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Medicament intermediate and preparation method of fluroxypyr 1-methylheptyl ester

A fluroxypyr sec-octyl ester and intermediate technology, applied in the field of organic synthesis, can solve the problems of unfavorable industrial production, limited raw materials, difficult operation, etc., and achieve the effects of avoiding product loss, low cost, and reasonable route design

Inactive Publication Date: 2017-11-03
CHONGQING HUAGE BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Comparing these five synthetic methods, they are either limited by the availability of raw materials, or the process is complicated, the operation is difficult, or they are dangerous and pollute, which are not conducive to industrial production.

Method used

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  • Medicament intermediate and preparation method of fluroxypyr 1-methylheptyl ester
  • Medicament intermediate and preparation method of fluroxypyr 1-methylheptyl ester
  • Medicament intermediate and preparation method of fluroxypyr 1-methylheptyl ester

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preparation example Construction

[0020] The embodiment of the present invention provides a kind of preparation method of pharmaceutical intermediate, it comprises:

[0021] In the presence of molecular sieves, the pentachloropyridine is successively reacted with a fluorination reagent and an amination reagent for fluorination and amination reactions by using a one-pot method to obtain a drug intermediate; wherein, the structural formula of the drug intermediate is

[0022] The drug intermediate has a wide range of applications and can be used to synthesize a variety of polychlorinated drug molecules, for example, fluroxypyr sec-octyl ester that can be used as a herbicide. In the prior art, a two-step method is usually adopted for the synthesis of the drug intermediate, that is, the fluorination reaction is first carried out to pentachloropyridine to obtain the intermediate dichlorotrifluoropyridine, and its structural formula is Then carry out amination reaction to dichlorotrifluoropyridine. Due to the co...

Embodiment 1

[0043] The present embodiment provides a kind of preparation method of pharmaceutical intermediate, and its reaction formula is

[0044]

[0045] Its preparation steps include:

[0046] S1. Weigh 500mmol of potassium fluoride in a reaction flask, dissolve it in 5000ml of N,N-dimethylacetamide, add 0.5mmol of benzyltriethylammonium chloride as a catalyst, and then add 100mmol of pentachloro Pyridine and 5 mmol of 4A molecular sieve were heated up to 120° C. for 3 h to obtain a solution containing dichlorotrifluoropyridine.

[0047] S2. Cool the above-mentioned solution containing dichlorotrifluoropyridine to 10°C, and slowly add 30wt% ammonia water dropwise at 10°C, and detect the reaction by TLC. After the reaction of dichlorotrifluoropyridine is complete, stop the reaction and separate to obtain White solid, the desired drug intermediate (yield 95.3%).

Embodiment 2

[0049] The present embodiment provides a kind of preparation method of pharmaceutical intermediate, and its reaction formula is

[0050]

[0051] Its preparation steps include:

[0052] S1. Weigh 1000mmol of sodium fluoride in a reaction flask, dissolve it in 5000ml of N,N-dimethylacetamide, add 5mmol of benzyltriethylammonium chloride as a catalyst, and then add 100mmol of pentachloropyridine and 50 mmol of 4A molecular sieves, heated to 150 ° C for 1 h to obtain a solution containing dichlorotrifluoropyridine.

[0053] S2. Cool the above-mentioned solution containing dichlorotrifluoropyridine to 0°C, and slowly feed ammonia gas into the solution at 0°C, and detect the reaction by TLC. After the reaction of dichlorotrifluoropyridine is complete, stop the reaction and separate A white solid, the desired drug intermediate, was obtained (yield: 92.7%).

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Abstract

The invention discloses a medicament intermediate and a preparation method of fluroxypyr 1-methylheptyl ester, and relates to the field of organic synthesis. The preparation method of the medicament intermediate has the advantages that a molecular sieve is added, a fluoridation reaction and next amination reaction of pentachloropyridine can be realized through one-pot reaction, complex separation steps are saved, product loss caused by the separation process is avoided, and the key medicament intermediate for preparing herbicide can be prepared at high yield. The preparation method is easy to operate, is low in equipment demand, contributes to lowering production cost, and is suitable for large-scale industrial production. The preparation method is characterized in that low-cost and readily-available pentachloropyridine is taken as an initial raw material, the fluoridation reaction and next amination reaction are implemented by adopting the one-pot method to obtain key medicament intermediate; on the basis of the medicament intermediate, a hydroxylation reaction and a condensation reaction are implemented to obtain efficient high-yield fluroxypyr 1-methylheptyl ester. The preparation method is reasonable in route design, is simple in steps, is convenient to operate, is low in cost, is low in pollution, and is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a pharmaceutical intermediate and fluroxypyr sec-octyl ester. Background technique [0002] Fluroxypyr 2-octyl ester is an organic heterocyclic herbicide developed by Dow Agrochemicals. It is a typical hormone herbicide, which can be quickly absorbed by plant leaves and roots, and quickly transmitted in the body. In the market, generally 95% fluroxypyr sec-octyl ester is the original drug, which is suitable for controlling broad-leaved weeds in wheat, barley, corn, grapes, orchards, pastures, woodlands, lawns and other places. [0003] Fluroxypyr 2-octyl, as a fluorine-containing herbicide with high efficiency, low toxicity and low residue, has been reported more abroad but less domestically. In the prior art, the synthesis methods of fluroxypyr sec-octyl mainly include: alkylation method, alcohol hydroxycarboxylate method, sodium methoxide method, chloro...

Claims

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Application Information

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IPC IPC(8): C07D213/73
Inventor 何小强陈志忠张春华顾福海吴承丽杨鑫瑶
Owner CHONGQING HUAGE BIOCHEM
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