JP2010519296A - ある種の置換スルフィルイミン類の調製方法 - Google Patents
ある種の置換スルフィルイミン類の調製方法 Download PDFInfo
- Publication number
- JP2010519296A JP2010519296A JP2009550885A JP2009550885A JP2010519296A JP 2010519296 A JP2010519296 A JP 2010519296A JP 2009550885 A JP2009550885 A JP 2009550885A JP 2009550885 A JP2009550885 A JP 2009550885A JP 2010519296 A JP2010519296 A JP 2010519296A
- Authority
- JP
- Japan
- Prior art keywords
- membered
- alkyl
- haloalkyl
- integer
- alkenyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 9
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 35
- -1 Cyano-substituted sulfilimines Chemical class 0.000 claims abstract description 22
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 23
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 150000004763 sulfides Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 33
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 6
- 229940001584 sodium metabisulfite Drugs 0.000 description 6
- 235000010262 sodium metabisulphite Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- NGPCQVZAFDWNQL-UHFFFAOYSA-N 5-(1-methylsulfanylethyl)-2-(trifluoromethyl)pyridine Chemical compound CSC(C)C1=CC=C(C(F)(F)F)N=C1 NGPCQVZAFDWNQL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012455 biphasic mixture Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000005555 sulfoximide group Chemical group 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical class [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical class ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- CRNHLPZBBWBNDN-UHFFFAOYSA-N 2-(dimethylamino)prop-2-enenitrile Chemical compound CN(C)C(=C)C#N CRNHLPZBBWBNDN-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- PBVZQAXFSQKDKK-UHFFFAOYSA-N 3-Methoxy-3-oxopropanoic acid Chemical class COC(=O)CC(O)=O PBVZQAXFSQKDKK-UHFFFAOYSA-N 0.000 description 1
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 description 1
- QZYSTPIBCDZBBH-UHFFFAOYSA-N 5-(1-methoxyethyl)-2-(trifluoromethyl)pyridine Chemical compound FC(C1=NC=C(C=C1)C(C)OC)(F)F QZYSTPIBCDZBBH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- OWGYCXXXFUULRH-UHFFFAOYSA-N [methyl-[1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-$l^{4}-sulfanylidene]cyanamide Chemical compound N#CN=S(C)C(C)C1=CC=C(C(F)(F)F)N=C1 OWGYCXXXFUULRH-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- 238000005660 chlorination reaction Methods 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本非仮出願は、2007年2月26日に出願された仮出願第60/903,471号の優先権を主張する。
Hetは、
Xは、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、NO2、SOmR6(式中、mは0〜2の整数である)、COOR4、またはCONR4R5を表し、
Yは、水素、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、NO2、SOmR1(式中、mは0〜2の整数である)、COOR4、CONR4R5、アリール、またはヘテロアリールを表し、
nは、0〜3の整数であり、
Lは、単結合、−CH(CH2)P−(この場合、R1とSとLは一緒になって、4員、5員、または6員環を表し、pは1〜3の整数である)、−CH(CH2OCH2)−(この場合、R1とSとLは一緒になって、6員環を表す)、または−CH−(この場合、LとR2とこれらが結合している共通の炭素とは一緒になって、最大1個までであるが1個以下のヘテロ原子を有する4員、5員、または6員環を表す)を表し、
R1は、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリールアルキル、ヘテロアリールアルキル、またはR1、S、およびLが一緒になって、4員、5員、もしくは6員環を表す場合に−CH2−を表し、
R2およびR3は、独立して、水素、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、SOmR6(式中、mは0〜2の整数である)、COOR4、CONR4R5、アリールアルキル、ヘテロアリールアルキルを表し、またはR2とR3とこれらが結合している共通の炭素とは、3〜6員環を形成し、
R4およびR5は、独立して、水素、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリール、ヘテロアリール、アリールアルキル、またはヘテロアリールアルキルを表し、
R6は、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリールアルキル、またはヘテロアリールアルキルを表す]を有するある種の置換スルフィルイミンを調製する方法であって、
式(II)のスルフィド
R1、R2、R3、L、Het、およびnは、先に定義する通りである]を、
反応条件に本質的に不活性である適当な有機溶媒中、約−40℃〜約30℃の温度でシアナミドおよび次亜塩素酸塩溶液と接触させるステップを含む方法に関する。
(1)Hetが(6−置換)ピリジン−3−イルであり、XがハロゲンまたはC1〜C2ハロアルキルであり、Yが水素である式(I)の化合物。
(2)R2およびR3が先に定義した通りであり、R1がメチルであり、nが1であり、Lが単結合である、下記の構造を有する式(I)の化合物。
[実施例]
上記(40mL)からのスルフィルイミン溶液の一部分を真空中で濃縮し、高真空に曝露して、濃いオレンジ/コハク色の油を得た。この油を10mLのEtOAcに溶解し、10mLのヘキサンを添加した。混濁した混合物に、1mLのEtOAcを添加して、透明溶液に戻した。フラスコをガラス棒で引っ掻いて、結晶化を誘導した。混合物を冷蔵庫で1時間冷却し、濾過し、高真空乾燥して、1.2gの白色粉末を得た。mp 115℃〜117℃、第1の溶離異性体のLC、>99%(面積);1H nmr (CDCl3): δ 8.72 (d, J=2 Hz, 1H), 8.04 (dd, J=2 Hz, 8 Hz, 1H), 7.81 (d, J=8 Hz, 1H), 4.41 (q, J=7 Hz, 1H), 2.62 (s, 3H), 1.90 (d, J=7 Hz, 3H).
