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[ CAS No. 616-47-7 ] {[proInfo.proName]}

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Chemical Structure| 616-47-7
Chemical Structure| 616-47-7
Structure of 616-47-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 616-47-7 ]

CAS No. :616-47-7 MDL No. :MFCD00005292
Formula : C4H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MCTWTZJPVLRJOU-UHFFFAOYSA-N
M.W :82.10 Pubchem ID :1390
Synonyms :

Calculated chemistry of [ 616-47-7 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 23.49
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : -0.06
Log Po/w (WLOGP) : 0.42
Log Po/w (MLOGP) : -0.47
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 0.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.93
Solubility : 9.69 mg/ml ; 0.118 mol/l
Class : Very soluble
Log S (Ali) : 0.14
Solubility : 113.0 mg/ml ; 1.37 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.68
Solubility : 17.1 mg/ml ; 0.208 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 616-47-7 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P210-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P361+P364-P370+P378-P403+P235-P405-P501 UN#:2922
Hazard Statements:H227-H302-H311-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 616-47-7 ]

* 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.

  • Upstream synthesis route of [ 616-47-7 ]
  • Downstream synthetic route of [ 616-47-7 ]

[ 616-47-7 ] Synthesis Path-Upstream   1~87

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Reference: [1] Australian Journal of Chemistry, 2004, vol. 57, # 2, p. 145 - 147
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
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YieldReaction ConditionsOperation in experiment
85.1% With ammonium hydroxide In water at 25 - 70℃; 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
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Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[2] The Journal of organic chemistry, 2002, vol. 67, # 17, p. 5913 - 5918
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Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 25, p. 3855 - 3857
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15207 - 15217
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 3, p. 239 - 244
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
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Reference: [1] Journal of Chemical Research, Miniprint, 1983, # 8, p. 1913 - 1941
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Reference: [1] Patent: US4435412, 1984, A,
  • 14
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YieldReaction ConditionsOperation in experiment
92% at 119.84℃; for 16 h; High pressure; Inert atmosphere To a solution of N-methyl-1H-imidazole (15.00 g, 0.18 M) in 20 mL anhydrous acetonitrile in a 100 mL polytetrafluoroethylene flask was added a solution of paraformaldehyde (30.00 g, 1.00 M) in 20 mL anhydrous acetonitrile with vigorous stirring under nitrogen. After placing in the sealed high pressure reactor and heating to 393 K for 16 h, the reaction was cooled to room temperature and evaporated under reduced pressure to dryness. The residue was poured into acetone (100 mL) to give a precipitate. The crude product was recrystallized from a solution of ethyl acetate and anhydrous methanol (v/v, 2 : 1). Colorless cubic crystals suitable for X-ray analysis were obtained in 92percent yield. Anal. Calcd for C5H8N2O: C, 53.56; N, 24.98; H, 7.19percent. Found: C, 53.36; N, 24.88; H, 7.31percent. 1H NMR (300 MHz, CDCl3): δH 6.86 (2H; CH-4,5), 4.63 (2H; CH2), 3.73 (3H, CH3); 13C NMR (500MHz, D2O): δC 32.74 (–CH3), 55.08 (CH2OH), 123.28 (CH-5), 126.32 (CH-4), 146.92 (CH-2).
80% at 120℃; for 12 h; 1-Methyl-imidazole (29.13 mL, 30.0 g, 0.365 mol) and paraformaldehyde (30.0 g, 1 equiv.) were mixed in 30 mL of CH3CN and heated in a pressure vessel at 120 oC for 12 h. The cooled products, which solidified, were rotavapped to remove the produced H2O and was crystallized from methanol and ethyl acetate to give 1-methyl-2-hydroxymethyl imidazole as crystals. Yield: 33g, 80percent. 1H NMR (CDCl3) δ ppm: 6.85 (s, 1H), 6.80 (s, 1H), 6.39 (bs, 1H), 4.6 (s, 2H), 3.72 (s, 3H). 3C NMR (CDCl3) δ ppm: 128, 126.2, 121.4, 55.2, 32.8. TOF-MS m/z: 113.0759 (M+H+, 32percent), 95.0653 (100percent). Molecular formula C5H8N2O, calculated m/z: 113.07 (M+H+)
63% at 110℃; for 24 h; Aton parr pressure vessel was charged with 30.0 g (0.36 mol) of n-methylimidazole,Add 30.0 g of paraformaldehyde and 50 mL of acetonitrileAnd the mixture was stirred for 24 hours while heating to 110 deg.After completion of the reaction, the resulting solids were removed with a vacuum filter, and the passing solution was collected and removed by distillation under reduced pressure.The concentrated product was dissolved in methanol and then excess ethyl acetate was added and precipitated at 0 & lt; 0 & gt; C.The precipitated solids were collected by vacuum filtration and vacuum dried to give 25.84 g of product (yield = 63percent). NMR and mass measurement results of the obtained ionic liquid are as follows.
Reference: [1] Journal of Coordination Chemistry, 2014, vol. 67, # 14, p. 2393 - 2404
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5308 - 5310
[3] Physical Chemistry Chemical Physics, 2011, vol. 13, # 48, p. 21503 - 21510
[4] European Journal of Medicinal Chemistry, 1992, vol. 27, # 5, p. 551 - 553
[5] ChemBioChem, 2016, vol. 17, # 4, p. 308 - 317
[6] Chemical Communications, 2005, # 30, p. 3832 - 3834
[7] Patent: KR2016/96254, 2016, A, . Location in patent: Paragraph 0175; 0178; 0179; 0180
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 19, p. 2291 - 2302
[9] RSC Advances, 2014, vol. 4, # 5, p. 2360 - 2367
[10] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
[11] Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 229 - 231
[12] Chemische Berichte, 1924, vol. 57, p. 956
[13] Journal of the Chemical Society, 1927, p. 3132
[14] Arzneimittel-Forschung/Drug Research, 1985, vol. 35, # 8, p. 1223 - 1224
[15] Medicinal Chemistry Research, 1997, vol. 7, # 2, p. 123 - 136
[16] Patent: US6646122, 2003, B1, . Location in patent: Page/Page column 9-10
[17] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 29
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YieldReaction ConditionsOperation in experiment
60% With hydrogenchloride In formaldehyd; ethanol Step A:
Preparation of N-methyl-2 -hydroxymethylimidazole hydrochloride
1-Methylimidazole (121 mmole, 10 gm) was dissolved in 35 ml of 38percent aqueous formaldehyde, decanted into a glass medium pressure tube and the tube sealed.
The glass pressure tube was heated to 130° C. for 14 hours.
The reaction mixture was cooled and added to 75 ml ethanol containing 18 ml concentrated hydrochloric acid.
The mixture was stirred for 10 minutes and then evaporated under reduced pressure.
The residue was dissolved in 50 ml of ethanol followed by removing the solvent under reduced pressure.
This procedure was repeated twice more.
The crude product was recrystallized from ethanol-ether to give 10.8 gm (60percent yield) of N-methyl-2-hydroxymethylimidazole, m.p. 158°-160° C.
Reference: [1] Patent: US4746669, 1988, A,
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859
[2] Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8783 - 8794
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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YieldReaction ConditionsOperation in experiment
73% With triethylamine In acetonitrile at -20 - 30℃; for 12.5 h; Inert atmosphere After replacing the inside of a 100 mL three-necked flask with an argon atmosphere, 22 mL of acetonitrile and 6.3 mL of methyl chloroformate were added and the mixture was cooled to -20 ° C. To this solution, a solution of 3.3 g of 1-methyl-1H-imidazole and 6.8 mL of triethylamine in 8 mL of acetonitrile was added in 30 minutes, followed by stirring at room temperature for 12 hours. After adding 50 mL of ethyl acetate to the reaction solution, insoluble matter was filtered off, and the residue was washed with 50 mL of ethyl acetate. The filtrate and the washing solution were combined, concentrated under reduced pressure,the concentrated residue was purified by column chromatography(Silica gel, hexane / ethyl acetate) to obtain 4.2 g (yield: 73percent) of methyl 1-methyl-1H-imidazole-2-carboxylate.
Reference: [1] Patent: JP2017/66077, 2017, A, . Location in patent: Paragraph 0059
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YieldReaction ConditionsOperation in experiment
79%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
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Reference: [1] Journal of Chemical Research, Miniprint, 1983, # 8, p. 1913 - 1941
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Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 1434
[2] Synthesis, 2011, # 17, p. 2859 - 2864
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Reference: [1] Synthesis, 2011, # 17, p. 2859 - 2864
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Reference: [1] Synthesis, 2011, # 17, p. 2859 - 2864
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YieldReaction ConditionsOperation in experiment
80% With triethylamine In acetonitrile at 0 - 20℃; for 16 h; (Reference Example 9) Synthesis of ethyl 1-methyl-1H-imidazole-2-carboxylate:
Triethylamine (3.40 mL, 24.4 mmol) and ethyl chloroformate (2.34 mL, 24.4 mmol) were added to a solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol) in acetonitrile (4.0 mL) at 0°C and the reaction liquid was stirred at room temperature for 16 hours.
The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure.
The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80percent) as a white solid.
1H-NMR (400 MHz, CDCl3) δ: 1.42 (3H, t, J=7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J=7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m).
ESI-MS: m/z= 155 (M+H)+.
71% With triethylamine In acetonitrile at -20 - 30℃; for 14 h; Inert atmosphere; Large scale (Comparative Examples 1 to 4) 1-methyl-1H-imidazole 3.3 g scaleAfter replacing the inside of a 100 mL three-necked flask with an argon atmosphere, 22 mL of acetonitrile, 3.3 g of 1-methyl-1H-imidazole and triethylamine in the amounts shown in Table 1 were added and cooled to -20 ° C. To this solution, a solution of ethyl chloroformate in the amount shown in Table 1 in 8 mL of acetonitrile was added at the addition time shown in Table 1. Thereafter, the mixture was stirred at room temperature for the reaction time shown in Table 1. To the reaction solution were added 20 mL of ethanol and 10 mL of water to dissolve the precipitate, and 1 mL was collected from the homogenized solution. The collected solution was diluted 1000-fold with acetonitrile and subjected to HPLC analysis, and the yield was calculated. The results are shown in Table 2.
68% With triethylamine In acetonitrile at -20 - 20℃; for 3.5 h; To a solution of N-methylimidazole (5 g, 0.06 mol), acetonitrile (32 mL) and triethylamine (15 mL), cooled to-20°C was added ethyl CHLOROFORMATE (13 mL, 0.137 mol), and the mixture allowed to slowly warm to room temperature and stirred for 3.5 hr. The solution was filtered (triethylamine hydrochloride) and concentrated under vacuum. The residue was purified by distillation under reduced pressure (0 Torr, 102°C) to yield the product as a white solid. Yield (6.26 g, 68percent) 1H NMR (DMSO): 8 7.44 (d, 1H, J=2. 8 Hz), 7.04 (d, 1H,. J=2. 8 Hz), 4.26 (q, 2H, J=3. 5 Hz), 3.91 (s, 3H), 1.26 (t, 3h, 7 3. 5 Hz). 13C (DMSO): 159.3, 129.1, 127.7, 61.0, 36.0, 14.5.
66% With triethylamine In acetonitrile at -30 - 20℃; N-methylimidazole-2-carboxaldehyde Dry acetonitrile (600 ML) was added to N-methylimidazole (150 g, 1.8 mol), followed by triethylamine (503 ML, 3.6 mol) in one portion, and the mixture cooled TO-30 °C. Neat ethyl chloroformate (350 mL, 3.6 mol) was added slowly over 15 min. The turbid mixture was then warmed to room temperature and maintained overnight. The solid triethyl ammonium chloride was filtered off, washed with EtOAc, and the filtrate concentrated in vacuo. Dichloromethane (500 ML) was added and the solution was extracted with water (300 mL), the organic phase dried with magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (SIO2, EtOAc) and recrystallization from ether/heptane (2: 1) to provide 188 g (66percent) of N-METHYLIMIDAZOLE-2-CARBOXY ethyl ester. This N-methylimidazole-2-carboxy ethyl ester (120 g, 0.77 mol) was treated with a solution of sodium hydroxide (37 g, 0.9 mol) in water (60 mL), and the mixture heated at reflux for 1 h. The mixture cooled to 50 °C, acidified to pH 2 with concentrated HC1, cooled further to 5 °C and the precipitate filtered. The solid was washed with ether, diluted into water (70 mL), heated gently under 60 °C, and upon cooling the product crystallizes to give 75 g (77percent) of N-METHYLIMIDAZOLE-2-CARBOXYLIC acid, which was converted into the corresponding aldehyde as described for Intermediate 23.
51% With triethylamine In acetonitrile at -30 - 10℃; Triethyl amine (5OmL) is added to a solution of methyl imidazol (16.3g, 199mmol) in acetonitrile (10OmL), then it is cooled to -300C. A solution of ethyl chloroformate (3ImL, 328mmol) in acetonitrile (5OmL) is added slowly keeping the temperature bellow 100C. The <n="74"/>reaction mixture is concentrated and diluted in water and extracted with chloroform, dried with MgSO4 anh, filtered and evaporated. Recrystallisation from ether yields l-Methyl-lH-imidazole-2- carboxylic acid ethyl ester as an orange oil (15.5g, 51percent).
37%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: With chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 1 h; Inert atmosphere
Stage #3: at -78 - 20℃; for 1 h; Inert atmosphere
A literature procedure for the synthesis of the title compound was adopted. 2 A solution of N-methyl-1H-imidazole (280 μL, 290 mg, 3.50 mmol) in anhydrous THF (7 mL) was cooled to -78°C and n-BuLi (2.5 M in hexanes, 2.2 mL, 3.60 mmol) was added dropwise by syringe under stirring. The resulting yellow solution was stirred for 30 minutes at -78°C where upon chlorotrimethylsilane (465 μL, 399 mg, 3.67 mmol) was added dropwise by syringe; after the addition the resulting reaction mixture was allowed to return to room temperature and the stirring was continued for 1 h. The reaction was then cooled back to -78°C, ethylchloroformiate (350 μL, 398 mg, 3.67 mmol) was added and the resulting mixture was allowed to warm up to room temperature and further stirred for 1h. The reaction was quenched with water (1 mL) and the solvents were evaporated under reduced pressure. The obtained crude product was dissolved in dichloromethane (100 mL), washed with water (3 x25 mL) and brine (1 x 25 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with EtOAc as eluent, the chromatographic fractions containing the required compound were collected and concentrated under reduced pressure, affording the title compound 1f as a colorless liquid(152 mg, 37percent).

Reference: [1] Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146
[2] Patent: EP3263565, 2018, A1, . Location in patent: Paragraph 0386; 0387
[3] Patent: JP2017/66077, 2017, A, . Location in patent: Page/Page column 7; 8; 9; 10; 11
[4] Patent: WO2005/33077, 2005, A1, . Location in patent: Page/Page column 53
[5] Patent: WO2004/58763, 2004, A1, . Location in patent: Page 43
[6] Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3493 - 3501
[7] Patent: WO2009/24585, 2009, A2, . Location in patent: Page/Page column 72-73
[8] Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 229 - 231
[9] Tetrahedron Letters, 2015, vol. 56, # 25, p. 3855 - 3857
[10] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
[11] Tetrahedron, 2013, vol. 69, # 36, p. 7847 - 7853
  • 35
  • [ 616-47-7 ]
  • [ 109-94-4 ]
  • [ 30148-21-1 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 14 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 36
  • [ 616-47-7 ]
  • [ 1003-91-4 ]
YieldReaction ConditionsOperation in experiment
29% With bromine; sodium acetate In acetic acid at 20℃; for 2.5 h; To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) at room temperature was added bromine (9.6 g, 60.07 mmol) dropwise as a solution in 20 mL acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo, the residue was suspended in 500 mL water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give 2,4,5-tribromo-l-methyl- lH-imidazole (1.82 g, 29percent - some product remained in the mother liquor) as a light yellow powder. Used without further characterization. To a suspension of the tribromide (1.82 g, 5.71 mmol) in 45 mL water was added sodium sulfite (13 g, 103 mmol) and the resulting mixture was stirred at rapid reflux for 24 h. After cooling to room temperature, organics were extracted with ether (3 χ 75 mL), dried over magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tri-, di- and monobromoimidazoles. This mixture was re-subjected to the reduction conditions (same quantity of sodium sulfite) using 15 mL of 3: 1 water/acetic acid as solvent and heating in a sealed vessel at 130 °C for 60 h. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 by addition of 2 N sodium hydroxide. Organics were extracted with ether (3 χ 50 mL), dried over magnesium sulfate, filtered and concentrated to give crude 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 62percent). Used without further characterization.. 4-Butyl-l -methyl- lH-imidazole (95 mg, 22 percent) was synthesized as in Example 3.1 using 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 3.53 mmol) in place of 5-bromo-2- formylfuran and propylboronic acid (372 mg, 4.24 mmol) in place of hexylboronic acid. Used without further characterization. To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at - 0°C was added -butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to -20 °C over 20 minutes. After cooling to -78 °C, 4-butyl-l -methyl- lH-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at -78 °C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3 χ 20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50percent ethyl acetate in hexanes) to give l -methyl-4-propyl-lH-imidazole-2-carbaldehyde (9 mg, 8percent) as an off-white solid. Used without further characterization
63.76 g With N-Bromosuccinimide In chloroform at 20℃; for 1.5 h; 2-(2-Ethynyl-1 -methyl-1 H-imidazol-4-yl)-thiazole    To a solution of compound N-methylimidazole (65.6 g, 0.8 mol) in CHCl3 (1 .5 L), N-bromosuccinimide (NBS; 476g,2.4 mol) was added in portion and then the mixture was stirred at roomtemperature for 1 .5 hour, filtered and concentrated, the residue was purifiedby column chromatography over silica gel (eluent: EA/PE 1/10) to afford 2,4,5-Tribromo-1 -methyl-1H-imidazole (63.76 g, 0.2 mol), which was dissolved in in dry THF (2L) andEtMgBr (220 ml_, 0.22 mol) was added slowly under N2 atmosphere at ambient temperature during 3 hourand stirred for another 2 hour. Then about 100ml_ water was added and filtered,concentrated and the residue was extracted with ethyl acetate, purified bycolumn chromatography over silica gel (eluent : EA/PE 1/10) to afford 2,4-dibromo-1 -methyl-1 H-imidazole (20 g, yield:41 .7percent). To a solution of 2,4-dibromo-1-methyl-1 H-imidazole (6 g, 25.6 mmol) in THF (26 ml_) was added Cul (0.2 g,1mmol), Et3N (12 ml_,86 mmol),Pd(dppf)CI2 (417 mg, 0.5 mmol),Ethynyl-trimethyl-silane (4.2 ml_,29.6 mmol), then the mixture was heated to40°C and stirred at this temperature for 40min. Then filtered, concentrated andpurified by column chromatography over silica gel (eluent: EA/PE 1/50), collectthe desire fraction and concentrated to give 4-Bromo-1-methyl-2-trimethylsilanylethynyl-1 H-imidazole (3.95 g, yield: 60percent). To a solution of 4-Bromo-1-methyl-2-trimethylsilanylethynyl-1 H-imidazole (5.14 g, 20 mmol) in toluene(100 ml_) , 2-Tributylstannanyl- thiazole (8.3 g, 22 mmol) was added followedwith Pd(PPh3) (1 .2 g, 1 mmol), then themixture was refluxed for 6 hour, when cooled, the mixture was filtered, thefiltrate was concentrated and purified by chromatography over silica gel (eluent :EA/PE 1/20 to 1/10) to afford 2-(1-Methyl-2-trimethylsilanylethynyl-1 H-imidazol-4-yl)-thiazole (2.5 g, yield:48percent). To the mixture of 2-(1 -Methyl -2-trimethylsilanylethynyl-1H-imidazol-4-yl)-thiazole in MeOH (50 ml_), Na2CO3 (1 .5 g, 18 mmol) was added quickly and stirred the mixture forabout one minutes, then filtered, concentrated and purified by column chromatographyover silica gel (eluent: EA PE 1/5) to afford 2-(2-Ethynyl-1 -methyl-1H-imidazol-4-yl)-thiazole (2 g, yield: 80percent). 1H NMR (CDCI3 400 MHz TMS):53.40 (s, 1 H), 3.80 (s, 3H), 7.27 (s, 1 H), 7.53 (s, 1 H), 7.26-7.27 (d, J=4.0Hz, 1 H).
95 g at 20℃; for 2.5 h; To a solution of Example 69a (82 g, 1.0 mol) and sodium acetate (125 g, 1.52 mol) in acetic acid (2.0 L) at room temperature was added bromine (480 g, 30 mmol) dropwise as a solution in 1.0L acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo; the residue was suspended in 1.5L water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give Example 69b (95.0 g, contained 30percent isomer) as light yellow powder. LCMS [M+H]+=319.1
Reference: [1] Synthesis, 1988, # 10, p. 767 - 771
[2] Tetrahedron Letters, 2006, vol. 47, # 12, p. 1949 - 1951
[3] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[4] Chemische Berichte, 1991, vol. 124, p. 1639 - 1650
[5] Patent: WO2013/192352, 2013, A1, . Location in patent: Page/Page column 116; 117
[6] Chemische Berichte, 1883, vol. 16, p. 546 Anm. 1
[7] Patent: WO2013/50527, 2013, A1, . Location in patent: Page/Page column 38; 39; 40
[8] Patent: WO2017/218960, 2017, A1, . Location in patent: Paragraph 00638
  • 37
  • [ 616-47-7 ]
  • [ 1003-50-5 ]
  • [ 1003-91-4 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 1569
  • 38
  • [ 616-47-7 ]
  • [ 67-66-3 ]
  • [ 7726-95-6 ]
  • [ 1003-50-5 ]
  • [ 1003-91-4 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 1569
  • 39
  • [ 616-47-7 ]
  • [ 541-41-3 ]
  • [ 22232-54-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7313 - 7317
  • 40
  • [ 616-47-7 ]
  • [ 37067-95-1 ]
YieldReaction ConditionsOperation in experiment
76% With 4-(3-methylimidazolium)butanesulfonate; iodine In water at 20℃; for 2 h; Sealed tube; Green chemistry General procedure: To a mixture of 2-phenylimidazo[1,2-a]pyridine (1a, 39 mg, 0.2 mmol), molecular I2 (50 mg, 1 equiv), and 4-(3-methylimidazolium)butane-1-sulfonate (I, 9 mg, 20 molpercent) in a sealed tube was added water (2 mL) and the mixture was stirred at r.t. for 2 h. After completion of the reaction (TLC), the mixture was extracted with EtOAc (20 mL). The organic phase was dried (anhyd Na2SO4) and concentrated under reduced pressure give the crude residue which was purified by column chromatography (silica gel, 60–120 mesh, petroleum ether/EtOAc, 9:1) to afford 2a as a white solid: yield: 58 mg (91percent); mp 132–134 °C.
55%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.0833333 h;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333 h;
a)
Synthesis of 2-iodine-1-methyl-imidazol
7.97 ml (100.0 mmol) 1-methyl-imidazol was dissolved in THF (100 ml) and cooled to -78° C. 40 ml (2.5 M in hexane, 100 mmol) BuLi was added in drops at this temperature.
After the end of addition, heating was performed for 5 min to 0° C., followed immediately by cooling to -78° C. A solution of 27.9 g (110.0 mmol) iodine (I2) in THF (60 ml) was added in drops at this temperature and stirring was performed for 20 min at RT.
Quenching was subsequently performed with a 5percent aq. Na2S2O3 sol (120 ml) and extraction with DCM (4*50 ml).
The collected organic phases were dried over MgSO4, filtered and concentrated in a vacuum. 11.5 g (55.2 mmol, 55percent) 2-iodine-1-methyl-imidazol was obtained by crystallisation of the residue from diethylether.
Reference: [1] Organic Letters, 2014, vol. 16, # 12, p. 3244 - 3247
[2] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 20, p. 2774 - 2781
[3] Organic Letters, 2003, vol. 5, # 18, p. 3209 - 3212
[4] Journal of Organometallic Chemistry, 2007, vol. 692, # 1-3, p. 635 - 644
[5] Synthesis (Germany), 2016, vol. 48, # 22, p. 4009 - 4015
[6] Chemical Communications, 2016, vol. 52, # 28, p. 4983 - 4986
[7] Patent: US2008/261996, 2008, A1, . Location in patent: Page/Page column 45
[8] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[9] Tetrahedron, 1997, vol. 53, # 21, p. 7237 - 7254
[10] Chemical Communications, 2004, # 11, p. 1306 - 1307
[11] CrystEngComm, 2013, vol. 15, # 47, p. 10157 - 10160
  • 41
  • [ 616-47-7 ]
  • [ 37067-95-1 ]
  • [ 86026-81-5 ]
YieldReaction ConditionsOperation in experiment
35% With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; potassium <i>tert</i>-butylate In toluene at 20℃; for 3 h; 1-methylimidazole (1 mmol, 82.1 mg),Perfluoro iodobutane (3.1 mmol, 1072 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (2.2 mmol, 246.9 mg) was addedAnd 5mL of toluene, stirring at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).The product 1 was obtained: 2-iodo-1-methylimidazole (white solid, 72 mg, 35percent).Product 2: 2,5-diiodo-1-methylimidazole (white solid, 210 mg, 63percent)
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[2] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0039; 0040
[3] Tetrahedron Letters, 2010, vol. 51, # 41, p. 5423 - 5425
  • 42
  • [ 616-47-7 ]
  • [ 67-66-3 ]
  • [ 14508-49-7 ]
  • [ 17180-94-8 ]
  • [ 51269-82-0 ]
  • [ 38180-46-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 43
  • [ 616-47-7 ]
  • [ 67-66-3 ]
  • [ 14508-49-7 ]
  • [ 17180-94-8 ]
  • [ 51269-82-0 ]
  • [ 68325-15-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 44
  • [ 75-31-0 ]
  • [ 616-47-7 ]
  • [ 4532-96-1 ]
YieldReaction ConditionsOperation in experiment
82% With ammonium carbonate; paraformaldehyde In methanol EXAMPLE 4
To a 200 ml RB flask was added 4.08 g (136 mmol) of paraformaldehyde and 20 ml of methanol.
After cooling to 0-5° C., there was added, in order, 7.65 g (129 mmol) i-propylamine, 10 ml methanol, 6.20 g (65 mmol) ammonium carbonate, 10 ml methanol, 9.07 g (43.1 mmol) trimeric glyoxal dihydrate and 25 ml methanol.
The reaction was stirred overnight at RT. A small aliquot was removed for NMR analysis. 1H-NMR (DMSO-d6, ppm): 1.352 (d, 6H, Me), 4.37 (sept., 1H, CH), 6.86 and 7.19 [1H each, CH(4,5)], 7.652 [1H, CH(2)].
This indicated 1-methylimidazole was produced in relatively high yield.
Volatiles were removed under reduced pressure and the reaction mixture was vacuum distilled to yield 12.16 g (82percent) of 1-i-propylimidazole, bp 97-99° C./2.7 kPa.
Reference: [1] Patent: US6177575, 2001, B1,
  • 45
  • [ 616-47-7 ]
  • [ 16681-59-7 ]
YieldReaction ConditionsOperation in experiment
63% With carbon tetrabromide; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 3 h; 1-methylimidazole (1 mmol, 82.1 mg),Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction. The mixture is poured into water and extracted with dichloromethane. The organic phase is collected, dried, and the dichloromethane is removed by rotary evaporation.Crude product. The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (volume ratio = 10:1) to obtain 2-Bromo-1-methylimidazole (red-brown liquid, 101.4 mg, yield 63percent).
Reference: [1] Chemical Communications, 2013, vol. 49, # 37, p. 3875 - 3877
[2] Australian Journal of Chemistry, 1999, vol. 52, # 3, p. 159 - 165
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[4] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0055; 0056
[5] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[6] Journal of Organometallic Chemistry, 2000, vol. 601, # 2, p. 233 - 236
  • 46
  • [ 616-47-7 ]
  • [ 5213-50-3 ]
  • [ 19183-20-1 ]
  • [ 1671-82-5 ]
YieldReaction ConditionsOperation in experiment
37% With nitronium tetrafluoborate In nitromethane at -20 - 125℃; for 3.16667 h; EXAMPLE 7; Preparation of 1-Methyl 2,4-5 Trinitroimidazole; Nitration of 1-methylimidazole with Nitronium Tetrafluoroborate; 1-Methylimidazole (0.77 g, 9.36 mmol) was dissolved in 10 ml of nitromethane. The solution was then cooled down to -20° C. NO2BF4 (3.0 g) was added with vigorous stirring. After 10 minutes, the cooling bath was replaced with oil bath (22° C.) and another portion of nitronium tetrafluoroborate (5.0 g, total 8.0 g, 60.0 mmol) was added with stirring. After being stirred at the temperature for 1.0 hour, the reaction mixture was heated to 125° C. within 1.0 hour while nitromethane was collected by distillation under atmosphere pressure. Then the reaction mixture was kept at that temperature for a further 1.0 hour and then poured onto ice. The resulting product mixture was extracted with methylene chloride (4.x.20 ml). The combined organic phase was washed successively with water (20 ml), 10percent aq. NaHCO3 (20 ml), and water (20 ml) and dried over Na2SO4. Evaporation of the solvent gave 0.945 g of oil. Proton NMR showed that it only contained three products with ratio of 2.8:1.0:0.18 (corresponding tol-methyl-4,5-dinitroimidazoel, 1-methyl-2,4,5-trinitroimidazole and 1-methyl-2-nitroimidazole). Thus the yield of 1-methyl-4,5-dinitroimidazole was about 37percent, 1-methyl-2,4,5-trinitroimidazole, 13percent and 1-methyl-2-nitroimidazole, 6percent based on the integration of the NMR spectrum.
Reference: [1] Patent: US7304164, 2007, B1, . Location in patent: Page/Page column 7
  • 47
  • [ 616-47-7 ]
  • [ 3034-41-1 ]
  • [ 5213-50-3 ]
  • [ 19183-20-1 ]
  • [ 1671-82-5 ]
YieldReaction ConditionsOperation in experiment
1% at 110 - 120℃; for 2 h; Nitration of 1-methylimidazole with Nitric Acid and Sulfuric Acid
Fuming nitric acid (1.5 ml, excess, d.1.544 g/ml) was added to 1-methylimidazole (100 mg, 1.22 mmol) at room temperature with stirring.
Then sulfuric acid (1.5 ml, excess, fuming 30percent SO3) was added slowly from the top of condenser.
After addition, the reaction mixture was heated to 110° C. and then the reaction temperature was maintained between 110-120° C. for 2.0 hrs.
The reaction mixture was cooled to room temperature and the resulting mixture of products was extracted with methylene chloride and the organic phase was dried with Na2SO4/NaHCO3.
