CN115785020A - Synthetic method of 2-chloro-5-chloromethyl thiazole - Google Patents
Synthetic method of 2-chloro-5-chloromethyl thiazole Download PDFInfo
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- CN115785020A CN115785020A CN202211495752.0A CN202211495752A CN115785020A CN 115785020 A CN115785020 A CN 115785020A CN 202211495752 A CN202211495752 A CN 202211495752A CN 115785020 A CN115785020 A CN 115785020A
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- chloromethylthiazole
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- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000010189 synthetic method Methods 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 51
- KLEYVGWAORGTIT-UHFFFAOYSA-N 2-chlorothiazole Chemical compound ClC1=NC=CS1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 30
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000001308 synthesis method Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 230000002194 synthesizing effect Effects 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 11
- 229910007926 ZrCl Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 231100000086 high toxicity Toxicity 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 239000012043 crude product Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 238000005660 chlorination reaction Methods 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CJSJMPBLJWVOEH-UHFFFAOYSA-N 2-chloro-1-isothiocyanatoprop-1-ene Chemical compound ClC(=CN=C=S)C CJSJMPBLJWVOEH-UHFFFAOYSA-N 0.000 description 2
- DGBFPSVUFUDQNA-UHFFFAOYSA-N 2-chloro-3-isothiocyanatoprop-1-ene Chemical compound ClC(=C)CN=C=S DGBFPSVUFUDQNA-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 239000005941 Thiamethoxam Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960002155 chlorothiazide Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a synthesis method of 2-chloro-5-chloromethyl thiazole, which takes 2-chloro thiazole as an initial raw material and prepares the 2-chloro-5-chloromethyl thiazole by mixing and reacting the 2-chloro thiazole, formaldehyde, hydrochloric acid and a catalyst. The 2-chloro-5-chloromethyl thiazole is synthesized by a one-step method, reagents with high toxicity and high pollution, such as chlorine gas, sulfonyl chloride and the like, are not needed, and the method is short in step, green and environment-friendly, few in by-products, high in yield and suitable for large-scale production.
Description
Technical Field
The invention relates to a synthetic method of 2-chloro-5-chloromethyl thiazole, belonging to the field of organic chemical synthesis.
Background
In recent years, plant diseases and insect pests are increasing, which brings great threat to plants, particularly crops, and further affects food safety, in order to reduce the plant diseases and insect pests, the use amount of pesticides is increasing day by day, but the pesticide resistance of some pests is also becoming stronger, so that designing and synthesizing novel chemical pesticides with high efficiency, low toxicity and low residue are becoming more and more important.
The german bayer company successfully developed the first commercial-scale neonicotinoid insecticide, "imidacloprid", in the mid-eighties of the last century. Practice proves that the pesticide has higher insecticidal activity, high selectivity and spectral environmental compatibility, so that more and more people research and develop the pesticide.
The thiamethoxam and chlorothiazide are second-generation neonicotinoid insecticides, and have higher insecticidal activity, wider insecticidal range, less environmental pollution and higher safety than the first-generation neonicotinoid insecticides.
2-chloro-5-chloromethyl thiazole is a key intermediate for synthesizing thiamethoxam and chlorothiazide, the efficient synthesis of the 2-chloro-5-chloromethyl thiazole is always concerned, and the synthesis methods of the 2-chloro-5-chloromethyl thiazole mainly comprise the following steps:
(1) Patent CN109776446a discloses: adding 2,3-dichloropropene and sodium thiocyanate into an organic solvent for reaction, and treating a reaction liquid to obtain a colorless liquid 2-chloropropenyl isothiocyanate; dissolving 2-chloropropenyl isothiocyanate in an organic solvent, adding hydrochloric acid, and electrolyzing to obtain 2-chloro-5-chloromethyl thiazole, wherein the reaction formula is shown as follows:
(2) The compound is prepared by taking 1-isothiocyanato-2-chloro-2-propylene as a key intermediate and chlorine as a chlorination reagent for chlorination reaction. However, the preparation process needs a highly toxic reagent chlorine gas, and has high risk coefficient, high cost and more reaction byproducts, and the reaction formula is as follows:
(3) 1-isothiocyanato-2-chloro-2-propene is used as a raw material, and SO is used 2 Cl 2 Used as a chlorinating agent to carry out chlorination reaction. The reaction process also has a large amount of SO 2 And HCl is released, increasing cost and also causing greater environmental pollution, the reaction formula is as follows:
(4) Patent CN112409289a discloses: placing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent for mixing to obtain a mixed solution; adding an oxidant into the mixed solution for reaction to obtain 2-chloro-5-chloromethylthiazole, wherein the reaction formula is as follows:
(5) Patent CN112661717a discloses: the synthesis method of photocatalytic chlorination is reported to synthesize 2-chloro-5-chloromethylthiazole, and the reaction formula is shown as follows:
(6) 5-methylene-1,3-thiazolidine-2-thioketone is used as a raw material, chlorine is used as a chlorination reagent, and 2-chloro-5-chloromethyl thiazole is synthesized by the following reaction formula:
in conclusion, it can be seen that the reported methods mainly have the disadvantages of complicated steps, use of highly toxic reagents, high cost, serious pollution, high temperature, many reaction byproducts, difficulty in separation and the like.
Disclosure of Invention
The invention aims to provide a synthetic method of 2-chloro-5-chloromethyl thiazole, so as to overcome the defects in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
the embodiment of the invention provides a synthetic method of 2-chloro-5-chloromethyl thiazole, which comprises the following steps:
reacting a mixed reaction system containing 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst to prepare the 2-chloro-5-chloromethylthiazole.
The catalyst in the embodiment of the invention comprises AlCl 3 、FeCl 3 、FeBr 3 、BF 3 、SnCl 2 、ZnCl 2 、ZrCl 2 And the like, or a combination of two or more thereof.
Further, the molar ratio of the 2-chlorothiazole to the catalyst is 1: 0.1-1: 10, preferably 1: 2-1: 8.
Further, the mol ratio of the 2-chlorothiazole to the formaldehyde is 1: 1-1: 10, preferably 1: 3-1: 5.
Further, the mol ratio of the 2-chlorothiazole to the hydrochloric acid is 1: 1-1: 10, preferably 1: 6-1: 10.
Further, the reaction temperature is 60-120 ℃, and the reaction time is 4-10 hours.
Compared with the prior art, the invention has the beneficial effects that:
1) The 2-chloro-5-chloromethyl thiazole is obtained by one-step synthesis by taking 2-chloro thiazole as a raw material, and the reaction steps are few.
2) The method provided by the invention does not need to use reagents with high toxicity and much pollution, such as chlorine, sulfonyl chloride and the like, and has the advantages of environmental protection and the like.
Detailed Description
Aiming at the defects of the prior art, the inventor of the present invention provides a technical scheme of the present invention through long-term research and a large amount of practice, wherein 2-chloro-thiazole is mainly used as an initial raw material, and reacts with formaldehyde under the conditions of hydrochloric acid and a catalyst to synthesize the 2-chloro-5-chloromethyl thiazole by a one-step method.
The technical solution, its implementation and principles, etc. will be further explained as follows. It is to be understood, however, that within the scope of the present invention, each of the above-described features of the present invention and each of the features described in detail below (examples) may be combined with each other to form new or preferred embodiments. Not to be reiterated herein, but to the extent of space.
One aspect of the embodiment of the invention discloses a synthesis method of 2-chloro-5-chloromethylthiazole, which comprises the step of mixing and reacting 2-chloro-thiazole, formaldehyde, hydrochloric acid and a catalyst to prepare the 2-chloro-5-chloromethylthiazole. The method provided by the invention has the characteristics of few reaction steps, easily obtained raw materials, high product purity and suitability for mass production.
The invention discloses a synthetic method of 2-chloro-5-chloromethyl thiazole, which comprises the following steps of
Reacting a mixed reaction system containing 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst to prepare the 2-chloro-5-chloromethylthiazole.
Specifically, the one-step method provided by the invention utilizes Friedel-crafts reaction to synthesize and obtain the 2-chloro-5-chloromethyl thiazole, and the specific reaction mechanism is as follows: formaldehyde and hydrochloric acid in the presence of metal salt catalyst form chloromethyl carbanion in situ, which can react with 2-chlorothiazole to produce Friedel-crafts chloromethylation reaction to obtain the target product.
Specifically, the synthetic route of the 2-chloro-5-chloromethylthiazole is as follows:
in some specific embodiments, the catalyst comprises AlC1 3 、FeCl 3 、FeBr 3 、BF 3 、SnCl 2 、ZnCl 2 、ZrCl 2 And the like, but not limited thereto.
In some embodiments, the molar ratio of 2-chlorothiazole to catalyst is from 1: 0.1 to 1: 10.
In some embodiments, the molar ratio of 2-chlorothiazole to formaldehyde is from 1: 1 to 1: 10.
In some embodiments, the molar ratio of 2-chlorothiazole to hydrochloric acid is from 1: 1 to 1: 10.
In some embodiments, the temperature of the reaction is 60-120 ℃ and the time of the reaction is 4-10 hours.
In some specific embodiments, the method for synthesizing 2-chloro-5-chloromethylthiazole comprises: adding 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst into a reaction device to form the mixed reaction system.
In some examples, the mixed reaction system is cooled and purified after the reaction is finished to obtain the 2-chloro-5-chloromethylthiazole.
In some embodiments, the synthesis method has a yield above 65%.
In some more specific embodiments, the method for synthesizing 2-chloro-5-chloromethylthiazole comprises:
adding 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst into a reactor, and reacting for a certain time at a certain temperature to obtain 2-chloro-5-chloromethylthiazole.
In conclusion, the 2-chloro-5-chloromethylthiazole is synthesized by one step by using the 2-chlorothiazole as the raw material, and reagents such as chlorine gas, sulfonyl chloride and the like which have high toxicity and high pollution are not needed.
The technical solutions of the present invention will be described in further detail with reference to several preferred embodiments, and it should be apparent that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. It is to be noted that the following examples are intended to facilitate the understanding of the present invention, and do not set forth any limitation thereto. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers.
Example 1
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to the reactor, 1mol of 2-chlorothiazole, 1mol of formaldehyde, 2mol of hydrochloric acid and 0.1mol of AlCl were added 3 And heating the system to 60 ℃, reacting for 10 hours, cooling, and distilling the crude product under reduced pressure to obtain a product, wherein the yield of the reaction is 65%.
The product obtained in this example was confirmed to be 2-chloro-5-chloromethylthiazole (conventional compound, CAS No. 105827-91-6).
Example 2
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to the reactor, 1mol of 2-chlorothiazole, 2mol of formaldehyde, 4mol of hydrochloric acid and 1mol of FeCl were added 3 And heating the system to 70 ℃, reacting for 8 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole with the reaction yield of 72 percent.
Example 3
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to the reactor, 1mol of 2-chlorothiazole, 3mol of formaldehyde, 6mol of hydrochloric acid and 2mol of BF were added 3 And heating the system to 80 ℃, reacting for 6 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole with the reaction yield of 86%.
Example 4
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to the reactor, 1mol of 2-chlorothiazole, 4mol of formaldehyde, 8mol of hydrochloric acid and 4mol of SnCl were added 2 And heating the system to 90 ℃, reacting for 5 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole with the reaction yield of 91 percent.
Example 5
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to the reactor, 1mol of 2-chlorothiazole, 5mol of formaldehyde, 10mol of hydrochloric acid and 8mol of ZnCl were added 2 And heating the system to 100 ℃, reacting for 4 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole, wherein the yield of the reaction is 95%.
Example 6
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to a reactor, 1mol of 2-chlorothiazole, 5mol of formaldehyde, 10mol of hydrochloric acid and 10mol of FeCl were added 3 And heating the system to 120 ℃, reacting for 4 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole, wherein the yield of the reaction is 70%.
Example 7
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
to a reactor, 1mol of 2-chlorothiazole, 10mol of formaldehyde, 1mol of hydrochloric acid and 8mol of ZnCl are added 2 And heating the system to 85 ℃, reacting for 6 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole with the reaction yield of 72 percent.
Example 8
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
into a reactor, 1mol of 2-chlorothiazole, 10mol of formaldehyde, 1mol of hydrochloric acid and 8mol of FeF were added 3 And heating the system to 85 ℃, reacting for 6 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole with the reaction yield of 69 percent.
Example 9
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
into a reactor, 1mol of 2-chlorothiazole, 10mol of formaldehyde, 1mol of hydrochloric acid and 8mol of ZrCl were charged 2 And heating the system to 85 ℃, reacting for 6 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole, wherein the yield of the reaction is 84%.
Comparative example
The process for synthesizing 2-chloro-5-chloromethylthiazole in this example specifically includes:
into a reactor, 1mol of 2-chlorothiazole, 12mol of formaldehyde, 15mol of hydrochloric acid and 0.05mol of FeCl were added 3 And heating the system to 130 ℃, reacting for 4 hours, cooling, and distilling the crude product under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole, wherein the yield of the reaction is 35%.
In addition, the inventors of the present invention have also made experiments with other materials, process operations, and process conditions described in the present specification with reference to the above examples, and have obtained preferable results.
It should be understood that the technical solution of the present invention is not limited to the above-mentioned specific embodiments, and all technical modifications made according to the technical solution of the present invention fall within the protection scope of the present invention without departing from the spirit of the present invention and the protection scope of the claims.
Claims (10)
1. A synthetic method of 2-chloro-5-chloromethyl thiazole is characterized by comprising the following steps:
reacting a mixed reaction system containing 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst to prepare the 2-chloro-5-chloromethylthiazole.
2. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the catalyst comprises AlCl 3 、FeCl 3 、FeBr 3 、BF 3 、SnCl 2 、ZnCl 2 、ZrCl 2 Any one or a combination of two or more of them.
3. The method for synthesizing 2-chloro-5-chloromethylthiazole according to claim 1, wherein the method comprises the following steps: the mol ratio of the 2-chlorothiazole to the catalyst is 1: 0.1-1: 10, preferably 1: 2-1: 8.
4. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the mol ratio of the 2-chlorothiazole to the formaldehyde is 1: 1-1: 10, preferably 1: 3-1: 5.
5. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the molar ratio of the 2-chlorothiazole to the hydrochloric acid is 1: 1-1: 10, preferably 1: 6-1: 10.
6. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the temperature of the reaction is 60-120 ℃.
7. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the reaction time is 4-10 hours.
8. The method of claim 1, comprising: adding 2-chlorothiazole, formaldehyde, hydrochloric acid and a catalyst into a reaction device to form the mixed reaction system.
9. The method of claim 1, comprising: and cooling the mixed reaction system after the reaction is finished, and distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
10. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein: the yield of the synthesis method is more than 65%.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101263130A (en) * | 2005-09-13 | 2008-09-10 | 詹森药业有限公司 | 2-aniline-4-aryl substituted thiazole derivatives |
| CN102276595A (en) * | 2010-04-16 | 2011-12-14 | 山东轩竹医药科技有限公司 | Oxazolidinone antibiotic containing five-membered heterocycles |
| CN108276357A (en) * | 2018-02-13 | 2018-07-13 | 浙江永太科技股份有限公司 | The synthetic method of 2- chloro-5-chloromethyl thiazoles |
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- 2022-11-24 CN CN202211495752.0A patent/CN115785020A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101263130A (en) * | 2005-09-13 | 2008-09-10 | 詹森药业有限公司 | 2-aniline-4-aryl substituted thiazole derivatives |
| CN102276595A (en) * | 2010-04-16 | 2011-12-14 | 山东轩竹医药科技有限公司 | Oxazolidinone antibiotic containing five-membered heterocycles |
| CN108276357A (en) * | 2018-02-13 | 2018-07-13 | 浙江永太科技股份有限公司 | The synthetic method of 2- chloro-5-chloromethyl thiazoles |
Non-Patent Citations (3)
| Title |
|---|
| 张执侯等: "有机化学", 30 June 1986, 上海科学技术出版社, pages: 466 * |
| 王彦林: "精细化工单元反应与工艺", 30 November 1996, 河南大学出版社, pages: 273 * |
| 莫羡忠 等: "吡虫啉相关化合物的合成及其杀虫效能", 精细化工, vol. 17, 31 August 2000 (2000-08-31), pages 447 - 449 * |
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