上記からの濾液を真空中で濃縮して、濃いコハク色油を得た(LCによる2つの異性体の面積比15:67)。この油をシリカフラッシュクロマトグラフィーにかけ、CHCl3中5%EtOHで溶離した。一部の少量の着色物質をまず廃棄した。次に、主なスルフィルイミン異性体(LCによる第2の溶離異性体)を回収し、真空中で濃縮し、高真空乾燥して、3.2gの濃いコハク色油を得た。この油をスラリーにし、20mLのEt2Oで引っ掻き、冷蔵庫で冷却し、濾過し、高真空乾燥して、2.48gの白色粉末を得た。mp 78℃〜80℃、第2の溶離異性体のLC、>99%(面積);1H nmr (CDCl3): δ 8.74 (d, J=2 Hz, 1H), 7.95 (dd, J=2 Hz, 8 Hz, 1H), 7.81 (d, J=8 Hz, 1H), 4.45 (q, J=7 Hz, 1H), 2.65 (s, 3H), 1.92 (d, J=7 Hz, 3H).
Claims (9)
- 式(I)のスルフィルイミン
Hetは、
Xは、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、NO2、SOmR6(式中、mは0〜2の整数である)、COOR4、またはCONR4R5を表し、
Yは、水素、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、NO2、SOmR1(式中、mは0〜2の整数である)、COOR4、CONR4R5、アリール、またはヘテロアリールを表し、
nは、0〜3の整数であり、
Lは、単結合、−CH(CH2)P−(この場合、R1とSとLは一緒になって、4員、5員、または6員環を表し、かつpは1〜3の整数である)、−CH(CH2OCH2)−(この場合、R1とSとLは一緒になって、6員環を表す)、または−CH−(この場合、LとR2とこれらが結合している共通の炭素とは一緒になって、最大1個までであるが1個以下のヘテロ原子を有する4員、5員、または6員環を表す)を表し、
R1は、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリールアルキル、ヘテロアリールアルキル、またはR1、S、およびLが一緒になって、4員、5員、もしくは6員環を表す場合に−CH2−を表し、
R2およびR3は独立に、水素、ハロゲン、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4アルキニル、C2〜C4ハロアルケニル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、CN、SOmR6(式中、mは0〜2の整数である)、COOR4、CONR4R5、アリールアルキル、ヘテロアリールアルキルを表し、またはR2とR3とこれらが結合している共通の炭素とは、3〜6員環を形成し、
R4およびR5は独立に、水素、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリール、ヘテロアリール、アリールアルキル、またはヘテロアリールアルキルを表し、
R6は、C1〜C4アルキル、C1〜C4ハロアルキル、C3〜C6アルケニル、C3〜C6アルキニル、C3〜C6ハロアルケニル、アリールアルキル、またはヘテロアリールアルキルを表す]を調製する方法であって、
式(II)のスルフィド
R1、R2、R3、L、Het、およびnは、先に定義した通りである]を、
反応条件に本質的に不活性である適当な有機溶媒中、約−40℃〜約30℃の温度でシアナミドおよび次亜塩素酸塩溶液と接触させるステップを含む方法。 - Hetが(6−置換)ピリジン−3−イルであり、XがハロゲンまたはC1〜C2ハロアルキルであり、Yが水素である、請求項1に記載の方法。
- 前記スルフィルイミンが下記の構造
請求項1に記載の方法。 - 前記スルフィルイミンが下記の構造
nは1であり、R1とSとLは一緒になって、Lが−CH(CH2)P−であり、pが1〜3の整数であり、かつR1が−CH2−であるような標準的な4員、5員、または6員環を形成し、Het、R2、およびR3は先に定義した通りである]を有する、
請求項1に記載の方法。 - 前記スルフィルイミンが下記の構造
nは0であり、R1とSとLは一緒になって、Lが−CH(CH2)P−であり、pが1〜3の整数であり、かつR1が−CH2−であるような標準的な4員、5員、または6員環を形成し、Hetは先に定義した通りである]を有する、
請求項1に記載の方法。 - 前記温度が約−10℃〜約10℃である、請求項1に記載の方法。
- 前記次亜塩素酸塩溶液が、水中に約5〜約6重量パーセントの次亜塩素酸ナトリウムを含有する市販のCloroxブリーチである、請求項1に記載の方法。
- 前記有機溶媒が、ハロゲン化脂肪族炭化水素または脂肪族ニトリルである、請求項1に記載の方法。
- ハロゲン化脂肪族炭化水素と水の混合物を含む二相溶媒系中で実施される、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US90347107P | 2007-02-26 | 2007-02-26 | |
US60/903,471 | 2007-02-26 | ||
PCT/US2008/001818 WO2008106006A1 (en) | 2007-02-26 | 2008-02-12 | Process for the preparation of certain substituted sulfilimines |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010519296A true JP2010519296A (ja) | 2010-06-03 |
JP5302221B2 JP5302221B2 (ja) | 2013-10-02 |
Family
ID=39523499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009550885A Active JP5302221B2 (ja) | 2007-02-26 | 2008-02-12 | ある種の置換スルフィルイミン類の調製方法 |
Country Status (16)
Country | Link |
---|---|
US (2) | US7868027B2 (ja) |
EP (1) | EP2114886B1 (ja) |
JP (1) | JP5302221B2 (ja) |
KR (1) | KR101437710B1 (ja) |
