N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and synthesis method thereof

A technology of phenylbenzoic acid and methyl, applied in the field of N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and its synthesis, can solve the problem of short residual effect time and toxicity. Low water solubility, low water solubility, etc.

Inactive Publication Date: 2018-12-07
ANKANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2-Methylbiphenyl compounds, due to the presence of a methyl group at the 2-position, the two benzene rings have a certain dihedral angle and are not on the same plane. The derivatives of this type of biphenyl have low toxicity and low water solubility. Environmentally friendly and other characteristics, such as biphenyl alcohol (2-methyl-3-phenylbenzyl alcohol) is often used as intermediates such as pesticides, hydrazide compounds have strong biological activity, such as N-tert-butyl- N'-(4-ethylbenzoyl)hydrazine and N-tert-butyl-N'-(2methyl-3-methoxybenzoyl)hydrazine are synthetic pesticides tebufenozide and methoxyfenonyl The intermediate of hydrazine, but this kind of hydrazine has the disadvantages of strong water solubility, strong fluidity and short residual effect time due to its good water solubility.

Method used

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  • N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and synthesis method thereof
  • N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and synthesis method thereof
  • N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of compound 2 (2-methyl-3-phenylbenzoic acid)

[0018] 40 g CrO 3 Pour into a volumetric flask containing 120 mL of water, and add 34.5 mL of concentrated H 2 SO 4 , shake well, and dilute with water to 150 mL to obtain Jones reagent; add 30 g of 2-methyl-3-phenylbenzyl alcohol, 32 mL of water, and 200 mL of acetone to a three-neck flask, place in an ice-water bath, and add 90 mL of Jones reagent dropwise. Reagents, control the reaction temperature at 25°C, react for 6 h, track the reaction with thin-layer chromatography, dichloromethane as the developer, wait for the disappearance of the substrate point and the aldehyde point, stop the reaction, and the reaction takes 6 h. Acetone was removed under reduced pressure, a large amount of precipitate was produced, suction filtered, the filter cake was washed with water until white, and dried to obtain 30 g of crude product with a yield of 99%. The crude product was dissolved in ethanol (the amount of...

Embodiment 2

[0019] Example 2 Synthesis of compound 3 (2-methyl-3-phenylbenzoyl chloride)

[0020] Add 5 g of compound 2 into a three-necked flask, add 1-2 drops of DMF, then add 10 mL of toluene, install a tail gas absorption device, raise the temperature to 80 °C, and then add 10 mL of SOCl 2 , after the dropwise addition, continue the constant temperature reaction for 1 h, cool to room temperature, and then remove excess SOCl 2 , the product compound 3 was obtained, which was directly used in the next step of synthesis without purification.

Embodiment 3

[0021] Example 3 Synthesis of Compound 4 (N-tert-butyl-N'-(2-methyl-3-phenylbenzoyl)hydrazine)

[0022] Weigh 3.9g of tert-butylhydrazine hydrochloride and 40 mL of dichloromethane into a four-neck flask, and under nitrogen protection, add 100 mL of 0.3 M sodium hydroxide aqueous solution dropwise at 0 °C. After the dropwise addition, simultaneously Add compound 3 and 100 mL of 0.3 M sodium hydroxide aqueous solution dropwise, keep the addition of the two synchronously, control the temperature of the whole reaction at 4-5 °C, follow the reaction by thin-layer chromatography, developer: dichloromethane: ethyl acetate ( 2:1), after 1.5 h, the temperature was raised to 30 °C to dissolve all the solids in the reaction system, and then the layers were separated, and the oil layer was separated. , suction filtration, and drying to obtain 5.5 g of the product, melting range: 186-189°C.

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Abstract

The invention discloses an N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and a synthesis method thereof. The compound is a white solid, has a melting range of 156 to 159 DEG C, is slightly soluble in water, and is easily soluble in organic solvents such as ethanol, dichloromethane and ethyl acetate. Compared with the derivatives of the existing tebufenozide intermediate N-tert-butylhydrazine, the compound has the advantages of low fluidity, long effective disinsection time, high efficiency, low toxicity, environmental friendliness, simple synthesis process and high yield.

Description

technical field [0001] The present invention relates to N-(2-methyl-3-phenylbenzoyl)-N'-tert-butylhydrazine and its synthesis method. Background technique [0002] 2-Methylbiphenyl compounds, due to the presence of a methyl group at the 2-position, the two benzene rings have a certain dihedral angle and are not on the same plane. The derivatives of this type of biphenyl have low toxicity and low water solubility. Environmentally friendly and other characteristics, such as biphenyl alcohol (2-methyl-3-phenylbenzyl alcohol) is often used as intermediates such as pesticides, hydrazide compounds have strong biological activity, such as N-tert-butyl- N'-(4-ethylbenzoyl)hydrazine and N-tert-butyl-N'-(2methyl-3-methoxybenzoyl)hydrazine are synthetic pesticides tebufenozide and methoxyfenonyl The intermediate of hydrazine, but this kind of hydrazine has disadvantages such as good water solubility, strong fluidity of the synthesized pesticide, and short residual effect time. In the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C241/04C07C243/38
CPCC07C51/305C07C51/60C07C241/04C07C243/38C07C63/72C07C63/331
Inventor 曹国标黄星星
Owner ANKANG UNIV
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