* 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.
In a wide-necked Erlenmeyer flask areintroduced 6.8g (0.1 mol) imidazole, 45.5g (0.1 mol)1-bromohexadecan, 2.4g (7.5mmol)tertiobutyllammoniumbromid (TBAB). The mixtureis adsorbed on mixture of potassium carbonate andpotassium hydroxide ratio 1:1 and then irradiatedin an open vessel in a domestic microwave oven300 Watt power for 3 min by period of 20 secondstill it changed to pasty.After dilution in dichloromethane followedby washing with water, the organic phase isseparated and dried over sodium sulfate. Afterfiltration, the solvent is evaporated under vacuum.
88.3%
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; Inert atmosphere
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 after stirring until a clear solution, to which was added dropwise 2.21 g (10.0 mmol) of bromo decane, the reaction of about 4 ~ 6 h, the reaction was poured into 10 mL of water and extracted with chloroform 3 × 10 mL, washed with water The chloroform layer was 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- decyl-imidazole 1.84 g, yield 88.3percent.
86%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; Inert atmosphere
General procedure: This compound was synthesized using a variation of the procedure previously reported [32]. Sodium hydride (60percent dispersion in mineral oil, 1.56 g, 39.0 mmol) was suspended in dry THF (50 mL) under Ar at 0 °C. Imidazole (2.16 g, 31.7 mmol) was dissolved in dry THF (20 mL) and added drop-wise. After 30 min, 1-bromodecane (5.41 g, 24.5 mmol) was added. The resulting reaction mixture was then stirred at room temperature overnight. After careful addition of a few drops of water to quench the remaining sodium hydride, the organic solvent was removed in vacuo, and diethyl ether (50 mL) was added. This solution was then washed with water (3 × 50 mL), dried over anhydrous MgSO4, filtered, concentrated, and then purified by flash chromatography (ethyl acetate/hexanes = 10/1 (v/v)) to give the product as a light yellow oil (yield: 4.38 g, 86percent). Spectroscopic and purity data matched those reported for this compound [32].
81.2%
Stage #1: With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2 h; Stage #2: for 4 h;
General 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.
76%
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：
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[2] Oriental Journal of Chemistry, 2015, vol. 31, # 4, p. 2391 - 2394
[3] Patent: CN103951702, 2016, B, . Location in patent: Paragraph 0049; 0050
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[7] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 3, p. 408 - 413
[8] Polyhedron, 2017, vol. 127, p. 68 - 83
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[27] Molecules, 2018, vol. 23, # 9,
2
[ 288-32-4 ]
[ 693-58-3 ]
[ 33529-02-1 ]
Yield
Reaction Conditions
Operation in experiment
70%
With potassium carbonate In acetoneReflux
General procedure: Briefly, a mixture of imidazole (100 mmol), alkyl bromide (100 mmol) and K2CO3 (200 mmol) inacetone (200 mL) was refluxed overnight. Upon filtration and solvent removal, the remaining residuewas subjected to flash chromatography with ethyl acetate to produce >90percent yield.
Reference：
[1] Molecules, 2018, vol. 23, # 9,
3
[ 288-32-4 ]
[ 1002-69-3 ]
[ 33529-02-1 ]
Reference：
[1] European Journal of Medicinal Chemistry, 1990, vol. 25, # 5, p. 449 - 454
[2] Heterocycles, 1997, vol. 45, # 4, p. 715 - 722
[3] ChemCatChem, 2015, vol. 7, # 4, p. 616 - 624
4
[ 288-32-4 ]
[ 2050-77-3 ]
[ 33529-02-1 ]
Reference：
[1] Journal of the American Chemical Society, 2008, vol. 130, # 38, p. 12590 - 12591
[2] Journal of Materials Chemistry A, 2013, vol. 1, # 22, p. 6572 - 6578
5
[ 927690-64-0 ]
[ 33529-02-1 ]
Reference：
[1] Journal of Surfactants and Detergents, 2014, vol. 17, # 3, p. 383 - 390
With tetrabutylammomium bromide; potassium carbonate; potassium hydroxide; at 50℃;Microwave irradiation;
In a wide-necked Erlenmeyer flask areintroduced 6.8g (0.1 mol) imidazole, 45.5g (0.1 mol)1-bromohexadecan, 2.4g (7.5mmol)tertiobutyllammoniumbromid (TBAB). The mixtureis adsorbed on mixture of potassium carbonate andpotassium hydroxide ratio 1:1 and then irradiatedin an open vessel in a domestic microwave oven300 Watt power for 3 min by period of 20 secondstill it changed to pasty.After dilution in dichloromethane followedby washing with water, the organic phase isseparated and dried over sodium sulfate. Afterfiltration, the solvent is evaporated under vacuum.
88.3%
With sodium hydroxide; In dimethyl sulfoxide; at 20 - 25℃;Inert atmosphere;
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 after stirring until a clear solution, to which was added dropwise 2.21 g (10.0 mmol) of bromo decane, the reaction of about 4 ~ 6 h, the reaction was poured into 10 mL of water and extracted with chloroform 3 × 10 mL, washed with water The chloroform layer was 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- decyl-imidazole 1.84 g, yield 88.3%.
86%
General procedure: This compound was synthesized using a variation of the procedure previously reported [32]. Sodium hydride (60% dispersion in mineral oil, 1.56 g, 39.0 mmol) was suspended in dry THF (50 mL) under Ar at 0 C. Imidazole (2.16 g, 31.7 mmol) was dissolved in dry THF (20 mL) and added drop-wise. After 30 min, 1-bromodecane (5.41 g, 24.5 mmol) was added. The resulting reaction mixture was then stirred at room temperature overnight. After careful addition of a few drops of water to quench the remaining sodium hydride, the organic solvent was removed in vacuo, and diethyl ether (50 mL) was added. This solution was then washed with water (3 × 50 mL), dried over anhydrous MgSO4, filtered, concentrated, and then purified by flash chromatography (ethyl acetate/hexanes = 10/1 (v/v)) to give the product as a light yellow oil (yield: 4.38 g, 86%). Spectroscopic and purity data matched those reported for this compound [32].
81.2%
General 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 %.
76%
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].
General procedure: These compoundswere obtained fromthe reaction of the sodium salt of imidazole and 1-bromoalkanes, as follows: to a 3-necked round-bottom flask, provided with a reflux condenser, dropping funnel, and inlet for dry nitrogen was added a solution of imidazole (7.49 g; 0.11 mol) in dry ethanol (25 mL). Small pieces of sodium (2.53 g, 0.11 mol), were slowly introduced, the mixture was vigorously stirred until the metal has dissolved and then heated under reflux for 2 h. The mixture was cooled to room temperature; the appropriate 1-bromoalkane (0.10 mol; 16.50 g, 17.91 g, 19.31 g, 22.12 g for R ¼ C6; C7; C8 and C10, respectively)was added slowly (ca. 30 min); then the mixture was refluxed for 2 h. The mixture was cooled to room temperature, the precipitated NaBr was filtered off; the ethanol evaporated, the residual oilwas washed with water, and then dried with anhydrous MgSO4. The N-(1-alkyl)imidazoles were purified by fractional distillation (yields before distillation ca. 98%); their purity was confirmed with 1H NMR spectroscopy (results not shown).
With potassium carbonate; potassium hydroxide; In acetonitrile; at 80℃; for 16h;
General procedure: The zwitterionic surfactants synthesis was performed by adaptation of a literature procedure [22],which consists of two steps: the synthesis of an akyl imidazole molecule followed an alkylationutilizing 1,3-propane sultone. An imidazole solution (1.30 g, 0.0191 mol) in acetonitrile (10 mL) was added to a round-bottom flask containing potassium hydroxide (0.76 g, 0.013 mol) and potassium carbonate (0.50 g, 0.0036 mol).Then, a solution of n-alkyl bromide (0.012 mol) was added dropwise to the mixture, and the reaction proceeded for 16 h at 80 C under continuous stirring. After this period, the solids were removed byfiltration and the solution was diluted in 100 mL of ethyl acetate and washed three times with 50 mLof distilled water. The organic phase was dried with anhydrous magnesium sulfate, filtrated and thesolvent was evaporated under vacuum, giving a yellow residue. The given product was characterizedby 1H-NMR in CDCl3.
