CN116425697A - Method for synthesizing 2-acetylthiazole - Google Patents
Method for synthesizing 2-acetylthiazole Download PDFInfo
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- CN116425697A CN116425697A CN202310047565.4A CN202310047565A CN116425697A CN 116425697 A CN116425697 A CN 116425697A CN 202310047565 A CN202310047565 A CN 202310047565A CN 116425697 A CN116425697 A CN 116425697A
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- reaction
- acetylthiazole
- synthesizing
- furan
- bromobutane
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- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical compound CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 14
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims abstract description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 238000004321 preservation Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012153 distilled water Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 32
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 230000021736 acetylation Effects 0.000 abstract description 2
- 238000006640 acetylation reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- -1 thiazole compound Chemical class 0.000 description 2
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 235000015223 cooked beef Nutrition 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 210000003462 vein Anatomy 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention relates to a method for synthesizing 2-acetyl thiazole, which belongs to the technical field of organic chemistry and comprises the following steps: dropwise adding a furan solution of bromobutane into furan-rinsed magnesium powder under the protection of nitrogen until the magnesium powder disappears, then carrying out heat preservation and reflux for 1-3 hours at 30-50 ℃ to obtain a Grignard reagent, sequentially dropwise adding N, N-dimethylacetamide and thiazole into the Grignard reagent, stirring at a low temperature for reaction to obtain a reaction product, and separating and purifying the reaction product to obtain the 2-acetylthiazole. Compared with the existing synthesis method, the method uses furan to replace diethyl ether to participate in the synthesis of the format reaction, so that the reaction safety is greatly improved; the invention also uses N, N-dimethylacetamide as an acetylation reagent, increases the reactivity, greatly shortens the reaction time, improves the reaction yield, and is suitable for industrial production.
Description
Technical Field
The invention relates to a method for synthesizing 2-acetylthiazole, belonging to the technical field of organic chemistry.
Background
The thiazole ring is an important five-membered aromatic heterocycle, contains nitrogen and sulfur heteroatoms, has rich electrons, is easy to form hydrogen bonds, coordinates with metal ions, and has pi-pi stacking, static electricity, hydrophobic effect and other non-covalent bond interactions, and the structure endows the thiazole compound with a plurality of special properties and has wide potential application in a plurality of fields. 2-acetylthiazole is a kind of edible spice which is naturally present in cooked beef, cooked pork liver, asparagus, potato, rice and has a fragrance similar to nuts, rice and popcorn. The use of the flavor is approved in the United states (FEMA registration number 3328), and the flavor is allowed to be used for foods in the state of GB 2760-1996.
At present, the production routes of 2-acetylthiazole are mainly divided into two types: (1) direct acylation method: the method takes thiazole as a raw material and reacts with an acetylating reagent such as acetyl chloride and the like in the presence of triethylamine to prepare the 2-acetylthiazole. As early as 1984, alessandro Medici mentioned this method in its article Additions and Cycloadditions of Ketenes to 1,3-Thiazole and Its Alkyl Derivatives. However, the method cannot be popularized because of long reaction time and low reaction yield. (2) indirect acylation method: the method refers to that 2-bromothiazole is subjected to silanization and aldol condensation to obtain 2-acetyl thiazole. The traditional method has the defects of complicated operation process and high raw material consumption, so that the method is not economical although the yield is improved.
Disclosure of Invention
The invention aims to solve the defects of the synthesis method of 2-acetylthiazole in the prior art and provides a method for synthesizing 2-acetylthiazole, which has the advantages of simple operation, short reaction time and high reaction yield.
Technical proposal
A method for synthesizing 2-acetylthiazole, comprising the steps of:
(1) Dropwise adding a furan solution of bromobutane into furan-rinsed magnesium powder under the protection of nitrogen until the magnesium powder disappears, and then carrying out heat preservation and reflux for 1-3 h at 30-50 ℃ to obtain a Grignard reagent;
(2) And (3) sequentially dripping N, N-dimethylacetamide and thiazole into the Grignard reagent in the step (1), stirring at a low temperature for reaction to obtain a reaction product, and separating and purifying the reaction product to obtain the 2-acetylthiazole.
In the step (1), the drop velocity of the bromobutane furan solution is 3-5 seconds per drop.
Further, in the step (1), in the furan solution of the bromobutane, the volume ratio of the bromobutane to the furan is 1:1.
In the step (1), the molar ratio of the bromobutane to the magnesium powder is (1.05-1.20): 1.
In the step (2), the molar ratio of the thiazole to the N, N-dimethylacetamide is 1 (1.1-1.5).
In the step (2), the temperature of the low-temperature stirring reaction is 0-5 ℃, and the reaction time is 0.5-2 h.
Further, in the step (2), the separation and purification method is as follows: extracting the organic phase, washing with distilled water, adding anhydrous Na 2 SO 4 Drying, and finally distilling under reduced pressure to collect the fraction of b.p.89-91 ℃/1.6 kPa.
The reaction equation of the synthesis method of the invention is as follows:
the invention has the beneficial effects that:
compared with the existing synthesis method, the method for synthesizing the 2-acetylthiazole uses furan to replace diethyl ether to participate in the synthesis of the format reaction, so that the reaction safety is greatly improved; the invention also uses N, N-dimethylacetamide as an acetylation reagent, increases the reactivity, greatly shortens the reaction time, improves the reaction yield, and is suitable for industrial production.
Detailed Description
The present invention will now be described more fully hereinafter with reference to the accompanying drawings.
Example 1
A method for synthesizing 2-acetylthiazole, comprising the steps of:
(1) Washing magnesium powder 0.9 and g with furan 4.2 and mL, then dropwise adding a furan solution of bromobutane (the mass of bromobutane is 5.4g, the volume ratio of bromobutane to furan is 1:1) into the magnesium powder under the protection of nitrogen until the magnesium powder disappears, increasing the dropwise acceleration to 40 ℃ per drop, and carrying out heat preservation and reflux for 2 hours to obtain a Grignard reagent;
(2) Dropwise adding 0.37g of N, N-dimethylacetamide and 0.3g of thiazole into the Grignard reagent in the step (1) in sequence, stirring and reacting for 1h at 5 ℃ to obtain a reaction product, extracting an organic phase in the reaction product, washing with distilled water, and then adding anhydrous Na 2 SO 4 Drying and finally distilling under reduced pressure, and collecting fractions of b.p.89-91 ℃/1.6 kPa to obtain 0.42g of 2-acetylthiazole.
In this example, the reaction yield was 94% and the purity of the product 2-acetylthiazole was 99%.
Comparative example 1
Direct acylation process to prepare 2-acetylthiazole: adding 0.3g thiazole and 30 mL benzene solution into a reaction bottle with a stirrer and a dropping funnel, adding 0.51 mL acetyl chloride under stirring, stirring for 30 min, slowly dropping 2.94 mL triethylamine to 2h, stirring 2 d, and then using saturated NaHCO 3 Washing with aqueous solution, extracting with benzene solution, separating oil layer, and using anhydrous Na 2 SO 4 And (5) drying. After filtering off the drying agent, the solution was moved to a reduced pressure. Then taking 100 mL diethyl ether, dripping 1 mL ammonia solution (about 40%) into the mixture, reacting for 20 min, adding proper diethyl ether, and using saturated NaHCO 3 Washing the reaction with aqueous solution, separating oil layer, and using anhydrous Na 2 SO 4 Drying, the solvent layer was removed under vacuum to give 50% mg of 2-acetylthiazole in 78% reaction yield.
Comparative example 2
The indirect acylation method for preparing the 2-acetyl thiazole comprises the following steps:
1) Adding 27L hot water, 5.6 kg sulfur vein and 15 kg of 40% chloroacetaldehyde solution into a reaction kettle, refluxing for 2h under stirring, cooling, adding 20% sodium hydroxide solution, adjusting the pH value to 8-9, and separating out 2-aminothiazole crystals; then diethyl ether is added to dissolve the mixture, and the mixture is separatedThe ether layer is taken out, washed by distilled water and added with anhydrous Na 2 SO 4 Drying, steaming and distilling to recover diethyl ether to obtain crude product; recrystallizing the crude product by ethanol to obtain yellow crystal 2-aminothiazole with the melting point of 92-93 ℃.
