JP5249219B2 - 2−置換−5−(1−アルキルチオ)アルキルピリジンの調製プロセス - Google Patents
2−置換−5−(1−アルキルチオ)アルキルピリジンの調製プロセス Download PDFInfo
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- JP5249219B2 JP5249219B2 JP2009523751A JP2009523751A JP5249219B2 JP 5249219 B2 JP5249219 B2 JP 5249219B2 JP 2009523751 A JP2009523751 A JP 2009523751A JP 2009523751 A JP2009523751 A JP 2009523751A JP 5249219 B2 JP5249219 B2 JP 5249219B2
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- alkyl
- membered saturated
- saturated ring
- haloalkyl
- substituted
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- 238000002360 preparation method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 150000002081 enamines Chemical class 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- -1 alkyl vinyl ethers Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LSGZGFUQRGHSSU-UHFFFAOYSA-N 1-(3-methylsulfanylbut-1-enyl)pyrrolidine Chemical compound CSC(C)C=CN1CCCC1 LSGZGFUQRGHSSU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NCBDFIPMWRKPDU-UHFFFAOYSA-N 3-(Methylthio)butanal Chemical compound CSC(C)CC=O NCBDFIPMWRKPDU-UHFFFAOYSA-N 0.000 description 2
- HXRCNDISMMOJDS-UHFFFAOYSA-N CSC(C)C=1C(=NC=CC1)C(F)(F)F Chemical compound CSC(C)C=1C(=NC=CC1)C(F)(F)F HXRCNDISMMOJDS-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
[ここで、R1およびR2はそれぞれ独立してH、C1〜C4アルキルを表し、あるいは、R1またはR2のいずれかはR3と共に4〜6員環飽和環を表し、あるいは、R1はR2と共に、OまたはN原子と必要に応じて置換された3〜6員環飽和環を表し、
R3はC1〜C4アルキルを表し、あるいは、R3はR1またはR2のいずれかと共に4〜6員環飽和環を表し、
R4は、C1〜C4アルキルまたはC1〜C4ハロアルキルを表す。]の調製プロセスに関し、
前記プロセスは、α、β−不飽和ケトンII
[ここで、Xは、ハロゲン、OR5OSO2R5、SR5、SOR5、SO2R5またはNR6R7を表し、
R5は、水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールを表し、
R6およびR7は、それぞれ独立して水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールを表し、あるいは、R6およびR7はNと共に、5または6員環飽和または不飽和環を表し、
R4は上記にて定義された通りである。]の、
エナミンIII
[ここで、R1、R2、R3、R6、R7は上記にて定義された通りである。]
での、アンモニアまたはアンモニアを生成可能な試薬の存在下における環化を含む。
[ここで、R1およびR2は、H、C1〜C4アルキルをそれぞれ独立して表し、あるいは、R1またはR2のいずれかはR3と共に4〜6員環飽和環を表し、あるいは、R1はR2と共にOまたはN原子と必要に応じて置換された3〜6員環飽和環を表し、
R3はC1〜C4アルキルを表し、あるいは、R3はR1またはR2と共に4〜6員環飽和環を表し、
R4は、C1〜C4アルキルまたはC1〜C4ハロアルキル(好適にはC1〜C4ハロアルキル)を表す。]
を有する新規な化合物である。
[ここで、R1およびR2はH、C1〜C4アルキルをそれぞれ独立して表し、または、R1またはR2のいずれかはR3と共に4〜6員環飽和環を表し、あるいは、R1はR2と共に、OまたはN原子と必要に応じて置換された3〜6員環飽和環を表し、
R3はC1〜C4アルキルを表し、あるいは、R3はR1またはR2のいずれかと共に4〜6員環飽和環を表し、
R4は、C1〜C4アルキルまたはC1〜C4ハロアルキルを表す。]は、
α、β−不飽和ケトンII
[ここで、Xは、ハロゲン、OR5OSO2R5、SR5、SOR5、SO2R5またはNR6R7を表し、
R5は、水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールを表し、
R6およびR7は、水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールをそれぞれ独立して表し、あるいは、R6およびR7はNと共に、5または6員環飽和または不飽和環を表し、
R4は上記にて定義された通りである。]を、
エナミンIII
[ここで、R1、R2、R3、R6、R7は上記にて定義された通りである。]
で環化することにより、調製される。
5−(1−メチルチオ)エチル−2−(トリフルオロメチル)ピリジンの調製
5−(1−メチルチオ)エチル−2−(トリフルオロメチル)ピリジンの調製
Claims (5)
- 2−置換−5−(1−アルキルチオ)アルキルピリジン(I)
[ここで、R1およびR2はそれぞれ独立してH、C1〜C4アルキルを表し、あるいは、R1またはR2のいずれかはR3と共に4〜6員環飽和環を表し、あるいは、R1はR2と共に、OまたはN原子と必要に応じて置換された3〜6員環飽和環を表し、
R3はC1〜C4アルキルを表し、あるいは、R3はR1またはR2のいずれかと共に4〜6員環飽和環を表し、
R4は、C1〜C4アルキルまたはC1〜C4ハロアルキルを表す。]
の調製プロセスであって、
前記プロセスは、α、β−不飽和ケトンII
[ここで、Xは、ハロゲン、OR5 、OSO2R5、SR5、SOR5、SO2R5またはNR6R7を表し、
R5は、水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールを表し、
R6およびR7は、水素、C1〜C8アルキル、C2〜C8アルケニル、C1〜C8アリールアルキル、C1〜C8ハロアルキル、C1〜C8アルコキシアルキル、C1〜C8アルキルアミノアルキル、アリールまたはヘテロアリールをそれぞれ独立して表し、あるいは、R6およびR7はNと共に、5または6員環飽和または不飽和環を表し、
R4は上記にて定義された通りである。]と、
エナミンIII
[ここで、R1、R2、R3、R6、R7は上記にて定義された通りである。]
とを、アンモニアまたはアンモニアを生成可能な試薬の存在下において環化する工程を含む、プロセス。 - R1およびR2はHまたはメチルをそれぞれ独立して表し、R3はメチルを表し、R4はトリフルオロメチルを表す、請求項1に記載のプロセス。
- 前記アンモニアを生成可能な試薬は有機酸のアンモニウム塩である、請求項1に記載のプロセス。
- 以下の化学式
[ここで、R1およびR2は、H、C1〜C4アルキルをそれぞれ独立して表し、あるいは、R1またはR2のいずれかはR3と共に4〜6員環飽和環を表し、あるいは、R1はR2と共にOまたはN原子と必要に応じて置換された3〜6員環飽和環を表し、
R3はC1〜C4アルキルを表し、あるいは、R3はR1またはR2と共に4〜6員環飽和環を表し、
R4は、C 1〜C4ハロアルキルを表す。]
の化合物。 - R1およびR2はHまたはメチルをそれぞれ独立して表し、R3はメチルを表し、R4はトリフルオロメチルを表す、請求項4に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83594006P | 2006-08-07 | 2006-08-07 | |
US60/835,940 | 2006-08-07 | ||
PCT/US2007/003827 WO2008018917A1 (en) | 2006-08-07 | 2007-02-09 | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010500346A JP2010500346A (ja) | 2010-01-07 |
JP5249219B2 true JP5249219B2 (ja) | 2013-07-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009523751A Active JP5249219B2 (ja) | 2006-08-07 | 2007-02-09 | 2−置換−5−(1−アルキルチオ)アルキルピリジンの調製プロセス |
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EP (1) | EP2049487B1 (ja) |
JP (1) | JP5249219B2 (ja) |
KR (1) | KR101368045B1 (ja) |
CN (1) | CN101516847B (ja) |
AU (1) | AU2007282148B2 (ja) |
BR (1) | BRPI0715408B8 (ja) |
CA (1) | CA2658593C (ja) |
CO (1) | CO6160226A2 (ja) |
DK (1) | DK2049487T3 (ja) |
ES (1) | ES2398382T3 (ja) |
HK (1) | HK1134085A1 (ja) |
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MX (1) | MX2009001347A (ja) |
MY (1) | MY147732A (ja) |
TW (1) | TWI383973B (ja) |
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Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW201309635A (zh) | 2006-02-10 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺(二) |
TWI381811B (zh) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
TWI383973B (zh) | 2006-08-07 | 2013-02-01 | Dow Agrosciences Llc | 用於製備2-取代-5-(1-烷硫基)烷基吡啶之方法 |