With tetraethylammonium iodide; sodium hydroxide; In toluene; for 10h;Reflux;
General procedure: A mixture of imidazole (22 mmol, 1 equiv) and the alkyl bromide (1equiv) in toluene (30 mL) in the presence of tetraethylammonium iodide(0.2 equiv) and sodium hydroxide (3 equiv) was heated at refluxtemperature for 10 h. The resulting mixture was cooled to room temperature,water was added, and the mixture extracted twice with ethylacetate. The combined organic extracts were washed with brine, driedover sodium sulfate, and concentrated. Purification by flash-columnchromatography on silica gel using ethyl acetate as an eluent, followedby drying under high vacuum gave the product.
1-Decylimidazole was synthesized according to previous literature. 1-Decylimidazole (5.49 g, 26.3 mmol) and 3-bromopropene (3.1 g, 26.3 mmol) were added to a 100 mL round-bottom flask containing 30 mL ethanol with condenser. The reaction mixture was stirred for 24 h. Solvent was then removed under reduced pressure. The crude product was washed three times with ether and dried in a vacuum oven at 50 C for 24 h to give the 1-allyl-3-decylimidazolium bromide (ADIm). 1-Allyl-3-decylimidazolium bromide: This compound was obtained in 97% as a yellow viscous oil. 1H NMR (DMSO-d6, 400 MHz): delta 9.30 (s, 1H, -N-CH-N-), 7.87 (s, 1H, -N-CH-CH-N-), 7.78 (s, 1H, -N-CH-CH-N-), 6.07 (m, 1H, -CH=CH2), 5.32 (dd, 2H, =CH2), 4.87 (d, 2H, -CH2-CH=CH2), 4.19 (t, 2H, -N-CH2-), 1.79 (m, 2H, -CH2-CH2-), 1.24 (broad, 14H, -CH2-CH3), 0.85 (t, 3H, -CH3).
86%
In neat (no solvent); at 20℃;
In a necked 50 ml equipped with acondenser, 4.9 ml (57 mmol) of allyl bromide areadded dropwise to 0.01 mol of 1a(2.92g) or 1b(2.08g) in room temperature and free solventconditions. The reaction mixture is refluxed andstirred until a solid slightly pasty appears. Thisresidue is triturated with ether and then filteredunder vacuum to obtain a solid dough.
1-decyl-3-methyl-1H-imidazolium tetrafluoroborate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
64%
In einem Autoklaven wurden 0,25 Mol 1-Decylimidazol, welches durch die Radziszewski-Reaktion aus Glyoxal, Formaldehyd, Ammoniak und 1-Decylamin zugaenglich ist (siehe Ullmann's Encyclopedia of Industrial Chemistry, 6th edition, 2000 electronic release, Chapter "IMIDAZOLE AND DERIVATIVES - Production), und 0,3 Mol Dimethylcarbonat in 100 ml Methanol zusammen mit 1,5 g Kaliumcarbonat und 0,1 g 18-Krone-6 12 Stunden auf 135C erhitzt. Nach dem Abkuehlen wurde der Reaktionsaustrag filtriert und mit 150 ml 50%iger waessriger Tetrafluoroborsaeure (Fa. Acros) versetzt. Nun wurde fuer eine Stunde unter Ruehren auf 50C erwaermt und anschliebetaend die waessrige Phase abgetrennt. Die verbleibende organische Phase wurde erneut mit 100 ml 50 %iger waessriger Tetrafluoroborsaeure versetzt, fuer eine weitere Stunde unter Ruehren auf 50C erwaermt und die waessrige Phase abgetrennt. Der organische Rueckstand wurde nun zweimal mit Cyclohexan extrahiert und danach im Vakuum bei 80C von Loesungsmittelresten befreit. Es wurden 0,16 Mol 1-Decyl-3-methylimidazolium-tetrafluoroborat erhalten, was einer Ausbeute von 64 % entspricht.
at 80℃; for 1h;Inert atmosphere; Microwave irradiation;
These ILs were obtained by the reaction of the appropriate N-(1-alkyl)imidazole with allyl chloride (3-chloro-1-propene), under microwave (MW) irradiation as follows, for 1-allyl-3-(1-hexyl) imidazolium chloride, AlHxImCl; 1-allyl-3-(1-heptyl)imidazolium chloride, AlHpImCl; 1-allyl-3-(1-octyl)imidazolium chloride AlOcImCl; 1-allyl-3-(1-decyl)imidazoliumchloride, AlDcImCl. N-(1-alkyl) imidazole (0.22 mol; 33.49 g, 36.58 g, 39.66 g, 45.8 g for R ¼ C6; C7; C8 and C10) and 3-chloro-1-propene (0.25 mol; 19.13 g) were mixed in a glass reactor, provided with a reflux condenser and inlet for dry nitrogen; the reactor was introduced in the cavity of the MWapparatus (Discover model DU-8316; CEM; Matthews) and irradiated under vigorous stirring for 1 h; 20W, 80 C. The product was dissolved in ethyl acetate (100 mL); the solution placed in a freezer (phase separation of the IL); the upper layer discarded; this process was repeated thrice. After removal of ethyl acetate, the IL was dried at 110 C,1 mmHg for 12 h. The yields were 98 1% (light yellow viscous liquid in all cases). 2.2.3.4 1-Allyl-3-(1-decyl)imidazolium chloride Light-yellow, viscous liquid. 1H NMR for C16H29N2Cl: 0.88 (3H, t, J = 7.2, H13), 1.19-1.40 (14H, m, H12), 1.92 (2H, dxt, J = 7.4, H11), 4.33 (2H, t, J = 7.6, H10), 5.07 (2H, d, J = 6.5, H6), 5.46 (1H, d, J = 7.6, H9), 5.48 (1H, s, H8), 6.02 (1H, m, H7) 7.20 (2H, s, H4 & H5), 11.03 (1H, s, H2). Calcd. for C16H29N2ClO4: C, 55.1%; H, 8.4%; N, 8.0%. Found: C, 55.1%; H, 8.5%; N, 8.1%.
α,ω-bis(3-decylimidazolium-1-yl)ethane bromide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
In acetonitrile; for 72h;Reflux;
A solution of <strong>[33529-02-1]1-decylimidazole</strong> (4.58 g, 22 mmol) and 1,2-dibromoethane (2.07 g, 11 mmol) in MeCN (20 mL) was refluxedfor 3 days. After cooling to room temperature, the precipitate wasfiltered and washed with THF three times. Drying in a vacuum ovengave colorless crystalline bromide salt (5.17 g, 78%). A solution ofthe bromide salt and NaI (4 equiv.) in deionized water was stirredfor 24 h at ambient temperature. The precipitate was filtered anddrying in a vacuum oven gave a colorless crystalline solid BII-10(5.36 g, 90% from the bromide salt). MP 265-267 C. 1H NMR(500 MHz, CDCl3, 23 C): delta 0.88 (t, J 8, 6H), 1.26-1.36 (m, 28H),1.96 (m, 4H), 4.26 (t, J 8, 4H), 5.30 (s, 4H), 7.47 (t, J 1.5, 2H), 8.52(t, J 1.5, 2H), 10.1 (s, 2H). 13C NMR (125 MHz, CDCl3, 23 C): delta 14,22, 26, 28.7, 29.0, 29.1, 29.2, 29.7, 32, 48, 51, 122, 124, 136.
3-decyl-1-[(±)-menthoxymethyl]imidazolium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
In hexane; at 20℃; for 3h;
General procedure: All reactions were performed under anhydrous conditions. A solution of freshly distilled trialkylamine, or 1-alkylimidazole, or 1-alkoxymethylimidazole (0.036mol) in hexane (30mL) was mixed. Chloromethyl (±)-menthyl ether (7.36g, 0.036mol) was added slowly and vigorously stirred for 60min at room temperature. After 120min, the phases were separated and the crude product was washed with dry hexane (3·30mL). The volatile materials were removed under reduced pressure at 60C overnight.
