CN116102517A - Synthesis method of 2-chloro-5-chloromethylthiazole - Google Patents
Synthesis method of 2-chloro-5-chloromethylthiazole Download PDFInfo
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- CN116102517A CN116102517A CN202211420632.4A CN202211420632A CN116102517A CN 116102517 A CN116102517 A CN 116102517A CN 202211420632 A CN202211420632 A CN 202211420632A CN 116102517 A CN116102517 A CN 116102517A
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- chloro
- chloromethylthiazole
- chlorothiazole
- solvent
- catalyst
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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 28
- 238000001308 synthesis method Methods 0.000 title claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 79
- KLEYVGWAORGTIT-UHFFFAOYSA-N 2-chlorothiazole Chemical compound ClC1=NC=CS1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000004820 halides Chemical group 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052796 boron Inorganic materials 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 238000004440 column chromatography Methods 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Chemical group 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- 229910007926 ZrCl Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000460 chlorine Substances 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 3
- 231100000086 high toxicity Toxicity 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RTEUDRWHKUPKJB-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-thiazole Chemical compound CC1=CN=C(Cl)S1 RTEUDRWHKUPKJB-UHFFFAOYSA-N 0.000 description 2
- 239000005941 Thiamethoxam 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
- -1 5-hydroxy methylthiazole-2-diazonium salt Chemical class 0.000 description 1
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
Abstract
The invention belongs to the field of organic chemical synthesis, and discloses a synthesis method of 2-chloro-5-chloromethylthiazole. Reacting 2-chlorothiazole, methylene dichloride and a catalyst at the temperature of-40 ℃ for 3-10 hours, removing a solvent after the reaction is finished, and purifying to obtain 2-chloro-5-chloromethylthiazole; the catalyst is a halide of metal or a halide of boron, and the metal is Al, fe, ti, zr, sn, zn or Cu; the mol ratio of the 2-chlorothiazole to the dichloromethane is 1: (5-50), and the mol ratio of the 2-chlorothiazole to the catalyst is 1: (0.5-4). The synthesis method of the invention takes 2-chlorothiazole and methylene dichloride as raw materials, and the 2-chloro-5-chloromethylthiazole is synthesized in one step, and chlorine sources with high toxicity and pollution such as chlorine, sulfonyl chloride, hydrochloric acid and the like are not needed.
Description
Technical Field
The invention belongs to the field of organic chemical synthesis, and particularly relates to a synthesis method of 2-chloro-5-chloromethylthiazole.
Background
The second generation neonicotinoid insecticide represented by 'imidaclothiz' and 'thiamethoxam' has higher safety, higher insecticidal activity and wider range than the first generation neonicotinoid insecticide, and is an insecticide superior to carbamate and organophosphorus insecticides.
The key intermediate of "imidaclothiz" and "thiamethoxam" is 2-chloro-5-chloromethylthiazole, and more researches on the compound are carried out.
The synthesis method of the 2-chloro-5-chloromethylthiazole mainly comprises the following steps:
(1) In the patent CN101370795B, the synthetic route is as follows, chlorine gas or sulfonyl chloride is taken as a chlorine source to react with 1-isothiocyanate-2-chloro-2-propylene to synthesize 2-chloro-5-chloromethylthiazole;
(2) In the patent CN1169800C, the synthesis route is as follows, 5-hydroxy methylthiazole-2-diazonium salt is adopted as a raw material, and is reacted with hydrochloric acid, chloride salt, acyl chloride or phosphorus pentachloride in sequence to synthesize 2-chloro-5-chloromethylthiazole;
(3) In the patent CN108276357B, the synthetic route is as follows, firstly, 2-amino-5-methylthiazole is taken as a raw material, firstly, the 2-chloro-5-methylthiazole is reacted with tert-butylsulfanitrile to obtain 2-chloro-5-methylthiazole, and then free radical chlorination is carried out, the route has harsh conditions, and the raw material is not easy to obtain;
(4) In CN112409289A, the synthetic route is as follows, 1-isothiocyanate-2-chloro-2-propylene and hydrochloric acid are subjected to oxidizing agent to obtain 2-chloro-5-chloromethylthiazole;
in summary, the reported methods have mainly the following disadvantages: high cost, serious pollution, complicated steps, use of highly toxic reagents, difficult separation and purification of products and the like.
