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Bisamide derivative intermediate and preparation method of bisamide derivative

A technology of derivatives and bisamides, applied in the field of compound synthesis, can solve the problems of complex preparation process, high safety risk, unfavorable large-scale production and the like, and achieve the effects of easy control of process conditions, simple process and simple raw materials

Pending Publication Date: 2022-07-29
上海陶术生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, technicians focus on the development of new bisamide insecticides and explore their specific mechanism of action, and little is involved in their synthesis and preparation. The traditional preparation process is complex, and some technologies require the use of highly toxic substances such as phosgene. High security risk, not conducive to mass production

Method used

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  • Bisamide derivative intermediate and preparation method of bisamide derivative
  • Bisamide derivative intermediate and preparation method of bisamide derivative
  • Bisamide derivative intermediate and preparation method of bisamide derivative

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preparation example Construction

[0060] In the traditional process for preparing benfluenzamide, the process is complicated, and highly toxic substances are often used, resulting in uncontrollable process and extremely high safety risk, which is not conducive to industrialized large-scale production, such as the use of dimethyl sulfate in one technology. The preparation of bisamide derivative intermediates from hazardous chemicals requires palladium to catalyze carbonylation, and the process conditions are severe, which is not conducive to large-scale scale-up experiments; in another technology, the use of hazardous triphosgene and palladium catalyzed hydrogenation to synthesize fenflubenilamide, which is safe The risk is extremely high, and the process conditions are severe, which is not conducive to large-scale scale-up experiments.

[0061] Based on this, those skilled in the present application propose to improve the above-mentioned synthetic route to obtain a synthetic route that is relatively simple and ...

Embodiment 1

[0172] (1) the synthesis of compound (2), the synthetic route is as follows:

[0173]

[0174] The specific steps are as follows: at 0 °C, to a mixture of 3-amino-2-fluorobenzoic acid (compound 1) (8.00 g, 51.5 mmol, 1 eq.) and concentrated sulfuric acid (50 mL) was added dropwise aqueous formaldehyde solution (9.29 g) , 37%purity, 309mmol, 8.52mL, 6eq), the internal temperature was maintained at about 30°C during the dropwise addition, after the dropwise addition, the mixture was stirred at 40°C for reaction, and LCMS was used to monitor the reaction at any time, and the reaction was 2 After one hour, solid sodium hydroxide was added to the reaction solution until pH=3, then extracted with ethyl acetate (25 mL*3), and the combined organic phases were concentrated to obtain the crude product.

[0175] The crude product was subjected to column chromatography (100-200 mesh silica gel, petroleum ether / ethyl acetate volume ratio=1:1) to obtain 2-fluoro-3-methylaminobenzoic acid...

Embodiment 2

[0216] Embodiment 2 is basically identical with embodiment 1, and difference is: step (2) is as follows:

[0217] Compound 2 (100 mg, 591.18 μmol, 1 eq) was dissolved in tetrahydrofuran (1.0 mL) to prepare a solution, then pyridine (93.52 mg, 1.18 mmol, 95.43 μL, 2 eq) and compound 3 (benzoyl chloride, 99.72 mg, 709.42 μmol were added) , 82.41 μL, 1.2eq), and then the reaction was stirred at 60 °C for 12 hours, and the results are shown in Table 1 below.

[0218] Table 1

[0219]

[0220] According to the analysis in Table 1, it can be seen that the substance with the retention time of 0.363 is compound 4, and the specific mass spectrum is as follows Figure 9 As shown, LC-MS for compound 4: (M+1)+: 274.0.

[0221] Combined with the above detection results, it can be known that the yield of compound 4 in the above steps is about 10%.

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Abstract

The present invention relates to a bisamide derivative intermediate and a bisamide derivative preparation method, the bisamide derivative intermediate preparation method comprises: carrying out an N-methylation reaction on a compound (1) to prepare a compound (2); carrying out condensation reaction on the compound (2) and a compound (3) to prepare a bisamide derivative intermediate as shown in a formula (4); the compound (3) is selected from one or more of benzoic acid and benzoyl chloride. According to the preparation method, raw materials are simple, cheap and easy to obtain, technological conditions in the preparation process are easy to control, highly toxic substances such as phosgene are not needed, the bisamide derivative intermediate shown in the formula (4) can be further used for synthesizing bisamide derivatives such as synthesis of flubendiamide and the like, and large-scale production of the bisamide derivatives is facilitated.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a bisamide derivative intermediate and a preparation method of the bisamide derivative. Background technique [0002] Bisamide insecticides are a class of insecticides that have opened up a new mechanism of action. Since the development of the first insecticide with a new structure, flufenprod in 1998, bisamide insecticides have attracted much attention. Broflanilide is a kind of m-benzamide-based benzamide insecticide, which was jointly developed by Japan's Mitsui Agrochemical Company and BASF. Common pests, bromine Current studies have shown that bromine has excellent activity on both larvae and adults. [0003] However, technicians focus on developing new bisamide insecticides and exploring their specific mechanism of action. There is very little involved in their synthesis and preparation. The traditional preparation process is complicated, and some technologies ...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/60C07C231/02C07C233/81C07C231/12C07C233/80
CPCC07C227/18C07C231/02C07C231/12C07C229/60C07C233/81C07C233/80
Inventor 段震王艾唐小伍杨小平
Owner 上海陶术生物科技有限公司
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