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Structure of 1739-84-0 * Storage: {[proInfo.prStorage]}
* 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.
As shown in Fig. 1, a high-pressure microreactor in which a micro mixer was incorporated at three locations was used.An aqueous solution of methylamine (0.33 mol / L) was fed from the tank 1 through the pump 1 at a flow rate of 0.68 mL / min, an aqueous solution of acetaldehyde (0.33 mol / L) At a flow rate of 63 mL / min, from the tank 3 via the pump 3AmmoniumNear water(0.33 mol / L) was flowed at a flow rate of 1.13 mL / min, an aqueous glyoxal solution (0.33 mol / L) was flowed from the tank 4 via the pump 4 at 0.56 mL / flow rate, and a reaction pressure of 30 MPa The reaction was carried out under pressure. The final flow rate was 8.0 mL / min. The temperature of the first micromixer and the reaction tube of 2.4 m is controlled in a thermostatic chamber 1 keeping the temperature at 25 ° C. The mixture and reaction of methylamine and acetaldehyde in the first micromixer and reaction tube Was done. In the next second micromixer in which the aqueous solution and ammonia water are mixed by this mixing, they are mixed in a thermostatic chamber 2 kept at a temperature of 25 ° C., and after sufficient mixing and reaction in a 0.1 m reaction tube After that, glyoxal was mixed, after which 1Sufficient reaction was carried out in a 0 m reaction tube. Next, the temperature of the reaction part was adjusted to 70 ° C., and the reaction was carried out in a 25 m reaction tube. Finally, it was cooled down to 5 ° C. with a heat exchanger, depressurized to normal pressure via a discharge pressure valve, and the aqueous solution obtained while cooling with ice water (0 ° C. to 4 ° C.) was collected. In this case, the reaction time (residence time in the reaction part) was 37 seconds. For the analysis, if necessary diluted 10 times with ice water and analyzed immediately using a gas chromatograph. The reaction tube was made of stainless steel (SUS 316) and had an inner diameter of 0.5 mm. As a result, the objective 1,2-dimethylimidazole was obtained in a yield of 85.1percent.For measurement of the above quantitative yield, a gas chromatograph (GC 6890, hydrogen flame ionization detector) manufactured by Agilent was used and the column was HP INNOWAX manufactured by J & W Co., inner diameter 0.32 mm, film thickness 0.25 μm, length Analysis was carried out using 30 m. The yield of each product was determined by preparing a calibration curve for each compound using various concentrations of the product (1,2-dimethylimidazole, 1-methylimidazole, 2-methylimidazole, imidazole) Concentration of each product obtained was converted from a calibration curve, and the yield of each product was calculated. The respective yields were 1,2-dimethylimidazole 85.1percent, 1-methylimidazole 6.27percent, 2-methylimidazole 6.59percent and imidazole 2.06percent.
Reference：
[1] Patent: JP2016/222615, 2016, A, . Location in patent: Paragraph 0051-0052
2
[ 693-98-1 ]
[ 616-38-6 ]
[ 1739-84-0 ]
Yield
Reaction Conditions
Operation in experiment
85%
at 120 - 145℃;
To 500 ml of the input three-mouth flask in 128g of 2 - methyl imidazole and 100 ml of DMF, oil bath heated to 120 °C, the temperature next adds by drops 280g dimethyl carbonate, control temperature at 135 - 140 °C, dropping time control in 5 - 6h, after dropping in the 145 °C preserving 2h, thermal insulation after the completion of the, gas chromatographic analysis of 2 - methyl imidazole conversion 98percent. In 4.0KPa, 90 °C conditions under reduced pressure distillation, evaporate the solvent. The use of the rectifying device, in 4.0KPa under vacuum, collecting 100 - 110 °C of distillate, high purity can be obtained of the 1, 2 - dimethyl imidazole of the finished product, yield 85percent, gas chromatographic analysis of the content of 99.5percent.
Reference：
[1] Synthesis, 1986, # 5, p. 382 - 383
[2] Liebigs Annalen der Chemie, 1987, p. 77 - 80
[3] Patent: CN106045912, 2016, A, . Location in patent: Paragraph 0020; 0021; 0023; 0024; 0025; 0026; 0027
3
[ 693-98-1 ]
[ 74-88-4 ]
[ 1739-84-0 ]
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1991, vol. 27, # 10, p. 1140 - 1144[2] Khimiya Geterotsiklicheskikh Soedinenii, 1991, vol. 27, # 10, p. 1414 - 1418
[3] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 193 - 197
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1995, # 1, p. 9 - 10
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 5, p. 547 - 550[3] Khimiya Geterotsiklicheskikh Soedinenii, 1994, # 5, p. 624 - 628
7
[ 79-20-9 ]
[ 107-15-3 ]
[ 534-26-9 ]
[ 1739-84-0 ]
[ 693-98-1 ]
Reference：
[1] J. Appl. Chem. USSR (Engl. Transl.), 1991, vol. 64, # 7.2, p. 1446 - 1447[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1991, vol. 64, # 7, p. 1590 - 1591
[3] J. Appl. Chem. USSR (Engl. Transl.), 1991, vol. 64, # 7.2, p. 1446 - 1447[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1991, vol. 64, # 7, p. 1590 - 1591
