1-Butyl-2-methyl-1H-imidazole

0.82 g of 2-methylimidazole (10 mmol) was dissolved in N, N-dimethylformamide (20 mL), heated to 40 ° C, and 0.84 g of potassium hydroxide (15 mmol) was added.After stirring for 15 min, 1.438 g of bromo n-butane (10.5 mmol) was added dropwise. After the addition was completed, the reaction was continued for 12 h.Cool to room temperature, dilute with water, extract 3 times with dichloromethane, combine the organic phase, wash 3 times with water, Adding water-removing agent anhydrous sodium sulfate to the organic phase, after standing for 1 h, suction filtration, and removing the solvent to obtain 1-butyl-2-methylimidazole, the yield is 97percent;0.82 g of 2-methylimidazole (10 mmol) was dissolved in N, N-dimethylformamide (20 mL), heated to 40 C, and 0.84 g of potassium hydroxide (15 mmol) was added.After stirring for 15 min, 1.438 g of bromo n-butane (10.5 mmol) was added dropwise. After the addition was completed, the reaction was continued for 12 h.Cool to room temperature, dilute with water, extract 3 times with dichloromethane, combine the organic phase, wash 3 times with water, Adding water-removing agent anhydrous sodium sulfate to the organic phase, after standing for 1 h, suction filtration, and removing the solvent to obtain 1.86 g (5 mmol) of dysprosium oxide was dissolved in about 51 mmol of a 25% by volume aqueous solution of nitric acid, Stirring until completely dissolved, Further, 2.76 g (20 mmol) of General procedure: Yield: 75%. Yellow oil. 1H NMR (400HMz, DMSO-d6, TMS) delta 9.63 (s, 1H), 7.79 (d, J = 4.0 Hz, 2H), 7.19 (t, J = 8.0 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 6.70 (d, J = 8.0 Hz, 2H), 5.36 (s, 2H), 4.14 (t, J = 8.0 Hz, 2H), 2.62 (s, 3H), 1.71 (t, J = 4.0 Hz, 2H), 1.28 (d, J = 8.0 Hz, 2H), 0.90 (t, J = 8.0 Hz, 3H). 13C NMR (100HMz, DMSO-d6, TMS) delta 157.83, 143.99, 135.79, 130.01, 121.78, 121.51, 117.95, 115.37, 114.33, 50.55, 47.43, 30.99, 18.91, 13.38, 9.53.General procedure: 2.3. Typical procedure for the synthesis of imidazolium ion tethered TsDPENs 5a. A solution mixture of the intermediate 3 (818 mg, 1.5 mmol) and 1, 2-dimethyl-1H-imidazole (173 mg, 1.8 mmol) in acetonitrile (2 mL) was heated at 70 C for 30 h. The solvent was removed under reduced pressure, and the residue was washed with a mixture solvent (hexane/ethyl acetate = 10:1) and dried in vacuo to give an intermediate 4a, to which HCl solution (3 mL, 4 M in dioxane) was added. The reaction mixture was stirred at room temperature for 5 h and the precipitation was filtered and washed with hexane to give the Boc deprotected intermediate, which was used for the next step directly without further characterization. The Boc-deprotected intermediate was subsequently neutralized by Na2CO3 (159 mg, 1.5 mmol) in MeOH (2 mL). The mixture was stirred for 5 h and the solvent was removed to dryness. The solid residue was dissolved in dry CH2Cl2 and filtered, and concentrated to give the product 5a as a white solid (550 mg, 68% yield for 2 steps).General procedure: A solution mixture of the intermediate 3 (818 mg, 1.5 mmol) and 1, 2-dimethyl imidazole (173 mg, 1.8 mmol) in acetonitrile (2 mL) was heated at 70 C for 30 h. The solvent was removed under reduced pressure, and the residue was washed with a mixture solvent (hexane/ethyl acetate = 10:1) and dried in vacuo to give an intermediate 4a, to which HCl solution (3 mL, 4 M in dioxane) was added. The reaction mixture was stirred at room temperature for 5 h and the precipitation was filtered and washed with hexane to give the Boc deprotected intermediate, which was used for the next step directly without further characterization. The Boc deprotected intermediate was subsequently neutralized by Na2CO3 (159 mg, 1.5 mmol) in MeOH (2 mL). The mixture was stirred for 5 h and the solvent was removed to dryness. The solid residue was dissolved in dry CH2Cl2 and filtered, and concentrated to give the product 5a as a white solid (550 mg, 68% yield for 2 steps).

Molecular Weight:138.21
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:138.115698455
Monoisotopic Mass:138.115698455
Topological Polar Surface Area:17.8
Heavy Atom Count:10
Complexity:93.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes