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Dicaryon benzimidazole ionic salt as well as preparation method and application thereof

A technology of nuclear benzimidazole and benzimidazole, which is applied in the field of binuclear benzimidazole ion salt and its preparation, and achieves the effects of high yield, strong coordination ability and good product purity

Inactive Publication Date: 2015-04-08
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are relatively few reports on its synthesis, and they are limited to mononuclear benzimidazolium salts

Method used

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  • Dicaryon benzimidazole ionic salt as well as preparation method and application thereof
  • Dicaryon benzimidazole ionic salt as well as preparation method and application thereof
  • Dicaryon benzimidazole ionic salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of N-benzylbenzimidazole:

[0021] In a 250mL three-necked round-bottomed flask with a reflux condenser, add 8.85g (0.075mol) benzimidazole, 40mL 40% NaOH solution and 3.22g (0.01mol) tetrabutylammonium bromide successively, after magnetic stirring for 30min, 11.27 mL (0.098 mol) of benzyl chloride was slowly added dropwise. After the dropwise addition, the reaction temperature was raised to the slight reflux of the system, and the reaction was continued for 8 hours. Cool the reaction mixture to room temperature, filter with suction, dissolve the filter cake in 60 mL of ethyl acetate and 45 mL of water, and separate the organic phase with a separatory funnel. After the organic phase was dried over anhydrous sodium sulfate, the solvent was spun off under reduced pressure to obtain the crude product as a tan solid. The crude product was recrystallized by adding 6 mL of toluene to obtain 10.3 g of a light yellow solid with a yield of 66% and a melting point of ...

Embodiment 2

[0023] Synthesis of N-benzylbenzimidazole:

[0024] Add 8.85g (0.075mol) benzimidazole, 40mL30%NaOH solution and 3.00g tetrabutylammonium chloride successively in the three-necked round-bottomed flask that has reflux condenser in 250ml, after magnetic stirring 30min, slowly add dropwise 11.65mL ( 0.098 mol) benzyl bromide. After the dropwise addition was completed, the reaction temperature was raised to the slight reflux of the system, and the reaction was continued for 8 hours. Cool the reaction mixture to room temperature, filter with suction, dissolve the filter cake in 60 mL of ethyl acetate and 45 mL of water, and separate the organic phase with a separatory funnel. The organic phase was dried by adding anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a tan solid. The crude product was recrystallized by adding 6 mL of toluene to obtain 10.78 g of a light yellow solid with a yield of 69% and a melting point of 116-117°C. 1 H N...

Embodiment 3

[0026] Synthesis of 3,3'-dibenzyl-1,1'-ethylenedibenzimidazolium dibromide:

[0027] Add 5.00g (0.024mol) 1-benzylbenzimidazole, 1.03mL (0.012mol) 1,2-dibromoethane and 60mL toluene to a 250mL three-necked round-bottomed flask equipped with a reflux condenser. The system was heated up to 100°C, and reacted for 72 hours under magnetic stirring. After the reaction was completed, the system was fully cooled. After rapid filtration, the filter cake was recrystallized from a mixed solution of 1 mL of acetonitrile, 25 mL of ethyl acetate and 5 mL of diethyl ether, and then recrystallized with absolute ethanol. 5.51 g of white solid was obtained with a yield of 76%. 1 H NMR (400MHz, TMS, CDCl 3 )δ: 10.11(s, 2H), 8.19(d, J=6.0Hz, 2H), 8.00(d, J=6.0Hz, 2H), 7.59(t, J=6.0Hz, 4H), 7.52-7.50( m,10H),5.84(s,4H),5.03(t,J=6.0Hz,4H); 13 C NMR (100MHz, DMSO) δ: 146.57, 134.60, 134.05, 132.36, 132.17, 131.73, 131.54, 130.29, 130.15, 117.37, 116.45, 53.25, 51.49; MS m / z: 443.3(M + ).

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Abstract

The invention provides a dicaryon benzimidazole ionic salt as well as a preparation method and application thereof, and relates to an imidazole compound. The preparation method comprises the following steps: carrying out reaction on benzyl bromide or benzyl chloride and benzimidazole under alkaline condition to synthesize N-benzyl benzimidazole; further carrying out reaction on the generated N-benzyl benzimidazole and dibromohydrocarbon to synthesize the dicaryon benzimidazole ionic salt. The dicaryon benzimidazole ionic salt and a catalyst palladium acetate are used as a composite system which shows favorable reaction activity in the Heck reaction of bromobenzene and butyl acrylate. The dicaryon benzimidazole ionic salt has numerous excellent characteristics of the ionic salts, such as heat stability, chemical stability, incombustibility, low vapor pressure and strong coordination capacity. The compound can be used as a reaction medium to synergize with metal catalysts to promote the organic carbon-carbon coupling reaction.

Description

technical field [0001] The invention relates to imidazole compounds, in particular to a dinuclear benzimidazolium ion salt and a preparation method and application thereof. Background technique [0002] Ionic molten salt, as a new type of green material, is a class of compounds composed of organic cations and inorganic anions with a melting point below 200 °C. In 1992, Wilkes et al. synthesized the first ionic compound 1-ethyl-3-methylimidazolium tetrafluoroborate, which is stable to both water and air. The research and application of ionic salts have attracted extensive attention. Ionic salts of cations and anions were synthesized sequentially. Especially in the last 15 years, under the stimulation of the demand for organic synthesis and green chemistry, ionic salts have excellent properties such as thermal stability, chemical stability, non-flammability, low vapor pressure, and controllable dissolution of organic and inorganic compounds. , there are continuous research r...

Claims

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Application Information

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IPC IPC(8): C07D235/06B01J31/02B01J31/04C07C67/343C07C69/618
CPCB01J31/0284B01J31/04B01J2231/4261C07C67/343C07D235/06C07C69/618
Inventor 王晓菊赵三虎张立伟冯丽恒
Owner SHANXI UNIV
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