2) 120g of 2-aminothiazole is weighed and placed in a reaction bottle, phosphoric acid 400 mL (the content is 85%) is added, stirring is carried out to dissolve and cool the mixture to-10 to 0 ℃, 80 mL concentrated nitric acid is dripped into the reaction bottle for about 20 to 30 min, then 20g sodium nitrite is dissolved in 150 mL distilled water solution to be slowly dripped into the reaction bottle, 3 min is needed, stirring is continued for 30 min after the adding, and the reddish brown diazonium salt solution and sodium bromide solution (200 g NaBr is dissolved in 250 mL distilled water) are respectively and slowly dripped into copper sulfate aqueous solution (200 g CuSO) at the same speed by using a dripping funnel 4 •5H 2 O is dissolved in 600 mL distilled water) for bromination reaction, maintained at 0-10 ℃, dropwise added with about 1h, reacted after the addition of 2h, then heated and stirred overnight to lead N to be 2 Removing, cooling, adding 750 mL of 33% NaOH solution for neutralization, adjusting the pH value of the solution to 6-7, then steaming the solution with water vapor to obtain an aqueous solution containing 2-bromothiazole, separating, extracting and steaming the aqueous solution, and adding 250 g of K 2 CO 3 Drying, and collecting b.p. 71-73 ℃/2.4 kPa flash distillation, obtaining 128.6 g with the yield of 73.5%.
3) Dropwise adding diethyl ether solution of 2-bromothiazole (25 g of 2-bromothiazole dissolved in 200 mL diethyl ether) into butyl lithium solution (140 mL,0.16 mol) about 0.5 h, stirring for 30 min after adding, reacting at low temperature, dropwise adding diethyl ether solution of ethyl acetate (25 g ethyl acetate dissolved in 50 mL diethyl ether) into the above solution, stirring for 1h after adding, extracting organic phase, washing with distilled water, adding anhydrous Na 2 SO 4 Drying, and then distilling under reduced pressure to collect the fraction of b.p. 89-91 ℃/1.6 kPa to obtain the 2-acetylthiazole with the purity of 17.76 and g being 92 percent.
Claims (7)
1. A method for synthesizing 2-acetylthiazole, comprising the steps of:
(1) Dropwise adding a furan solution of bromobutane into furan-rinsed magnesium powder under the protection of nitrogen until the magnesium powder disappears, and then carrying out heat preservation and reflux for 1-3 h at 30-50 ℃ to obtain a Grignard reagent;
(2) And (3) sequentially dripping N, N-dimethylacetamide and thiazole into the Grignard reagent in the step (1), stirring at a low temperature for reaction to obtain a reaction product, and separating and purifying the reaction product to obtain the 2-acetylthiazole.
2. The method for synthesizing 2-acetylthiazole according to claim 1, wherein in the step (1), the drop velocity of the furan solution of bromobutane is 3 to 5 seconds per drop.
3. The method for synthesizing 2-acetylthiazole according to claim 1, wherein in the step (1), the volume ratio of bromobutane to furan in the furan solution of bromobutane is 1:1.
4. The method for synthesizing 2-acetylthiazole according to claim 1, wherein in the step (1), the molar ratio of the bromobutane to the magnesium powder is (1.05-1.20): 1.
5. The method for synthesizing 2-acetylthiazole according to claim 1, wherein in the step (2), the molar ratio of thiazole to N, N-dimethylacetamide is 1 (1.1-1.5).
6. The method for synthesizing 2-acetylthiazole according to claim 1, wherein in the step (2), the temperature of the low-temperature stirring reaction is 0-5 ℃ and the reaction time is 0.5-2 h.
7. The method for synthesizing 2-acetylthiazole according to any one of claims 1 to 6, wherein in the step (2), the method for separation and purification is: extracting the organic phase, washing with distilled water, adding anhydrous Na 2 SO 4 Drying, and finally distilling under reduced pressure to collect the fraction of b.p.89-91 ℃/1.6 kPa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117209446A (en) * | 2023-09-15 | 2023-12-12 | 济南悟通生物科技有限公司 | Method for preparing 2-acetylthiazole by micro-channel method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117209446A (en) * | 2023-09-15 | 2023-12-12 | 济南悟通生物科技有限公司 | Method for preparing 2-acetylthiazole by micro-channel method |
| CN117209446B (en) * | 2023-09-15 | 2024-05-10 | 济南悟通生物科技有限公司 | Method for preparing 2-acetylthiazole by micro-channel method |
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