1-Dodecylimidazole

Clourless Liquid

Imidazole 1 (0.68 g, 10 mmol), bromododecane (2.5 g, 10 mmol)Anhydrous potassium carbonate (2.76 g, 20 mmol) was placed in a 50 mL round-bottomed flask and dissolved in 20 mL of acetone.The combined solution was heated at reflux for 7 h. The acetone solvent was removed by rotary evaporation and subjected to column chromatography(Ethyl acetate as eluent), the ethyl acetate solvent was removed by rotary distillation under reduced pressure, and dried in vacuo, The yield of purified N-dodecylimidazole was 90percent.Equipped with a stirrer, a thermometer, a three-necked flask was added 0.440 g (11.0 mmol) NaOH, 0.714 g (10.5 mmol) of imidazole and 10 mL of dimethyl sulfoxide (DMSO), at 20 ° C ~ 25 ° C under nitrogen atmosphere stir until a clear solution, to which was added dropwise 2.49 g (10.0 mmol) of bromo dodecane, reacted for about 4 ~ 6 h, the reaction was poured into 10 mL of water and extracted with chloroform 3 × 10 mL, and then washed with water The chloroform layer was washed 4 to 5 times, and then dried over anhydrous MgSO 4, filtered to obtain a filtrate, the chloroform was removed to give a pale yellow liquid N- dodecyl imidazole 2.08 g, yield 88.1percent.imidazole in an eggplant-shaped flask (2.05g, 30mmol) was dissolved in tetrahydrofuran (15mL), there sodium hydroxide solution (sodium hydroxide 2.47g, 62 mmol, water 5g) was added and stirred for 1 hour at room temperature.Here bromo dodecane (7.48 g, 30 mmol) was added and stirred for 1 day at 55 ° C..After the reaction solution was washed with ethyl acetate, neutralized with hydrochloric acid, it was subjected to three washes with subsequent water.The organic layer was dried over anhydrous magnesium sulfate, filtration using a filter paper and evaporated after removing the magnesium sulfate SiOGeneral procedure: N-Dodecylimidazole was obtained following the procedure ofliterature [45]. To a solution of imidazole (0.7 g, 10 mmol) in NaOH(50percent) solution (1.0 g, 11 mmol), a solution of 1-bromododecane(2.5 g, 10 mmol) in THF (10 mL) was added dropwise. The obtainedmixture was refluxed for three days. After cooling, THF wasremoved by a rotary evaporator. The residue was extracted withdichloromethane three times. The combined organic layer waswashed with water and then dried over anhydrous Na2SO4. The fil-trate was concentrated and purified by a column chromatographyto produce clear yellow oil (2.0 g, 81percent).1H NMR (CDCl3): (ppm) = 0.83 (t, J = 5.1 Hz, 3H, CH3), 1.10–1.21(m, 18H, CH2), 1.69 (br, J = 7.0 Hz, 2H, CH2), 3.84 (t, J = 6.2 Hz, 2H, CH2), 6.89 (s, 1H, ImH), 7.04 (s, 1H, ImH), 7.44 (s, 1H, ImH).13C NMR(CDCl3): (ppm) = 13.7, 22.3, 26.1, 28.7, 28.9, 29.0, 29.2, 20.7, 31.5, 46.5, 118.3, 128.2, 136.6General procedure: A solution of imidazole 3 (30 mmol) in THF (60 mL) was treated with NaOH (25 mL, 40percent aq) and the alkyl bromide (30 mmol), and the reaction was refluxed overnight. The solvent was evaporated and the crude reaction mixture was extracted with CHGeneral procedure: A mixture of imidazole (30 mmol, 2.04 g), potassiumhydroxide (30 mmol, 1.68 g) and dimethyl sulfoxide(10 mL) was stirred for 2 h at room temperature. Afterthat, alkyl bromide (25.0 mmol of 1-bromohexane, 1-bromooctane, 1-bromodecane, 1-bromododecane, 1-bromotetradecane, 1-bromohexadecane, or 1-bromooctadecane)was dropped in slowly and the mixture was stirred for anadditional 4 h. Upon completion, water (30 mL) was addedto the resulting mixture followed by extraction with chloroform(5 x 30 mL). The combined organic layer wasdried over anhydrous magnesium sulfate and the filtratewas concentrated under reduced pressure. The residue wassubjected to flash chromatography with ethyl acetate aseluent to give N-alkyl imidazole. The respective yields ofN-hexyl imidazole, N-octyl imidazole, N-decyl imidazole, N-dodecyl imidazole, N-tetradecyl imidazole, N-hexadecylimidazole and N-octadecyl imidazole are 84.6, 82.3, 81.2, 80.5, 80.4, 79.8 and 79.6 percent.(2) Add 30 g of ethanol to a four-neck round bottom flask.Further, 32.6 g (0.064 mol) of N, N-dimethyl(1-iodopropyl)dodecyl ammonium iodide and 15.89 g (0.0672 mol) of N-dodecylimidazole were added.1 g of tetrabutylammonium iodide, The mixture was stirred and heated to 70 C, and the reaction was stirred for 36 hours. The ethanol was distilled off under reduced pressure, the solid was washed three times with chloroform, and the cake was vacuum dried at 60 C for 5 hours to obtain a crude product;The crude product was recrystallized three times from acetone to give the product 1-(N, N-dimethyldodecylammonium) propyl-3-dodecylimidinium iodide salt in a yield of 85%.A mixture of A mixture of A mixture of Add in a round bottom flask at a molar ratio of 2:1N-dodecyl imidazole and 2 were subjected to microwave reaction (80 W, 5 min). After the reaction was completed, the mixture was washed with ethyl acetate for 2-3 times, and the precipitate was collected by filtration, dried, and then added with anhydrous ethanol and heated to 50 ° C. Filtration while hot, collecting the filtrate, removing the solvent by rotary evaporation, and drying to give a white solid.That is, Cph-phC-Min-C, the yield is about 24.4percent.

A N-alkylated derivative of imidazole as antibacterial agent.

Molecular Weight:236.40
XLogP3:5.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:11
Exact Mass:236.225248902
Monoisotopic Mass:236.225248902
Topological Polar Surface Area:17.8
Heavy Atom Count:17
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes