CN105153054A - Synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone - Google Patents
Synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone Download PDFInfo
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- CN105153054A CN105153054A CN201510653265.6A CN201510653265A CN105153054A CN 105153054 A CN105153054 A CN 105153054A CN 201510653265 A CN201510653265 A CN 201510653265A CN 105153054 A CN105153054 A CN 105153054A
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- Prior art keywords
- ethyl ketone
- triazolyl
- chloro
- chlorine cyclopropyl
- cyclopropyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone. In the synthetic method, 2-chloro-1-(1-chloro-cyclopropyl)ethanone and 1,2,4-triazole are adopted as raw materials, and the method comprises the following steps: under the action of an acid-binding agent, carrying out a nucleophilic substitution reaction between 2-chloro-1-(1-chloro-cyclopropyl)ethanone and 1,2,4-triazole in an inert organic solvent to remove one molecule of hydrogen chloride to generate 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone, wherein the molar ratio of the acid-binding agent to 2-chloro-1-(1-chloro-cyclopropyl)ethanone is (1.0-3.0):1. The method is high in yield, simple in process, and mainly used for synthesis of 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone as a pesticide intermediate.
Description
Technical field
The present invention relates to a kind of synthetic method of pesticide intermediate, be specifically related to a kind of 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone.
Background technology
Prothioconazoles (Prothioconazole) is a kind of New-type wide-spectrum triazolinthione series bactericidal agent, be mainly used in control cereal crop as numerous diseases of wheat, barley, rape, peanut, paddy rice and legume crop etc., have toxicity low, without teratogenesis, without mutagenicity, to embryo's nontoxicity, to the human and environment plurality of advantages such as safely, it is one of generally acknowledged promising triazole bactericidal agent of most.1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) ethyl ketone is intermediate required in prothioconazoles building-up process.The existing synthetic technology of this intermediate is less, and yield is also lower.
Summary of the invention
The technical problem to be solved in the present invention is, for the deficiencies in the prior art, provides a kind of technique simple, the 1-(1-chlorine cyclopropyl that yield is high)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone.
For solving the problems of the technologies described above, technical scheme of the present invention is as follows:
A kind of 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) structural formula of ethyl ketone is as follows:
With 2-chloro-1-(1-chlorine cyclopropyl) ethyl ketone, 1,2,4-triazole is raw material, comprises the following steps: respectively by chloro-for 2-1-(1-chlorine cyclopropyl) ethyl ketone, 1,2,4-triazole is dissolved in solvent separately and makes solution, under nitrogen protection and room temperature condition, by 1,2,4-triazole solution and acid binding agent join in flask, more slowly add 2-chloro-1-(1-chlorine cyclopropyl) ethyl ketone solution, mixed; Then stoichiometric number hour is carried out in heating, and underpressure distillation goes out solvent, is carried out by residue extracting, washes, dry, obtains 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) ethyl ketone product.
Claims (6)
1. a 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) structural formula of ethyl ketone is as follows:
With 2-chloro-1-(1-chlorine cyclopropyl) ethyl ketone, 1,2,4-triazole is raw material, comprises the following steps: respectively by chloro-for 2-1-(1-chlorine cyclopropyl) ethyl ketone, 1,2,4-triazole is dissolved in solvent separately and makes solution, under nitrogen protection and room temperature condition, by 1,2,4-triazole solution and acid binding agent join in flask, more slowly add 2-chloro-1-(1-chlorine cyclopropyl) ethyl ketone solution, mixed;
Then stoichiometric number hour is carried out in heating, and underpressure distillation goes out solvent, is carried out by residue extracting, washes, dry, obtains 1-(1-chlorine cyclopropyl)-2-(1,2,4-triazolyl) ethyl ketone product.
2. according to 1-(1-chlorine cyclopropyl according to claim 1)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, it is characterized in that: the solvent reacting used is all conventional inert organic solvents, solvent prioritizing selection ketone, as acetone; Nitrile, as acetonitrile.
