CN102382068A - 一种制备1-(1,2,4-三唑-1-基)-2-芳基-2-烷基醇的方法 - Google Patents
一种制备1-(1,2,4-三唑-1-基)-2-芳基-2-烷基醇的方法 Download PDFInfo
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- CN102382068A CN102382068A CN2011102268251A CN201110226825A CN102382068A CN 102382068 A CN102382068 A CN 102382068A CN 2011102268251 A CN2011102268251 A CN 2011102268251A CN 201110226825 A CN201110226825 A CN 201110226825A CN 102382068 A CN102382068 A CN 102382068A
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- aryl
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- triazol
- alkyl alcohol
- triazole
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- 238000000034 method Methods 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 239000000460 chlorine Substances 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005757 Cyproconazole Substances 0.000 claims abstract description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 150000003851 azoles Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- 238000004811 liquid chromatography Methods 0.000 claims description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- -1 aryl alkyl ketone Chemical class 0.000 claims description 2
- 238000010606 normalization Methods 0.000 claims description 2
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 abstract 1
- 150000004983 alkyl aryl ketones Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000010025 steaming Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- IFOXIBCJKDKKIJ-UHFFFAOYSA-N 1-(1,6-dichlorocyclohexa-2,4-dien-1-yl)pentan-2-one Chemical compound ClC1(C(C=CC=C1)Cl)CC(CCC)=O IFOXIBCJKDKKIJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N C(C1)CN=C2N1CCCCC2 Chemical compound C(C1)CN=C2N1CCCCC2 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- YMVOFDYXJIUUFD-UHFFFAOYSA-N CC(CCC)=O.ClC1=C(C=CC=C1)Cl Chemical compound CC(CCC)=O.ClC1=C(C=CC=C1)Cl YMVOFDYXJIUUFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241001515786 Rhynchosporium Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- DNVPQKQSNYMLRS-APGDWVJJSA-N ergosterol group Chemical group [C@@H]1(CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002512 suppressor factor Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
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Claims (4)
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CN2011102268251A CN102382068B (zh) | 2011-08-09 | 2011-08-09 | 一种制备1-(1,2,4-三唑-1-基)-2-芳基-2-烷基醇的方法 |
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CN2011102268251A CN102382068B (zh) | 2011-08-09 | 2011-08-09 | 一种制备1-(1,2,4-三唑-1-基)-2-芳基-2-烷基醇的方法 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103588730A (zh) * | 2013-11-14 | 2014-02-19 | 江苏剑牌农化股份有限公司 | 一种制备三唑类杀菌剂式(iii)化合物的合成方法 |
CN106243054A (zh) * | 2016-09-23 | 2016-12-21 | 三峡大学 | 一种三唑酰胺醇类杀菌剂及其合成方法 |
CN109020905A (zh) * | 2017-06-09 | 2018-12-18 | 华东理工大学 | 两种环丙唑醇的多晶型及其制备方法 |
CN112204016A (zh) * | 2018-03-06 | 2021-01-08 | Upl有限公司 | 用于制备杀真菌活性三唑化合物的方法 |
CN113582979A (zh) * | 2021-08-20 | 2021-11-02 | 浙江禾本科技股份有限公司 | 一种由异构体合成丙环唑的方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105820128B (zh) * | 2015-01-05 | 2018-01-19 | 江西华士药业有限公司 | 一种环唑醇的制备方法 |
Citations (5)
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US4898954A (en) * | 1983-04-29 | 1990-02-06 | Bayer Aktiengesellschaft | Process for the preparation of oxiranes |
CN1760187A (zh) * | 2005-11-08 | 2006-04-19 | 湖南大学 | 高纯度戊唑醇的制备方法 |
CN101565406A (zh) * | 2009-04-29 | 2009-10-28 | 江苏七洲绿色化工股份有限公司 | 环唑醇的制备工艺 |
CN101798290A (zh) * | 2010-04-02 | 2010-08-11 | 北京欧凯纳斯科技有限公司 | 一种手性环唑醇的合成方法 |
CN101805300A (zh) * | 2010-04-02 | 2010-08-18 | 北京欧凯纳斯科技有限公司 | 一种制备手性己唑醇的方法 |
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2011
- 2011-08-09 CN CN2011102268251A patent/CN102382068B/zh not_active Expired - Fee Related
Patent Citations (5)
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US4898954A (en) * | 1983-04-29 | 1990-02-06 | Bayer Aktiengesellschaft | Process for the preparation of oxiranes |
CN1760187A (zh) * | 2005-11-08 | 2006-04-19 | 湖南大学 | 高纯度戊唑醇的制备方法 |
CN101565406A (zh) * | 2009-04-29 | 2009-10-28 | 江苏七洲绿色化工股份有限公司 | 环唑醇的制备工艺 |
CN101798290A (zh) * | 2010-04-02 | 2010-08-11 | 北京欧凯纳斯科技有限公司 | 一种手性环唑醇的合成方法 |
CN101805300A (zh) * | 2010-04-02 | 2010-08-18 | 北京欧凯纳斯科技有限公司 | 一种制备手性己唑醇的方法 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103588730A (zh) * | 2013-11-14 | 2014-02-19 | 江苏剑牌农化股份有限公司 | 一种制备三唑类杀菌剂式(iii)化合物的合成方法 |
CN103588730B (zh) * | 2013-11-14 | 2016-01-20 | 江苏剑牌农化股份有限公司 | 一种制备三唑类杀菌剂式(iii)化合物的合成方法 |
CN106243054A (zh) * | 2016-09-23 | 2016-12-21 | 三峡大学 | 一种三唑酰胺醇类杀菌剂及其合成方法 |
CN106243054B (zh) * | 2016-09-23 | 2018-06-26 | 三峡大学 | 一种三唑酰胺醇类杀菌剂及其合成方法 |
CN109020905A (zh) * | 2017-06-09 | 2018-12-18 | 华东理工大学 | 两种环丙唑醇的多晶型及其制备方法 |
CN109020905B (zh) * | 2017-06-09 | 2022-12-23 | 华东理工大学 | 两种环丙唑醇的多晶型及其制备方法 |
CN112204016A (zh) * | 2018-03-06 | 2021-01-08 | Upl有限公司 | 用于制备杀真菌活性三唑化合物的方法 |
EP3762369A4 (en) * | 2018-03-06 | 2022-06-15 | UPL Ltd | PROCESSES FOR THE PREPARATION OF FUNGICIDICALLY ACTIVE TRIAZOLE COMPOUNDS |
CN113582979A (zh) * | 2021-08-20 | 2021-11-02 | 浙江禾本科技股份有限公司 | 一种由异构体合成丙环唑的方法 |
CN113582979B (zh) * | 2021-08-20 | 2023-02-24 | 浙江禾本科技股份有限公司 | 一种由异构体合成丙环唑的方法 |
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