CN108997164A - 2- methyl -3- phenylbenzohydrazide and its synthetic method - Google Patents
2- methyl -3- phenylbenzohydrazide and its synthetic method Download PDFInfo
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- CN108997164A CN108997164A CN201810924001.3A CN201810924001A CN108997164A CN 108997164 A CN108997164 A CN 108997164A CN 201810924001 A CN201810924001 A CN 201810924001A CN 108997164 A CN108997164 A CN 108997164A
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- methyl
- phenylbenzohydrazide
- phenylbenzoate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses 2- methyl -3- phenylbenzohydrazide and its synthetic methods, the preparation method of the compound is using 2- methyl -3- Phenylbenzoic acid as raw material, synthesis 2- methyl -3- phenylbenzoate is reacted with alcohol, thionyl chloride, then 2- methyl -3- phenylbenzoate and hydration hydrazine reaction are prepared.The compounds of this invention water solubility is small, is soluble in the organic solvents such as alcohol, ethyl acetate, methylene chloride, have Antifungal activities, there is similar hydrazides to compare, have many advantages, such as that efficacy is strong, not easily run off, residual effect it is strong.
Description
Technical field
The present invention relates to 2- methyl -3- phenylbenzohydrazide and its synthetic method, belong to body technique neck among organic agricultural chemicals
Domain.
Background technique
2- methyl -3- phenylbenzohydrazide can be used as many important organic molecules (such as heterocycle, drug, dyestuff and liquid crystal material
Material etc.) synthesis precursor or intermediate, derivative has antiviral and antitumor, anti-malarial, desinsection, sterilization etc. extensive raw
Object and physiological activity.
Compared with the 2- methyl -3- methoxybenzoyl hydrazine of similar structures, 2- methyl -3- phenylbenzohydrazide 3- are benzene
Base synthesizes obtain for the first time for inventor, due on the phenyl ring of benzoyl 2- with the presence of a methyl, 3- phenyl due to
The rotation of singly-bound can collide with 2- methyl hydrogens, so that the compound and its derivative of this biphenyl structural have toxicity
Small, water solubility reduces, oil-soluble enhancing, and pesticide synthesized by the intermediate especially as pesticide has environmental-friendly, is not easy
It is lost, the advantages that drug residual effect is strong, such as agricultural chemical insecticide Biphenthrin just uses 2- methyl -3- phenyl in the synthesis process
Benzyl alcohol is as intermediate, and the pesticide is not soluble in water, and mobility is extremely low, and drug residual effect is strong, and low toxicity, environmentally friendly,
It is widely used in the insecticidal materials in farmland and prevents termite.
Summary of the invention
The object of the present invention is to provide 2- methyl -3- phenylbenzohydrazide and its synthetic methods.
The present invention realizes that process is as follows:
Compound shown in structure formula (I),
。
The preparation method of compound shown in structure formula (I), includes the following steps:
(1) 2- methyl -3- Phenylbenzoic acid, with C1-C4ROH alcohol and thionyl chloride be raw material react be made 2- methyl -3-
Phenylbenzoate；
(2) 2- methyl -3- phenylbenzoate and hydrazine hydrate back flow reaction obtain 2- methyl -3- phenylbenzohydrazide.
In above-mentioned steps (1), the ROH alcohol is ethyl alcohol.
In above-mentioned steps (2), the molar ratio of 2- methyl -3- phenylbenzoate and hydrazine hydrate is 1:1.1~1.5, preferably
For 1:1.3.
2- methyl -3- the phenylbenzohydrazide that the present invention synthesizes be white solid, melting range: 117-119 DEG C, slightly soluble
Yu Shui, is soluble in ethyl alcohol, methanol, and the organic solvents such as ethyl acetate, methylene chloride have very high chemical reactivity, can use
The synthesis precursor or intermediate for making many important organic molecules (such as heterocycle, drug, dyestuff and liquid crystal material), with similar hydrazides
Compare, have many advantages, such as that efficacy is strong, not easily run off, residual effect it is strong, derivative have antiviral and antitumor, anti-malarial, kill
The extensive biology such as worm, sterilization and physiological activity.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of 2- methyl -3- phenylbenzohydrazide；
Fig. 2 is the infrared spectrum of 2- methyl -3- phenylbenzohydrazide.
Specific embodiment
The synthesis of 1 2- methyl -3- Phenylbenzoic acid ethyl ester of embodiment
It weighs 2g 2- methyl -3- Phenylbenzoic acid to be added in three-necked flask, 10 mL dehydrated alcohols is added, in ice-water bath
Under, 2 mL SOCl are added dropwise in stirring2 , reflux is warming up to after dripping, at 54 DEG C, solid all dissolves, thin-layer chromatography tracking
Reaction stops reaction until acid point disappears, and decompression removes extra ethyl alcohol and thionyl chloride, stands, room temperature is cooled to, with 0.1%
NaHCO3Aqueous solution tune pH value to 8, be then extracted with ethyl acetate, extract liquor dried, filtered with anhydrous calcium chloride,
Filtrate decompression is distilled, ethyl acetate is removed, obtains 2- methyl -3- Phenylbenzoic acid ethyl ester crude product 1.9g.
The synthesis of 2 2- methyl -3- phenylbenzohydrazide of embodiment
1.9g 2- methyl -3- Phenylbenzoic acid ethyl ester is added in three-necked flask, then is separately added into 2 mL dehydrated alcohols, 10
ML hydrazine hydrate flows back at 102 DEG C, and thin-layer chromatography (methylene chloride makees solvent) tracking reaction to ester point disappears, and stops reaction,
Decompression removal ethyl alcohol and extra hydrazine hydrate, it is dry, obtain 1.7 g of white solid 2- methyl -3- phenylbenzohydrazide crude product.
Fig. 1 is the nuclear magnetic spectrogram of 2- methyl -3- phenylbenzohydrazide, and Fig. 2 is the infrared of 2- methyl -3- phenylbenzohydrazide
Spectrogram, it was demonstrated that successfully synthesis obtains 2- methyl -3- phenylbenzohydrazide.
3 following equation of embodiment is Biphenthrin synthetic reaction formula
。
Claims (6)
1. compound shown in structure formula (I),
。
2. the preparation method of compound shown in claim 1, it is characterised in that include the following steps:
(1) 2- methyl -3- Phenylbenzoic acid, with C1-C4ROH alcohol and thionyl chloride react be made 2- methyl -3- phenyl benzene first
Acid esters；
(2) 2- methyl -3- phenylbenzoate and hydrazine hydrate back flow reaction obtain 2- methyl -3- phenylbenzohydrazide.
3. preparation method according to claim 2, it is characterised in that: in step (1), the ROH alcohol is ethyl alcohol.
4. preparation method according to claim 2, it is characterised in that: in step (2), 2- methyl -3- phenylbenzoate with
The molar ratio of hydrazine hydrate is 1:1.1~1.5.
5. preparation method according to claim 4, it is characterised in that: 2- methyl -3- phenylbenzoate and hydrazine hydrate rub
You are than being 1:1.3.
6. application of the compound shown in claim 1 as pesticide intermediate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810924001.3A CN108997164A (en) | 2018-08-11 | 2018-08-11 | 2- methyl -3- phenylbenzohydrazide and its synthetic method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810924001.3A CN108997164A (en) | 2018-08-11 | 2018-08-11 | 2- methyl -3- phenylbenzohydrazide and its synthetic method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108997164A true CN108997164A (en) | 2018-12-14 |
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|---|---|---|---|
| CN201810924001.3A Pending CN108997164A (en) | 2018-08-11 | 2018-08-11 | 2- methyl -3- phenylbenzohydrazide and its synthetic method |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113058567A (en) * | 2021-02-09 | 2021-07-02 | 深圳世纪盛源环境科技有限公司 | Hydrogen bond induced high-stability porous covalent organogel material and preparation method thereof |
Citations (7)
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| US20060122428A1 (en) * | 2004-11-08 | 2006-06-08 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Hydroxynaphthoic acid hydrazide compound and method for preparing the same |
| CN101606522A (en) * | 2009-05-26 | 2009-12-23 | 上海师范大学 | N-aroyl tetrahydropyrimidineinsecticide insecticide and preparation method thereof |
| CN103193769A (en) * | 2013-04-15 | 2013-07-10 | 南开大学 | 4-methyl-1,2,3-thiadiazole-5-triazole compound as well as preparation method and use thereof |
| CN103408454A (en) * | 2013-08-16 | 2013-11-27 | 兰州大学 | Preparation method of hydrazide compound |
| CN103694179A (en) * | 2013-12-04 | 2014-04-02 | 上海工程技术大学 | Bishydrazide compound and preparation method thereof |
| CN105348141A (en) * | 2015-09-25 | 2016-02-24 | 海南医学院 | Preparation and application of benzoyl hydrazine derivative |
| CN107216291A (en) * | 2017-06-05 | 2017-09-29 | 杨子辉 | Fragrant phenoxy group propionic acid compounds containing bishydrazide and preparation method and application |
-
2018
- 2018-08-11 CN CN201810924001.3A patent/CN108997164A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060122428A1 (en) * | 2004-11-08 | 2006-06-08 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Hydroxynaphthoic acid hydrazide compound and method for preparing the same |
| CN101606522A (en) * | 2009-05-26 | 2009-12-23 | 上海师范大学 | N-aroyl tetrahydropyrimidineinsecticide insecticide and preparation method thereof |
| CN103193769A (en) * | 2013-04-15 | 2013-07-10 | 南开大学 | 4-methyl-1,2,3-thiadiazole-5-triazole compound as well as preparation method and use thereof |
| CN103408454A (en) * | 2013-08-16 | 2013-11-27 | 兰州大学 | Preparation method of hydrazide compound |
| CN103694179A (en) * | 2013-12-04 | 2014-04-02 | 上海工程技术大学 | Bishydrazide compound and preparation method thereof |
| CN105348141A (en) * | 2015-09-25 | 2016-02-24 | 海南医学院 | Preparation and application of benzoyl hydrazine derivative |
| CN107216291A (en) * | 2017-06-05 | 2017-09-29 | 杨子辉 | Fragrant phenoxy group propionic acid compounds containing bishydrazide and preparation method and application |
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| ALEXANDRA BASILIO LOPES等: "Characterization of Amide Bond Conformers for a Novel Heterocyclic Template of N-acylhydrazone Derivatives", 《MOLECULES》 * |
| T.MUKAI等: "THE REACTION OF 2,6-DISUDSTITUTED TROPONES WITH HYDRAZINE", 《TETRAHEDRON LETTERS》 * |
| 王晓庆等: "室温下三光气作环合剂合成5-取代-1，3,4-噁二唑-2-酮类化合物", 《化学研究与应用》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113058567A (en) * | 2021-02-09 | 2021-07-02 | 深圳世纪盛源环境科技有限公司 | Hydrogen bond induced high-stability porous covalent organogel material and preparation method thereof |
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Application publication date: 20181214 |