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Synthesis method of diafenthiuron impurity C

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

Pending Publication Date: 2021-07-27
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

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  • Synthesis method of diafenthiuron impurity C
  • Synthesis method of diafenthiuron impurity C
  • Synthesis method of diafenthiuron impurity C

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preparation example Construction

[0029] The invention provides the preparation method of diafenthiuron impurity C, such as figure 1 , including the following steps:

[0030] Step S1: Dissolve 2,6-isopropylaniline in pyridine, then add 4-toluenesulfonyl chloride to obtain the first reaction solution, heat to reflux until the reaction is complete, mix the cooled first reaction solution with a sufficient amount of HCl The solution was mixed uniformly, and the first solid was obtained by suction filtration, and the first solid was dissolved in ethanol, and compound 3 was obtained by recrystallization;

[0031] Step S2: HNO 3 , the compound 3, AcOH, NaNO 2 sequentially added to H 2 Obtain the second reaction solution in 0, stir and react at the first temperature for a period of time, then raise the temperature to the second temperature and stir the reaction until the reaction is complete, mix the cooled first reaction solution with a sufficient amount of HCl solution, and pump Solid compound 4 was obtained by ...

Embodiment 1

[0039] This embodiment provides the preparation method of compound 3 (i.e. step S1):

[0040] Compound 1 (2,6-isopropylaniline, 0.2mol, 35.4g) was dissolved in 75ml of pyridine (Pyridine), and compound 2 (4-toluenesulfonyl chloride, 0.22mol, 41.91g) was added to obtain the first reaction solution, Heated to reflux for 4h, TLC detected that the reaction was complete, cooled, poured into 2mol / L HCl solution, stirred for 0.5h, and filtered to obtain a solid, which was dissolved in ethanol (EA) and recrystallized to obtain compound 3 (50g, yield : 79%).

[0041] The prepared compound 3 was detected by proton nuclear magnetic spectrum:

[0042] 1 HNMR (300MHz, CDCl 3 )δ0.91(d,12H),2.37(s,3H),3.08-3.11(m,2H), 7.10(d,2H),7.20(t,1H),7.38(d,2H),7.60(d ,2H),9.35(s,1H)

Embodiment 2

[0044]This embodiment provides the preparation method of compound 4 (i.e. step S2):

[0045] 30ml concentrated HNO 3 (concentration 65%) was added to 160ml H 2 O, then sequentially added compound 3 (7g, 0.021mol), 140ml AcOH, NaNO 2 (2.23g, 0.032mol) to obtain the second reaction solution, stirred at room temperature for 24h, then heated up to 100°C for 4h, TLC detected that the reaction was complete, cooled, poured into 500ml H 2 O, stirred for 0.5 h, and was filtered with suction to obtain solid compound 4 (4 g, yield: 50%).

[0046] The prepared compound 4 was carried out by proton nuclear magnetic spectrum detection:

[0047] 1 HNMR (300MHz, CDCl 3 )δ1.02(d,12H),2.44(s,3H),3.10-3.22(m,2H), 6.24(s,2H),7.28(d,2H),7.61(d,2H),7.98(s ,1H)

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Abstract

The invention provides a preparation method of a diafenthiuron impurity C. According to the preparation method of the diafenthiuron impurity C, 2, 6-isopropylaniline, 4-toluenesulfonyl chloride, phenol, N, N-diisopropylethylamine and the like 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 impurities in diafenthiuron production, and the impurities are controlled within a safe and reasonable limit range, so that the quality standard of 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 C. 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. It has contact killing, stomach poisoning, systemic and fumigation effects, and has a certain ovicidal effect. It is transformed into a substance with insecticidal activity under ultraviolet light, and has strong activity against pests that have developed severe drug resistance on vegetables. It can control aphids, whiteflies, leafhoppers, noctuidae pests and harmful mites on a variety of crops and ornamental plants. [0003] [0004] Diafenthiuron impurity C is a by-product produced during the production of diafenthiuron. Due to its low content, it is difficult to enrich it by means of purification. At present, there is...

Claims

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Application Information

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IPC IPC(8): C07C335/18
CPCC07C335/18C07C213/02C07C201/12C07C209/62C07C303/40C07C303/38C07C217/90C07C205/38C07C205/12C07C211/52C07C311/21
Inventor 李春成闫强朱宁吴正军
Owner LONGXINING SHANGHAI PHARMA TECH CO LTD
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