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An improved process for the preparation of trifloxystrobin

A technology of trifloxystrobin and solvent, which is applied in the field of trifloxystrobin, and can solve problems such as waste water generation, unsuitability for the preparation of trifloxystrobin, and increased production cost of trifloxystrobin

Active Publication Date: 2020-06-16
HIKAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Few reported synthetic routes use more expensive starting materials
In addition, due to the long synthesis route, a large amount of waste water is produced, thus increasing the preparation cost of trifloxystrobin
Based on the above disadvantages, the prior art process may not be suitable for the preparation of trifloxystrobin for commercial scale operation

Method used

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  • An improved process for the preparation of trifloxystrobin
  • An improved process for the preparation of trifloxystrobin
  • An improved process for the preparation of trifloxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: One-step preparation of (E)-2-methoxyimine-2-(o-tolyl)acetic acid (compound 5)

[0064] A can

[0065] A four necked round bottom flask equipped with mechanical stirrer, thermopocket and water condenser was set up. Water (3.0 volumes relative to o-toluidine) was added with stirring, followed by concentrated hydrochloric acid (3.0 volumes relative to o-toluidine), and the reaction was cooled to 0°C to 5°C. With stirring at 0°C to 5°C, o-toluidine (1.0 eq.) was added dropwise to the reaction over 30 minutes to form an off-white slurry. The reaction mixture (RM) was stirred for 30 min. NaNO 2 (1.0 eq.) solution was added portionwise to the reaction mixture over 30 minutes. After complete addition, the solution was used in the next step.

[0066] B tank

[0067] Under stirring, to a four-necked round bottom flask equipped with a mechanical stirrer, heating mantle, water condenser and addition funnel, was added glyoxylic acid (1.5 eq.), methoxylamine hy...

Embodiment 2

[0069] Example 2: One-step preparation of (E)-2-methoxyimine-2-(o-tolyl)acetic acid (compound 5)

[0070] A can

[0071] Under stirring, add water (3 times the volume relative to o-toluidine), concentrated hydrochloric acid (3.0 times the volume relative to o-toluidine) to a four-necked round bottom flask equipped with a mechanical stirrer, a heating mantle, and a water condenser, The solution was then cooled to 0 °C. With stirring at 0°C, o-toluidine (1.0 eq.) was added dropwise to the reaction over 30 minutes to form an off-white slurry, and stirred for a further 30 minutes. At -5°C to 0°C, NaNO in water (1.0 volume relative to o-toluidine) 2 (1.0 eq.) solution was added dropwise to the reaction mixture over 30 minutes. After complete addition, the solution was used in the next step.

[0072] B tank

[0073] Under stirring, to a four-neck round bottom flask equipped with a mechanical stirrer, heating mantle, water condenser and addition funnel was added glyoxylic ...

Embodiment 3

[0074] Example 3: Preparation of (E)-2-methoxyimine-2-(o-tolyl)methyl acetate (compound 6)

[0075] To a four necked round bottom flask equipped with a mechanical stirrer, air condenser, heating mantle and water bath was added a solution of Compound 5 (1.0 eq.) in MeOH (3-5 volumes relative to Compound 5). At 25°C to 30°C, the concentrated H 2 SO 4 (0.8eq.) was slowly added dropwise to the reaction mixture over 15min and heated to reflux temperature for 12h. The reaction mixture was cooled to 50°C to 55°C, and water (3.0 volumes relative to compound 5) was added portionwise over 1 hour. After complete addition of water, the reaction mixture was stirred at 20°C to 25°C for 3 h and filtered with a Buchner funnel, the solid was washed with water and the crude product was dried. The crude product was dissolved in isopropanol (1.43 volumes relative to Intermediate 5), and the mixture was heated to 60°C. The solution was cooled to room temperature, stirred for 1 h, and further c...

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Abstract

The present invention relates to an improved process for the preparation of trifloxystrobin of formula (I), which is simple, economical, efficient, user and environment friendly, moreover commerciallyviable with higher yield and chemical purity.

Description

Technical field [0001] The present invention relates to an improved method for preparing trifloxystrobin (trifloxystrobin) of formula (I) in an environmentally friendly and commercially feasible manner with high yield and chemical purity. [0002] Background technique [0003] Trifloxystrobin is a member of the strobilurin class of fungicides. Trifloxystrobin is chemically called [(E)-methoxyimino]{2-[l-(3-trifluoromethyl-phenyl)-(E)-ethyleneaminooxymethyl] Phenyl]acetic acid methyl ester ([(E)-methoxyimino]-{2-[l-(3-trifluoromethyl-phenyl)-eth-(E)-ylideneaminooxy methyl]-phenyl}-acetic acid methyl ester), as shown in the formula (I) is shown. It is now known to have broad fungicidal action and to have good preventive and healing properties. Considering the broad activity spectrum and commercial interest, many methods for the synthesis of trifloxystrobin and intermediates have been reported in the literature. This is summarized in the following discussion. [0004] U...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/53
CPCC07C247/16C07C249/08C07C249/12C07C251/36C07C251/48B01J31/0237B01J2231/005B01J2531/002C07C245/20C07C251/60
Inventor 卡姆利什·坎蒂拉尔·洛德哈桑地普·波帕特拉奥·乌达万特迪帕克·巴巴萨海布·帕哈萨拉孔达·纳加拉萨达·拉奥桑托什·库马尔·高希苏迪尔·南比亚尔
Owner HIKAL
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