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Preparation method of imidazole chiral ionic liquid replaced by C-2

A chiral ionic liquid, imidazole technology, applied in the direction of organic chemistry, etc., can solve the problem of single synthesis method, and achieve the effects of simple preparation method, easy availability of raw materials, and broad development prospects.

Inactive Publication Date: 2012-06-27
中国人民解放军63975部队
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  • Abstract
  • Description
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Problems solved by technology

[0004] The present invention aims to overcome the shortcomings of the single synthesis method of the current C-2-substituted imidazole chiral ionic liquid, and utilizes the chiral pool method to introduce an acid chloride at the C-2 position of methylimidazole through an acylation reaction, and then through an esterification reaction Introduce chiral menthol to obtain chiral fragments, react with halogenated hydrocarbons, and obtain a C-2 substituted imidazole chiral ionic liquid through microwave-assisted catalysis

Method used

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  • Preparation method of imidazole chiral ionic liquid replaced by C-2
  • Preparation method of imidazole chiral ionic liquid replaced by C-2
  • Preparation method of imidazole chiral ionic liquid replaced by C-2

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Embodiment 1

[0023] Synthesis of trichloroacetyl chloride: add 32.7g (0.2mol) of trichloroacetic acid and 32.1g (0.26mol) of thionyl chloride into a two-necked bottle equipped with a thermometer and a spherical condenser (connected to the drying tube), drop into dimethyl DMF 0.286g, the condenser tube was connected to the calcium chloride drying tube, reacted for 3h, and collected 31g of fractions at 119°C to 120°C by atmospheric distillation, with a yield of 90%.

Embodiment 2

[0025] Synthesis of 2-trichloroacetyl-1-methylimidazole: under nitrogen protection, add 7mL (11.2g, 61mmol) trichloroacetyl chloride and 40mLCH to a 100mL three-necked flask 2 Cl 2 . Charge 5 mL (5.00 g, 63 mmol) of 1-methylimidazole (3) and 30 mL of CH into a constant pressure funnel 2 Cl 2 , Slowly drop into the three-necked flask, about 2h after the dropwise addition, continue to stir at room temperature for 8h. The reaction mixture was cooled to 0° C. with an ice-water bath, 8.8 mL of triethylamine was added dropwise, and stirred for another 1 h. After filtration, the solvent was removed from the filtrate under reduced pressure, and recrystallized (n-hexane was used as solvent) to obtain 9.43 g of white crystals, with a yield of 68%. mp76℃~77℃. MS (EI) m / z 226 (M + , C 6 h 5 N 2 OCl 3 The theoretical value of 226).

Embodiment 3

[0027] Synthesis of menthyl 1-methylimidazole-2-carboxylate (2): Add 7.13g (0.03mol) 2-trichloroacetyl-1-methylimidazole and 4.68g (0.03mol) menthol to a 15mL two-neck bottle . Magnetic stirring was performed at 80° C. for 5 h, the generated chloroform was removed under reduced pressure, and recrystallized (n-hexane or ethyl acetate) to obtain 4 g of a white solid with a yield of 57%. MS (EI) m / z 264 (M + , C 15 h 24 N 2 The theoretical value of O is 264). IR (KBr) 3105, 2951, 2933, 2871, 2846, 1705, 1477, 1419, 1414, 1130, 1259, 982, 957, 924, 785, 667. 1 H NMR (DCCl 3 , 500MH Z )7.26(s, 1H), 4.95(m, 3H, J=26.5), 4.00(s, 3H), 2.00(m, 2H, J=43.5), 0.77(m, 3H, J=7). 13 C NMR (CDCl 3 , 500H Z )δ159.0, 136.9, 129.3, 126.0, 77.0, 46.6, 40.8, 35.9, 34.15, 31.5, 26.0, 23.2, 22.0, 20.7, 16.0.

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Abstract

The invention relates to a preparation method of imidazole chiral ionic liquid replaced by C-2, which comprises the following steps of: acylating 1-methylimidazole and trichloroacetic chloride, esterfying with chiral menthol and carrying out chiral fragment reaction at 1-methylimidazole C-2. According to the preparation method of the imidazole chiral ionic liquid replaced by the C-2, natural menthol is introduced into a chiral center by adopting a green chemical thinking method and utilizing a chiral pool method to prepare the imidazole chiral ionic liquid replaced by the C-2 under the microwave-assisted catalysis. The preparation method has the advantages of simplicity, easiness for raw material obtaining, low cost and short reaction time, thereby having a wide development prospect.

Description

technical field [0001] The invention relates to a preparation method of a C-2 substituted imidazole chiral ionic liquid. Background technique [0002] Ionic liquids are green substances that have attracted extensive attention from academia and industry in recent years. Chiral ionic liquids have the advantages and characteristics of both chiral and ionic liquids. They can be used as chiral solvents or chiral inducers in chiral synthesis, It has great application potential in chiral separation and chiral catalysis. [0003] The introduction of the chirality of C-2 imidazole chiral ionic liquids has been obtained by attacking the N atom of the imidazole nitrogen heterocycle with a chiral alkylation reagent for a long time, but the preparation cost is relatively high. Bao et al. (Bao.W.; Wang, Z.; Li, Y.J.Org.Chem.2003, 68, 591-593) reported for the first time the synthesis of imidazole chiral ionic liquids with side chains using natural chiral amino acids. Due to the advantag...

Claims

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Application Information

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IPC IPC(8): C07D233/90
Inventor 肖军华刘瑛
Owner 中国人民解放军63975部队
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