* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1 h; Stage #2: at 20℃; for 16 h;
(Reference Example 18) Synthesis of 1-propyl-1H-imidazole: Sodium hydride (55percent, 0.966 g, 22.1 mmol) was added to a solution of imidazole (1.37 g, 20.1 mmol) in tetrahydrofuran (50.0 mL) at room temperature. The reaction liquid was stirred at the same temperature for 1 hour, and then, 1-bromopropane (5.48 mL, 60.3 mmol) was added at room temperature. The reaction liquid was stirred at the same temperature for 16 hours. The reaction liquid was filtered through Celite and washed with tetrahydrofuran, and then the filtrate and the washing solution were concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, chloroform/methanol) to obtain 1-propylimidazole (2.07 g, 18.8 mmol, 93percent) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ: 0.93 (3H, t, J=7.2 Hz), 1.81 (2H, td, J=7.2, 14.4 Hz), 3.90 (2H, t, J=7.2 Hz), 6.91 (1H, s), 7.06 (1H, s), 7.46 (1H, s).
86%
Stage #1: With sodium hydride In tetrahydrofuran; hexane at 20℃; Stage #2: at 60 - 65℃; Reflux
General procedure: A THF solution of imidazole (1 equivalent) is added to a suspension of NaH (1.1 equivalents) (60 percent in paraffin oil) previously stirred in n-hexane for 15 min. The imidazole solution is added dropwise over a period of 25–30 min at 5–10 °C to avoid vigorous liberation of H2 gas. Once H2 gas evolution ceased, the suspension of imidazole sodium is stirred at RT for 2–3 h to favor complete formation of NaIm salt. To this suspension, corresponding R–Br (0.90 equivalents), was added dropwise over a period of 30 min and further stirred for 3 h or longer to achieve uniform mixing indicated by vertex formation. The thoroughly stirred reaction mixture then was refluxed overnight at 60–65 °C. The reaction mass was then allowed to cool and filtered to remove NaBr salt. THF is removed under a rotary evaporator and DCM is added to the resultant brownish liquid followed by the addition of activated charcoal and anhydrous Na2SO4, stirred for 2–3 h and filtered over Celite. A Celite bed was washed with DCM and DCM removed under vacuum leading to a pale yellowish liquid. The NMR spectra checked in CDCl3 and matches with literature reports [20].
78%
Stage #1: With sodium hydroxide In dimethyl sulfoxide at 20℃; for 1.5 h; Stage #2: at 20℃;
General procedure: Imidazole (3)/benzimidazole(5) (10 mmol) was dissolved in 10 ml of DMSO and solid NaOH(15 mmol) was then added it. The resulting pale yellow suspensionwas stirred in air at room temperature for 1.5 h, after which, thealkyl bromides or benzyl chlorides (15 mmol) were added andallowed to react until completion (TLC). Water (50 ml) was thenadded and the products were extracted with ethyl acetate. Combinedorganic layers were washed several times with water, thenwith brine, dried over Na2SO4 and subjected to chromatographicpurification over silica (100–200 mesh) using MeOH: EtOAc 5:95(v/v) as the mobile phase. Compounds 4a-f were isolated as yellowoils whereas, the compounds 7a-e were white solid. Spectroscopic data of the N-alkyl imidazoles are in accord with earlier literatureand thus are not shown here [30].
