1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE

off-white to beige powder

In a flask, the imine(3 g, 10 mmol) was dissolved in tetrahydrofuran(25 ml), followed by dropwise addition of chloromethyl ethyl ether(1.04 g, 11 mmol), the mixture was stirred under N2 at 40 °C for 18 h, and then ethyl ether(25 ml) was added to separate white solid, the solid was filtered and washed with ethyl ether, the white solid was dried under vacuum affording 2.2 g IMes*HCl in 65percent yield. 1H NMR(CDCl3, 400 MHz): δ 2.15(s, 12H), 2.33(s, 6H), 7.00(s, 4H), 7.70(s, 2H), 10.73(s, 1H); 13C NMR(CDCl3, 100 MHz): δ 17.6, 21.1, 124.8, 129.8, 130.7, 134.1, 139.2, 141.1.In a flask, the imine (3.0 g, 10 mmol) was dissolved in tetrahydrofuran (25 ml), followed by dropwise addition of chloromethyl ethyl ether (1.04 g, 11 mmol), the mixture was stirred under NChloromethylethyl ether (0.300 g, 3.17 mmol) in THF (1 mL) was added to a solution of glyoxal-bis(2, 4, 6-trimethylphenyl)imine (0.900 g, 3.08 mmol) in THF (10 mL). After 30 min stirring under nitrogen at room temperature, a white solid precipitated, which was collected by suctionfiltration and recrystallized from n-hexane to yield product as a white powder (0.49 g, 48 percent).Charging a 1 L round bottom flask with methanol (500 mL), 2, 4, 6-trimethylaniline (97 mL, 689 mmol), glyoxal (40 wt percent solution in water, 38.8 mL, 313.5 mmol), and formic acid (1 mL).Stirring the resulting mixture for 3 hours at room temperature.Filtering the yellow precipitate formed, (1) Diagram D.Washing precipitate with cold methanol.Drying precipitate in vacuo overnight (91.0percent, 74.5 g, 313.5 mmol).Charging a 5 L round bottom flask with 1 (100 g, 342 mmol) and ethyl acetate (2000 mL).Cooling solution to 0° C.Charging a 500 mL Erlenmeyer flask with paraformaldehyde (13.35 g, 445 mmol) and HCl (4N in dioxane, 136.9 mL, 548 mmol, ).Stirring this solution for 10 minutes then add it to the cooled solution of 1.Stirring the reaction mixture for a total reaction time of 2.5 hours.Collecting the beige precipitate formed by filtration.Drying the precipitate.Dissolving precipitate in 100 ml of dichloromethane.Adding Sodium bicarbonate (10.0 g) to the solution.Stirring the mixture for 1 hour or until the solution stopped bubbling.Filtering the solution to remove the solids.Precipitating the product with 100 ml of diethyl etherCollecting product by filtrationWashing product with etherDrying product in vacuo to yield IMes.HCl (2) as an off-white powder (66percent, 77.1 g, 226 mmol). Synthesizing of l, 3-Bis(2, 4, 6-trimethylphenyl)imidazoliιim chloride (IMes HCI, 2) by:; Charging a IL round bottom flask with methanol (500 mL), 2, 4, 6- 5 trimethylaniline (97 mL, 689 mmol), glyoxal (40 wt percent solution in water, 38.8 mL, 313.5 mmol), and formic acid (ImL).Stirring the resulting mixture for 3 hours at room temperature. Filtering the yellow precipitate formed, (1) Diagram D. Washing precipitate with cold methanol. 0 Drying precipitate in vacuo overnight (91.0percent, 74.5 g, 313.5 mmol).Charging a 5 L round bottom flask with 1 (100 g, 342 mmol) and ethyl acetate (2000 mL).Cooling solution to O

Important pharmaceutical intermediates

Molecular Weight:340.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:340.1706265
Monoisotopic Mass:340.1706265
Topological Polar Surface Area:8.8
Heavy Atom Count:24
Complexity:335
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes