CN100497311C - Preparation method of 2-amido-3-5-trifluoro picoline - Google Patents
Preparation method of 2-amido-3-5-trifluoro picoline Download PDFInfo
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- CN100497311C CN100497311C CNB200610044598XA CN200610044598A CN100497311C CN 100497311 C CN100497311 C CN 100497311C CN B200610044598X A CNB200610044598X A CN B200610044598XA CN 200610044598 A CN200610044598 A CN 200610044598A CN 100497311 C CN100497311 C CN 100497311C
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Abstract
The process of preparing 2-amino-3-chloro-5-trifluoromethylpyridine as one new type of pesticide intermediate includes the following steps: aminolysis of 2, 3-dichloro-5-trifluoromethyl pyridine in refluxing organic solvent at 123-135 deg.c and 2.0-3.5 MPa, eliminating organic solvent, water washing, centrifuging, and stoving to obtain product. The process of the present invention is simple, easy to operate, and favorable to industrial production, and the obtained product has purity not lower than 99 %, yield of 90 % and low production cost.
Description
Technical field
The present invention relates to the preparation method of pesticide intermediate 2-amino-3-chloro-5-5-flumethiazine.
Background technology
2-amino-3-chloro-5-5-flumethiazine is the key intermediate of synthetic pesticide, it is a kind of sterilant of succeeding in developing the nineties by U.S. a company that is used to prevent and treat diseases and pests of agronomic crop, be mainly used in the control of land for growing field crops disease and pests such as cotton, soybean, rape, effect is remarkable.Drug effect is renderd a service strong, and the mu consumption is few, the characteristics of hypotoxicity, low residue.
2-amino-3-chloro-5-5-flumethiazine is not only as the novel agrochemical intermediate, and is also of many uses at organic synthesis and dyestuff, field of medicaments.In recent years, it is found that owing to introduce the lipotropy that trifluoromethyl can improve compound on the heterocycle, the electron attractivity when thereby raising is reacted to the perviousness of organism film and tissue and with organism, strengthen the physiologically active of compound, compound 2-amino-3-chloro-5-5-flumethiazine is exactly to have introduced trifluoromethyl on the pyridine ring.At present, 2-amino-3-chloromethylpyridine fields such as widespread use agricultural chemicals, medicine, dyestuff.
Prior art is to be main raw material with 3-chloro-5-5-flumethiazine by the 2-amino-3-chloro-5-5-flumethiazine of U.S. a company exploitation, carries out nitration reaction under sulfuric acid, nitric acid nitration mixture, and the spent acid, the waste water that are produced are too many, and environmental protection is difficult to resolve determines.
Summary of the invention
Technical problem to be solved by this invention provides the preparation method of 2-amino-3-chloro-5-5-flumethiazine, and technology is simple to operation, does not have waste water, waste residue, product purity height, yield height.
The preparation method of 2-amino of the present invention-3-chloro-5-5-flumethiazine is characterized in that comprising the steps:
(1) in the presence of organic solvent, 2, in the 3-two chloro-5-5-flumethiazines logical liquefied ammonia at 125-135 ℃, under the pressure 2.0-3.5Mpa ammonolysis reaction 8-15 hour, with 2,3-two chloro-5-5-flumethiazine meters, with the mol ratio of liquefied ammonia be 1:10～18;
(2) reaction solution removes organic solvent by distillation, washing then, the centrifugal product that obtains.The described organic solvent of step 1 can adopt methyl alcohol, ethanol, Virahol, ether etc.2, the mass ratio of 3-two chloro-5-5-flumethiazines and organic solvent is 1:2-10.
The described organic solvent of step (1) can adopt methyl alcohol, ethanol, Virahol or ether, and 2, the mass ratio of 3-two chloro-5-5-flumethiazines and organic solvent is 1:0.5-10.
Advantage of the present invention:
Technology is simple to operation, is beneficial to suitability for industrialized production, does not have waste water, waste residue.Obtain the product purity height, purity 〉=99%, yield are about 90%, and production cost is low.
The physico-chemical property of 2-amino-3-chloro-5-5-flumethiazine is:
Molecular formula: C
6H
4F
3N
2Cl
Structural formula:
Molecular weight: 196.5
Fusing point: 90-92 ℃
Embodiment:
Describe the present invention in detail below in conjunction with embodiment, but do not limit the present invention.
Embodiment 1:
(1) ammonia is separated
Suction 2 in 5 liters autoclave, 3-two chloro-5-5-flumethiazine 1000g, methyl alcohol 1500g, liquefied ammonia 935g.Open stirring, chuck is opened electrically heated, and design temperature is at 135 ℃, when temperature in the kettle reaches 135 ℃, equipment stops heating (when being lower than 135 ℃ as temperature, equipment heats up automatically) automatically, and pressure is 3.5MPa, at this moment kept 8 hours, begin cooling (stopping electrically heated) after the time, when temperature was reduced to 40 ℃, beginning row pressure (beating the tail gas absorption system simultaneously) pressure was to 0.0Mpa, bubbling air catches up with gas more than 2 hours, till not having to ammonia.
With reaction solution suction methyl alcohol still kettle, normal pressure steams and removes methyl alcohol, when ammonia is separated in the material methanol content less than 10% the time, stop distillation, be cooled to 40 ℃, in still, add big water gaging and wash (starting stirring simultaneously) and put into whizzer and dry, put into drying baker, oven dry back sampling analysis (G.C detection) content 〉=99%, the packing warehouse-in.