Reference：
[1] Dalton Transactions, 2013, vol. 42, # 5, p. 1385 - 1393
[2] Patent: EP3263565, 2018, A1, . Location in patent: Paragraph 0433; 0434
[3] Research on Chemical Intermediates, 2016, vol. 42, # 6, p. 5587 - 5596
[4] New Journal of Chemistry, 2007, vol. 31, # 6, p. 879 - 892
[5] Polyhedron, 2017, vol. 127, p. 68 - 83
[6] Crystal Growth and Design, 2013, vol. 13, # 7, p. 3068 - 3077
[7] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 17, p. 2863 - 2865
[8] New Journal of Chemistry, 2012, vol. 36, # 3, p. 702 - 722
[9] Chemische Berichte, 1882, vol. 15, p. 646[10] Justus Liebigs Annalen der Chemie, 1882, vol. 214, p. 309,320
[11] Bioscience, Biotechnology, and Biochemistry, 1992, vol. 56, # 1, p. 161 - 162
[12] Chemistry Letters, 2005, vol. 34, # 3, p. 442 - 443
[13] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 423 - 427
[14] Journal of the Chinese Chemical Society, 2013, vol. 60, # 7, p. 745 - 754
[15] Chemical Biology and Drug Design, 2014, vol. 83, # 3, p. 278 - 288
[16] Molecules, 2014, vol. 19, # 8, p. 11741 - 11759
2
[ 288-32-4 ]
[ 107-08-4 ]
[ 35203-44-2 ]
Reference：
[1] Synthetic Communications, 2010, vol. 40, # 15, p. 2291 - 2301
[2] Journal of Materials Chemistry A, 2013, vol. 1, # 22, p. 6572 - 6578
3
[ 31410-01-2 ]
[ 35203-44-2 ]
Reference：
[1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1300 - 1303
(Reference Example 18) Synthesis of 1-propyl-1H-imidazole: Sodium hydride (55%, 0.966 g, 22.1 mmol) was added to a solution of imidazole (1.37 g, 20.1 mmol) in tetrahydrofuran (50.0 mL) at room temperature. The reaction liquid was stirred at the same temperature for 1 hour, and then, 1-bromopropane (5.48 mL, 60.3 mmol) was added at room temperature. The reaction liquid was stirred at the same temperature for 16 hours. The reaction liquid was filtered through Celite and washed with tetrahydrofuran, and then the filtrate and the washing solution were concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, chloroform/methanol) to obtain 1-propylimidazole (2.07 g, 18.8 mmol, 93%) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 0.93 (3H, t, J=7.2 Hz), 1.81 (2H, td, J=7.2, 14.4 Hz), 3.90 (2H, t, J=7.2 Hz), 6.91 (1H, s), 7.06 (1H, s), 7.46 (1H, s).
86%
General procedure: A THF solution of imidazole (1 equivalent) is added to a suspension of NaH (1.1 equivalents) (60 % in paraffin oil) previously stirred in n-hexane for 15 min. The imidazole solution is added dropwise over a period of 25-30 min at 5-10 C to avoid vigorous liberation of H2 gas. Once H2 gas evolution ceased, the suspension of imidazole sodium is stirred at RT for 2-3 h to favor complete formation of NaIm salt. To this suspension, corresponding R-Br (0.90 equivalents), was added dropwise over a period of 30 min and further stirred for 3 h or longer to achieve uniform mixing indicated by vertex formation. The thoroughly stirred reaction mixture then was refluxed overnight at 60-65 C. The reaction mass was then allowed to cool and filtered to remove NaBr salt. THF is removed under a rotary evaporator and DCM is added to the resultant brownish liquid followed by the addition of activated charcoal and anhydrous Na2SO4, stirred for 2-3 h and filtered over Celite. A Celite bed was washed with DCM and DCM removed under vacuum leading to a pale yellowish liquid. The NMR spectra checked in CDCl3 and matches with literature reports [20].
78%
General procedure: Imidazole (3)/benzimidazole(5) (10 mmol) was dissolved in 10 ml of DMSO and solid NaOH(15 mmol) was then added it. The resulting pale yellow suspensionwas stirred in air at room temperature for 1.5 h, after which, thealkyl bromides or benzyl chlorides (15 mmol) were added andallowed to react until completion (TLC). Water (50 ml) was thenadded and the products were extracted with ethyl acetate. Combinedorganic layers were washed several times with water, thenwith brine, dried over Na2SO4 and subjected to chromatographicpurification over silica (100-200 mesh) using MeOH: EtOAc 5:95(v/v) as the mobile phase. Compounds 4a-f were isolated as yellowoils whereas, the compounds 7a-e were white solid. Spectroscopic data of the N-alkyl imidazoles are in accord with earlier literatureand thus are not shown here [30].
A. 1-[4-(4-Chlorophenyl)butyl]-3-propylimidazolium chloride Add 7.13 g (0.035 mole) of 1-chloro-4-(4-chlorobutyl)benzene to 3.52 g (0.032 mole) of <strong>[35203-44-2]1-propyl-1H-imidazole</strong> and heat to 130° C. for 18 hours. Follow the progress of reaction by NMR (CDCl3). At the completion of the reaction, cool to room temperature to obtain the title compound.
(4-nitrophenyl)[2-(1-propyl)imidazolyl]methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a solution of <strong>[35203-44-2]<strong>[35203-44-2]1-propylimidazol</strong>e</strong> (8.0 g) in dry THF (100 ml), 1.6M n-butyllithium hexane solution (54.5 ml) was at 0°C under argon atmosphere. After the mixture was allowed to be at room temperature and was stirred for 2 hours, a solution of 4-nitrobenzaldehyde (9.97 g) in dry THF (100 ml) was added dropwise to the mixture at -78°C. The mixture was allowed to be at room temperature and was stirred overnight, and then, 1N hydrochloric acid was added to the mixture at 0°C. The mixture was neutralized with potassium carbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from ethyl acetate-diisopropyl ether, to give (4-nitrophenyl)[2-(1-propyl)imidazolyl]methanol (5.26 g) as brown crystals. 1H-NMR (200 MHz, CDCl3) delta 0.77 (3H, t, J = 7.4 Hz), 1.42 to 1.72 (2H, m), 3.70 (2H, t, J = 7.4 Hz), 5.99 (1H, s), 6.86 (1H, s), 6.94 (1H, s), 7.54 (2H, d, J = 8.8 Hz), 8.20 (2H, d, J = 8.8 Hz). Elemental Analysis C13H15N3O3 Calcd. C, 59.76; H, 5.79; N, 16.08; Found. C, 59.85; H, 7.73; N, 16.04.
2-(4-nitrophenyl)-1-(1-propylimidazol-2-yl)ethanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a solution of <strong>[35203-44-2]<strong>[35203-44-2]1-propylimidazol</strong>e</strong> (13.5 g) in dry tetrahydrofuran (200 ml) was added dropwise n-butyllithium(1.6 m hexane solution, 91.9 ml) under argon atmosphere at -78°C,. The mixture as it is was stirred for 30 minutes, and added dropwise to a solution of N-methoxy-N-methyl-2-(4-nitrophenyl)acetoamide (27.5 g) in dry tetrahydrofuran (300 ml) under argon atmosphere at -78°C,. The mixture was allowed to be at room temperature and stirred overnight, and 6N hydrochloric acid (30 ml) was added to the mixture at 0°C. The mixture was neutralized with potassium carbonate, extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate = 2:1). The obtained solid was washed with hexane-diisopropyl ether to give 2-(4-nitrophenyl)-1-(<strong>[35203-44-2]1-propylimidazol</strong>-2-yl)ethanone (1.25 g) as red crystals. m.p. 95.0 to 96.0°C 1H-NMR (200 MHz, CDCl3) delta 0.90 (3H, t, J = 7.6 Hz), 1.68 to 1.85 (2H, m), 4.32 (2H, t, J = 7.4 Hz), 4.56 (2H, s), 7.14 (1H, d, J = 0.8 Hz), 7.22 (1H, d, J = 0.8 Hz), 7.52 (2H, d, J = 8.6 Hz), 8.19 (2H, d, J = 8.6 Hz). Elemental Analysis for C14 h15N3O3 Calcd. C, 61.53; H, 5.53; N, 15.38: Found C, 61.70; H, 5.56; N, 15.06.