[5] J. Appl. Chem. USSR (Engl. Transl.), 1991, vol. 64, # 7.2, p. 1446 - 1447[6] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1991, vol. 64, # 7, p. 1590 - 1591
8
[ 24134-09-6 ]
[ 1739-84-0 ]
Reference：
[1] Tetrahedron Letters, 1989, vol. 30, # 11, p. 1409 - 1412
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 4, p. 919 - 924
9
[ 122676-65-7 ]
[ 1739-84-0 ]
[ 56499-56-0 ]
Reference：
[1] Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7247 - 7257
10
[ 91631-71-9 ]
[ 1739-84-0 ]
[ 1066-40-6 ]
Reference：
[1] Journal of the American Chemical Society, 1984, vol. 106, # 20, p. 5979 - 5984
11
[ 694-48-4 ]
[ 6338-45-0 ]
[ 1739-84-0 ]
Reference：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 24, p. 8325 - 8334
12
[ 24134-13-2 ]
[ 1739-84-0 ]
Reference：
[1] Tetrahedron Letters, 1989, vol. 30, # 11, p. 1409 - 1412
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 4, p. 919 - 924
13
[ 861362-00-7 ]
[ 1739-84-0 ]
Reference：
[1] Helvetica Chimica Acta, 1924, vol. 7, p. 714
14
[ 900640-98-4 ]
[ 1739-84-0 ]
Reference：
[1] Chemische Berichte, 1924, vol. 57, p. 956
[2] Chemische Berichte, 1924, vol. 57, p. 956
15
[ 694-31-5 ]
[ 10447-93-5 ]
[ 1739-84-0 ]
[ 60375-51-1 ]
Reference：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 24, p. 8325 - 8334
16
[ 19225-92-4 ]
[ 1739-84-0 ]
Reference：
[1] Chemische Berichte, 1924, vol. 57, p. 956
17
[ 693-98-1 ]
[ 74-88-4 ]
[ 1739-84-0 ]
[ 36432-31-2 ]
Reference：
[1] Chemische Berichte, 1883, vol. 16, p. 488
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 5, p. 547 - 550[2] Khimiya Geterotsiklicheskikh Soedinenii, 1994, # 5, p. 624 - 628
20
[ 694-31-5 ]
[ 6338-45-0 ]
[ 10447-93-5 ]
[ 1739-84-0 ]
Reference：
[1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1937 - 1940
21
[ 603-35-0 ]
[ 1739-84-0 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 597 - 609
22
[ 1739-84-0 ]
[ 13230-04-1 ]
[ 551-92-8 ]
Reference：
[1] Journal of the Chemical Society, 1925, vol. 127, p. 1835
23
[ 1739-84-0 ]
[ 24134-09-6 ]
Yield
Reaction Conditions
Operation in experiment
3.78 g
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 3 h; Inert atmosphere
To a solution of 1,2-dimethyl-1H-imidazole (1a) (96 mg, 1 mmol) in DMF (5 mL), was added NBS (169 mg, 0,95 mmol) and the resulting reaction mixture was stirred in the dark at room temperature for 3 h. The orange-yellowish solution thus obtained was diluted with EtOAc (50 mL), washed with a 10percent aqueous solution of NaOH (2 x 50 mL), water (50 mL) and brine (50 mL). The aqueous phases were back-extracted with EtOAc (50 mL) and the combined organic phases dried over Na2SO4 and filtered. The solvent was removed at reduced pressure, affording the title compound as colorless crystals (3.78 g, 76percent).
Reference：
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 597 - 609
[2] Tetrahedron, 2004, vol. 60, # 37, p. 8065 - 8071
[3] Patent: US2014/107097, 2014, A1, . Location in patent: Paragraph 0332
[4] Tetrahedron Letters, 2015, vol. 56, # 25, p. 3855 - 3857
24
[ 1739-84-0 ]
[ 109-65-9 ]
[ 227617-70-1 ]
Reference：
[1] Synthesis, 2003, # 17, p. 2626 - 2628
General procedure: The synthesis of 1-methyl-3-propylimidazolium iodide [1-MPrIM][I] is depicted in Scheme 1. Under microwave exposure,a mixture of 1-methylimidazole (7.78 mL, 100 mmol) and propyliodide (9.74 mL, 50 mmol) was heated for 3 min at 120° C. The yield of this reaction was 87percent. The reaction mixture was evaporated at reduced pressure and the product was washed repeatedly with diethyl ether (5Χ 20 mL) to remove any excess propyl iodide. Then the solvent was removed and the product was dried under vacuum for 8 h to obtain a product with high purity. The resulting 1-methyl-3-propylimidazolium iodide was obtained as a yellowish viscous liquid. 1,2-Dimethyl-3-propylimidazolium iodide [1,2-DMPrIM][I] was synthesized in a similar way as the [1-MPrIM][I] ionic liquid. The yield of the synthesis was 92percent. The compound was obtained as a slightly yellow liquid at room temperature
Reference：
[1] Journal of Molecular Structure, 2017, vol. 1134, p. 582 - 590
[2] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 2, p. 370 - 374
3 5.1.3. 4,5-Dibromo-1,2-dimethyl-1H-imidazole (49)
To a solution of 1,2-dimethyimidazole 48 (10.0 g, 104 mmol) in CHCl3 (400 mL) was added NBS (40.7 g, 229 mmol) portion wise. The reaction was stirred for 16 h, after which 5.0 M HCl (100 mL) was added. The aqueous layer was extracted with water (3 * 100 mL), and then neutralised with NaOH(aq) (4.0 M). The precipitate was filtered and dried to afford the title compound 49 as a white solid (21.6 g, 81%). mp = 95-97 °C; νmax = 2924, 1506, 1396, 1222, 974, 658 cm-1; 1H NMR (300 MHz, CDCl3) δ 3.47 (s, 3H), 2.33 (s, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 145.6, 114.5, 102.9, 32.8, 14.2 ppm; HRMS for C5H7Br2N2 calc. 252.8976 found 252.8988.