CN (1) | CN101641331B (ja) |
AR (1) | AR065471A1 (ja) |
AU (1) | AU2008219748B2 (ja) |
BR (1) | BRPI0807702B8 (ja) |
CA (1) | CA2678028C (ja) |
CL (1) | CL2008000564A1 (ja) |
DK (1) | DK2114886T3 (ja) |
HK (1) | HK1141013A1 (ja) |
IL (1) | IL200520A (ja) |
TW (1) | TWI393706B (ja) |
WO (1) | WO2008106006A1 (ja) |
ZA (1) | ZA200905012B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015507018A (ja) * | 2012-02-16 | 2015-03-05 | ダウ アグロサイエンシィズ エルエルシー | スルフィルイミン化合物の製造方法 |
JP2016504304A (ja) * | 2012-12-11 | 2016-02-12 | ダウ アグロサイエンシィズ エルエルシー | |n−シアノ−s−[1−(ピリジン−3−イル)エチル]−s−メチルスルフィルイミンの改良された製造方法 |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8193222B1 (en) | 2007-02-26 | 2012-06-05 | Dow AgroSciences, L.L.C. | Process for the preparation of certain substituted sulfilimines |
ES2589006T3 (es) | 2008-12-26 | 2016-11-08 | Dow Agrosciences, Llc | Composiciones insecticidas estables y métodos para producirlas |
NZ624786A (en) * | 2008-12-26 | 2015-12-24 | Dow Agrosciences Llc | Stable sulfoximine-insecticide compositions |
EP2223602A1 (de) * | 2009-02-23 | 2010-09-01 | Bayer CropScience AG | Verfahren zur verbesserten Nutzung des Produktionspotentials genetisch modifizierter Pflanzen |
EP2381781B1 (de) | 2008-12-29 | 2016-06-08 | Bayer Intellectual Property GmbH | Verfahren zur verbesserten nutzung des produktionspotentials genetisch modifizierter pflanzen |
EP2223598A1 (de) | 2009-02-23 | 2010-09-01 | Bayer CropScience AG | Insektizide Zusammensetzungen mit verbesserter Wirkung |
US20110306643A1 (en) | 2010-04-23 | 2011-12-15 | Bayer Cropscience Ag | Triglyceride-containing dormancy sprays |
EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
BR112014020123B8 (pt) | 2012-02-21 | 2021-02-09 | Bayer Ip Gmbh | composto 3-(sulfin/sulfonimidoil) benzamida, composição herbicida, seus usos e método para o controle de plantas indesejadas |
JP6084988B2 (ja) | 2012-02-21 | 2017-02-22 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 除草剤スルフィンイミドイル−およびスルホンイミドイルベンゾイル誘導体 |
JP6242392B2 (ja) | 2012-06-30 | 2017-12-06 | ダウ アグロサイエンシィズ エルエルシー | ピリジンn−オキシドおよびそれらの製法 |
CA2876192C (en) | 2012-06-30 | 2021-01-05 | Dow Agrosciences Llc | Production of n-substituted sulfoximine pyridine n-oxides |
EP2873668A1 (en) | 2013-11-13 | 2015-05-20 | Syngenta Participations AG. | Pesticidally active bicyclic heterocycles with sulphur containing substituents |
CN108026074A (zh) | 2015-09-28 | 2018-05-11 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
CN109311849B (zh) | 2016-06-13 | 2021-02-26 | 吉利德科学公司 | 调节fxr(nr1h4)的化合物 |
CA2968836A1 (en) | 2016-06-13 | 2017-12-13 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
TWI735573B (zh) * | 2016-06-21 | 2021-08-11 | 美商陶氏農業科學公司 | 生產某些經取代硫亞胺之方法 |
WO2018016643A1 (ja) | 2016-07-22 | 2018-01-25 | 住友化学株式会社 | 除草剤組成物および雑草防除方法 |
CN110023287B (zh) | 2016-12-01 | 2023-11-24 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
KR20220119520A (ko) | 2017-03-28 | 2022-08-29 | 길리애드 사이언시즈, 인코포레이티드 | 간 질환을 치료하기 위한 치료 조합물 |
US10894792B2 (en) | 2017-05-02 | 2021-01-19 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2019219689A1 (en) | 2018-05-18 | 2019-11-21 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
WO2019229089A1 (en) | 2018-05-31 | 2019-12-05 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
MX2020013188A (es) | 2018-06-06 | 2021-02-26 | Syngenta Crop Protection Ag | Derivados heterociclicos activos como plaguicidas con sustituyentes que contienen sulfoximina. |
AR115495A1 (es) | 2018-06-06 | 2021-01-27 | Syngenta Crop Protection Ag | Derivados heterocíclicos con sustituyentes que contienen azufre activos como plaguicidas |
TW202035404A (zh) | 2018-10-24 | 2020-10-01 | 瑞士商先正達農作物保護公司 | 具有含亞碸亞胺的取代基之殺有害生物活性雜環衍生物 |
CN113302190A (zh) | 2019-01-15 | 2021-08-24 | 吉利德科学公司 | Fxr(nr1h4)调节化合物 |
US11524005B2 (en) | 2019-02-19 | 2022-12-13 | Gilead Sciences, Inc. | Solid forms of FXR agonists |
CA3201212A1 (en) | 2020-12-14 | 2022-06-23 | Rizwan Shabbir SHAIKH | Sulfoximine pesticides |
WO2022253841A1 (en) | 2021-06-02 | 2022-12-08 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007532568A (ja) * | 2004-04-08 | 2007-11-15 | ダウ アグロサイエンシィズ エルエルシー | 殺虫性n−置換スルホキシイミン類 |
JP2009526074A (ja) * | 2006-02-10 | 2009-07-16 | ダウ アグロサイエンシィズ エルエルシー | 殺虫性n置換(6−ハロアルキルピリジン−3−イル)アルキルスルホキシイミン |
-
2008
- 2008-02-12 DK DK08725445.4T patent/DK2114886T3/da active
- 2008-02-12 JP JP2009550885A patent/JP5302221B2/ja active Active
- 2008-02-12 ZA ZA200905012A patent/ZA200905012B/xx unknown
- 2008-02-12 CN CN2008800045382A patent/CN101641331B/zh active Active
- 2008-02-12 CA CA2678028A patent/CA2678028C/en not_active Expired - Fee Related
- 2008-02-12 KR KR1020097017664A patent/KR101437710B1/ko active IP Right Grant
- 2008-02-12 WO PCT/US2008/001818 patent/WO2008106006A1/en active Application Filing
- 2008-02-12 AU AU2008219748A patent/AU2008219748B2/en active Active
- 2008-02-12 US US12/069,627 patent/US7868027B2/en active Active
- 2008-02-12 EP EP08725445.4A patent/EP2114886B1/en active Active
- 2008-02-12 BR BRPI0807702A patent/BRPI0807702B8/pt active IP Right Grant
- 2008-02-21 TW TW097106047A patent/TWI393706B/zh not_active IP Right Cessation
- 2008-02-25 CL CL200800564A patent/CL2008000564A1/es unknown
- 2008-02-25 AR ARP080100777A patent/AR065471A1/es active IP Right Grant
-
2009
- 2009-08-20 IL IL200520A patent/IL200520A/en active IP Right Grant
-
2010
- 2010-07-31 HK HK10107320.4A patent/HK1141013A1/xx not_active IP Right Cessation
- 2010-11-18 US US12/949,213 patent/US20110077409A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007532568A (ja) * | 2004-04-08 | 2007-11-15 | ダウ アグロサイエンシィズ エルエルシー | 殺虫性n−置換スルホキシイミン類 |
JP2009526074A (ja) * | 2006-02-10 | 2009-07-16 | ダウ アグロサイエンシィズ エルエルシー | 殺虫性n置換(6−ハロアルキルピリジン−3−イル)アルキルスルホキシイミン |
Non-Patent Citations (2)
