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Preparation method of furantefenozide, intermediate and preparation method thereof

A technology of furanfenozide and intermediates, which is applied in the field of pesticide compounds, can solve the problems of high cost, low reaction selectivity, and low yield, and achieve the effects of low total cost, good reaction selectivity, and safe and reliable reaction

Inactive Publication Date: 2019-05-21
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Purpose of the invention: the object of the present invention is to provide a kind of high-purity furafenozide and its synthetic technology for the existence of the reaction selectivity of the above-mentioned furofenozide is not high, the yield is lower and the cost is higher. Preparation

Method used

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  • Preparation method of furantefenozide, intermediate and preparation method thereof
  • Preparation method of furantefenozide, intermediate and preparation method thereof
  • Preparation method of furantefenozide, intermediate and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Embodiment 1: the synthesis of N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine (I)

[0062] Add tert-butoxycarbonyl-2-tert-butylhydrazine (189g, 1.00mol) and toluene (600ml) into the reaction flask, cool down to 5-8°C, stir, and dropwise add 3,5-dimethylbenzoyl chloride (168g , 0.99mol) and sodium hydroxide aqueous solution (mass concentration is 30%, 132g, 0.99mol), the dropwise process control temperature is lower than 10 ℃. After the addition, the reaction was continued for 2 hours. Cool to 0°C and filter. The filter cake was washed twice with water. Add methanol (900ml) to the filter cake and stir to heat up to 30°C, add dropwise concentrated hydrochloric acid (180g, 1.77mol) with a mass concentration of 36%, control the reaction temperature at 30-35°C, and continue the reaction for 6 hours after the addition. Add sodium carbonate to adjust the pH to 6-8, filter, wash the filter cake twice with water, and dry to obtain N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine ...

Embodiment 2

[0064] Example 2: Synthesis of N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine (I)

[0065] Add tert-butyl 2-tert-butylcarbazinate (189g, 1.00mol) and toluene (600ml) into the reaction flask, cool down to 5-8°C, stir, and dropwise add 3,5-dimethylbenzoyl chloride (168g , 0.99mol) and sodium hydroxide aqueous solution (mass concentration is 30%, 132g, 0.99mol), dropwise process control temperature is lower than 10 ℃, after adding, continue insulation reaction for 2 hours, cool to 0 ℃, filter. Wash the filter cake twice with water, add ethanol (900ml) to the filter cake and stir the temperature to 30°C, add dropwise concentrated hydrochloric acid (36%, 180g, 1.77mol) with a mass concentration of 36%, and control the reaction temperature at 30-35°C. After the addition was complete, the reaction was continued for 6 hours. After the reaction, add sodium carbonate to adjust the pH to 6-8, filter, wash the filter cake twice, and dry to obtain N-(3,5-dimethylbenzoyl)-N-tert-butylhydraz...

Embodiment 3

[0066] Example 3: Synthesis of N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine (I)

[0067] Add tert-butoxycarbonyl-2-tert-butylhydrazine (189g, 1.00mol) and toluene (600ml) into the reaction flask, cool down to 5-8°C, stir, and dropwise add 3,5-dimethylbenzoyl chloride (130g , 0.80mol) and sodium hydroxide aqueous solution (mass concentration is 30%, 107g, 0.80mol), the dropwise addition process controls the temperature -10 ℃. After the addition, the reaction was continued for 2 hours. Warm up to 0°C and filter. The filter cake was washed twice with water. Add methanol (900ml) to the filter cake and stir to heat up to 30°C, add dropwise concentrated hydrochloric acid (180g, 1.77mol) with a mass concentration of 36%, control the reaction temperature at 40-50°C, and continue the reaction for 5 hours after the addition is complete. Add sodium carbonate to adjust the pH to 6-8, filter, wash the filter cake twice with water, and dry to obtain N-(3,5-dimethylbenzoyl)-N-tert-butylh...

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Abstract

The invention discloses a preparation method of furanfenozide and a preparation method of a furanfenozide intermediate, wherein the preparation method of the furanfenozide comprises the following steps: tert-butoxycarbonyl-2-tert-butylhydrazine reacts with 3, 5-dimethylbenzoyl chloride, then the removal of tert-butoxycarbonyl groups is carried out to obtain N-(3, 5-dimethylbenzoyl)-N-tert-butylfluorene; 2, 7-dimethyl-2, 3-dihydrobenzofuran-6-carboxylic acid and acylating reagent are reacted to obtain 2, 7-dimethyl-2, 3-dihydrobenzofuran-6-formyl chloride; N-(3, 5-dimethylbenzoyl)-N-tert-butylhydrazine reacts with 2, 7-dimethyl-2, 3-dihydrobenzofuran-6-formyl chloride to obtain furanyl hydrazide. The preparation method has the advantages of safe and reliable reaction, simple operation, no need of special equipment and suitability for industrial production. And the product is high in efficiency, low in toxicity and environment-friendly.

Description

technical field [0001] The invention relates to a pesticide compound, in particular to a preparation method of furanfenozide, an intermediate and a preparation method thereof. Background technique [0002] The chemical name of Fufenozide (Code: JS118) is N-(2,3-dihydro-2,7-dimethyl-benzofuran-6-formyl)-N'-tert-butyl-N' -(3,5-Dimethylbenzoyl)-hydrazine is a new type of insecticide with independent intellectual property rights, high efficiency and safety, created and invented by Jiangsu Pesticide Research Institute Co., Ltd. in 2001. It has the function of regulating the growth of insects with bionic properties, and is one of the very few agricultural insecticides invented in China. [0003] Indoor bioactivity tests and field efficacy tests have shown that it has high insecticidal activity against various Lepidoptera pests such as diamondback moth, corn borer, beet armyworm, armyworm, cotton bollworm, and rice stem borer. Effect of Fufenozide on Acute Oral LD ​​in Rats 50 &...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79C07C241/04C07C243/38
Inventor 张洪全曹庆亮马海军刘廷王天赐
Owner JIANGSU PESTICIDE RES INST
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