Evaporation of the solvent gave 61 mg of oil.
Proton NMR showed that the ratio of the products was 7:25:45:2:1 (corresponding to 1-methyl-4-nitroimidazole, 1-methyl-2-nitroimidazole, 1-methyl-4,5-dinitroimidazole, 1-methyl-2,4-dinitroimidazole, and 1-methyl-2,4,5-trinitroimidazole).
The yield of 1-methyl-2,4,5-trinitroimidazole is less then 1percent based on the integration of the NMR.
Reference: [1] Patent: US7304164, 2007, B1, . Location in patent: Page/Page column 7
  • 48
  • [ 616-47-7 ]
  • [ 19183-20-1 ]
  • [ 1671-82-5 ]
  • [ 19183-15-4 ]
Reference: [1] Synthesis, 2011, # 17, p. 2859 - 2864
  • 49
  • [ 616-47-7 ]
  • [ 68-12-2 ]
  • [ 27258-33-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 11, p. 1409 - 1414
  • 50
  • [ 616-47-7 ]
  • [ 143-33-9 ]
  • [ 66121-69-5 ]
  • [ 66121-66-2 ]
  • [ 45515-45-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 10, p. 3693 - 3696
  • 51
  • [ 616-47-7 ]
  • [ 68-12-2 ]
  • [ 13750-81-7 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.5 h;
Stage #2: at -70 - 0℃; for 2 h;
To a solution of 1- methylimidazole (8.2 g, 100 mmol) in dry THF (100 mL) cooled to -70 0C, was added dropwise a solution of nBuLi in THF. After stirring for 30 min at the same temperature, the solution was treated with freshly distilled DMF (7.3 g, 100 mmol). The resultant yellow suspension was stirred at 0 0C for 2 h, and quenched with ice- water. The mixture was extracted with EtOAc, and the organic extracts dried (Na2SO4) before evaporation to afford an oily residue, which was distilled under reduced pressure to afford the title product (68percent yield). 1H-NMR (CDCl3) 69.76 (s, EPO <DP n="82"/>IH, CHO), 7.22 (s, IH, Im-CH), 7.07 (s, IH, Im-CH), 3.96 (s, 3H, CH3). EI-HRMS: m/z calcd for C5H6N2O 110.0480, found 110.0481 (100percent), 82.0493 (60percent).
Reference: [1] Inorganica Chimica Acta, 2011, vol. 375, # 1, p. 213 - 219
[2] Dalton Transactions, 2015, vol. 44, # 17, p. 8013 - 8020
[3] Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12735 - 12740
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  • 52
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  • [ 67-56-1 ]
  • [ 68-12-2 ]
  • [ 62366-53-4 ]
  • [ 13750-81-7 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
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YieldReaction ConditionsOperation in experiment
53% With sodium dihydrogenphosphate; diisopropylamine In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide Synthesis of 1-Methyl-1H-imidazole-2-carbaldehyde (BB5)
To a solution of 1-methyl imidazole (57 g, 0.7 mmol) in THF (250 mL) was added LDA (2 M solution in THF, 348 mL) at -60° C. and the stirred for 3 h.
The reaction mixture was cooled -78° C., DMF (75 mL) was added rapidly, and the reaction mixture was slowly allowed to room temperature and stirred at ambient temperature overnight.
The reaction mixture was cooled to 0° C., a solution of NaH2PO4 (100 g in 350 mL H2O) was added and the resulting mixture was stirred for 30 min.
The mixture was filtered to remove insoluble material and the filtrate was extracted with DCM (4*400 mL).
The combined organic extracts were concentrated in vacuo and the crude residue was purified by column chromatography (silica gel, 100-200 mesh, 30percent EtOAc/pet. ether) to provide (BB5) (41 g, 53percent) as a yellow solid. Rf: 0.3 (15percent MeOH/CHCl3).
1H NMR (400 MHz, CDCl3): δ 9.82 (1H, s), 7.28 (1H, app d), 7.13 (1H, app d), 4.04 (3H, s); m/z 111 (MH)+.
Reference: [1] Patent: US2012/322722, 2012, A1,
[2] Liebigs Annalen der Chemie, 1980, # 4, p. 542 - 556
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  • 57
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  • [ 60-56-0 ]
YieldReaction ConditionsOperation in experiment
82.54%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1.5 h;
Stage #2: With sulfur In tetrahydrofuran; hexane for 9 h; Reflux
N-methylimidazole 8.21 g (100 mmol) and 80 ml of tetrahydrofuran were added to a three-necked reaction flask and then cooled to -5 ° C. A solution of n-butyllithium-n-hexane (50 ml, n-butyllithium, MOL / L). After the dropwise addition, the reaction was incubated at -5 ° C for 1 hour. Then, 4.16 g (130 mmol) of elemental sulfur was added portionwise at the same temperature, and the temperature was raised for 8 hours. Thin layer chromatography was used to detect the raw material spots, and then quenched in an ice-water bath. The pH was adjusted to 6.0 to 6.5 by the addition of dilute hydrochloric acid, and then the reaction system was concentrated to dryness under pressure. The concentrated solid was dissolved in ethyl acetate and activated carbon. The reaction mixture was decolorized by refluxing for about 1 hour. The filtrate was concentrated under reduced pressure to give 9.41 g of methimazole as a pale yellow solid. The yield was 82.54percent and the purity was 100percent (gas chromatography).
Reference: [1] Patent: CN105541724, 2016, A, . Location in patent: Paragraph 0029; 0031; 0032
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[2] Synthetic Communications, 2013, vol. 43, # 21, p. 2913 - 2925
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  • [ 16427-44-4 ]
  • [ 35487-17-3 ]
YieldReaction ConditionsOperation in experiment
98% at 10 - 20℃; for 4 h; Example 1-(1); Synthesis of Ethylene Glycol Monomethyl Ether Methanesulfonate; 1-Methylimidazole (50 g) and methanesulfonyl chloride (66 g) were mixed in dichloromethane in a 500 mL two-bulb flask. After adding ethylene glycol monomethyl ether (42 g) dropwise at 10° C., the mixture was stirred at room temperature for 4 hours. After the reaction was completed, water was added. After stirring for 10 minutes, the solvent layer in which the product was dissolved was separated from the aqueous layer in which the byproduct was dissolved. The product was yielded by removing the solvent at room temperature using an evaporator (yield: 98percent), and the byproduct 1-methylimidazolium chloride was recovered as 1-methylimidazole using 40 wt percent NaOH aqueous solution and used again (yield: 95percent).
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  • [ 74-96-4 ]
  • [ 65039-08-9 ]
YieldReaction ConditionsOperation in experiment
98% at 40℃; for 24 h; Schlenk technique; Inert atmosphere General procedure: The ligands (except 3) were all synthesized by adaptation of the methods of Starikova et al. [20]. A typical and generic procedure is described. Spectroscopic and analyses data are presented. N-monosubstituted azole (0.1mmol) and dry toluene were placed in a two-neck flask and stirred until a homogeneous solution was formed; then alkyl halide (0.3mmol) was added drop wise with continuous stirring. After addition of the alkyl halide, the mixture was stirred while heating at 40°C for 24h. The solvent was removed and the ligand was dried under vacuum. 2.2.2
1-Methyl-3-ethylimidazolium bromide (2)
White solid.
Yield (4.70 g, 98percent). IR (ATR cm-1): 3065, 2975, 1670, 1571, 1467, 1172, 1101, 856, 789, 649, 789, 621, 417; δH (400 MHz, CDCl3): 1.47 (3H, t, J 7.3 Hz, CH3), 3.97 (3H, s, NCH3), 4.32 (2H, q, NCH2), 7.54 (2H, s, NCH) and 10.07 ppm (1H, s, CH); δC (100 MHz, CDCl3): 15.64 (CH3), 36.63 (NCH3), 45.18 (NCH2), 122.01 (NCH), 123.71 (NCH) and 136.73 ppm.; m/z (ESI) 111.5 (M+-Br-). HRMS (ESI) calcd for C6H11BrN2, 111.09222 (M+-Br-); found, 111.09196 (M+-Br-).
95% at 80℃; for 0.0333333 h; Microwave irradiation The intermediate 1-ethyl-3-methylimidazolium bromide[EMIM]Br was prepared with equimolar bromoethane(>99percent) and 1-methylimidazolium (>99percent) in a closed glass reactor and the reaction was enhanced by microwave(Milestone microwave lab station, Italy). Firstly, the reactor was heated to 80°C (80 w) during a period of 30 seconds and the temperature was kept for another 90 seconds(100 w) to complete this reaction. The forming of AlCl3/[EMIM]Br was prepared by slow addition of known amounts of AlCl3 (anhydrous, grain, >99percent) to the formerintermediate ([EMIM]Br) in a long beaker. The temperaturewas controlled carefully in case of decomposition of the ionic liquid
90% at 50 - 80℃; for 4 h; Step 1"; Synthesis of l-ethyl-3-methylimidazolium bromide; Into a flask equipped with a thermometer, a nitrogen gas inlet tube, a reflux condenser tube, a stirrer, and a dropping funnel, methylimidazole 82 g (1.0 mol) and 2-butanone(hereinafter, described as MEK) 400 g were charged. While the mixture was maintained at 50°C under nitrogen flow, ethyl bromide163.5 g (1.5 mol) was added dropwise into the mixture over 2 hours. Then, the mixture was maintained at 80°C for 2 hours and then the reaction was completed. Then, the reaction liquid was filtered to obtain l-ethyl-3-methylimidazolium bromide (hereinafter, described as EMImBr) whichwas a slight brown-white crystal. Then, this crystal was washed with MEK two times in a glove box, the inside of which was substituted with nitrogen, to obtain white EMImBr 172g (yield of 90percent) .
86% Inert atmosphere; Schlenk technique General procedure: The salts 15a-15e were prepared by the reported procedures. The reactions of neat alkyl halides with 1-methyl imidazole were carried out under nitrogen atmosphere. The white solid compounds were formed in the reaction mixture. These reaction mixtures were evaporated to dryness in vacuum to give white solid salts in good yield. The solid salts were highly hygroscopic in nature. All salts 15a-15e were characterized by common spectroscopic techniques.
85% at 35℃; for 5 h; Ionic liquid 1-ethyl-3-methylimidazolium bromidePreparation of the compound:In a 100 ml three-necked flask with a condensing reflux unit,Add 1-methylimidazole (8.2 g, 0.1 mol),Ethyl bromide (11.99 g, 0.11 mol) was stirred at 35 ° C for 5 hours.A white crystalline powder was obtained which was washed with ethyl acetate to remove ethyl bromide.Dry at 80 ° C for 3 h under vacuum. The yield was 85percent.
49.7% at 70 - 80℃; for 10 h; Reflux 0.82g (10 mmol) 1-methylimidazole and 1.09 g (10 mmol) bromoethane were slowly added to 50 mL acetonitrile under stirring with continuous heating at 70–80C and refluxing for 10 h. It was then filtered off and recrystallized with methanol and ether, and dried under vacuum. The yield of MLDE ¢Brreached about 49.7percent. The synthesis method can be showedas the followed Scheme 2.

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YieldReaction ConditionsOperation in experiment
100% ultrasound 4.89 g of methylimidazole (0.059 mol) and 8.98 g of butyl bromide (0.065 mol) are introduced into a beaker. The beaker is placed under ultrasound, adjusted to have a pulsation of 2 seconds, with an instantaneous power of 15 W. The butylmethylimidazolium bromide is obtained with 100percent yield. This product is then added dropwise at ambient temperature to a mixture containing 50 ml of water and an equimolar quantity of lithium bis(trifluorosulphonyl)imide. The mixture is then maintained for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70° C. for 30 minutes. The overall yield is 94percent.
100% at 50℃; for 12 h; Inert atmosphere N-methyl imidazole (8.21 g, 0.1 mol) and n-bromobutane (20.55 g, 0.15 mol) were added into the Schlenk tube under nitrogen atmosphere. The reaction mixture was firstly stirred at room temperature for 30 min and followed by heating slowly to 50 oC for another 12 h. After completed, the mixture was washed thrice with redistilled petroleum and ethyl acetate (1:1, 50 mL.x.3). The great amount of white solid was generated during the washing with solvents. Then the product was drained at room temperature under vacuum for 2 h and dried continuously at 50 oC under vacuum for another 6 h. Finally, the white waxy solid BmimBr was obtained in nearly quantitative yield (21.99 g).
99% for 24 h; Reflux General procedure: 1-Butyl-3-methylimidazolium bromide was synthesized. 1-Bromobutane (1.1 mol) was added dropwise into 1-methylimidazole (1 mol) with agitation at 70 °C. The reaction mixture was refluxed for 24 h, and when cooled to room temperature, ethyl acetate was added to the mixture. The ethyl acetate was removed by a separating funnel followed by the addition of fresh ethyl acetate, and this step was repeated four times. The remaining ethyl acetate was removed by rotary evaporation, and the solution was dried under high vacuum at (343–353)K for at least 6 h to get 1-butyl-3-methylimidazolium bromide ([C4mim] [Br]) at very high yield (99percent) (Scheme 1).
96.3% at 70℃; for 24 h; An oil bath with a stirred flask containing equimolar amounts of commercially available 1-methylimidazole and 1-bromobutane in toluene was heated at 70 °C for 24 h. After cooling to room temperature, the reaction mixture was separated and the upper toluene phase was recycled. The lower phase was washed with ethyl acetate and chloroform, and the residue was dried under vacuum to give the product (white crystals), yield: 96.3percent, mp: 77-78 °C. 1H NM (D2O, 400 MHz) δ: 1.68 (t, J = 14.8 Hz, 3H, CH3), 2.06 (m, 2H, CH2), 2.61 (m, 2H, CH2), 4.95 (t, J = 14.4 Hz, 2H, NCH2), 5.54 (s, 3H, NCH3), 8.16-8.25 (m, 2H, C3H3N2 4,5-H), 9.48 (s, 1H, C3H3N2 2-H).
96.23% at 45 - 90℃; for 4.83333 h; Large scale A method for preparing 1-butyl-3-methylimidazolium bromide comprises the following steps:(1) take the reaction raw material bromobutane 30Kg 80L reactor was added to the reactor by passing a water bath into the reactor bromine butyl bromide was heated until heated to 55 ~ 60 ° C;(2) After the raw material is heated and stirred in step (1), the water bath is turned off and 16Kg of N-methylimidazole is added dropwise to the reaction vessel, and the dropwise addition is completed within 4 hours;(3) After the addition of N-methylimidazole in step (2),The temperature is controlled at 80 ~ 90 °C and stirring is continued for 50 minutes.Ethyl acetate 16L was added after stirring was completed.The temperature is lowered by passing tap water into the reaction vessel sandwich.And continue to stir until the temperature of the reactor is lowered to 45-55°C to complete the reaction; then the material is discharged from the outlet of the reactor (the discharge temperature is 45-55°C); the discharged material is transported to the cover through the material conveying pipeline. Centrifuge with feed port, and then added ethyl acetate through the feed port on the cover of the centrifuge to wash the discharged material, centrifuge while washing (centrifuge speed is 350r/min), washing is completed (will not be reacted After the raw material is washed, a white solid is obtained;(4) The white solid obtained after rinsing and centrifuging as described in step (3) is vacuum-steamed under the condition of 40-50° C. (vacuum degree in vacuum rotary evaporation is −0.08 MPa) to remove residual ethyl acetate. That is, 1-butyl-3-methylimidazolium bromide white solid particles are obtained. After testing, the yield of the obtained product is 96.23percent; the purity is 99.80percent and its water content is 1660 ppm; that is, the product prepared by this method has a high yield and purity, and the water content is low and meets the requirements.
95% at 60 - 70℃; for 2 h; A mixture of 0.04 mol N-methyl imidazole, 0.04 mol butyl bromide, and 25 mL of toluene was reuxed at 60-70C for 2 h. After cooling to room temperature, the lower phase, which contained the product, was separated from the upper phase. The product was washed a few more times with toluene and yellowish viscous liquid was obtained in 95percent yield.
94% at 90℃; for 24 h; Inert atmosphere Freshly distilled 1-methylimidazole (8.21g, 0.1mol) and n-butylbromide (13.7g, 0.1mol) were combined in 100 mL round bottom flask equiped with a reflux condenser. The reaction mixture was heated to reflux (90°C) under N2 atmosphere for 24h. The product was washed with ethyl acetate (3×30 mL) to remove starting material. The residual ethyl acetate was removed from product under vacuum pressure. The yellow solid was dissolved in water (50 mL) and decolorizing charcoal (2g) was added. This solution was heated at 70°C for 24h, cooled and filtered. The water was removed using rotavapor. The resulting solid was heated under high vacuum for 48h at 70°C. The product was obtained as a white solid.Yield: 94percent,
94% at 40℃; for 12 h; The ionic liquid [C4mim]Br was prepared according to the procedure described in the literature [30]. 1-Bromobutane (13.7g, 0.1mol) was slowly added to freshly distilled 1-methylimidazole (8.2g, 0.1mol) in a 100mL round-bottom flask fitted with a reflux condenser. This mixture was then stirred with a magnetic stirrer at 40°C for 12h, during a yellowish viscous liquid formed. The liquid was then purified by moderate amount of ethyl acetate, gave the white solid product with a 94percent yield.
94% for 24 h; Reflux 10 mL (0.13 mol) of 1-methylimidazole, 16 mL (0.15 mol) of 1-bromobutane and 50 mL ofacetonitrile were added to the round-bottomed flask fitted with a reflux condenser and refluxed for24 hours. After removal of the solvent, the residual liquid was diluted with 50 mL of deionizedwater. The solution was washed with 50 mL of ethyl acetate three times. After the water phasewas evaporated, the residual liquid was further dried in vacuo (under 0.1mbar) at 60°C for 24 hours,producing a pale yellow viscous liquid (yield: 25.8g, 94percent).
92% at 70℃; for 24 h; To a clean, dry round-bottomed flask were added 1-methylimidazole (29.4 mL, 0.37 mol) and 1-bromobutane (44.1 mL, 0.41 mol). The reaction mixture was stirred at 70 °C for 24 h. During this time, an emulsion formed, followed by the formation of the colourless ionic liquid. The crude ionic liquid was washed with Et2O (3 .x. 30 mL) to remove excess 1-bromobutane, then dried in vacuo (50 °C, 40 mbar) for 2 h. On cooling to room temperature, the colourless, viscous ionic liquid crystallised to form a white solid. Yield: 74.1 g (92percent); 1H NMR (DMSO-d6) δ 0.86 (3H, t, J = 7.2 Hz), 1.23 (2H, m), 1.74 (2H, m), 3.86 (3H, s), 4.19 (2H, t, J = 7.2 Hz), 7.78 (1H, t, J = 1.8 Hz), 7.86 (1H, t, J = 1.8 Hz), 9.36 (1H, t, J = 1.8 Hz); 13C NMR (DMSO-d6) δ 13.4, 18.9, 31.5, 35.9, 48.6, 122.4, 123.7, 136.7 ppm.
87% at 70℃; for 24 h; General procedure: C4mimBr was synthesized according to the reported literatures.1 In a 100 mL round-bottom flask, 1-methylimidazole (8.21 g, 0.1 mol) was mixed with n-butyl bromide (16.44 g, 0.12 mol) and allowed to reflux for 24 h at 70 °C. The excess n-butyl bromide was distilled off under reduced pressure and the residue was finally extracted thoroughly 2-3 times (50 mL each) with diethyl ether to remove the traces of unreacted starting materials. A white solid of 1-n-butyl-3-methylimidazolium bromide was obtained in 87percent yield.
86% at 60 - 70℃; Inert atmosphere For the synthesis of IL [bmim][Br], slight excess of 1-bromobutane(10 g, 73 mmol) was added drop wise to 1-methylimidazole (5.7 g,69 mmol) in a round bottom flask followed by refluxing the solutionat about 60–70 °C for 24 h under N2 atmosphere. It was then cooledto room temperature followed by washing of the product obtainedusing diethyl ether several times. After this slight yellow viscous productis obtained which was dried under vacuum to get 1-butyl-3-methylimidazolium bromide [bmim][Br], with 86percent yield. Karl–Fisherexamination of the IL indicated that the water content reduced tob400 ppm.1H NMR (400 MHz, D2O, δ-ppm): 0.846(t, 3H), 1.241(m, 2H),1.771(m, 2H), 3.810(s, 3H), 4.116(t, 2H), 7.344(d, 1H), 7.393(d, 1H).8.625(s, 1H).
82% at 0 - 40℃; for 12 h; Inert atmosphere Under inert conditions, 1-methyl-imidazole (1 eq) was addedto neat 1-bromobutane (2 eq) at 0°C. The mixture wasstirred during 12 hours under 40°C. The resulting salt was dried to give yellowoil and a white solid was obtained by several wash with diethyl ether. The final product was dried during 12 hours at roomtemperature. Yield: 82percent. 1H NMR (DMSO-d6, 300 MHz): δ (ppm) = 9.24 (s,1H,Im+), 7.77 (d,2H,Im+), 4.17(t,2H,-CH2Im+), 3.86 (s,3H, CH3Im+),1.76 (m,2H,-CH2-) 1.25 (m,2H,-CH2-), 0.89 (t,3H,-CH3).13C NMR (DMSO-d6, 125 MHz): δ(ppm) = 136.99(Im+); 124.05(Im+); 122.72(Im+);48.91(CH3Im+); 36.23(-CH2Im+);31.82(-CH2-); 19.22(-CH2-); 13.74(-CH3). HR MS(ESI) m/z: [M*+](calcd for C8H15N2+):139.123 found: 139.124. Elementalanalysis: Calcd for C8H15BrN2: N 12.78; C43.85; H 6.90. Found: N 12.73; C 43.91; H 7.02.
50% at 80℃; Schlenk technique To a 50 mL Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-bromobutane(13.5g, 0.1 mol, 2equiv) and distilled toluene (20 mL), the mixture were heated and stirred at 80 °C oil bath overnight, after reaction, all the versitile were removed under vacuo, the residue red oil were washed with 2-methoxy-2-methylpropane (5 * 20 mL), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium bromide ( NHC precursor F ) as colorless oil (50percent, 5g)

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  • 71
  • [ 616-47-7 ]
  • [ 74-96-4 ]
  • [ 301-04-2 ]
  • [ 143314-17-4 ]
YieldReaction ConditionsOperation in experiment
92 %Spectr. at 50℃; for 0.5 h; Microwave irradiation Synthesis of 1-ethyl-3-methylimidazolium acetate ([Emim] Ac) in one step To a 500 ml round bottom flask was added 1.2 mol of bromoethane and 0.5 mol of lead acetate, To the constant-pressure dropping funnel was added 1 mol of N-methylimidazole, The reaction was carried out in an ultrasonic microwave combined reactor, The knob of the constant-pressure dropping funnel was controlled so that 1 mol of N-methylimidazole was dropped in one minute, The left through the cooling water, Set the ultrasonic power to 1000W, Microwave heating power of 900W, The reaction was carried out at 50 ° C for 30 minutes. The content of the target product [Emim] Ac in the reaction mixture was determined to be 92percent by nuclear magnetic resonance (NMR) and liquid chromatography-mass spectrometry.
Reference: [1] Journal of Molecular Liquids, 2012, vol. 165, p. 173 - 176
[2] Patent: CN105315215, 2016, A, . Location in patent: Paragraph 0013; 0014; 0015
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  • [ 64-17-5 ]
  • [ 64-19-7 ]
  • [ 143314-17-4 ]
YieldReaction ConditionsOperation in experiment
17% at 165℃; for 72 h; Autoclave Acetic acid 44 ml was added to a 250 ml Erlenmeyer flask containing 43 ml Ethanol. 6 ml 1-Methylimidazol was then added slowly to the stirred mixture. The mixture was then sealed inside a parr reactor whit continuous stirring for 72 hours at a temperature of 165 °C. The resulting dark liquid was placed in a rotary evaporator at 50 °C water bath. The mixture was then fed to a vacuum distillation equipment to remove the precursor and excess acetic acid. The still remaining liquid was then finally purified by Flash chromatography in a C18 pre-packet column with water as the eluent . The light yellow fractions were saved. This step was repeated 4 times. The final product was dissolved twice in 99,5percent ethyl alcohols and subjected to vacuum treatment. Yield 17percent. 13C-NMR (400HHz, DMSO) δ 175.0, 138.7, 124.6, 123.1, 44.9, 36.4, 26.4, 16.3.
Reference: [1] Journal of Molecular Structure, 2012, vol. 1028, p. 156 - 163
  • 73
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  • [ 253453-91-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: With hexachloroethane In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
A literature procedure for the synthesis of the title compound was adopted.1 A solution of N-methyl-1H-imidazole (1.5 mL, 1.56 g, 19 mmol) in anhydrous THF (12 mL) was cooled to -78 °C and n-BuLi (2.5 M in hexanes, 14 mL, 21 mmol) was added dropwise by syringe understirring. The resulting yellow solution was stirred for 30 minutes where upon a solution of hexachloroethane (5.00 g, 21 mmol) in anhydrous THF (12 mL) was added dropwise by syringe resulting in the formation of a pale grey solid. The reaction mixture was stirred for 1h at -78 °C, then a saturated solution of aqueous ammonium chloride (25 mL) was added.The resulting mixture was allowed to return at room temperature, and diluted with ethylacetate (150 mL). The organic layer was separated, washed with water and brine, and driedover anhydrous Na2SO4. After filtration, the solvents were evaporated under reducedpressure, the residue was dissolved in hexane (50 mL) and HCl (20percent, 50 mL) was added. The resulting mixture was stirred at room temperature for 30 minutes, then the organic layer was separated and extracted with HClaq 20percent (2 x 10 mL). The collected acidic aqueous extracts were neutralized with solid KOH, filtered and extracted with diethyl ether (3 x 25mL). The organic extracts were then concentrated under reduced pressure to afford the desired product 1e (1.97 g, 90percent).
80% With n-butyllithium; hexachloroethane In tetrahydrofuran; hexane at -78℃; for 1.5 h; Step A: Preparation of 2-Chloro-1-methyl-1H-imidazole. To a 300-mL, three-necked, round-bottomed flask equipped with a magnetic stirrer, and nitrogen inlet was added N-methylimidazole (4.1 g, 0.05 mol) and anhydrous THF (25 mL). The stirrer was started and the solution was cooled to -78° C. n-BuLi (2.5 M in hexanes, 22 mL, 0.055 mol) was added via syringe resulting in a golden yellow solution. This solution was stirred for 30 min whereupon a solution of hexachloroethane (13 g, 0.055 mol) in THF (25 mL) was slowly added via syringe. The reaction mixture was stirred for 1 h and then was quenched with satd. aq. NH4Cl (25 mL). The cooling bath was removed and when the reaction flask reached rt the contents were transferred to a 500 mL separatory funnel, washing with EtOAc (150 mL). The organic layer was separated, washed with water, brine, and dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure resulting in an oily residue. This crude product was distilled under reduced pressure to afford 2-chloro-1-methyl-1H-imdazole (4.75 g, 80percent) as a colorless liquid. bp 54° C./2 Torr. IR (film): 1515, 1420, 1367, 1277,1127, 912, 740, 689, 665 cm-1. 1H NMR (400 MHz, CDCl3): δ6.92 (d, J=1.5 Hz, 1H), 6.85 (d, J=1.5 Hz, 1H), 3.55 (s, 3H). 13C NMR (100 MHz, CDCl3): δ132.4, 128.0, 122.3, 33.5. HRMS (EI): m/z calcd for C4H6ClN2 [M+H]+, 117.0223; found, 117.0220
60%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: With hexachloroethane In tetrahydrofuran at -78℃; Inert atmosphere
To a solution of 1-methyl-1H-imidazole (200 g, 2.44 mol) in anhydrous THF (2 L) was added dropwise n-BuLi (2.5M, 1.07 L, 2.68 mol) at -78 ° C with stirring over 2 h. Then perchloroethane (800 g, 0.845 mol) in dry THF (1L) was added dropwise to above solution over 1h at the same temperature. After the starting material was consumed, the mixture was poured into saturated ammonium hydrochloride, extracted with ethyl acetate (800 mL x 3), washed with brine, the organic phase was dried and concentrated to give crude product which was purified by column chromatography on silca gel (PE/ EtOAc = 20:1~5:1) to give the title compound (170 g, 60percent) as a yellow oil.
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[2] Patent: US2005/250948, 2005, A1, . Location in patent: Page/Page column 41
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  • 74
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  • [ 109-69-3 ]
  • [ 79917-90-1 ]
YieldReaction ConditionsOperation in experiment
92% at 90℃; Schlenk technique To a 50ml Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-chlorobutane (9.2g, 0.1 mol, 2 equiv) and distilled toluene (20 ml), the mixture were heated and stirred at 90 °C oil bath for overnight, after reaction, all the versitile were removed under vacuo. the residue were washed with 2-methoxy-2-methylpropane (3* 20 ml), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium chloride (NHC precursor E) as white solid (92percent, 8g)
90% at 40℃; for 24 h; 1) N-Methylimidazole (4 g, 48.7 mmol)In a single-necked flask,And then weighed1-Chloromethane6.68 g (72.2 mmol)(The molar ratio of 1-methyl chloride to N-methyl imidazole was about 1.48: 1). After the dropwise addition, the reaction was carried out at 40 ° C for 24 hours. The reaction was monitored by thin layer chromatography , The excess of 1-methyl chloride distillation, the white solid is chlorinated 1-butyl-3-methyl imidazole, the yield of 90percent;
90% at 150℃; Microwave irradiation In a MW vial, 4 mL of 1-methylimidazole(0.0484 mol) and 7.6 mL of 1-chlorobutane (0.0726 mol) were consecutively added; then, the mixturewas irradiated (200 W) at 150 °C for 25 min. Then, the supernatant 1-chlorobutane was removedand the mixture was then washed with hexane and diluted with CH2Cl2 to be transferred in a roundbottom flask for the removal of solvent under vacuum. The desired product 5 was obtained in 90percentyield. 1H-NMR (200 MHz, CDCl3, ppm): δ = 9.71 (s, 1H), 7.99 (m, 1H), 7.89 (m, 1H), 4.24 (t, 2H,J = 7.0 Hz), 3.91 (s, 3H), 1.77 (m, 2H), 1.30 (m, 2H), 0.88 (t, 3H, J = 7.2 Hz).
88.6% for 48 h; Reflux Synthesis of 1-butyl-3-methylimidazolium chloride: A mixture of 1-methylimidazole (70.0 g, 0.853 mol), ethanenitrile (50 mL) and 1-chlorobutane (102 g, 1.10 mol) are heated under reflux with vigorous stirring for 48 hrs. 1-chlorobutane (99.5percent) is sourced from a commercial supplier (Sigma-Aldrich). Volatile substances are removed in a first step under reduced pressure (ca. 50° C., 20 mbar), and finally, in vacuo (ca. 80° C., 0.01 mbar) during 16 hrs, yielding 1-butyl-3-methylimidazolium chloride ([C4mim]Cl, 131.8 g, 88.6percent) as a pale yellow viscous liquid which crystallizes upon cooling to room temperature.
88% at 60 - 65℃; for 24 h; An amount of 1-methylimidazole (10 mmol, 1.745 g) and n-butylchloride (11 mmol, 1.018 g) were sequentially added into a 25 mL round-bottom flask assembled with the condenser. The reaction mixture was stirred magnetically with 250 rpm speed at 60–65 °C for 24 h. After cooling down to room temperature, the reaction mixture was washed with diethyl ether(5 x 10 mL) until no trace of n-butyl chloride, as well as 1-methylimidazole in a solution of diethylether were detected by thin layer chromatography (TLC) and gas chromatography (GC). The othersolution containing recyclable [Bmim]Cl was evaporated under reduced pressure at 80 °C for 30 minto afford a light yellow liquid in high yield (88percent). The identity and purity of [Bmim]Cl obtainedwere analyzed by 1H-NMR, 13C-NMR and LC/MS spectroscopy. In continuation of the preparationof [Bmim]Cl*2AlCl3, an amount of aluminum chloride (4 mmol, 0.534 g) was added slowly into a10 mL round-bottom flask containing [Bmim]Cl (2 mmol, 0.349 g). After that, the reaction mixturewere stirred magnetically at room temperature for 12 h. The identity and purity of acidic catalyst,[Bmim]Cl*2AlCl3, were checked by 1H-NMR and integrated as follows: 1H-NMR (500 MHz, D2O): δ (ppm) 8.65 (s, 1H), 7.43 (s,1H), 7.38 (s, 1H), 4.14 (t, J = 7.0 Hz, 2H), 3.84 (s, 3H), 1.77–1.82 (m, 2H),1.23–1.30 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H).
86% at 110℃; for 24 h; To a vigorously stirred solution of 1-methylimidazole (1.25 mol) in toluene (125 mL) at 0 °C, 1-chlorobutane (1.38 mol) was added.
The solution was heated to reflux at 110 °C for 24 h, after which it was placed in a freezer at - 20 °C for 12 h.
The toluene was decanted and the remaining viscous oil/semi-solid was recrystallized from acetonitrile.
Again it was repeatedly recrystallized from ethyl acetate to yield a white crystalline solid, which was further dried under reduced pressure to give [Bmim]Cl in approximately 86percent yield. 1H NMR (400 MHz, DMSO-d6): δ = 10.54 (1H, s), 7.55 (1H, m), 7.40 (1H, m), 4.26 (2H, t, J = 7.3 Hz), 4.11 (3H, s), 1.82 (2H, m), 1.30 (2H, m), 0.89 (3H, t, J = 7.3 Hz).
Chloride ion is 21.10 wtpercent
85% at 80℃; 1-Butyl-3-methylimidazolium chloride was prepared from the reaction of N-methylimidazole with n-butylchloride at 80 °C under neat conditions.
82% at 75℃; for 48 h; Inert atmosphere 1-butyl-3-methylimidazolium chloride [bmim][Cl] synthesized accordingto organic synthesis [39]. A mixture of 1-methylimidazole(1 eq) and 1-chlorobutane (1.3 eq) in dry acetonitrile was stirred at75 °C for 48 h under nitrogen.The mixture was cooled to room temperature.The volatile material was removed under reduced pressure andthe remaining light-yellow oil dissolved in appropriate acetonitrileand added dropwise to a flask containing dry ethyl acetate dry ethyl acetatecontaining flask to give [bmim][Cl] as a white crystal in approximately82percent yeild.
80% Reflux; Inert atmosphere Two chloride-based ionic liquids, [BMIM]Cl and [AMIM]Cl, were synthesized according to the literature methods [10,11], respectively. Reactions were carried out under nitrogen atmosphere and followed by ESI-MS and 1H NMR. Produced ILs were dried overnight in a high vacuum at 50–70 °C and stored in a desiccator. Water content of the IL determined by the Mettler Toledo DL36 Karl Fischer coulometer was <0.1percent (w/w). (0012) [BMIM]Cl was prepared from butyl chloride (159.5 g, 1.72 mol) and N-methylimidazole (103.0 g, 1.25 mol) in a 500 ml flask by mixing and refluxing until all methylimidazole had reacted (24–48 h). The crude product was then recrystallized from an ethyl acetate–acetonitrile mixture (55:45). The yield of white [BMIM]Cl was 174.8 g (80percent). 1H NMR (200 MHz, CDCl3): δ 0.96 (3H, t, JHH = 7.3 Hz), 1.41 (2H, m), 1.89 (2H, m), 4.13 (3H, s), 4.34 (2H, t, JHH = 7.3 Hz), 7.47 (1H, t, JHH = 1.8 Hz), 7.62 (1H, t, JHH = 1.8 Hz),10.67 (1H,s). MS(ESI+) [m/z (rel. int. (percent))]: 139 (100, [BMIM]). MS(ESI) [m/z (rel. int. (percent))]: 210 (100, Cl[BMIM]Cl)
72% at 70℃; for 24 h; General procedure: C4mimBr was synthesized according to the reported literatures.1 In a 100 mL round-bottom flask, 1-methylimidazole (8.21 g, 0.1 mol) was mixed with n-butyl bromide (16.44 g, 0.12 mol) and allowed to reflux for 24 h at 70 °C. The excess n-butyl bromide was distilled off under reduced pressure and the residue was finally extracted thoroughly 2-3 times (50 mL each) with diethyl ether to remove the traces of unreacted starting materials. A white solid of 1-n-butyl-3-methylimidazolium bromide was obtained in 87percent yield.
72.4% at 75℃; for 48 h; Equipped with a blender,Reflux condenser and a thermometer 500mL three-necked flask was added 68.60g N-methyl imidazole and 85.65g chlorobutane,And were added 80mL cyclohexane and toluene as the reaction medium,Control the temperature inside the bottle is 70 ,After stirring for 48h, the upper solvent and the unreacted raw materials were removed by pouring,The lower oily liquid was hot with ethyl acetate 4 times (each time the amount of 20mL)Remove the liquid transfer to a single mouth flask,Rotate under reduced pressure (water bath temperature was controlled at 70 ) to remove part of the solvent and raw materials unreacted raw materials.Turn the steam transfer to the vacuum drying oven,The temperature is 70 ,Vacuum dried 36h,That is to obtain the intermediate l-butyl-3-methylimidazolium chloride [Bmim] Cl,Yield 68.6percent.
70.2% at 80℃; for 36 h; 500 mL equipped with a stirrer, reflux condenser and thermometerThree-necked flask was added 68.60gN-methylimidazole and85.65g chlorobutane, and were added 80mL cyclohexane and toluene as the reaction medium,Control the temperature inside the bottle is 80 ,After stirring for 36h, the upper solvent and the unreacted raw materials were removed by pouring,The lower oily liquid was hot with ethyl acetate 4 times (each time the amount of 20mL)Remove the liquid transfer to a single mouth flask,Rotate under reduced pressure (water bath temperature was controlled at 70 ) to remove part of the solvent and raw materials unreacted raw materials. Turn the steam transfer to a vacuum oven, the temperature is 70 ,Drying in vacuo for 36 h gave the intermediate productL-butyl-3-methylimidazolium chloride[Bmim] Cl, yield 70.2percent.
68.2% at 70℃; for 48 h; In the presence of a stirrer,Reflux condenser and a thermometer was charged 68.60 g of N-methylimidazole in a 500 mL three-necked flaskAnd 85.65 g of chlorobutane,And adding 80mL of cyclohexane and toluene as reaction intermediates,The temperature in the control bottle is 70 ° C,After stirring for 48 h, the upper layer solvent and the unreacted starting material were removed by the pouring method,The lower oily liquid was washed 4 times with ethyl acetate (20 mL each)Remove the liquid from the lower layer to the vial,Vacuum distillation (water bath temperature control at 70 ° C) to remove part of the solvent and raw materials in the unreacted raw materials.Steaming finished transferred to a vacuum oven,The temperature is 70 ° C, vacuum drying 36h,To give the intermediate 1-butyl-3-methylimidazolium chloride[Bmim] C1, yield 68.2percent.
61% at 65℃; for 11 h; 9.27g (0.1mol) 1-chlorobutane was added dropwise to 11.50g (0.14mol) 1-methylimidazole. The mixture was heated at 65°C under stirring for 11h. Phase separation occurred and the viscous yellow liquid obtained was washed with ethyl acetate (60 mL for three times). Then the product was filtered and dried in vacuum dryness case until constant weigh. 10.80g [bmim]Cl was obtained, and the yield of colorless liquid was 61percent.

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  • [ 74-96-4 ]
  • [ 155371-19-0 ]
YieldReaction ConditionsOperation in experiment
92% at 70℃; for 336 h; In einen 1 I Schlenkkolben werden 92,1 g (1,20 mol) 1-Methylimidazol, 261,5 (2,40 mol) Ethylbromid und 302,3 g (1,80 mol) Natriumhexafluorophosphat gegeben und bei 70°C ca. 2 Wochen geruehrt. Der entstandene weisse Feststoff wird ueber eine Schutzgasfritte abfiltriert. Der Filterkuchen wird zwei mal mit je 400 ml Methylenchlorid gewaschen, die Phasen vereinigt und von dem Methylenchlorid befreit. Danach wird der weisse Feststoff ueber Nacht bei 60°C im HV getrocknet. Man erhaelt 1-Ethyl-3-methyl-imidazolium hexafluorophosphat in 92 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 g des Produktes in ca. 5 ml Wasser geloest und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Niederschlags spricht fuer die komplette Abwesenheit von Chloridresten. 1H-NMR (300 MHz, CDCl3):δ=9.6 ppm (s,1H,Ha); δ=7.26 ppm (d,1H,Hc); δ=7.24 ppm (d,1H,Hd); δ=3.9 ppm (q,2H,He); δ=3.6 ppm (s,3H,Hb); δ=1.2 ppm (t,3H,Hf). 13C-NMR (75 MHz, CDCl3):δ=137 ppm (C1); δ=124-122 ppm (C3,C4); δ=45 ppm (C5); δ=36 ppm (C2); δ=16 ppm (C6). 31P-NMR (121 Mhz):-143.08 (Heptett, J=710 Hz). 19F-NMR (281 Mhz): -72.5 (d, J=710 Hz).
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: for 0.25 h;
Stage #2: With sodium hexaflorophosphate In water
In einen 2 I Schlenkkolben werden 410,5 g (5 mol) 1-Methylimidazol vorgelegt und 770,95g (5 mol) Diethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Der Kolbeninhalt wird danach in ein 5I Becherglas ueberfuehrt und zu einer Mischung von 839,7g (5 mol) Natriumhexafluorophosphat in 2 Liter Wasser gegeben. Sofort bildet sich ein weisser Feststoff, der durch Filtration isoliert wird. Die waessrige Phase wird noch zweimal mit je 1 Liter CH2Cl2extrahiert, die organischen Phasen vereinigt und von Methylenchlorid befreit. Das Produkt wird ueber Nacht bei 60°C am HV getrocknet. Man erhaelt 1-Ethyl-3-methyl-imidazoliumhexafluorophosphat in 82 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 g des Produktes in ca. 5 ml Wasser geloest und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Silberchlorid-Niederschlags spricht fuer die komplette Abwesenheit von Halogenidionen. 1H-NMR (300 MHz, CDCl3):δ=9.6 ppm (s,1H,Ha); δ=7.26 ppm (d,1H,Hc); δ=7.24 ppm (d,1H,Hd); δ=3.9 ppm (q,2H,He); δ=3.6 ppm (s,3H,Hb); δ=1.2 ppm (t,3H,Hf).13C-NMR (75 MHz, CDCl3):δ=137 ppm (C1); δ=124-122 ppm (C3,C4); δ=45 ppm (C5); δ=36 ppm (C2); δ=16 ppm (C6).31P-NMR (121 Mhz):-143.08 (Heptett, J=710 Hz).19F-NMR (281 Mhz): -72.5 (d, J=710 Hz).
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YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 80℃; for 12 h;
81.89 g (1.0 mol) of 1-methylimidazole, 128.95 g (1.0 mol) of and 92.0 g (1.0 mol) of potassium hexafluorophosphate in a 500 ml three necked round bottom flask with a reflux condenser at 80 °C for 12 h. 1-bromobutane De-ionized water (100 ml) was added and a bi-phase was formed. The immiscible ionic liquid layer was separated from the water phase with a separating funnel. The ionic liquid was washed with de-ionized water (2 × 50 ml) until the water phase did not react with 0.001 M aqueous silver nitrate (AgNO3). Diethyl ether(2 × 30ml) was added to the ionic liquid and separated in a separating funnel. The ionic liquid was dried in vacuum for 2 h. A colorless liquid was obtained Yield (86percent). The ionic liquid was characterized and by1H and 13C NMR FTIR and by TGA. 1H NMRof the ionic liquid sample (300MHz,DMSO) contains peaks at δ: 9.05 (s, 1H-imidazole), 7.77 (s, 1H-imidazole), 7.65 (s, 1H-imidazole),4.16 (s, N–CH3), 3.8 (s, N–methyl), 1.8 (s, CH2), 1.30 (s, CH2), and 0.92(t, methyl).13C NMR in Fig. 4.4 (300 MHz, DMSO) δ: 19.2 (qt, CH3), 32.3 (q, CH2), 35.69, (q, CH2), 40.55 (tq, N-methyl), 48.5 (t, N–CH2),0.120.3(dm, imidazole CH), 122.5 (d, imidazole CH), 135.4 (d, imidazole CH).
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  • [ 174501-64-5 ]
YieldReaction ConditionsOperation in experiment
92% at 70℃; for 336 h; In einen 1 I Schlenkkolben werden 92,1 g (1,20 mol) 1-Methylimidazol, 222,2 g (2,40 mol) Butylchlorid und 302,3 g (1,80 mol) Natriumhexafluorophosphat gegeben und bei 70°C ca. 2 Wochen geruehrt. Der entstandene weisse Feststoff wird ueber eine Schutzgasfritte abfiltriert und die sich gebildeten zwei Phasen voneinander mit Hilfe eines Scheidetrichters getrennt. Die untere gelbliche Phase wird ueber Nacht bei 60°C im HV getrocknet. Man erhaelt 1-Butyl-3-methylimidazoliumhexafluorophosphat in 92 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 ml des Produktes mit ca. 5 ml Wasser versetzt und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Niederschlags spricht fuer die komplette Abwesenheit von Chloridresten. 1H-NMR (300 MHz, CDCl3):0,77 (3 H, tr, J=5,8 Hz, Ha); 1,05-1,17 (2 H, m, Hb); 1,50-1,59 (2 H, m, Hc); 3,51 (3 H, s, Hh); 3,75 (2 H, tr, J=5,8 Hz, Hd); 6,95-7,26 (je 1 H, s, Hf,g); 7,97 (1 H, s, He). 13C-NMR (75 MHz, CDCl3):13,3 (a); 19,4-35,7 (b, c, d); 49,5 (h); 122,2-123,5 (f,g); 135,7 (e). 31P-NMR (121 MHz, CDCl3):-143,08 (Heptett, J=710Hz) 19F-NMR (281 MHz, CDCl3):-72,5 (d, J=710 Hz)
92%
Stage #1: for 48 h; Reflux
Stage #2: With potassium hexafluorophosphate In toluene
N-methylimidazole, pyridine, N-methylmorpholine, N-methylpyrrole and other cyclic tertiary amine compounds (referred to as cyclic tertiary amine) and excess n-butyl chloride were added and refluxed in toluene for 48 hours to obtain corresponding chloride salts. The chloride salts and KBF4, KPF6, CH3COOK, KHSO4, potassium p-toluenesulfonate (p-TSAK) and the like are subjected to ion exchange reaction. The resulting product was filtered to remove the product, extracted with CH2Cl2, vacuum dried to obtain ionic liquid IL1-IL13. The reaction conditions and results are shown in Table 1.
Reference: [1] Patent: EP1182197, 2002, A1, . Location in patent: Page 9-10
[2] Patent: CN104672053, 2016, B, . Location in patent: Paragraph 0048; 0049; 0052-0054
[3] Molecules, 2008, vol. 13, # 1, p. 149 - 156
[4] Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5312 - 5319
[5] Synthesis, 2003, # 17, p. 2626 - 2628
[6] Analytical Chemistry, 2004, vol. 76, # 17, p. 5039 - 5044
[7] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3337 - 3340
[8] Journal of Chemical and Engineering Data, 2003, vol. 48, # 3, p. 486 - 491
[9] Mendeleev Communications, 2011, vol. 21, # 6, p. 329 - 330
[10] Journal of Materials Chemistry A, 2013, vol. 1, # 11, p. 3706 - 3712
  • 82
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  • [ 542-69-8 ]
  • [ 174501-64-5 ]
Reference: [1] Synthesis, 2003, # 17, p. 2626 - 2628
  • 83
  • [ 616-47-7 ]
  • [ 109-65-9 ]
  • [ 90076-65-6 ]
  • [ 174899-83-3 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1553 - 1557
[2] Journal of Organic Chemistry, 2007, vol. 72, # 20, p. 7790 - 7793
[3] Journal of Solution Chemistry, 2010, vol. 39, # 3, p. 371 - 383
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  • [ 109-69-3 ]
  • [ 90076-65-6 ]
  • [ 174899-83-3 ]
Reference: [1] Molecules, 2008, vol. 13, # 1, p. 149 - 156
  • 85
  • [ 616-47-7 ]
  • [ 544-10-5 ]
  • [ 304680-35-1 ]
YieldReaction ConditionsOperation in experiment
87% at 70℃; for 336 h; In einen 1 I Schlenkkolben werden 82,9 g (1,08 mol) 1-Methylimidazol, 260,5 g (2,16 mol) Hexylchlorid und 272,1 g (1,62 mol) Natriumhexafluorophosphat gegeben und bei 70°C ca. 2 Wochen geruehrt. Der entstandene weisse Feststoff wird ueber eine Schutzgasfritte abfiltriert und die sich gebildeten zwei Phasen voneinander mit Hilfe eines Scheidetrichters getrennt. Die untere gelbliche Phase wird ueber Nacht bei 60°C im HV getrocknet. Man erhaelt 1-Hexyl-3-methyl-imidazolium hexafluorophosphat in 87 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 ml des Produktes mit ca. 5 ml Wasser versetzt und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Niederschlags spricht fuer die komplette Abwesenheit von Chloridresten. 1H-NMR (300 MHz, CDCl3):δ=9.9 ppm (s,1H,Ha); δ=7.26 ppm (d,1H,Hc); δ=7.24 ppm (d,1H,Hd); δ=4.1 ppm (t,2H,He); δ=3.9 ppm (s,2H,Hb); δ=1.6 ppm (m,2H,Hf); δ=1.2 ppm (m,6H,Hg,h,i); δ=0.8 ppm (t,3H,Hj). 13C-NMR (75 MHz, CDCl3):δ=137 ppm (C1); δ=124-122 ppm (C3,C4); δ=48 ppm (C5); δ=35 ppm (C2); δ=29-24 ppm (C6-C8); δ=20 ppm (C9); δ=13 ppm (C10). 31P-NMR (121 Mhz):-143.08 (Heptett, J=710 Hz). 19F-NMR (281 Mhz): -72.5 (d, J=710 Hz).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 51, p. 9223 - 9224
[2] Patent: EP1182197, 2002, A1, . Location in patent: Page 10
[3] Analytical Chemistry, 2004, vol. 76, # 17, p. 5039 - 5044
[4] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3337 - 3340
[5] Journal of Chemical and Engineering Data, 2003, vol. 48, # 3, p. 486 - 491
  • 86
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  • [ 111-25-1 ]
  • [ 304680-35-1 ]
Reference: [1] Synlett, 2007, # 13, p. 2065 - 2068
[2] Synthesis, 2003, # 17, p. 2626 - 2628
[3] Journal of Fluorine Chemistry, 2008, vol. 129, # 2, p. 108 - 111
[4] Analytical Chemistry, 2001, vol. 73, # 15, p. 3737 - 3741
  • 87
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  • [ 81-07-2 ]
  • [ 482333-74-4 ]
Reference: [1] Patent: WO2004/35599, 2004, A1, . Location in patent: Page 9
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3270 - 3275
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