1-propyl-3-(4-phenoxybutyl)-1H-imidazol-3-ium bromide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
In toluene; at 80℃; for 5h;Sonication; Green chemistry;
General procedure: Alkylimidazole (1 eq) and the appropriate alkyl bromide (1 eq) were placed in a closedvessel and exposed to irradiation for 5 h at 80 °C using a sonication bath. The product was thencollected as described in the conventional procedure outlined earlier.
In acetone; at 100℃; for 12h;Autoclave; High pressure;
General procedure: All of the imidazolium salts were synthesized with good yields (>85percent, see Supporting Information online) by thequaternization of N-substituted imidazole with corresponding iodide alkane, according to Scheme 1. Take 1-hexadecyl-3-methylimidazolium iodide (1a) for example: the mixture of 1-methylimidazole and 1-iodohexadecane was dissolved in acetone. Then the solution was placed into a 58 mL Teflon-lined, stainless-steel autoclave and heated at 100 °C for 12 h. The final product was obtained by multiple crystallizations from diethyl ether. The purity of all the imidazolium salts was confirmed by 1H NMR and elemental analysis (see Supporting Information online).
In acetone; at 100℃; for 12h;Autoclave; High pressure;
General procedure: All of the imidazolium salts were synthesized with good yields (>85percent, see Supporting Information online) by thequaternization of N-substituted imidazole with corresponding iodide alkane, according to Scheme 1. Take 1-hexadecyl-3-methylimidazolium iodide (1a) for example: the mixture of 1-methylimidazole and 1-iodohexadecane was dissolved in acetone. Then the solution was placed into a 58 mL Teflon-lined, stainless-steel autoclave and heated at 100 °C for 12 h. The final product was obtained by multiple crystallizations from diethyl ether. The purity of all the imidazolium salts was confirmed by 1H NMR and elemental analysis (see Supporting Information online).
1,2-bis(1-propylimidazol-3-ium-3-yl)ethane*2Br-[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
In toluene; at 100℃; for 24h;Reflux;
General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.
1,3-bis(1-propylimidazol-3-ium-3-yl)propane*2Br-[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
In toluene; at 100℃; for 24h;Reflux;
General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.
In ethanol; at 69.99℃; for 24h;Inert atmosphere;
General procedure: The dicationic imidazolium-based ionic compounds were synthesized, as shown in Scheme 1 [29]. Typically, the reaction flask was charged with 1-methylimidazole and 1,2-dibromoethane (molar ratio of 2:1) in ethanol (15mL). Then the miscible liquids were heated to 343.15K, stirred for 24h under dry nitrogen. Then, the volatile material is removed from the resulting solution under reduced pressure at 323.15K. The water was then added. The aqueous phase was extracted three times with dichloromethane. The extract was recrystallized from ethyl acetate to obtain a white solid. The solid product was dried in vacuum for 24h in 313K, and the ILs with a yield of about 90.4percent was obtained [30,31]. The rest of the ionic compounds were synthesized in a similar way.
1,4-bis(1-propylimidazol-3-ium-3-yl)butane*2Br-[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
In toluene; at 100℃; for 24h;Reflux;
General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.
[Zn(1-propylimidazole)3]2V4O12 monohydrate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
In water; at 20 - 120℃; for 74h;Autoclave;
General procedure: A mixture of Zn(CH3COO)22H2O (0.1705 g, 0.8 mmol), NH4VO3(0.1404 g, 0.8 mmol), eIM (0.3 mL), and H2O (8 mL) was heated at about 120 °C for 72 h. After the mixture was cooled to room temperature, yellow crystals were isolated from the mixture.Yield: 76percent (based on NH4VO3); Anal. Calcd. for C30H48Zn2N12V4O12(percent): C, 32.63; H, 4.35; N, 15.23. Found: C, 32.76; H, 4.41; N, 15.21.
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