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The preparation method of sartan biphenyl

A technology of sartan biphenyl and o-chlorobenzonitrile, which is applied in the field of preparation of sartan biphenyl, can solve problems such as unfavorable continuous large-scale industrial production, difficult recovery of catalysts, harsh reaction conditions, etc., and achieve great implementation value and social Economic benefits, low production costs, and easy availability of raw materials

Active Publication Date: 2014-10-08
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patents such as European Patent 470765 in 1992 and WO310106 in 1993 describe the Suzuki coupling with borane, but the catalyst used is an expensive organometallic palladium catalyst, which is difficult to recycle, thus limiting the application of industrial production
[0004] The reported synthesis method has the disadvantages of high raw material cost, harsh reaction conditions, long reaction time and unfavorable continuous large-scale industrial production

Method used

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  • The preparation method of sartan biphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Dissolve 2 mmol of [Bmim] Im in 250 mL of purified water, mix well, add 0.13 g of nickel chloride (0.001 mol), and stir at 23±3°C for 30 min. In flask, add 13.76g (0.1mol) o-chlorobenzonitrile, 13.92g (0.11mol) p-chlorotoluene, stir 10min at 20 ℃, then the above-mentioned [Bmim]Im ionic liquid loaded with nickel chloride catalyst is added to In the mixed solution of o-chlorobenzonitrile and p-chlorobenzonitrile, stir and react at 25±3°C for 3h, then let stand for 0.5h. 19.0 g (yield: 98.45%) of a white solid was obtained by filtration with a purity of 99.4%. Mp: 48~49℃, 1 HNMR (500MHz, CDCl 3 ): (δppm): 2.45 (s, 3H), 7.25-7.35 (t, 2H), 7.41-7.58 (m, 4H), 7.61-7.82 (m, 2H).

Embodiment 2

[0025] Dissolve 2 mmol of [Bmim] Im in 300 mL of purified water, mix well, add 1.3 mg of nickel chloride (0.01 mmol), and stir at 25±3°C for 25 min. In flask, add 13.78g (0.1mol) o-chlorobenzonitrile, 13.94g (0.11mol) p-chlorotoluene, stir 15min at 20 ℃, then the above-mentioned [Bmim]Im ionic liquid loaded with nickel chloride catalyst is added to In the mixed solution of o-chlorobenzonitrile and p-chlorobenzonitrile, stir and react at 27±3°C for 5h, then let stand for 0.5h. 19.11 g (yield: 99.02%) of a white solid was obtained by filtration with a purity of 99.5%. Mp and 1 HNMR is the same as in Example 1.

Embodiment 3

[0027] Dissolve 2 mmol of [Bmim] Im in 250 mL of purified water, mix well, add 0.13 g of nickel chloride (0.001 mol), and stir at 24±3°C for 30 min. In flask, add 13.78g (0.1mol) o-chlorobenzonitrile, 15.19g (0.12mol) p-chlorotoluene, stir 15min at 22 ℃, then the above-mentioned [Bmim]Im ionic liquid loaded with nickel chloride catalyst is added to In the mixed solution of o-chlorobenzonitrile and p-chlorobenzonitrile, stir and react at 25±3°C for 6.5h, then let stand for 0.5h. 19.06 g (yield: 98.76%) of a white solid was obtained by filtration with a purity of 99.1%. Mp and 1HNMR are the same as in Example 1.

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Abstract

The invention belongs to the field of chemical synthesis and specifically relates to a preparation method of sartanbiphenyl. The preparation method comprises the following steps of: carrying out coupled reaction by taking chlorobenzonitrile and p-chlorotoluene as raw materials and taking nickel chloride loaded on the basic ionic liquid as a catalyst in an imidazole radical-1-butyl-3-methylimidazole basic ionic liquid / H2O system, and filtering, thus obtaining a product. According to the preparation method, raw materials are easily available, a 'one-pot' method is adopted for reaction, the operation is simple, convenient and safe, and reaction conditions are mild. The imidazole radical-1-butyl-3-methylimidazole basic ionic liquid is used for replacing an organic solvent, and the damage of the organic solvent on environments is avoided. The production cost is low; the catalyst can be recycled and reused; and the decomposition and loss of the catalyst are avoided. After reaction is ended, products can be transferred to a water phase, then the products can be obtained through simple filtration, and large-scale production is facilitated.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of sartan biphenyl. Background technique [0002] Sartan biphenyl is an important pharmaceutical intermediate, which is widely used in the synthesis of many new sartan antihypertensive drugs. Sartan antihypertensive drugs have become the most commonly used clinical drugs for more than ten years because of their obvious antihypertensive effect and good tolerance. One of the most popular antihypertensive drugs, it has attracted widespread clinical attention, and the incidence of adverse reactions such as dry cough, drug withdrawal rebound and orthostatic hypotension after long-term use is low. It has been recommended by multiple WTO treatment guidelines First-line antihypertensive drugs in hypertensive patients with urine. [0003] At present, the coupling reactions commonly used in the market to produce biphenyl drug intermediates are o-methoxybenzoic acid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30
CPCY02P20/584
Inventor 田廷璀张立明
Owner YIYUAN XINQUAN CHEM
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