Title |
---|
JPN5010003226; J. C. JOCHIMS: CHEMISCHE BERICHTE V116 N11, 198311, P3692-3701 * |
JPN5010003227; D. SWERN: TETRAHEDRON LETTERS V13 N26, 1972, P2635-2638, ELSEVIER SCIENCE PUBLISHERS * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015507018A (ja) * | 2012-02-16 | 2015-03-05 | ダウ アグロサイエンシィズ エルエルシー | スルフィルイミン化合物の製造方法 |
JP2016504304A (ja) * | 2012-12-11 | 2016-02-12 | ダウ アグロサイエンシィズ エルエルシー | |n−シアノ−s−[1−(ピリジン−3−イル)エチル]−s−メチルスルフィルイミンの改良された製造方法 |
Also Published As
Publication number | Publication date |
---|---|
AR065471A1 (es) | 2009-06-10 |
BRPI0807702A2 (pt) | 2014-05-27 |
DK2114886T3 (da) | 2014-06-30 |
CL2008000564A1 (es) | 2008-08-29 |
IL200520A0 (en) | 2010-04-29 |
TW200844097A (en) | 2008-11-16 |
AU2008219748A1 (en) | 2008-09-04 |
CA2678028C (en) | 2015-02-03 |
CA2678028A1 (en) | 2008-09-04 |
KR101437710B1 (ko) | 2014-09-03 |
AU2008219748B2 (en) | 2012-05-03 |
IL200520A (en) | 2014-02-27 |
ZA200905012B (en) | 2010-10-27 |
TWI393706B (zh) | 2013-04-21 |
BRPI0807702B1 (pt) | 2016-11-01 |
US7868027B2 (en) | 2011-01-11 |
CN101641331A (zh) | 2010-02-03 |
US20080207910A1 (en) | 2008-08-28 |
WO2008106006A1 (en) | 2008-09-04 |
KR20090113870A (ko) | 2009-11-02 |
BRPI0807702B8 (pt) | 2022-06-28 |
CN101641331B (zh) | 2012-06-27 |
EP2114886A1 (en) | 2009-11-11 |
US20110077409A1 (en) | 2011-03-31 |
EP2114886B1 (en) | 2014-03-26 |
JP5302221B2 (ja) | 2013-10-02 |
HK1141013A1 (en) | 2010-10-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5302221B2 (ja) | ある種の置換スルフィルイミン類の調製方法 | |
EP2114885B1 (en) | Process for the oxidation of certain substituted sulfilimines to insecticidal sulfoximines | |
US7511149B2 (en) | Process for the oxidation of certain substituted sulfilimines to insecticidal sulfoximines | |
JP6633539B2 (ja) | 2−(2,4−ジフルオロフェニル)−1,1−ジフルオロ−1−(5−置換−ピリジン−2−イル)−3−(1h−テトラゾール−1−イル)プロパン−2−オールおよびその調製工程 | |
JP2014508143A (ja) | 4−アミノ−5−フルオロ−3−ハロ−6−(置換)ピコリネートの調製方法 | |
US20120165538A1 (en) | Process for the preparation of certain substituted sulfilimines | |
KR20150095785A (ko) | 4-아미노-5-플루오로-3-클로로-6-(치환된)피콜리네이트의제조 방법 | |
EP3112350A1 (en) | Method for producing pyrazole compound | |
EP1873145B1 (en) | Method for producing nicotinic acid derivative or salt thereof | |
JP2020537680A (ja) | 除草性ピリダジノン化合物を製造するプロセス | |
JP7489390B2 (ja) | スルホンアミド除草剤プロセス中間生成物の調製 | |
JP5206931B2 (ja) | ジオキサジニルピラゾール化合物の製造方法および中間体 | |
JP2007246476A (ja) | ジオキサジニルピラゾール化合物の製造方法および中間体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110210 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130305 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130305 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130410 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130618 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130620 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5302221 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |