CN111303059A - 一种丙硫菌唑的合成方法 - Google Patents
一种丙硫菌唑的合成方法 Download PDFInfo
- Publication number
- CN111303059A CN111303059A CN202010353807.9A CN202010353807A CN111303059A CN 111303059 A CN111303059 A CN 111303059A CN 202010353807 A CN202010353807 A CN 202010353807A CN 111303059 A CN111303059 A CN 111303059A
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- CN
- China
- Prior art keywords
- prothioconazole
- ferric trichloride
- synthesizing
- reaction
- hydrogen peroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 239000005825 Prothioconazole Substances 0.000 title claims abstract description 43
- 238000001308 synthesis method Methods 0.000 title claims abstract description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 40
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 13
- 230000001590 oxidative effect Effects 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960002089 ferrous chloride Drugs 0.000 claims abstract description 10
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 230000003647 oxidation Effects 0.000 abstract description 5
- 238000006477 desulfuration reaction Methods 0.000 abstract description 4
- 230000023556 desulfurization Effects 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 4
- 239000007800 oxidant agent Substances 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- XUKUURHRXDUEBC-SXOMAYOGSA-N (3s,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-SXOMAYOGSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QPDUQKTYZRXRBC-UHFFFAOYSA-N triazole-4-thione Chemical compound S=C1C=NN=N1 QPDUQKTYZRXRBC-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
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CN202010353807.9A CN111303059B (zh) | 2020-04-29 | 2020-04-29 | 一种丙硫菌唑的合成方法 |
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CN111303059A true CN111303059A (zh) | 2020-06-19 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112255342A (zh) * | 2020-10-14 | 2021-01-22 | 合肥海关技术中心 | 一种马铃薯中丙硫菌唑及其代谢物硫酮菌唑残留量的测定方法 |
CN112295608A (zh) * | 2020-11-19 | 2021-02-02 | 河北威远生物化工有限公司 | 一种用于三唑类化合物芳香化的三氯化铁再生循环套用方法 |
CN113788778A (zh) * | 2021-10-09 | 2021-12-14 | 河北威远生物化工有限公司 | 一种含氮杂环化合物的芳香化方法 |
CN114736165A (zh) * | 2022-05-18 | 2022-07-12 | 绍兴上虞新银邦生化有限公司 | 一种丙硫菌唑的合成方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749057A (zh) * | 2016-12-30 | 2017-05-31 | 南京工业大学 | 一种中间体化合物以及丙硫菌唑的合成方法 |
CN109553584A (zh) * | 2018-12-22 | 2019-04-02 | 耿丹风 | 一种合成丙硫菌唑连续流氧化方法 |
-
2020
- 2020-04-29 CN CN202010353807.9A patent/CN111303059B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749057A (zh) * | 2016-12-30 | 2017-05-31 | 南京工业大学 | 一种中间体化合物以及丙硫菌唑的合成方法 |
CN109553584A (zh) * | 2018-12-22 | 2019-04-02 | 耿丹风 | 一种合成丙硫菌唑连续流氧化方法 |
Non-Patent Citations (1)
Title |
---|
余波: "丙硫菌唑的合成工艺优化", 《农药》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112255342A (zh) * | 2020-10-14 | 2021-01-22 | 合肥海关技术中心 | 一种马铃薯中丙硫菌唑及其代谢物硫酮菌唑残留量的测定方法 |
CN112255342B (zh) * | 2020-10-14 | 2023-10-13 | 合肥海关技术中心 | 一种马铃薯中丙硫菌唑及其代谢物硫酮菌唑残留量的测定方法 |
CN112295608A (zh) * | 2020-11-19 | 2021-02-02 | 河北威远生物化工有限公司 | 一种用于三唑类化合物芳香化的三氯化铁再生循环套用方法 |
CN112295608B (zh) * | 2020-11-19 | 2023-05-19 | 河北威远生物化工有限公司 | 一种用于三唑类化合物芳香化的三氯化铁再生循环套用方法 |
CN113788778A (zh) * | 2021-10-09 | 2021-12-14 | 河北威远生物化工有限公司 | 一种含氮杂环化合物的芳香化方法 |
WO2023056714A1 (zh) * | 2021-10-09 | 2023-04-13 | 河北威远生物化工有限公司 | 一种含氮杂环化合物的芳香化方法 |
CN113788778B (zh) * | 2021-10-09 | 2023-11-17 | 河北威远生物化工有限公司 | 一种含氮杂环化合物的芳香化方法 |
CN114736165A (zh) * | 2022-05-18 | 2022-07-12 | 绍兴上虞新银邦生化有限公司 | 一种丙硫菌唑的合成方法 |
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Effective date of registration: 20230620 Address after: 21444 No.7, Runhua Road, Ligang Town, Jiangyin City, Wuxi City, Jiangsu Province Patentee after: JIANGYIN SULI CHEMICAL Co.,Ltd. Address before: No.7-1, Runhua Road, Lingang street, Jiangyin City, Wuxi City, Jiangsu Province Patentee before: JIANGSU SULI FINE CHEMICAL Co.,Ltd. |
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Effective date of registration: 20240109 Address after: 750409 Suli Road, Ningdong Energy and Chemical Industry Base, Yinchuan City, Ningxia Hui Autonomous Region Patentee after: Suli (Ningxia) New Materials Technology Co.,Ltd. Address before: 21444 No.7, Runhua Road, Ligang Town, Jiangyin City, Wuxi City, Jiangsu Province Patentee before: JIANGYIN SULI CHEMICAL Co.,Ltd. |