3. according to 1-(1-chlorine cyclopropyl according to claim 1)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, it is characterized in that: the acid binding agent reacting used is conventional inorganic or organic bases, can prioritizing selection metal carbonate, as sodium carbonate and salt of wormwood; Alkali metal hydroxide, as sodium hydroxide and potassium hydroxide; Alkali metal alcoholate, as sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, potassium tert.-butoxide; Also has more rudimentary alkyl tertiary amine, Cycloalkyl amine and alkylamine, especially triethylamine.
4. according to 1-(1-chlorine cyclopropyl according to claim 1)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, it is characterized in that: react raw materials used 1,2,4-triazole and 2-chloro-1-(1-chlorine cyclopropyl) mol ratio of ethyl ketone is 1.0-4.0:1; Acid binding agent and 2-chloro-1-(1-chlorine cyclopropyl) mol ratio of ethyl ketone is 1.0-3.0:1.
5. according to 1-(1-chlorine cyclopropyl according to claim 1)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, it is characterized in that: temperature of reaction fluctuates up and down in the collection temperature range of this material, usually this temperature of reaction is 0-120 DEG C, prioritizing selection 20-100 DEG C; This reaction is carried out at ambient pressure.
6. according to 1-(1-chlorine cyclopropyl according to claim 1)-2-(1,2,4-triazolyl) synthetic method of ethyl ketone, it is characterized in that: the reaction times of this reaction is 2-16h, prioritizing selection 4-14h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510653265.6A CN105153054A (en) | 2015-10-12 | 2015-10-12 | Synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510653265.6A CN105153054A (en) | 2015-10-12 | 2015-10-12 | Synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone |
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| CN105153054A true CN105153054A (en) | 2015-12-16 |
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| CN201510653265.6A Pending CN105153054A (en) | 2015-10-12 | 2015-10-12 | Synthetic method for 1-(1-chloro-cyclopropyl)-2-(1,2,4-triazolyl)ethanone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440428A (en) * | 2018-05-10 | 2018-08-24 | 长乐智高生物科技有限公司 | A kind of 1- (1- chlorine cyclopropyl) -2-（1,2,4- triazolyls) ethyl ketone synthetic method |
| CN108479821A (en) * | 2018-05-10 | 2018-09-04 | 长乐智高生物科技有限公司 | A kind of catalyst and its application for synthesizing prothioconazoles intermediate |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308781A2 (en) * | 1987-09-25 | 1989-03-29 | Bayer Ag | Antimycotic preparations |
| DE4205081A1 (en) * | 1992-02-20 | 1993-08-26 | Bayer Ag | New 1-acyloxy-2-azolyl-ethane derivs. - useful as fungicides for plant protection |
| US5252582A (en) * | 1992-02-18 | 1993-10-12 | Bayer Aktiengesellschaft | Microbiocidal triazolo-pyridine derivatives |
| CN103664808A (en) * | 2013-11-26 | 2014-03-26 | 中国农业大学 | Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof |
-
2015
- 2015-10-12 CN CN201510653265.6A patent/CN105153054A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308781A2 (en) * | 1987-09-25 | 1989-03-29 | Bayer Ag | Antimycotic preparations |
| US5252582A (en) * | 1992-02-18 | 1993-10-12 | Bayer Aktiengesellschaft | Microbiocidal triazolo-pyridine derivatives |
| DE4205081A1 (en) * | 1992-02-20 | 1993-08-26 | Bayer Ag | New 1-acyloxy-2-azolyl-ethane derivs. - useful as fungicides for plant protection |
| CN103664808A (en) * | 2013-11-26 | 2014-03-26 | 中国农业大学 | Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 王美娟，等: "丙硫菌唑的合成", 《农药》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440428A (en) * | 2018-05-10 | 2018-08-24 | 长乐智高生物科技有限公司 | A kind of 1- (1- chlorine cyclopropyl) -2-（1,2,4- triazolyls) ethyl ketone synthetic method |
| CN108479821A (en) * | 2018-05-10 | 2018-09-04 | 长乐智高生物科技有限公司 | A kind of catalyst and its application for synthesizing prothioconazoles intermediate |
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