74%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h; Darkness;
4,5-Dibromo-1,2-dimethyl-1H-imidazole (2)
A modification of a literature procedure for the synthesis of the title compound was adopted.23 A solution of 1,2-dimethyl-1H-imidazole (1; 1.33 mL, 1.44 g, 15 mmol) and NBS (5.34 g, 30 mmol) in EtOAc or DMF (75 mL) was stirred overnight in the open air and in the dark at r.t. The clear orange-yellowish solution thus obtained was washed with a 10% aq NaOH (2 50 mL), 10% aq Na2SO3 (2 50 mL), H2O (50 mL), and brine (50 mL). The aqueous phases were back-extracted with EtOAc (50 mL) and the combined organic phases were dried (Na2SO4). The solvent was removed under reduced pressure, affording the title compound as a colorless solid; yield: 2.83 g (74%); mp 86-88 °C (Lit.24 mp 88-90 °C). 1H NMR (200 MHz, CDCl3): δ = 3.54 (s, 3 H), 2.40 (s, 3 H). EI-MS: m/z (%) = 256 (48), 254 (100), 252 (52), 175 (74), 173 (82), 134 (55), 132 (61), 94 (17), 82 (14), 80 (14), 52 (16). The physical and spectral properties of this compound were in agreement with those reported in the literature.(24,25)
54%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 16h;
4, 5-Dibromo-1, 2-dimethyi-1H-imidazole (IM 2)
To a solution of 1 ,2-dimethylimidazole (8.71 g, 90.67 mmol) in CHCI3 (300 ml) was added 1 ,3-dibromo-5,5-dimethylhydantoin (28.51 g, 99.73 mmol) in one portion. The resulting mixture was stirred for 16 hatroom temperature, following which 100 ml of 2.0 M HCI was added. The resulting mixture was extractedwith water (3 x 100 ml), and the pH of the combined aqueous layers was adjusted to 7.0 using Aq. sat.20 NaHC03 . The resulting white precipitate was filtered, dissolved in CH2CI2 and concentrated in vacuo toafford the target dibrominated imidazole lm 2 as a white solid (12.3209 g, 48.5222 mmol 54%). mp = 77-80 oc (lit 77-78 °C); IR (vmax) = 3054, 2986, 1421 em- 1H NMR (300 MHz, CDCI3) o 3.53 (s, 3H), 2.40(s, 3H) ppm; 13C NMR (75 MHz, CDCI3) o 145.66, 114.54, 102.96, 32.80, 14.19 ppm; HRMS calcd. forCsH7N2Br2 (ES+) 252.8976 found 252.8988 (4.8 ppm).
50%
With bromine; potassium hydrogencarbonate; N,N-dimethyl-formamide In N,N-dimethyl-formamide at 0 - 100℃; for 3h;
35%
With N-Bromosuccinimide; n-butyllithium In diethyl ether; hexane 1.) -78 deg C, 30 min, 2.) room temperature;
Stage #1: 1,2-dimethyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -5 - 0℃; for 0.5h;
Stage #2: oxirane In tetrahydrofuran; hexane at 0 - 20℃;
With N-Bromosuccinimide; In dichloromethane; at 0℃; for 2h;
A mixture of 1,2-dimethyl-1H-imidazole (2.80 g, 29.1 mmol) and NBS (5.40 g, 30.3 mmol) in dichloromethane (100 mL) was stirred for 2 hours at 0 C. and diluted with 100 mL of dichloromethane. The mixture was washed with 3×200 mL of H2O, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel column, 10:1 CH2Cl2/MeOH) to give the title compound as a pink solid.
3.78 g
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 25℃; for 3h;Inert atmosphere;
To a solution of 1,2-dimethyl-1H-imidazole (1a) (96 mg, 1 mmol) in DMF (5 mL), was added NBS (169 mg, 0,95 mmol) and the resulting reaction mixture was stirred in the dark at room temperature for 3 h. The orange-yellowish solution thus obtained was diluted with EtOAc (50 mL), washed with a 10% aqueous solution of NaOH (2 x 50 mL), water (50 mL) and brine (50 mL). The aqueous phases were back-extracted with EtOAc (50 mL) and the combined organic phases dried over Na2SO4 and filtered. The solvent was removed at reduced pressure, affording the title compound as colorless crystals (3.78 g, 76%).
1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In acetonitrile; at 110℃; under 7500.75 Torr; for 6h;Inert atmosphere;
General procedure: In a typical run, the appropriate volumes of the reagents (see Table 1 ) were charged into PTFE-coated stainless-steel reactor and heated at 110C for 6h under constant stirring and pressure (N2, 10bar). After cooling to room temperature and removal of acetonitrile, the IL (as chloride; (IL-Cl- IL-Cl- )) was purified by vigorously stirring with cold ethyl acetate (three times, 75mL each time); separated (lower layer) and dried at 40C under reduced pressure over P4O10 for 72h. The IL-OAc- IL-OAc- was obtained by anion exchange (IL-Cl- IL-Cl- ? IL-OH- IL-OH- ; methanol solvent), followed by neutralization of the IL-OH- IL-OH- with acetic acid. The completeness of the (Cl-/OH-) ion-exchange was assured by testing a dilute aqueous solution of the IL-OH- IL-OH- with AgNO3/HNO3 solution. After neutralization, methanol was evaporated under reduced pressure and the IL was dried at 40C under reduced pressure over P4O10 for 96h. The final yield for each IL is shown in Table 1. The structure of the IL was confirmed by 1H NMR spectroscopy
94 Preparation Of An Organoclay Composition Comprising the 1,2-Dimethyl-3-hexadecylimidazolium Cation
Example 94 Preparation Of An Organoclay Composition Comprising the 1,2-Dimethyl-3-hexadecylimidazolium Cation To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer were added 1-chlorohexadecane (260 g, 1.00 moles), 1,2 dimethylimidazole (91.0 g, 0.95 moles), and CH3CN (500 mL) and the two-phase reaction mixture was vigorously stirred in an oil bath at 80° C. After 72 h, the reaction mixture was cooled to room temperature and the product was crystallized overnight. The crystallized solid was filtered, thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days to give 1,2-dimethyl-3-hexadecylimidazolium chloride as a slightly off-white solid, 220 g, 62% yield.