1-(4-vinylbenzyl)-3-decylimidazolium bis(trifluoromethylsulfonyl)amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
4-Vinylbenzyl chloride (1.00 g, 6.55 mmol) and <strong>[33529-02-1]1-decylimidazole</strong> (1.50 g, 7.20 mmol) were stirred in acetonitrile (40 mL) at reflux for 18 h. Upon cooling, the reaction mixture was concentrated to form a yellow viscous oil and washed with Et2O (3 × 40 mL). The resulting oil was then dissolved in H2O (40 mL). LiTf2N (2.26 g, 7.87 mmol) was added, and then the resulting mixture stirred at room temperature for 12 h. A yellow oil was then extracted from this aqueous mixture with CH2Cl2 (3 × 50 mL). The CH2Cl2 layer was then washed with H2O (3 × 100 mL), dried over anhydrous MgSO4, filtered, and concentrated to give monomer 2c as a light yellow oil (yield: 3.49 g, 88%). 1H NMR (300 MHz, CDCl3): delta8.88 (s, 1H), 7.44 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 7.24 (dt, J = 12.0, 2.0 Hz, 2H), 6.69 (dd, J = 17.6, 10.9 Hz, 1H), 5.78 (d, J = 17.6, 1H), 5.31 (d, J = 10.8, 1H), 5.31 (s, 2H), 4.16 (t, J = 7.4 Hz, 2H), 1.93-1.76 (m, 2H), 1.39-1.17 (m, 14H), 0.87 (t, J = 7.0 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta139.19, 135.83, 135.58, 131.69, 129.29, 127.41, 122.45, 122.24, 122.08, 117.82, 115.76, 53.46, 50.49, 31.95, 30.18, 29.51, 29.40, 29.34, 28.96, 26.24, 22.77, 14.21. IR (neat): 3146.88, 2927.24, 2856.85, 1560.77, 1456.43, 1348.21, 1182.03, 1133.87, 1053.89, 990.02, 914.86, 830.80, 788.70, 739.55, 653.29. HRMS (ES) calcd. for C24H33F6N3O4S2 (M+ Tf2N-): 605.1817; observed: 605.2435. Since imidazolium-based ionic liquid compounds are known in the literature to have combustion issues for C, H, and N elemental analysis [34], the 1H and 13C NMR spectra for isolated 2c are provided in the Supplementary Data to help confirm its purity.
With potassium carbonate; potassium hydroxide; In acetone; at 0 - 20℃; for 120h;
General procedure: A solution of 1,3-propane sultone (1.34 g, 0.011 mol) in acetone (12 mL) was slowly added to the flask containing the akyl imidazole (0.012 mol) at 0 C. The reaction mixture was heated to the room temperature and, then, stirred for 5 days. After that, the reaction solution was filtrated giving the product as a solid. The solid was washed two times with a mixture of 1:1 hexane/dichloromethane and driedunder vacuum, giving the zwitterionic surfactant in 51% yield. The given product was characterized by 1H-NMR in CDCl3.
1-propargyl-3-decyl-1,3-diazanyl-2,4-cyclopentadiene bromide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
In ethanol; at 50℃; for 24h;
N-alkyl derivatized yne monomers were synthesized via the quaternization reaction represented in Scheme 1 . Alkyl imidazoles 2a-d were prepared following the method in literature with modifications [17] . An example synthesis procedure for 3a is given as follows. 1-Hexylimidazole 2a and 3-bromopropyne (mole ratio 1:1) were added to anhydrous ethanol. The synthesis was carried out in a round bottom flask equipped with a stirrer and a condenser at 50 C for 24 h. Then, solvent was removed using a rotary evaporator. The crude product was washed three times with ether and dried in a vacuum oven at 50 C for one day to obtain yne monomer 3a. This same procedure was used to synthesize modified yne monomers 3b-d.
1-(4-bromobutyl)-3-decylimidazolium bromide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76.8%
In acetone; at 50℃;Inert atmosphere;
General procedure: 1,4-dibromobutane (36.0 mmol, 7.70 g) was dissolved indry acetone (50 mL) and the obtained N-alkyl imidazole(9.0 mmol of N-hexyl imidazole, N-octyl imidazole, Ndecylimidazole, or N-dodecyl imidazole) was addedgradually. The reaction mixture was refluxed at 50 Cunder nitrogen atmosphere and the reaction was monitoredby TLC analysis. After the reaction finished, the solventwas removed under reduced pressure, and subsequently theun-reacted 1, 4-dibromobutane was washed thoroughlywith hexane. The collected viscous liquid was purified bysilica column chromatography with mixtures of acetone/methanol (10:1, by vol) as eluent to afford 1-(4-bromobutyl)-3-alkylimidazolium bromide. The yields of 1-(4-bromobutyl)-3-hexylimidazolium bromide, 1-(4-bromobutyl)-3-octylimidazolium bromide, 1-(4-bromobutyl)-3-decylimidazolium bromide and 1-(4-bromobutyl)-3-dodecylimidazoliumbromide are 72.5, 74.1, 76.8 and 80.3 %,respectively.
1-decyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2H-1λ4,3λ4-imidazol-2-ylium iodide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In neat (no solvent); at 120℃; for 6h;
General procedure: In a 250 mL two-neck round bottom flask equipped with a condenser linked to the vacuum-argon line, N-butylimidazole (title 99% w/w, Alfa Aesar) (4.2 g, 33.4 mmol) was charged and after degassing with three vacuum/argon cycles, 1H,1H,2H,2H-perfluorooctyliodide 96% w/w, Aldrich) (23.8 g, 50.1 mmol) was added. After three more vacuum/argon cycles the temperature of the oil bath was increased from 25 C to 120 C in 10 min. After heating for 6 h, NMR analysis of the crude reaction mixture (Fig. 6S, ESI) showed that the reaction went to completion and the occurrence, together with the target molecule C4-I, of the by-products N-butyl-imidazolium iodide and 1H,1H,2H-perfluoro-1-octene ( Scheme 1 ) typical of a Hofmann elimination of the imidazolium salts [29-31]. By cooling the presence of two phases was observed: a viscous red liquid (containing C4-I, N-butyl-imidazolium iodide and C6F13CH = CH2) at the top and a pale yellow liquid (the unreacted 1H,1H,2H,2H-perfluorooctyl iodide with C6F13CH = CH2) at the bottom. The phases were separated by decantation and the viscous red liquid washed three times with petroleum ether (3 * 50 mL) and three times with diethyl ether (3 * 50 mL). The solvent and the volatile by-product C6F13CH = CH2 (bp = 102-104) were eliminated under vacuum (30 C/53 Pa). After the work-up 1H NMR of the red oil showed peaks of C4-I (75%) and of N-butyl-imidazolium iodide (25%). The raw product (20 g) was dissolved in 20 mL of dichloromethane and filtered under argon on anhydrous celite (40 g) previously wetted with 200 mL of dichloromethane. The filtration was repeated two times. Celite was then washed with 80 mL of dichloromethane. Evaporation of the solvent (30 C/53 Pa) gives a red sticky wax with a yield of 75.1% (15.0 g, 25 mmol).
Equipped with a stirrer, a thermometer, a three-necked flask was added 1.67 g (8.0 mmol) N- decyl-imidazole, 0.56 g (4.4 mmol) 1,3- dichloro-2-propanol, at 115 ~ 125 C The reaction was stirred after, TLC tracking progress of the reaction, the reaction of about 8 ~ 12 h, the crude product was mixed with chloroform and ethyl acetate solvent was recrystallized to give a white powdery solid 1,1'-didecyl-3,3 '- (2- hydroxy-1,3-propylene) imidazole hydrochloride 1.42 g, yield 65.2%.
General procedure: A mixture of 9-bromo-10-(bromomethyl)anthracene (2) (1 mmol) and the relevant N-alkyl imidazoles(4a-f) or N-benzyl benzimidazoles (7a-e) in THF (15 ml)was refluxed at open condition for 24 h. By this time the products8a-f and 9a-e appeared as yellow precipitates which were isolatedby filtration, washed with little THF, then with ether and were airdried.Yield: 85-89% (imidazolium salts) and 80-87% (benzimidazoliumsalts).
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