Product yield: 90%
Embodiment 2:
Technological operation step with embodiment 1.Different condition is:
The ammonolysis reaction organic solvent adopts ethanol 1800g, liquefied ammonia amount 1000g, temperature of reaction 120-130 ℃, pressure 3Mpa, 16 hours reaction times.
Product purity is more than 99%, yield 88%.
Embodiment 3:
Technological operation step with embodiment 1.Different condition is:
It is Virahol 2000g that the ammonolysis reaction stage is adopted organic solvent, liquefied ammonia amount 1100g, temperature of reaction 120-130 ℃, pressure 3.5Mpa, 18 hours reaction times.
Product purity is more than 99%, yield 89%.
Embodiment 4:
Technological operation step with embodiment 1.Different condition is:
It is methyl alcohol 2000g that the ammonolysis reaction stage is adopted organic solvent, and the liquefied ammonia amount is 1200g, temperature of reaction 125-135 ℃, and pressure 3.5Mpa, 20 hours reaction times.
Product purity is more than 99%, yield 86%.
Claims (2)
1, the preparation method of a kind of 2-amino-3-chloro-5-5-flumethiazine is characterized in that comprising the steps:
(1) in the presence of organic solvent, 2, in the 3-two chloro-5-5-flumethiazines logical liquefied ammonia at 125-135 ℃, under the pressure 2.0-3.5Mpa ammonolysis reaction 8-15 hour, with 2,3-two chloro-5-5-flumethiazine meters, with the mol ratio of liquefied ammonia be 1:10～18;
(2) reaction solution removes organic solvent by distillation, washing then, the centrifugal product that obtains.
2, the preparation method of 2-amino according to claim 1-3-chloro-5-5-flumethiazine, it is characterized in that the described organic solvent of step (1) adopts methyl alcohol, ethanol, Virahol or ether, 2, the mass ratio of 3-two chloro-5-5-flumethiazines and organic solvent is 1:0.5-10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200610044598XA CN100497311C (en) | 2006-05-29 | 2006-05-29 | Preparation method of 2-amido-3-5-trifluoro picoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200610044598XA CN100497311C (en) | 2006-05-29 | 2006-05-29 | Preparation method of 2-amido-3-5-trifluoro picoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101081833A CN101081833A (en) | 2007-12-05 |
| CN100497311C true CN100497311C (en) | 2009-06-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB200610044598XA Expired - Fee Related CN100497311C (en) | 2006-05-29 | 2006-05-29 | Preparation method of 2-amido-3-5-trifluoro picoline |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITBS20100012A1 (en) * | 2010-01-28 | 2011-07-29 | Finchimica Srl | PROCEDURE FOR THE PREPARATION OF FLUAZINAM |
| CN102911115B (en) * | 2012-11-19 | 2015-01-07 | 江苏优嘉化学有限公司 | Method for preparing fluazinam intermediate 2-amino-3-chloro-5-trifluoromethyl pyridine |
| CN106866518A (en) * | 2017-04-16 | 2017-06-20 | 内蒙古佳瑞米精细化工有限公司 | A kind of synthetic method of the trifluoromethyl pyridine of 2 amino, 3 chlorine 5 |
| CN110143916B (en) * | 2019-05-12 | 2020-08-21 | 大连九信精细化工有限公司 | Synthesis process of fluazinam |
| CN115181060B (en) * | 2022-08-19 | 2024-03-19 | 江苏禾裕泰化学有限公司 | Clean production process for producing 2-amino-3-chloro-5-trifluoromethyl pyridine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681369A (en) * | 1970-04-20 | 1972-08-01 | George O P Doherty | 2,6-BIS (TRIFLUOROMETHYL)-1H-IMIDAZO{8 4,5-b{9 PYRIDINE |
| GB1417349A (en) * | 1972-10-10 | 1975-12-10 | Dow Chemical Co | Substituted aminohalopyridines |
| EP0031218A1 (en) * | 1979-12-24 | 1981-07-01 | Ishihara Sangyo Kaisha Ltd. | A 2-amino-trifluoromethyl-halogenopyridine compound and a process for producing the same |
| US4331670A (en) * | 1979-12-25 | 1982-05-25 | Ishihara Sangyo Kaisha, Ltd. | Pyridylanilines |
| US4349681A (en) * | 1979-12-24 | 1982-09-14 | Ishihara Sangyo Kaisha, Ltd. | 2-Amino-3-chloro-5-trifluoromethylpyridine |
-
2006
- 2006-05-29 CN CNB200610044598XA patent/CN100497311C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681369A (en) * | 1970-04-20 | 1972-08-01 | George O P Doherty | 2,6-BIS (TRIFLUOROMETHYL)-1H-IMIDAZO{8 4,5-b{9 PYRIDINE |
| GB1417349A (en) * | 1972-10-10 | 1975-12-10 | Dow Chemical Co | Substituted aminohalopyridines |
| EP0031218A1 (en) * | 1979-12-24 | 1981-07-01 | Ishihara Sangyo Kaisha Ltd. | A 2-amino-trifluoromethyl-halogenopyridine compound and a process for producing the same |
| US4349681A (en) * | 1979-12-24 | 1982-09-14 | Ishihara Sangyo Kaisha, Ltd. | 2-Amino-3-chloro-5-trifluoromethylpyridine |
| US4331670A (en) * | 1979-12-25 | 1982-05-25 | Ishihara Sangyo Kaisha, Ltd. | Pyridylanilines |
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| CN101081833A (en) | 2007-12-05 |
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Granted publication date: 20090610 Termination date: 20120529 |