Stage #1: 1,2-dimethyl-1H-imidazole With n-butyllithium In diethyl ether; hexane at 20℃; for 1.5h;
Stage #2: With N,N-dimethyl-formamide In diethyl ether; hexane for 2 - 5h;
109.A PREPARATIVE EXAMPLE 109
[2748] To a stirred solution of 1,2-dimethylimidazole, compound 958 (1.92 g, 1 eq. 20 mmol) in 50 ml of Et2O, was added BuLi (2.5 M in Hexanes, 1 eq. 20 mmol, 8 ml) and stirred at room temperature, a yellow suspension results. Stirred for 1.5 hr, more precipitate forms. Reaction mixture was treated with 3.5 ml of DMF, stirred for 2-5 hours or until reaction was complete. Quench reaction with NH4Cl solution and extract with CH2Cl2, wash organic 3×with brine. Isolate organic and evaporate to dryness to obtain product as a crude. Purification from Prep Plate Chromatography 10:1 CH2Cl2: MeOH:2N NH3 afforded 0.52 g of compound 959, 21%.
Multi-step reaction with 2 steps
1: 47 percent / acetic acid, sodium acetate / 72 h / Heating
2: 77 percent / conc. nitric acid / 4 h / Heating
With potassium carbonate; In N,N-dimethyl-formamide;
Preparation 5 A mixture of <strong>[3819-88-3]1-fluoro-3-iodo-5-nitrobenzene</strong> (2.45g), 1,2-dimethylimidazole (1.77g), potassium carbonate (2.54g), palladium (II) acetate (103mg), and N,N-dimethylformamide (60ml) were stirred at 140C for 14 hours. After cooling, the reaction mixture was poured into water (100ml) and extracted with ethyl acetate (twice, 100ml each time). The combined extracts were washed with water (twice, 200ml each time) and brine (100ml). The separated organic layer was dried over magnesium sulfate, decolored (activated carbon), and filtered. The solvent wasevaporated to give a residue which was purified by silica gel chromatography (dichloromethane-methyl alcohol) to give 5-(3-fluoro-5-nitrophenyl)-1, 2-dimethyl-1H-imidazole (1.01g) as yellow crystals. MS:236(M+1) NMR(DMSO, delta):2.37(3H,s), 3.62(3H,s), 7.17(1H,s), 7.8-7.9(1H,m), 8.0-8.2(2H,m)
In chloroform at 50℃; Inert atmosphere; Schlenk technique;
90%
In acetonitrile at 40℃; for 167h;
10 4.1. Chlorides, general procedure A
General procedure: A solution of amine (1 eq) in MeCN was placed in two-neck roundbottomedflask equipped with a reflux condenser in one neck and septuminthe other and heated to 40 °Cwith simultaneous stirring on magneticstirrer. Then 4-vinylbenzyl chloride (1 eq) was added dropwise(with addition rate 5 mL/h). A resulting mixture was stirred at 40 °Cfor time required to complete the reaction. Next, the solvent was evaporatedusing rotary evaporator, and obtained product waswashed withAcOEt (30 mL) in order to remove unreacted substrates and dried undervacuum to furnish pure ionic liquid.
2 Synthesis of 1,2-dimethyl-3-octylimidazolium chloride [odmim][Cl]
For the synthesis of 1,2-dimethyl-3-octylimidazolium chloride [odmim][Cl], initially a slight excess of 1-chlorooctane (16.1 g,108 mmol) was added drop wise to 1,2-dimethylimidazole (10 g,104 mmol) in a round bottom flask followed by refluxing the solution at about 60-70 °C for 24 h under N2 atmosphere and then cooled to room temperature for 12 h. The resultant compound was washed with ether several times to get a solid, which was dried in vacuum to get 1,2-dimethyl-3-octylimidazolium chloride [odmim][Cl], with 85%yield. Karl-Fisher examination of the IL indicated that the water content reduced to less than 280 ppm. The product obtained was flushed with N2 and stored in a dry place before use. 1H NMR (400 MHz, CDCl3, δ-ppm): 0.762(t, 3 H), 1.1745(m, 10 H),1.696(m, 2 H), 2.476(s, 3 H), 3.659(s, 3 H), 3.997(t, 2 H), 7.206(d,1 H), 7.235(d, 1 H).
In acetonitrile for 48h; Reflux;
General Procedure for the Synthesis of Ionic Liquids withan Alkyl Substituent in the Cation (I-V)
General procedure: Quaternization of 1,2-dimethylimidazole withalkyl halides was performed in acetonitrile (50% solution)at the boiling point of the solvent and an equimolarratio of the starting reagents for 48 h. The solvent was then removed, and lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30% solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. The desired product precipitated from water into the lower liquid phase. The upper aqueous layer was decanted, methylene chloride (equal volume) was added to the lower layer, and the resulting solution was washed again with distilled water till negative reaction to Cl- with AgNO3. The ionic liquids were dried by azeotropic distillation of absolute methylene chloride, then the traces of the organic solvent were removed in vacuum by heating (3 h at 100°C).
at 60 - 70℃; for 24h;
Synthesis of 1,2-Dimethyl-3-Octylimidazolium Chloride[Odmim][Cl]
The IL was synthesized according to the procedure reportedin the literature (Dupont et al., 2003). A slight excess of1-chlorooctane was refluxed with 1,2-dimethylimidazolium in a round bottom flask, at 60-70 C for 24 h. The resultantcompound was washed several times with ether to removeany unreacted material. A yellow waxy solid product wasobtained after washing. This was dried in a vacuum overnightto remove traces of solvent. Later, Karl-Fisher titrationwas performed to measure the water content. Watercontent was found to be less than 280 ppm. The final productwas stored under dry conditions. The characterizationof the IL was done using 1H NMR and the chemical shiftvalues of the corresponding protons are given below:1H NMR (CDCl3, 400 MHz, δ-ppm): 0.762 (t, 3H),1.1745 (m, 10H), 1.696 (m, 2H), 2.476 (s, 3H), 3.659 (s,3H), 3.997 (t, 2H), 7.206(d, 1H), 7.235(d, 1H).
