR (75 MHz, d6-DMSO): δ 141.8, 86.9. The spectroscopicdata matched that reported in the literature.43Preparation 70 Imidazole (8.4 g, 0.12 mol) and sodium hydroxide (14 g, 0.35 mol) are dissolved in 0.4 Lwater in an 1 L round bottom flask. Potassium iodide (80 g, 0.48 mol) and iodine (55 g, 0.22mol) are dissolved in 0.2 L water. This solution is added dropwise to the imidazole/sodium hydroxide mixture at room temperature. A white solid precipitates and the solution is stirred over night. Acetic acid and sodium thiosulfate are added until the solution is clear and neutral.The white solid is filtered and washed with water. Recrystallization from ethanol leads to finewhite crystals. (16 g, 41 percent). (14 g, 40 mmol) is dissolved in thf. An equimolar amount of potassium tert-butoxide (5.0 g, 44 mmol) is added to the solution at 0 C and the solution is stirred for 1h at that temperature. An equimolar amount of methyl iodide (2.7 mL, 44 mmol) is addeddrop wise to the solution at 0 C. A white solid precipitates and the otherwise clear solution is stirred at room temperature over night. The white solid is filtered and washed withdichloromethane. The solvent is removed from the filtrate and the resulting yellow solid isdissolved in dichloromethane and filtered. The solvent is removed from the filtrate and thesolid is dried under vacuum. (14 g, 94 %).To a solution of This compound was prepared following a literature procedure.23The mixture of

suzuki reaction

Molecular Weight:319.87
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:319.83074
Monoisotopic Mass:319.83074
Topological Polar Surface Area:28.7
Heavy Atom Count:7
Complexity:68
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes