A kind of method using benzimidazole ionic liquid to prepare sartan biphenyl

A technology of benzimidazole and ionic liquid, applied in the field of preparation of sartan biphenyl, can solve the problems of high toxicity, high cost, low yield and the like, and achieve the effect of strong electron donating ability

Active Publication Date: 2016-08-17
陕西煤业化工技术开发中心有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention solves the problems of high toxicity, high cost and low yield in the synthesis method of sartan biphenyl in the prior art, and further provides a kind of sartan biphenyl which is environmentally friendly, economical and efficient, and suitable for industrial production synthesis method

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  • A kind of method using benzimidazole ionic liquid to prepare sartan biphenyl
  • A kind of method using benzimidazole ionic liquid to prepare sartan biphenyl
  • A kind of method using benzimidazole ionic liquid to prepare sartan biphenyl

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Embodiment 1

[0028] The method for preparing sartan biphenyl using polyethylene glycol functionalized benzimidazole ionic liquid described in this embodiment comprises the following steps:

[0029] (1) Under nitrogen protection, add 2.4 mg of nickel chloride hexahydrate and 23.1 mg of polyethylene glycol-functionalized benzimidazole ionic liquid Ia to 8 mL of deionized water, and stir at 25° C. for 1 h to obtain a mixed solution;

[0030] (2) Add 137 mg of o-chlorobenzonitrile, 162 mg of 4-methylphenylboronic acid, and 80 mg of sodium hydroxide in sequence to the mixed solution, and stir at 100°C for reaction. After 4 hours, the reaction is completed, and the reaction solution is cooled to room temperature. , the reaction solution was extracted with ethyl acetate, the organic phase was collected, the organic phase was concentrated, the residue was separated by column chromatography, the eluent was petroleum ether: ethyl acetate=99:1 (v / v), and white 191 mg of solid is the target product, s...

Embodiment 2

[0040] The method for preparing sartan biphenyl using polyethylene glycol functionalized benzimidazole ionic liquid described in this embodiment comprises the following steps:

[0041] (1) Under nitrogen protection, add 1.2 mg of nickel chloride hexahydrate and 34.8 mg of polyethylene glycol-functionalized benzimidazole ionic liquid Ib to 10 mL of deionized water, and stir at 20° C. for 0.5 h to obtain a mixed solution;

[0042] (2) Add 182 mg of o-bromoxynil, 202 mg of 4-methylphenylboronic acid and 690 mg of potassium carbonate in sequence to the mixed solution, stir and react at 90°C, the reaction is completed after 7 hours, and the reaction solution is cooled to room temperature, The reaction liquid was extracted with ethyl acetate, the organic phase was collected, and the organic phase was concentrated, and the residue was separated by column chromatography, the eluent was petroleum ether: ethyl acetate=99:1 (v / v), and a white solid was obtained 185 mg, which is the targe...

Embodiment 3

[0050] The method for preparing sartan biphenyl using polyethylene glycol functionalized benzimidazole ionic liquid described in this embodiment comprises the following steps:

[0051] (1) Under nitrogen protection, add 1.2 mg of nickel chloride hexahydrate and 25.8 mg of polyethylene glycol-functionalized benzimidazole ionic liquid Ic to 10 mL of deionized water, and stir at 20° C. for 0.5 h to obtain a mixed solution;

[0052] (2) Add 182 mg of o-bromoxynil, 202 mg of 4-methylphenylboronic acid and 690 mg of potassium carbonate in sequence to the mixed solution, stir and react at 90°C, the reaction is completed after 7 hours, and the reaction solution is cooled to room temperature, The reaction liquid was extracted with ethyl acetate, the organic phase was collected, and the organic phase was concentrated, and the residue was separated by column chromatography, the eluent was petroleum ether: ethyl acetate=99:1 (v / v), and a white solid was obtained 189 mg, which is the targe...

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Abstract

The invention provides application of a polyethyleneglycol-functionalized benzimidazole ionic liquid disclosed as Formula (I) in preparing 2-cyano-4'-methylbiphenyl and a method for preparing 2-cyano-4'-methylbiphenyl by using the polyethyleneglycol-functionalized benzimidazole ionic liquid. The method comprises the following step: by using nickelous chloride as a catalyst and the polyethyleneglycol-functionalized benzimidazole ionic liquid as an accelerator, carrying out coupling reaction on ortho-halo cyanophenyl and 4-methylphenylboronic acid in a pure water solvent to obtain the 2-cyano-4'-methylbiphenyl. The method has the advantages of low cost and environmental protection, and is convenient for purification and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of sartan biphenyl, in particular to a method for preparing sartan biphenyl by using polyethylene glycol functionalized benzimidazole ionic liquid, and belongs to the technical field of organic catalysis. technical background [0002] As an angiotensin II (AT II) receptor antagonist, sartan drugs achieve the purpose of lowering blood pressure by inhibiting the vasoconstriction and blood pressure elevation caused by AT II. With the advantages of stability, significant curative effect, good tolerance, and high safety performance, the market share of sartan drugs has been continuously increasing, and they have become the first-line antihypertensive clinical drugs widely used in recent years, such as valsartan, losartan, Temisartan, Iprosartan, etc. However, the price of these drugs is as high as tens of thousands of dollars per ton, which greatly hinders the treatment of diseases by patients. Therefore, it is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/50
Inventor 宋双田饶小峰尚建选邬慧雄王振宇张蕾杨凯宁李铖赵迪
Owner 陕西煤业化工技术开发中心有限责任公司
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