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Synthesis method of diafenthiuron impurities A and B

A technology of diafenthiuron and impurities, applied in the field of medicinal chemistry, to achieve the effect of improving quality standards

Pending Publication Date: 2021-08-03
LONGXINING SHANGHAI PHARMA TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This has brought a lot of inconvenience to the production and declaration of pesticides

Method used

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  • Synthesis method of diafenthiuron impurities A and B
  • Synthesis method of diafenthiuron impurities A and B

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preparation example Construction

[0027] The invention provides the preparation method of diafenthiuron impurity A, such as figure 1 shown, including the following steps:

[0028] Step S1, dissolving 2,6-isopropylaniline in DMF to obtain the first reaction solution, adding the DMF solution of NBS dropwise, reacting for a period of time, adding water and ethyl acetate and mixing evenly, separating the liquids to obtain the first organic phase, The first organic phase was washed with water, dried and concentrated to obtain compound 2;

[0029] Step S2, dissolving the compound 2, potassium carbonate, phenol, cuprous chloride, and 1-methylimidazole in an organic solvent to obtain a second reaction solution, heating to reflux until the reaction is complete, adding water and ethyl acetate to mix evenly, Separation to obtain a second organic phase, which was washed with alkali, dried, concentrated, and column chromatographed to obtain compound 3;

[0030] Step S3, adding and dissolving the compound 3 and DIPEA in T...

Embodiment 1

[0038] This embodiment provides the preparation method of compound 2 (i.e. step S1):

[0039] Take 2,6-isopropylaniline (compound 1, 53g, 0.3mol), dissolve it in N,N-dimethylformamide (DMF, 500ml), lower the temperature to 0-5°C to obtain the first reaction solution, drop Add N-bromosuccinimide (NBS 63g, 0.36mol) in DMF (200ml) solution, after the dropwise addition is completed, react at 0-5°C for 0.5 hours, TLC detection confirms that the reaction is complete, add water and ethyl acetate and stir After 10 minutes, the liquid was separated, the organic phase was washed twice with water, dried and concentrated to obtain compound 2 (70 g, yield 98%);

[0040] The prepared compound 2 was detected by proton nuclear magnetic spectrum:

[0041] 1H NMR(300MHz,DMSO)δ6.93(s,2H),4.76(s,2H),2.93–3.04(m,2H), 1.10(d,J=6.9Hz,12H)

Embodiment 2

[0043] This embodiment provides the preparation method of compound 3 (i.e. step S2):

[0044]Take compound 2 (30g, 0.11mol), potassium carbonate (32.4g, 0.23mol), phenol (13.2g, 0.14mol), cuprous chloride (0.58mol), 1-methylimidazole (4.7ml) was dissolved in di The second reaction liquid was obtained in toluene (300ml), heated to reflux for 12 hours, added water and ethyl acetate after cooling, stirred for 10 minutes, separated, the organic phase was washed with potassium carbonate aqueous solution, dried over sodium sulfate, concentrated, and subjected to column chromatography Obtain compound 3 (23g, yield 72%)

[0045] The prepared compound 3 was detected by proton nuclear magnetic spectrum:

[0046] 1H NMR (300MHz,DMSO)7.21-7.23(m,2H),6.93-7.01(m,1H),6.79-6.86(m,2H),6.60(s,2H),4.50(s,2H),2.98- 3.09(m,2H), 1.11(d,J=6.9Hz,12H)

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Abstract

The invention provides a preparation method of the diafenthiuron impurities A and B. 2, 6-isopropylaniline, phenol, triphosgene, tert-butylamine and tert-butyl formamidine hydrochloride are used as raw materials, a material basis is provided for normatively researching the impurities, and the method can also be used for qualitative and quantitative analysis of the impurities in diafenthiuron production. And the impurities are controlled within a safe and reasonable limit range, so that the quality standard of the diafenthiuron can be improved, and important guiding significance is provided for safe medication of the masses.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing diafenthiuron impurity A and diafenthiuron impurity B. Background technique [0002] Diafenthiuron (also known as difenthiuron, compound I with the following structure) is a new type of thiourea insecticide and acaricide developed by Ciba-Geigy in the 1980s. The drug is a selective insecticide with systemic and fumigating effects. [0003] [0004] Diafenthiuron impurities A and B are two by-products produced during the production of diafenthiuron. Due to their low content, it is difficult to enrich them by means of purification. At present, there is no literature reporting its synthesis method. This has brought a lot of inconvenience to the production and declaration of pesticides. [0005] In order to standardize the research on impurities, control them within a safe and reasonable limit, and improve the quality and safety of diafenthiuron, it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/74C07C211/52C07C213/06C07C217/90C07C263/10C07C265/12C07C273/18C07C275/36C07C275/50
CPCC07C209/74C07C213/06C07C263/10C07C273/1827
Inventor 闫强李春成朱宁吴正军
Owner LONGXINING SHANGHAI PHARMA TECH CO LTD
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