1,2-dimethyl-5-(2-naphthyl)-1H-imidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
With PdCl(C<SUB>3</SUB>H<SUB>5</SUB>)(1,4-bis(diphenylphosphino)butane); potassium acetate In pentan-1-ol at 150℃; for 20h; Inert atmosphere;
General procedure for coupling reactions
General procedure: In a typical experiment, the aryl bromide (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb)17 (0.012 g, 0.02 mmol) were dissolved in pentan-1-ol or 3-methylbutanol (5 mL) (see tables) in a Schlenk tube under an argon atmosphere. The reaction mixture was stirred at 150 for 20 h. The solvent was removed in vacuo, then the crude mixture was purified by silica gel column chromatography.
77%
With potassium acetate; palladium diacetate In ISOPROPYLAMIDE at 150℃; for 17h; Inert atmosphere; regioselective reaction;
With potassium carbonate In glycerol at 130℃; for 17h; Green chemistry; regioselective reaction;
2.1. Typical procedure for direct C-5 Arylation of imidazole derivatives
General procedure: 1-methyl-1H-imidazole (2.0 mmol) or 1, 2- dimethyl-1H-imidazole(2.0 mmol), aryl halide (1.0 mmol), MRGO DAP-Pdll catalyst (25 mg,containing Pd 0.3 mol%) were weighed and placed in a reaction tube.DES (1 ml) was added. The resulting heterogeneous reaction mixturewas stirred at 130 °C under aerobic conditions. The reaction wasmonitored by TLC. After the completion of reaction (17 h), the mixturewas cooled to room temperature and after water addition, the catalystseparated by magnetic. This mixture was extracted with EtOAc(3×30 ml), dried over Na2SO4 and evaporated under reduced pressure.Purification of crude product was carried out by column chromatography(hexane: ethyl acetate=9:1).
73%
With potassium acetate; palladium diacetate In ISOPROPYLAMIDE at 150℃; for 17h; Inert atmosphere; regioselective reaction;
61%
With C40H40Cl3N3Pd; oxygen; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;
With C40H40Cl3N3Pd; oxygen; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;
83%
With C23H23ClN4OPd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 10h; Sealed tube;
75%
With potassium acetate; palladium diacetate In ISOPROPYLAMIDE at 150℃; for 17h; Inert atmosphere; regioselective reaction;
70%
With palladium diacetate; caesium carbonate In d<SUB>7</SUB>-N,N-dimethylformamide; N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere; regioselective reaction;
70%
With potassium carbonate In glycerol at 130℃; for 17h; Green chemistry; regioselective reaction;
2.1. Typical procedure for direct C-5 Arylation of imidazole derivatives
General procedure: 1-methyl-1H-imidazole (2.0 mmol) or 1, 2- dimethyl-1H-imidazole(2.0 mmol), aryl halide (1.0 mmol), MRGO DAP-Pdll catalyst (25 mg,containing Pd 0.3 mol%) were weighed and placed in a reaction tube.DES (1 ml) was added. The resulting heterogeneous reaction mixturewas stirred at 130 °C under aerobic conditions. The reaction wasmonitored by TLC. After the completion of reaction (17 h), the mixturewas cooled to room temperature and after water addition, the catalystseparated by magnetic. This mixture was extracted with EtOAc(3×30 ml), dried over Na2SO4 and evaporated under reduced pressure.Purification of crude product was carried out by column chromatography(hexane: ethyl acetate=9:1).
2.5 Preparation of PEG-functionalized ILs [54]
General procedure: In a typical reaction, DBN (20.0 mmol) and BrPEG150Br (20.0 mmol) were added to dry toluene (2 mL) in a round-bottomed flask under N2. The mixture was heated under reflux under N2 for 24 h, upon two layers were formed. The flask was allowed to cool to room temperature and was then cooled to -10 °C overnight, during which time yellow oil was formed. The excess toluene was decanted. The resulting product was washed with dry Et2O for five times and then dried in vacuo for 24 h.
General procedure: The synthesis of 1-methyl-3-propylimidazolium iodide [1-MPrIM][I] is depicted in Scheme 1. Under microwave exposure,a mixture of 1-methylimidazole (7.78 mL, 100 mmol) and propyliodide (9.74 mL, 50 mmol) was heated for 3 min at 120 C. The yield of this reaction was 87%. The reaction mixture was evaporated at reduced pressure and the product was washed repeatedly with diethyl ether (5Chi 20 mL) to remove any excess propyl iodide. Then the solvent was removed and the product was dried under vacuum for 8 h to obtain a product with high purity. The resulting 1-methyl-3-propylimidazolium iodide was obtained as a yellowish viscous liquid. 1,2-Dimethyl-3-propylimidazolium iodide [1,2-DMPrIM][I] was synthesized in a similar way as the [1-MPrIM][I] ionic liquid. The yield of the synthesis was 92%. The compound was obtained as a slightly yellow liquid at room temperature
With PdCl(1,4-bis(diphenylphosphino)butane)(C<SUB>3</SUB>H<SUB>5</SUB>); potassium acetate In N,N-dimethyl acetamide at 150℃; for 24h; Schlenk technique; Inert atmosphere; Green chemistry; regioselective reaction;
With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150℃; for 8h;Microwave irradiation;
119: 6-(1 ,2-Dimethyl-1 H-imidazol-5-yl)-2-methoxypyridin-3-amine A suspension of <strong>[89466-18-2]6-bromo-2-methoxypyridin-3-amine</strong> (96 mg, 0.473 mmol), 1 ,2- dimethyl-1 H-imidazole (91 mg, 0.946 mmol), Pd(OAc)2 (4.3 mg, 0.019 mmol), KOAc (93 mg, 0.95 mmol) in DMA (3 mL) was stirred at 150 ^0 under microwave irradiation for 8 hours. The reaction mixture was filtered, diluted with NaCI solution and extracted with EtOAc. The organic layer was purified by eluting through an SCX-2 column using 2M NH3/MeOH followed by Biotage silica gel column chromatography eluting with 0-4% MeOH/EtOAc to give the title compound as pink solid (17 mg, 16%). 1 H NMR (500 MHz, CDCI3): 5 7.1 1 (s, 1 H), 6.98 (d, J = 7.1 A Hz, 1 H), 6.91 (d, J = 7.74 Hz, 1 H), 4.00 (s, 3H), 3.85 (s, 3H), 2.45 (s, 3H). [00409] LCMS (ESI) Rt = 1 .10 minutes MS m/z 219 [M+H]+
With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150℃; for 8h;Microwave irradiation;
120: 5-(1 ,2-Dimethyl-1 H-imidazol-5-yl)-3-methoxypyridin-2-amine A suspension of <strong>[42409-58-5]5-bromo-3-methoxypyridin-2-amine</strong> (55.5 mg, 0.273 mmol), 1 ,2-dimethyl-1 H-imidazole (52.6 mg, 0.547 mmol), Pd(OAc)2 (2.5 mg, 0.01 1 mmol), KOAc (53.7 mg, 0.55 mmol) in DMA (3 mL) was stirred at 150C under microwave irradiation for 8 hours. The reaction mixture was filtered, diluted with NaCI solution and extracted with EtOAc. The organic layer was purified by eluting through an SCX-2 column using 2M NH3/MeOH followed by Biotage silica gel column chromatography eluting with 0-12% MeOH/EtOAc to give the title compound as yellow waxy solid (9 mg, 15%). 1 H NMR (500 MHz, CDCI3): delta 7.67 (d, = 1.78 Hz, 1 H), 6.92 (s, 1 H), 6.88 (d, J = 1.78 Hz, 1 H), 4.83 (s, 2H), 3.88 (s, 3H), 3.50 (s, 3H), 2.46 (s, 3H). LCMS (ESI) Rt = 0.42 minutes MS m/z 219 [M+H]+
Stage #1: 4-(hydroxymethyl)-4'-methyl-2,2'-bipyridine With methanesulfonyl chloride; triethylamine In dichloromethane at 25℃; for 1h;
Stage #2: 1,2-dimethyl-1H-imidazole In dichloromethane at 25℃; for 16h;
Stage #3: With potassium hexafluorophosphate In water
Synthesis of IL-1-IL-3
A glass ampoule was charged with 0.1 mol of thecorresponding disiloxane, 25 mL of acetonitrile, and21.15 g (0.22 mol) of 1,2-dimethylimidazole. Theampoule was sealed under vacuum after degassingand was held for 72 h at 100°C. After cooling, theprecipitated crystals were washed with smallamounts of acetonitrile, and then three times with1,2-dichloroethane and dried in vacuum. The yieldswere about 80%.
In acetonitrile for 72h; Heating;
The second stage is the synthesis of chloride ILs 1, 2, 4, 5, 10, and 11.
General procedure: An alkyl-substituted imidazole (1,2-dimethylimidazole, 1-methylimidazole, and 1-(2-methoxyethyl)-2-methylimidazole) was quaternized with a symmetrical disiloxane in acetonitrile(50% solution) at an equimolar ratio of the initial reagents at boiling temperature for 72 hours.After that, the precipitate was collected and dried in a vacuum.
In acetonitrile for 72h; Reflux;
Step 3. Synthesis of chloride ILs 3a-f
General procedure: Alkyl-substituted imidazole was quaternized with 1,1,3,3-tetralkyl-1,3-bis(chloroalkyl)disiloxanes 2a-c or 6 in refluxed acetonitrile (50% solution)at an equimolar ratio of the starting reagents for 72 h. The liquid phase was decanted, and the precipitate was dried in vacuo.
1-(methyl)-2-(methyl)-3-((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-imidazol-3-ium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
In N,N-dimethyl-formamide at 90℃; for 8h;
8 4.3. General procedure for the preparation of imidazolium (1a-3c) and benzimidazolium chlorides (5a-g)
General procedure: 1-Alkylimidazole or compound 4 (2 mmol) were dissolved infive mililiters of DMF. Two milimoles of corresponding alkyl chlorideswas added to this solution and the resulting mixture washeated for eight hours at 90 C. Later, the mixture was allowed tocool to ambient temperature. Ten mililiters of diethyl ether wasadded and precipitate was collected by fltration, The crude productwas washed with hexane (2 10 mL) and diethyl ether(2 10 mL) the dried under reduced procedure. The suitable crystalsof 2b and 2c for X-ray diffraction analysis was obtained fromrecrystallization of 2b and 2c from ethanol/diethyl ether.
2.2. Synthesis of [C12bmim]Cl
The synthesis of ionic liquid 1-dodecyl-2,3-dimethylimidazoliumchloride, [C12bmim][Cl], was done by reacting 1-chlorododecane with1,2-dimethylimidazole and refluxing the solution at 100 °C for 4 days.The final product was washed many timeswith ethyl acetate to removethe unreacted reactants. Excess ethyl acetate was decanted, the left ethyl acetate was eliminated by evaporating it under vacuum, and the product was then recrystallized from THF to obtain the crystalline solid product. The water content was estimated to be b280 ppm byusing Karl-Fisher titrator from Analab Scientific Instruments Pvt. Ltd.The characterization of SAIL was done by 1H NMR with frequency of 300 MHz in D2O whose δ values in ppm are given below which agreed well with those reported in [38]:[C12bmim][Cl]: 0.85 (3H, t), 1.26 (18H, m), 1.83 (2H, t), 2.61 (3H, s),3.80 (3H, s), 4.17 (2H, t), 7.38 (1H, d), 7.50 (1H, d).