US7863303B2 (en) * | 2006-09-01 | 2011-01-04 | Dow Agrosciences Llc | Insecticidal N-substituted (2-substituted-1,3-thiazol)alkyl sulfoximines |
TWI387585B (zh) * | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(雜芳基)烷基烴基硫亞胺 |
TWI409256B (zh) * | 2006-09-01 | 2013-09-21 | Dow Agrosciences Llc | 殺蟲性之n-取代(雜芳基)環烷基磺醯亞胺 |
TWI383970B (zh) * | 2006-11-08 | 2013-02-01 | Dow Agrosciences Llc | 多取代的吡啶基磺醯亞胺及其作為殺蟲劑之用途 |
TWI395737B (zh) * | 2006-11-08 | 2013-05-11 | Dow Agrosciences Llc | 作為殺蟲劑之雜芳基(取代的)烷基n-取代的磺醯亞胺 |
US7709648B2 (en) * | 2007-02-09 | 2010-05-04 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
AR066366A1 (es) * | 2007-05-01 | 2009-08-12 | Dow Agrosciences Llc | Mezclas sinergicas plaguicidas |
CA2693253C (en) * | 2007-07-20 | 2015-03-24 | Jonathan Babcock | Increasing plant vigor |
MX2010009748A (es) | 2008-03-03 | 2010-11-30 | Dow Agrosciences Llc | Plaguicidas. |
WO2010002577A1 (en) * | 2008-07-01 | 2010-01-07 | Dow Agrosciences Llc | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines |
WO2010021855A1 (en) * | 2008-08-19 | 2010-02-25 | Dow Agrosciences Llc | Improved process for the addition of thiolates to alfa, beta-unsaturated carbonyl or sulfonyl compounds |
ES2622872T3 (es) * | 2008-08-27 | 2017-07-07 | Dow Agrosciences Llc | Composiciones plaguicidas que comprenden sulfoximinas N-sustituidas |
CN104222135B (zh) * | 2008-12-26 | 2017-04-26 | 美国陶氏益农公司 | 稳定的亚磺酰亚胺杀虫剂组合物 |
JP5718249B2 (ja) | 2008-12-26 | 2015-05-13 | ダウ アグロサイエンシィズ エルエルシー | 安定な殺虫剤組成物およびその製造方法 |
BR112013013290B1 (pt) * | 2010-12-03 | 2018-02-14 | Dow Agrosciences Llc | Processo aperfeiçoado para a preparação de 2- trifluorometil-5-(1-substituído)alquilpiridinas |
CN104602527B (zh) | 2012-06-30 | 2018-09-25 | 美国陶氏益农公司 | 吡啶n-氧化物及其制备方法 |
NZ702435A (en) | 2012-06-30 | 2016-07-29 | Dow Agrosciences Llc | Insecticidal n-substituted sulfilimine and sulfoximine pyridine n-oxides |
WO2014004094A1 (en) | 2012-06-30 | 2014-01-03 | Dow Agrosciences Llc | Production of n-substituted sulfoximine pyridine n-oxides |
EP3246313A1 (en) * | 2016-05-19 | 2017-11-22 | Solvay Sa | Process for the manufacture of 2-substituted-5-(1-methylthio)alkylpyridines |
Family Cites Families (15)
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NO912475L (no) * | 1990-06-27 | 1991-12-30 | Sankyo Co | Tiazolidinkarboksylsyreamidderivater med antiallergisk aktivitet, og fremgangsmaate til fremstilling derav. |
DE10208955A1 (de) * | 2002-02-28 | 2003-09-11 | Bayer Ag | Verfahren zur Herstellung von 2-Halogenalkylnicotinsäuren |
AU2003300791A1 (en) * | 2002-12-13 | 2004-07-09 | Neurogen Corporation | Combination therapy for the treatment of pain |
AU2005310314B2 (en) * | 2004-04-08 | 2011-07-21 | Corteva Agriscience Llc | Insecticidal N-substituted sulfoximines |
TW201309635A (zh) | 2006-02-10 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺(二) |
TWI381811B (zh) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
TWI383973B (zh) * | 2006-08-07 | 2013-02-01 | Dow Agrosciences Llc | 用於製備2-取代-5-(1-烷硫基)烷基吡啶之方法 |
TWI409256B (zh) | 2006-09-01 | 2013-09-21 | Dow Agrosciences Llc | 殺蟲性之n-取代(雜芳基)環烷基磺醯亞胺 |
TWI387585B (zh) | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(雜芳基)烷基烴基硫亞胺 |
TW200820902A (en) | 2006-11-08 | 2008-05-16 | Dow Agrosciences Llc | Use of N-substituted sulfoximines for control of invertebrate pests |
TWI395737B (zh) | 2006-11-08 | 2013-05-11 | Dow Agrosciences Llc | 作為殺蟲劑之雜芳基(取代的)烷基n-取代的磺醯亞胺 |
TWI383970B (zh) | 2006-11-08 | 2013-02-01 | Dow Agrosciences Llc | 多取代的吡啶基磺醯亞胺及其作為殺蟲劑之用途 |
EP2364971B1 (en) | 2006-11-30 | 2014-04-30 | Dow AgroSciences LLC | 2,5-Disubstituted pyridines for the preparation of 2-substituted 5-(1-alkylthio)-alkylpyridines |
US7511149B2 (en) | 2007-02-09 | 2009-03-31 | Dow Agrosciences Llc | Process for the oxidation of certain substituted sulfilimines to insecticidal sulfoximines |
US7709648B2 (en) | 2007-02-09 | 2010-05-04 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
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Also Published As
Publication number | Publication date |
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CA2658593A1 (en) | 2008-02-14 |
MY147732A (en) | 2013-01-15 |
ES2398382T3 (es) | 2013-03-15 |
EP2049487B1 (en) | 2012-11-07 |
EP2049487A1 (en) | 2009-04-22 |
CA2658593C (en) | 2014-07-08 |
IL196875A (en) | 2014-02-27 |
BRPI0715408B1 (pt) | 2016-07-26 |
WO2008018917A1 (en) | 2008-02-14 |
AU2007282148B2 (en) | 2011-12-22 |
BRPI0715408A2 (pt) | 2012-12-25 |
KR101368045B1 (ko) | 2014-02-26 |
AU2007282148A1 (en) | 2008-02-14 |
US8129539B2 (en) | 2012-03-06 |
US7709650B2 (en) | 2010-05-04 |
US7541469B2 (en) | 2009-06-02 |
HK1134085A1 (ja) | 2010-04-16 |
ZA200900551B (en) | 2010-04-28 |
TW200808725A (en) | 2008-02-16 |
MX2009001347A (es) | 2009-02-16 |
DK2049487T3 (da) | 2013-02-18 |
KR20090035698A (ko) | 2009-04-10 |
IL196875A0 (en) | 2009-11-18 |
CN101516847A (zh) | 2009-08-26 |
JP2010500346A (ja) | 2010-01-07 |
US20080033180A1 (en) | 2008-02-07 |
TWI383973B (zh) | 2013-02-01 |
CN101516847B (zh) | 2011-11-16 |
BRPI0715408B8 (pt) | 2022-06-28 |
US20090163720A1 (en) | 2009-06-25 |
US20100168436A1 (en) | 2010-07-01 |
CO6160226A2 (es) | 2010-05-20 |
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