Disclosure of Invention
Aiming at the technical problems existing in the prior art, the invention aims to provide a synthesis method of 2-chloro-5-chloromethylthiazole, which has the advantages of few reaction steps, easily available raw materials, high product purity and suitability for mass production.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the synthesis method of the 2-chloro-5-chloromethylthiazole comprises the following synthesis routes:
the synthesis steps are as follows: reacting 2-chlorothiazole, methylene dichloride and a catalyst at the temperature of-40 ℃ for 3-10 hours, removing a solvent after the reaction is finished, and purifying to obtain 2-chloro-5-chloromethylthiazole; the catalyst is a halide of metal or a halide of boron, and the metal is Al, fe, ti, zr, sn, zn or Cu; the mol ratio of the 2-chlorothiazole to the dichloromethane is 1: (5-50), and the mol ratio of the 2-chlorothiazole to the catalyst is 1: (0.5-4).
Preferably, the catalyst is AlCl 3 、FeCl 3 、FeBr 3 、BF 3 、TiCl 4 、ZrCl 4 、SnCl 2 、ZnCl 2 Or CuCl 2 。
Preferably, the purification treatment is column chromatography separation, the eluent adopted is a mixed solution of a solvent A and a solvent B according to the volume ratio of 1:1-20, the solvent A is dichloromethane, ethyl acetate or chloroform, and the solvent B is n-pentane, n-hexane, petroleum ether or methanol.
The beneficial effects are that: the synthesis method of the invention takes 2-chlorothiazole and methylene dichloride as raw materials, and the 2-chloro-5-chloromethylthiazole is synthesized in one step, and chlorine sources with high toxicity and pollution such as chlorine, sulfonyl chloride, hydrochloric acid and the like are not needed.
Detailed Description
The present invention will be described in detail with reference to examples, but the scope of the present invention is not limited to the examples.
Example 1
Adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at-40 ℃, and adding AlCl 3 After reaction 10 h, filtering the obtained reaction liquid, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing dichloromethane and n-hexane according to the volume ratio of 1:10, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 65%; wherein, the 2-chlorothiazole is mixed with dichloromethane and AlCl 3 The molar ratio is 1:5:0.5.
And (3) carrying out nuclear magnetic characterization on a target product, wherein the result is as follows:
1 H NMR (400 MHz, DMSO d6 ): δ 6.72(s, 1H), 4.62 (s, 2H)。
melting point: 146-147 ℃.
Density: 1.83 g/cm 3 。
Example 2
Adding 2-chlorothiazole and methylene dichloride into a reactor, maintaining the temperature of the system at-30 ℃, and adding FeCl 3 Filtering the obtained reaction liquid after the reaction of 8 and h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing ethyl acetate and n-hexane according to the volume ratio of 1:5, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 72%; wherein, 2-chlorothiazole, methylene dichloride and FeCl 3 The molar ratio is 1:10:0.5.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 3
Adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at-20 ℃, and adding FeBr 3 Filtering the obtained reaction liquid after the reaction of 5 h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing dichloromethane and methanol according to the volume ratio of 1:1, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 76%; wherein, 2-chlorothiazole, dichloromethane and FeBr 3 The molar ratio is 1:15:1.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 4
Adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at-10 ℃, adding BF 3 Filtering the obtained reaction liquid after reaction 10 h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing ethyl acetate and petroleum ether according to the volume ratio of 1:8, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole with the yield of 81%; wherein, 2-chlorothiazole, dichloromethane and BF 3 The molar ratio is 1:20:2.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 5
After adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at 0 ℃, and adding TiCl 4 Filtering the obtained reaction liquid after the reaction of 7 and h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing chloroform and methanol according to the volume ratio of 1:1, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 85%; wherein, 2-chlorothiazole, methylene dichloride and TiCl 4 The molar ratio is 1:25:3.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 6
After adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at 20 ℃, adding ZnCl 2 Filtering the obtained reaction liquid after the reaction of 4 h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing ethyl acetate and n-hexane according to the volume ratio of 1:15, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 87%; wherein, 2-chlorothiazole, methylene dichloride and ZnCl 2 The molar ratio is 1:30:4.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 7
After adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at 40 ℃, adding SnCl 2 Filtering the obtained reaction liquid after the reaction of 5 h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing dichloromethane and n-pentane according to the volume ratio of 1:6, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 63%; wherein, 2-chlorothiazole, methylene dichloride and SnCl 2 The molar ratio is 1:40:2.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 8
Adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at-15 ℃, and adding ZrCl 4 After the reaction is finished 6 h, filtering the obtained reaction solution, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography separation is a silica gel column, an eluent is a mixed solution obtained by mixing dichloromethane and petroleum ether according to the volume ratio of 1:10, distilling the obtained fraction containing the target product under reduced pressure to remove the solvent, thus obtaining the target product 2-chloro-5-chloromethylthiazole, and collecting the target productThe rate is 92%; wherein, 2-chlorothiazole, methylene dichloride and ZrCl 4 The molar ratio is 1:50:3.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Example 9
After adding 2-chlorothiazole and methylene dichloride into a reactor, keeping the temperature of the system at 10 ℃, adding CuCl 2 Filtering the obtained reaction liquid after the reaction of 3 h, distilling the filtrate under reduced pressure to remove the solvent, separating the obtained product by column chromatography, wherein a chromatographic column for column chromatography is a silica gel column, an eluent is a mixed liquid obtained by mixing dichloromethane and petroleum ether according to the volume ratio of 1:20, and distilling the obtained fraction containing the target product under reduced pressure to remove the solvent to obtain the target product 2-chloro-5-chloromethylthiazole, wherein the yield is 75%; wherein, 2-chlorothiazole, methylene dichloride and CuCl 2 The molar ratio is 1:30:3.
The nuclear magnetic data, melting point and density of the target product of this example are the same as those of example 1.
Claims (3)
1. A synthesis method of 2-chloro-5-chloromethylthiazole is characterized in that: reacting 2-chlorothiazole, methylene dichloride and a catalyst at the temperature of-40 ℃ for 3-10 hours, removing a solvent after the reaction is finished, and purifying to obtain 2-chloro-5-chloromethylthiazole; the catalyst is a halide of metal or a halide of boron, and the metal is Al, fe, ti, zr, sn, zn or Cu; the mol ratio of the 2-chlorothiazole to the dichloromethane is 1: (5-50), and the mol ratio of the 2-chlorothiazole to the catalyst is 1: (0.5-4).
2. The method for synthesizing 2-chloro-5-chloromethylthiazole according to claim 1, wherein: the catalyst is AlCl 3 、FeCl 3 、FeBr 3 、BF 3 、TiCl 4 、ZrCl 4 、SnCl 2 、ZnCl 2 Or CuCl 2 。
3. The method for synthesizing 2-chloro-5-chloromethylthiazole according to claim 1, wherein: the purification treatment is column chromatography separation, the adopted eluent is a mixed solution of a solvent A and a solvent B according to the volume ratio of 1:1-20, the solvent A is dichloromethane, ethyl acetate or chloroform, and the solvent B is n-pentane, n-hexane, petroleum ether or methanol.
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| CN202211420632.4A CN116102517A (en) | 2022-11-14 | 2022-11-14 | Synthesis method of 2-chloro-5-chloromethylthiazole |
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| CN202211420632.4A CN116102517A (en) | 2022-11-14 | 2022-11-14 | Synthesis method of 2-chloro-5-chloromethylthiazole |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016941A (en) * | 2014-03-17 | 2014-09-03 | 江苏辉腾生物医药科技有限公司 | Preparation method of 2-chlorine-5-chloromethylthiazole |
| 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 |
| CN112409289A (en) * | 2020-09-17 | 2021-02-26 | 江西邦浦医药化工有限公司 | Synthetic method of 2-chloro-5-chloromethyl thiazole |
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- 2022-11-14 CN CN202211420632.4A patent/CN116102517A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016941A (en) * | 2014-03-17 | 2014-09-03 | 江苏辉腾生物医药科技有限公司 | Preparation method of 2-chlorine-5-chloromethylthiazole |
| 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 |
| CN112409289A (en) * | 2020-09-17 | 2021-02-26 | 江西邦浦医药化工有限公司 | Synthetic method of 2-chloro-5-chloromethyl thiazole |
Non-Patent Citations (1)
| Title |
|---|
| 王积涛等: "有机化学", vol. 3, 31 December 2009, pages: 153 - 154 * |
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