1
As shown in Fig. 1, a high-pressure microreactor in which a micro mixer was incorporated at three locations was used.An aqueous solution of methylamine (0.33 mol / L) was fed from the tank 1 through the pump 1 at a flow rate of 0.68 mL / min, an aqueous solution of acetaldehyde (0.33 mol / L) At a flow rate of 63 mL / min, from the tank 3 via the pump 3AmmoniumNear water(0.33 mol / L) was flowed at a flow rate of 1.13 mL / min, an aqueous glyoxal solution (0.33 mol / L) was flowed from the tank 4 via the pump 4 at 0.56 mL / flow rate, and a reaction pressure of 30 MPa The reaction was carried out under pressure. The final flow rate was 8.0 mL / min. The temperature of the first micromixer and the reaction tube of 2.4 m is controlled in a thermostatic chamber 1 keeping the temperature at 25 ° C. The mixture and reaction of methylamine and acetaldehyde in the first micromixer and reaction tube Was done. In the next second micromixer in which the aqueous solution and ammonia water are mixed by this mixing, they are mixed in a thermostatic chamber 2 kept at a temperature of 25 ° C., and after sufficient mixing and reaction in a 0.1 m reaction tube After that, glyoxal was mixed, after which 1Sufficient reaction was carried out in a 0 m reaction tube. Next, the temperature of the reaction part was adjusted to 70 ° C., and the reaction was carried out in a 25 m reaction tube. Finally, it was cooled down to 5 ° C. with a heat exchanger, depressurized to normal pressure via a discharge pressure valve, and the aqueous solution obtained while cooling with ice water (0 ° C. to 4 ° C.) was collected. In this case, the reaction time (residence time in the reaction part) was 37 seconds. For the analysis, if necessary diluted 10 times with ice water and analyzed immediately using a gas chromatograph. The reaction tube was made of stainless steel (SUS 316) and had an inner diameter of 0.5 mm. As a result, the objective 1,2-dimethylimidazole was obtained in a yield of 85.1%.For measurement of the above quantitative yield, a gas chromatograph (GC 6890, hydrogen flame ionization detector) manufactured by Agilent was used and the column was HP INNOWAX manufactured by J & W Co., inner diameter 0.32 mm, film thickness 0.25 μm, length Analysis was carried out using 30 m. The yield of each product was determined by preparing a calibration curve for each compound using various concentrations of the product (1,2-dimethylimidazole, 1-methylimidazole, 2-methylimidazole, imidazole) Concentration of each product obtained was converted from a calibration curve, and the yield of each product was calculated. The respective yields were 1,2-dimethylimidazole 85.1%, 1-methylimidazole 6.27%, 2-methylimidazole 6.59% and imidazole 2.06%.
General procedure for the synthesis of hydroxyl-containing ILs 1, 2, 4, and 5
General procedure: Quaternization was carried out in acetonitrile (50% solution) at the boiling point of the solvent and equimolar ratio of the starting reagents for 48 h. Then the solvent was removed, lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30 % solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. Target product precipitated from water into the lower phase. The upper aqueous layer was decanted and the bottom layer was washed with water to purify target product from the lithium salts. The ILs were dried in vacuo at 100 °C for 10 h.
In acetonitrile for 48h; Reflux;
General Procedure for the Synthesis of Hydroxyl-Containing Ionic Liquids (1, 2, 4, 5)
General procedure: Quaternization of 1,2-dimethylimidazole with chloroalcohols was performed in acetonitrile (50% solution) at the boiling point of the solvent and an equimolar ratio of the starting reagents for 48 h. After the solvent was distilled off in vacuum, lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30% solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. The desired product was separated as a water-insoluble lower liquid phase. The resulting IL was repeatedly washed with small portions of distilled water until negative reaction to the chloride ion with AgNO3 and then dried in vacuum, gradually increasing the temperature to 100°C for 10 h.
1,4-bis(1,2-dimethylimidazol-5-yl)-2,5-difluorobenzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
66%
With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150℃; for 48h;Inert atmosphere;
Under argon stream, 1,2-dimethylimidazole (385 mg, 4.0 mmol), <strong>[327-51-5]1,4-dibromo-2,5-difluorobenzene</strong> (272 mg, 1.0 mmol)Potassium acetate (393 mg, 4.0 mmol) and palladium acetate (11 mg, 0.05 mmol) were suspended in dimethylacetamide (DMAc, 5.0 mL) and stirred at 150 C. for 48 hours. After allowing to cool, water was added to the reaction mixture, the precipitated solid was collected by filtration,Washing with water yielded the desired 1,4-bis(1,2-dimethylimidazol-5-yl)-2,5-difluorobenzene as a milky white solid (198 mg, 66%).
General procedure: Quaternization of 1,2-dimethylimidazole withalkyl halides was performed in acetonitrile (50% solution)at the boiling point of the solvent and an equimolarratio of the starting reagents for 48 h. The solvent was then removed, and lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30% solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. The desired product precipitated from water into the lower liquid phase. The upper aqueous layer was decanted, methylene chloride (equal volume) was added to the lower layer, and the resulting solution was washed again with distilled water till negative reaction to Cl- with AgNO3. The ionic liquids were dried by azeotropic distillation of absolute methylene chloride, then the traces of the organic solvent were removed in vacuum by heating (3 h at 100C).
3-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1,2-dimethyl-1H-imidazol-3-ium iodide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
In tetrahydrofuran for 122h; Inert atmosphere; Reflux;
Procedure for the preparation of 3-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1,2-dimethyl-1H-imidazol-3-ium iodide (2e)
To a solution of triethylene glycol monomethyl ether (3.0×10-3 mol) in THF (20mL) were added triphenylphosphine (0.97g, 3.7×10-3 mol, 1.2 equiv) and imidazole (0.61g, 9.0×10-3 mol, 3.0 equiv). The mixture was stirred under nitrogen atmosphere at room temperature for 3min. Then the reaction mixture was cooled to -20°C and I2 (1.01g, 3.98×10-3 mol, 1.2 equiv) was added. After stirring at this temperature for 15min the cooling bath was removed, and the mixture stirred at room temperature for 2h until the total consumption of triethylene glycol monomethyl ether was verified. This monitoring was carried out by TLC, in an eluent of hexane and ethyl acetate (8:2) (spray reagent: phosphomolybdic acid solution). The reaction was quenched at 0°C with an aqueous saturated solution of NaHCO3 (20mL). The reaction mixture was filtered through out celite several times until all white precipitate formed was removed. The aqueous phase was extracted with diethyl ether and the combined organic phases were washed with a saturated solution of Na2S2O5 (20mL) and brine, dried over Na2SO4 anhydrous, filtered and evaporated. The residue was purified by chromatography on silica gel using as eluent a mixture of hexane and ethyl acetate (8:2), affording 3-{2-[2-(2-methoxyethoxy)ethoxy]ethyl} iodide (0.58g, 77%) as a yellow oil. In a round bottom flask equipped with magnetic stir bar was added 3-{2-[2-(2-methoxyethoxy)ethoxy]ethyl} iodide (0.57g, 2.1×10-3 mol, 1.4 equiv) and the 1,2-dimethylimidazol (0.14g, 1.5×10-3 mol) in dry THF. The reaction mixture was stirred and refluxed for 122h under nitrogen atmosphere until the total consumption of the 1,2-dimethylimidazol was verified. This monitoring was carried out by TLC, in an eluent of dichloromethane/MeOH (95:5) (spray reagent: Dragendorff-Munier solution). The reaction mixture was evaporated and washed with diethyl ether, affording 3-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1,2-dimethyl-1H-imidazol-3-ium iodide (2e) (0,40g, 75%) as a yellow oil; 1H NMR (CDCl3, 400MHz) δ: 7.72 (d, J=2.0Hz, 1H, H-4), 7.49 (d, J=2.4Hz, 1H, H-5), 4.48-4.43 (t, 2H, J=4.8Hz, H-1″a), 3.94 (s, 3H, H-6), 3.89-3.86 (t, 2H, 4.8Hz, H-2″a), 3.61-3.59 (m, 2H, CH2), 3.56-3.55 (m, 4H, 2xCH2), 3.53-3.48 (m, 2H, 2xCH2), 3.35 (s, 3H, CH3), 2.80 (s, 3H, CH3) ppm. 13C NMR (CDCl3, 100MHz) δ: 144.86 (C-2), 122.56 (CH), 121.94 (CH), 71.81 (CH2), 70.38 (CH2), 70.26 (2xCH2), 69.30 (CH2), 58.98 (OCH3), 49.18 (CH2), 36.44 (CH3-6), 11.62 (CH3-7) ppm. IR νmax (cm-1): 2897 (νs C-H aliphatic), 1095 (νas C-O-C), 1586 (w, C=N). HRMS (ESI-TOF) m/z: [M+H]+ Calc for C12H23N2O3 243.1706, found 243.1703.
3-[(3,5-di-tert-butylphenyl)methyl]-1,2-dimethyl-1H-imidazolium hydroxide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Stage #1: 1,2-dimethyl-1H-imidazole; 3,5-di-tert-butylbenzyl bromide In toluene at 96℃; for 24h;
Stage #2: With hydroxide exchange resin In water
1 Synthesis of 3-[(3,5-di-tert-butylphenyl)methyl]-1,2-dimethyl-1H-imidazolium Hydroxide
A 100 mL round bottom flask equipped with a magnetic stir bar was charged with 8 g of 3,5-di-tert-butylbenzyl bromide, 2.99 g of 1,2-dimethylimidazole and 60 mL of toluene. A reflux condenser was then attached, and the mixture heated at 96° C. for 24 hours. After cooling, the mixture was filtered, and the solid residue was washed with ethyl acetate. The solids were then dried under vacuum. (0050) The resulting bromide salt was exchanged to the corresponding hydroxide salt by stirring it with hydroxide exchange resin in deionized water overnight. The solution was filtered, and the filtrate was analyzed for hydroxide concentration by titration of a small sample with a standard solution of 0.1 N HCl.
Stage #1: 1,2-dimethyl-1H-imidazole; sulfuric acid dibutyl ester at 45℃; for 6h;
Stage #2: With barium hydroxide octahydrate In water for 1h;
12 Example 12
The experimental equipment is mainly a three-necked round-bottom flask, a magnetic stirrer and a constant temperature heating device. 9.62g (0.10mol) of 1,2-dimethylimidazole and 25.24g (0.12mol) of dibutyl sulfate were mixed, and stirred at 45°C for 6 hours. After the reaction was completed, an imidazolium salt mixture was formed. Dissolve 37.86g (0.12mol) of barium hydroxide octahydrate in water to prepare a barium hydroxide solution with a concentration of 10% by mass (that is, a total weight of 378.60g). Under the condition of continuous stirring, the barium hydroxide solution was added to the cooled imidazolium salt mixture, and stirring was continued for 1 hour. After the reaction, the white precipitate was removed by centrifugation and washed with n-pentane three times to obtain a clear solution of 1-butyl-2,3-dimethylimidazolium hydroxide.The actual yield measured by hydrochloric acid titration was 99.92%.
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