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Intermediate of benzovindiflupyr and preparation method and application thereof

A technology for reaction and reaction kettle, applied in the field of intermediates of benzofluconazole, can solve the problems of long steps, difficult to obtain raw materials, low yield and the like

Active Publication Date: 2017-04-26
杭州百昂锐地科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the currently reported routes have the disadvantages of low yield, difficult access to raw materials, poor stability of intermediates, complex operation, harsh reaction conditions, and unsuitability for large-scale industrial production.
[0005] The synthetic route reported in WO2011131546 is the shortest synthetic route seen in the literature so far, but the starting material 6,6-dichlorofulvene is unstable and needs to be synthesized by itself, so the steps are still relatively long and the overall yield is relatively low; Secondly, this method is a laboratory process, so it is not suitable for large-scale industrial production.

Method used

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  • Intermediate of benzovindiflupyr and preparation method and application thereof
  • Intermediate of benzovindiflupyr and preparation method and application thereof
  • Intermediate of benzovindiflupyr and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1 Synthesis of N-(1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-phenol-5-yl-)-phthalimide (VI) .

[0061] The molar ratio of the feed materials is 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol:phthalic anhydride=1:1.05.

[0062] In a 500ml four-necked bottle equipped with mechanical stirring and a thermometer, add 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol (99.8g, 0.57mol ), phthalic anhydride (88.5g, 0.59mol), the temperature was raised to 130°C, and stirred for 1.5h. After the reaction was completed, 200ml of toluene was added dropwise while hot. 1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol-5-yl-)-phthalimide (VI) 167.3g, yield 96.2%, The melting point is 148.9-149.7°C.

Embodiment 2

[0063] Example 2 Synthesis of N-(1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol-5-yl-)-phthalimide (VI) .

[0064] The molar ratio of the feed materials is 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol:phthalic anhydride=1:1.01.

[0065] In a 500ml four-necked bottle equipped with mechanical stirring and a thermometer, add 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol (99.8g, 0.57mol ), phthalic anhydride (85.8g, 0.58mol), the temperature was raised to 150°C, and stirred for 1.5h. After the reaction was completed, 200ml of toluene was added dropwise while hot. 1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol-5-yl-)-phthalimide (VI) 158.2g, yield 90.1%, The melting point is 148.8-149.9°C.

Embodiment 3

[0066] Example 3 Synthesis of N-(1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-phenol-5-yl-)-phthalimide (VI) .

[0067] The molar ratio of the feed materials is 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol:phthalic anhydride=1:1.2.

[0068] In a 500ml four-necked bottle equipped with mechanical stirring and a thermometer, add 5-amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol (99.8g, 0.57mol ), phthalic anhydride (100.6g, 0.68mol), the temperature was raised to 120°C, and stirred for 1.5h. After the reaction was completed, 200ml of toluene was added dropwise while hot. 1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol-5-yl-)-phthalimide (VI) 162.6g, yield 93.5%, The melting point is 148.9-149.9°C.

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Abstract

The invention provides an intermediate of benzovindiflupyr and a preparation method and application thereof. The compound is N-(1,2,3,4-tetrahydro-1,4- methanonaphthalene-naphthalene-9-phenol-5-yl-)- phthalimide, and the chemical formula (VI) is defined in the following description. According to the preparation method, the compound, namely 5-amino-1,2,3,4-tetrahydro-1,4-methanonaphthalene-naphthalene-9-phenol and phthalic anhydride react under a high-temperature molten state, then an organic solvent is added, and the compound in the formula (VI) is prepared. The preparation method is easy and convenient to operate, easy to implement, mild in reaction condition, good in product quality and suitable for large-scale industrialized production.

Description

technical field [0001] The present invention relates to the intermediate of benzovinfluconazole, namely the new compound N-(1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol-5-yl- )-phthalimide, and preparation method and application thereof. Background technique [0002] Benzovindiflupyr (also known as SYN545192, trade name Solatenol) is a succinate dehydrogenase fungicide with a new mode of action. Benzofenfluconazole is broad-spectrum, high-efficiency, and has a longer-lasting bactericidal effect. It can widely control foliar diseases and soil pathogens. It is an important tool for resistance management. It is used in many crops such as wheat, corn, and special crops. Demonstrated outstanding control effect on major diseases. The product has a good control effect on wheat leaf blight, peanut black spot, wheat take-all and wheat base rot, especially on wheat powdery mildew, corn small spot and gray mold, and on Asian soybean Rust has excellent control effect and has n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D231/14C07C201/12C07C205/26C07C213/02C07C215/70
CPCC07C201/12C07C213/02C07D209/48C07D231/14C07C205/26C07C215/70
Inventor 姜正金谭志勇李振华王波华
Owner 杭州百昂锐地科技有限公司
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