CN106905260A - 用于制备除草剂氟噻草胺中间体tda‑砜的方法 - Google Patents
用于制备除草剂氟噻草胺中间体tda‑砜的方法 Download PDFInfo
- Publication number
- CN106905260A CN106905260A CN201710120067.2A CN201710120067A CN106905260A CN 106905260 A CN106905260 A CN 106905260A CN 201710120067 A CN201710120067 A CN 201710120067A CN 106905260 A CN106905260 A CN 106905260A
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- CN
- China
- Prior art keywords
- thiadiazoles
- reaction
- trifluoromethyl
- microwave
- ultrasonic
- Prior art date
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- Granted
Links
- 238000000034 method Methods 0.000 title abstract description 19
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 title description 19
- 239000005531 Flufenacet Substances 0.000 title description 18
- 230000002363 herbicidal effect Effects 0.000 title description 6
- 239000004009 herbicide Substances 0.000 title description 6
- 150000003457 sulfones Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- 238000010189 synthetic method Methods 0.000 claims abstract description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- 239000002994 raw material Substances 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000004945 emulsification Methods 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 238000003541 multi-stage reaction Methods 0.000 claims description 12
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 claims description 10
- 230000004044 response Effects 0.000 claims description 10
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 8
- 210000000481 breast Anatomy 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 150000003851 azoles Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- -1 methyl mercapto Chemical class 0.000 abstract description 11
- 230000035484 reaction time Effects 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 6
- 150000004867 thiadiazoles Chemical class 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 2
- 230000002776 aggregation Effects 0.000 abstract description 2
- 150000002978 peroxides Chemical class 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 10
- 238000012545 processing Methods 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000010586 diagram Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005507 Diflufenican Substances 0.000 description 2
- 239000005582 Metosulam Substances 0.000 description 2
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000005583 Metribuzin Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- OYVABZRZDZPVQD-UHFFFAOYSA-N [F].C=1C=CSC=1 Chemical compound [F].C=1C=CSC=1 OYVABZRZDZPVQD-UHFFFAOYSA-N 0.000 description 2
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 2
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 244000131316 Panax pseudoginseng Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- GLCYMSPOJRDUEE-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=CC=C1.[F] Chemical compound [N+](=O)([O-])C1=CC=CC=C1.[F] GLCYMSPOJRDUEE-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
Description
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CN201710120067.2A CN106905260B (zh) | 2017-03-02 | 2017-03-02 | 用于制备除草剂氟噻草胺中间体tda-砜的方法 |
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CN201710120067.2A CN106905260B (zh) | 2017-03-02 | 2017-03-02 | 用于制备除草剂氟噻草胺中间体tda-砜的方法 |
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CN106905260A true CN106905260A (zh) | 2017-06-30 |
CN106905260B CN106905260B (zh) | 2019-01-11 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110651783A (zh) * | 2018-06-28 | 2020-01-07 | 江苏龙灯化学有限公司 | 一种农药液体组合物的制备方法及基于该方法制备的农药液体组合物及其用途 |
CN113402481A (zh) * | 2021-05-20 | 2021-09-17 | 西华大学 | 一种环氧乙烷衍生物的合成方法 |
CN115043791A (zh) * | 2021-03-09 | 2022-09-13 | 北京颖泰嘉和生物科技股份有限公司 | 连续氧化制备2-甲砜基-5-三氟甲基-1,3,4-噻二唑的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1162413C (zh) * | 1998-09-16 | 2004-08-18 | 美国拜尔公司 | 用于将tda转化成tda砜的改进的方法 |
CN103664824A (zh) * | 2013-11-19 | 2014-03-26 | 泸州东方农化有限公司 | 噻二唑酰胺类化合物的制备方法 |
-
2017
- 2017-03-02 CN CN201710120067.2A patent/CN106905260B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1162413C (zh) * | 1998-09-16 | 2004-08-18 | 美国拜尔公司 | 用于将tda转化成tda砜的改进的方法 |
CN103664824A (zh) * | 2013-11-19 | 2014-03-26 | 泸州东方农化有限公司 | 噻二唑酰胺类化合物的制备方法 |
Non-Patent Citations (1)
Title |
---|
黎育生等: "氟噻草胺的合成", 《现代农药》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110651783A (zh) * | 2018-06-28 | 2020-01-07 | 江苏龙灯化学有限公司 | 一种农药液体组合物的制备方法及基于该方法制备的农药液体组合物及其用途 |
CN115043791A (zh) * | 2021-03-09 | 2022-09-13 | 北京颖泰嘉和生物科技股份有限公司 | 连续氧化制备2-甲砜基-5-三氟甲基-1,3,4-噻二唑的方法 |
CN113402481A (zh) * | 2021-05-20 | 2021-09-17 | 西华大学 | 一种环氧乙烷衍生物的合成方法 |
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Publication number | Publication date |
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CN106905260B (zh) | 2019-01-11 |
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Effective date of registration: 20210120 Address after: Room 201, No.5, Lane 3399, Kangxin Road, Pudong New Area, Shanghai Patentee after: SHANGHAI LINKCHEM TECHNOLOGY Co.,Ltd. Address before: 233000 Room 102 north, No.11, No.2 building, liukm Huayuan commercial building, Changqing Township, Yuhui District, Bengbu City, Anhui Province Patentee before: Anhui Licha Information Technology Co.,Ltd. |
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Address after: Room 201, No. 5, Lane 3399, Kangxin Road, Pudong New Area, Shanghai, 201318 Patentee after: Shanghai Lingkai Technology Co.,Ltd. Country or region after: China Address before: Room 201, No.5, Lane 3399, Kangxin Road, Pudong New Area, Shanghai Patentee before: SHANGHAI LINKCHEM TECHNOLOGY Co.,Ltd. Country or region before: China |