EA013842B1 - Способ получения промежуточных продуктов - Google Patents

Способ получения промежуточных продуктов Download PDF

Info

Publication number: EA013842B1
Authority: EA; Eurasian Patent Office
Prior art keywords: group; alkyl; alkoxy; alkynyl; alkenyl
Prior art date: 2005-02-09

Application number

EA200701616A

Other languages

English (en)

Russian (ru)

Other versions

EA200701616A1 (ru

Inventor

Линьсуа Ван

Кристин Андерсон Долбир

Франки Ли Оудом

Original Assignee

Зингента Партисипейшнс Аг

Priority date (The priority date 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 date listed.)

2005-02-09

Filing date

2006-02-07

Publication date

2010-08-30

2006-02-07 Application filed by Зингента Партисипейшнс Аг filed Critical Зингента Партисипейшнс Аг

2008-02-28 Publication of EA200701616A1 publication Critical patent/EA200701616A1/ru

2010-08-30 Publication of EA013842B1 publication Critical patent/EA013842B1/ru

Links

238000000034 method Methods 0.000 title claims abstract description 35
238000002360 preparation method Methods 0.000 title abstract description 14
239000000543 intermediate Substances 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
238000010533 azeotropic distillation Methods 0.000 claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 13
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
238000004519 manufacturing process Methods 0.000 claims abstract 2
-1 nitro, amino Chemical group 0.000 claims description 72
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 23
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 20
125000003277 amino group Chemical group 0.000 claims description 20
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
239000007864 aqueous solution Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
238000004821 distillation Methods 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000005133 alkynyloxy group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000001301 oxygen Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229910052717 sulfur Chemical group 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
239000005749 Copper compound Substances 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000006227 byproduct Substances 0.000 claims description 6
150000001880 copper compounds Chemical class 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 5
125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 5
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 5
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 5
229910001507 metal halide Inorganic materials 0.000 claims description 5
150000005309 metal halides Chemical class 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 2
125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 2
125000005109 alkynylthio group Chemical group 0.000 claims description 2
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
239000011780 sodium chloride Substances 0.000 claims description 2
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 claims description 2
239000012414 tert-butyl nitrite Substances 0.000 claims description 2
125000005090 alkenylcarbonyl group Chemical group 0.000 claims 3
150000007529 inorganic bases Chemical class 0.000 claims 3
230000003472 neutralizing effect Effects 0.000 claims 3
238000005191 phase separation Methods 0.000 claims 3
238000000746 purification Methods 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
ATHVAWFAEPLPPQ-VRDBWYNSSA-N 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC ATHVAWFAEPLPPQ-VRDBWYNSSA-N 0.000 claims 1
125000005091 alkenylcarbonylamino group Chemical group 0.000 claims 1
125000005136 alkenylsulfinyl group Chemical group 0.000 claims 1
125000005108 alkenylthio group Chemical group 0.000 claims 1
125000005088 alkynylcarbonylamino group Chemical group 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
229940078552 o-xylene Drugs 0.000 claims 1
230000008520 organization Effects 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 9
229910052802 copper Inorganic materials 0.000 abstract description 6
239000010949 copper Substances 0.000 abstract description 6
238000006193 diazotization reaction Methods 0.000 abstract description 5
238000000197 pyrolysis Methods 0.000 abstract description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 4
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 29
125000004432 carbon atom Chemical group C* 0.000 description 10
239000000243 solution Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
QWIITRRSNVBPDK-UHFFFAOYSA-N 2-bromo-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Br QWIITRRSNVBPDK-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
150000001555 benzenes Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
150000001989 diazonium salts Chemical class 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
CQKJMEVQJREFRF-UHFFFAOYSA-N 2-chloro-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Cl CQKJMEVQJREFRF-UHFFFAOYSA-N 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
OIXUMNZGNCAOKY-UHFFFAOYSA-N 2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=CC(CC)=C1N OIXUMNZGNCAOKY-UHFFFAOYSA-N 0.000 description 3
239000011260 aqueous acid Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000006125 ethylsulfonyl group Chemical group 0.000 description 2
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
125000004438 haloalkoxy group Chemical group 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 1
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 1
125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
125000006023 1-pentenyl group Chemical group 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
VIMIAQYISZGMEJ-UHFFFAOYSA-N 2,4-dibromo-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=C(Br)C(CC)=C1Br VIMIAQYISZGMEJ-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical class 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000002704 decyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
125000003438 dodecyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
125000005291 haloalkenyloxy group Chemical group 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
125000000232 haloalkynyl group Chemical group 0.000 description 1
125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
FEVKBWGLRAAJCR-UHFFFAOYSA-N n,2-diethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1CC FEVKBWGLRAAJCR-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000001326 naphthylalkyl group Chemical group 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
125000001400 nonyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical class 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material 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
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
125000002948 undecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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US65117505P	2005-02-09	2005-02-09
PCT/EP2006/001068 WO2006084663A1 (en)	2005-02-09	2006-02-07	Process for the preparation of intermediates

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Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101492343B (zh) *	2008-12-30	2011-08-10	中钢集团鞍山热能研究院有限公司	3,5-二甲基溴苯的制备方法
DK2406205T3 (en)	2009-03-12	2017-02-27	Bayer Ip Gmbh	PROCEDURE FOR MANUFACTURING CHLOR AND BROMAROMATS
WO2012165648A1 (en)	2011-05-30	2012-12-06	Sumitomo Chemical Company, Limited	Cyclohexanone compounds and herbicides comprising the same
CN104768374B (zh)	2012-11-08	2016-08-24	住友化学株式会社	除草用组合物
MX2019000753A (es)	2016-07-22	2019-06-03	Syngenta Participations Ag	Proceso para preparacion de dinitrilos del acido fenilmalonico.
CN109336762B (zh) *	2018-11-30	2021-03-16	江苏富鼎化学有限公司	2-(2,6-二乙基-4-甲基苯)丙二酸二乙酯的合成方法
CN114907181B (zh) *	2021-02-09	2024-04-23	北京颖泰嘉和生物科技股份有限公司	用于桑德迈尔反应的装置和连续制备2,6-二乙基-4-甲基溴苯的方法
WO2023044364A1 (en)	2021-09-15	2023-03-23	Enko Chem, Inc.	Protoporphyrinogen oxidase inhibitors

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE600706C (de) *	1933-03-24	1934-07-30	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung aromatischer, im Kern fluorierter Verbindungen
DE1695659B1 (de) *	1967-12-18	1971-12-16	Ruetgerswerke Ag	Verfahren zur Herstellung von 2-Chlorpyridinen
EP0214068A1 (fr) *	1985-08-19	1987-03-11	Rhone-Poulenc Chimie	Procédé de préparation de composés aromatiques fluorés
JPH01283230A (ja) *	1988-05-09	1989-11-14	Mitsui Toatsu Chem Inc	芳香族弗素化合物の製造方法
WO2000078712A1 (en) *	1999-06-16	2000-12-28	Syngenta Participations Ag	Substituted arylmalonic acid dinitriles as intermediates for the prepartion of herbicides

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59112965A (ja)	1982-12-20	1984-06-29	Koei Chem Co Ltd	４−クロルピリジン塩酸塩の製造法
US4822927A (en) *	1987-11-24	1989-04-18	Mallinckrodt, Inc.	Continuous decomposition of diazonium fluorides
BR9205752A (pt)	1991-03-19	1994-11-08	Ciba Geigy Ag	Novos compostos herbicidamente, acaricidamente e inseticidamente ativos
DE4109208A1 (de)	1991-03-21	1992-09-24	Bayer Ag	3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate
DE4111214A1 (de)	1991-04-06	1992-10-08	Bayer Ag	Verfahren zur herstellung von 2-chlorpyridinen
WO1995001971A1 (de)	1993-07-05	1995-01-19	Bayer Aktiengesellschaft	Substituierte aryl-ketoenolheterocyclen
WO1996021652A1 (en)	1995-01-13	1996-07-18	Novartis Ag	4-aryl- and 4-heteroaryl -5-oxopyrazoline derivatives having pesticidal properties
AU4715896A (en)	1995-02-13	1996-09-04	Bayer Aktiengesellschaft	2-phenyl-substituted heterocyclic 1,3-ketonols as herbicides and pesticides
DE19517186A1 (de) *	1995-05-11	1996-11-14	Bayer Ag	Verfahren zur Herstellung substituierter 2-Fluor-pyrimidine
TR199701740T1 (xx)	1995-06-30	1998-04-21	Bayer Ag.	Herbisitler ve pestisitler olarak kullan�lmak �zere dialkil fenil halit ikameli ketoenoller.
JP3652986B2 (ja)	1998-03-13	2005-05-25	シンジェンタパーティシペーションズアクチェンゲゼルシャフト	殺草活性な３−ヒドロキシ−４−アリール−５−オキソピラゾリン誘導体
AR029166A1 (es)	1999-06-16	2003-06-18	Syngenta Participations Ag	Proceso para la preparacion de derivados de 3-hidroxi-4-aril-5-oxopirazolina sustituidos y compuestos relacionados
JP4222837B2 (ja)	2001-04-05	2009-02-12	住友化学株式会社	２，６−ジハロゲノプリンの製法
AR042282A1 (es)	2002-12-05	2005-06-15	Syngenta Participations Ag	Proceso para la preparacion de dinitrilos de acido fenilmalonico

2006
- 2006-02-07 WO PCT/EP2006/001068 patent/WO2006084663A1/en not_active Ceased
- 2006-02-07 EP EP06704443.8A patent/EP1848678B1/en not_active Expired - Lifetime
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2007
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Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE600706C (de) *	1933-03-24	1934-07-30	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung aromatischer, im Kern fluorierter Verbindungen
DE1695659B1 (de) *	1967-12-18	1971-12-16	Ruetgerswerke Ag	Verfahren zur Herstellung von 2-Chlorpyridinen
EP0214068A1 (fr) *	1985-08-19	1987-03-11	Rhone-Poulenc Chimie	Procédé de préparation de composés aromatiques fluorés
JPH01283230A (ja) *	1988-05-09	1989-11-14	Mitsui Toatsu Chem Inc	芳香族弗素化合物の製造方法
WO2000078712A1 (en) *	1999-06-16	2000-12-28	Syngenta Participations Ag	Substituted arylmalonic acid dinitriles as intermediates for the prepartion of herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch, Week 198951 Derwent Publications Ltd., London, 6B; Class B05, AN 1989-375646 XP002382741 & JP 01 283230 A (MITSUI TOATSU CHEM INC) 14 November 1989 (1989-11-14) abstract -& PATENT ABSTRACTS OF JAPAN vol. 014, no. 057 (C-0684), 2 February 1990 (1990-02-02) & JP 01 283230 A (MITSUI TOATSU CHEM INC), 14 November 1989 (1989-11-14) abstract *

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Publication number	Publication date
EP1848678A1 (en)	2007-10-31
KR101355873B1 (ko)	2014-02-03
CA2596590A1 (en)	2006-08-17
ES2546960T3 (es)	2015-09-30
JP5411319B2 (ja)	2014-02-12
JP2008529986A (ja)	2008-08-07
KR20070110290A (ko)	2007-11-16
CN102603444A (zh)	2012-07-25
AR053123A1 (es)	2007-04-25
US8030529B2 (en)	2011-10-04
PL1848678T3 (pl)	2015-11-30
HUE027652T2 (en)	2016-11-28
CN101115704B (zh)	2012-03-28
BRPI0606976A2 (pt)	2009-07-28
ZA200705880B (en)	2008-08-27
AU2006212397B2 (en)	2011-05-12
JP5254625B2 (ja)	2013-08-07
TW200640830A (en)	2006-12-01
EP1848678B1 (en)	2015-07-22
CA2596590C (en)	2014-01-21
AU2006212397A1 (en)	2006-08-17
MX2007009341A (es)	2007-09-21
TWI360533B (en)	2012-03-21
CN101115704A (zh)	2008-01-30
US20090023964A1 (en)	2009-01-22
EA200701616A1 (ru)	2008-02-28
DK1848678T3 (en)	2015-09-21
BRPI0606976B1 (pt)	2015-12-08
JP2012167122A (ja)	2012-09-06
IL184715A (en)	2013-03-24
UA89218C2 (ru)	2010-01-11
PT1848678E (pt)	2015-10-12
IL184715A0 (en)	2007-12-03
WO2006084663A1 (en)	2006-08-17

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CN1140528C (zh)	2004-03-03	制备除草剂衍生物的方法
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EP1185506A1 (en)	2002-03-13	Substituted arylmalonic acid dinitriles as intermediates for the preparation of herbicides
JP5667913B2 (ja)	2015-02-12	２，３−ジクロロピリジンの製造方法
JP5140776B1 (ja)	2013-02-13	１−置換−３−フルオロアルキルピラゾール−４−カルボン酸エステルの製造方法
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CN109982997A (zh)	2019-07-05	3-(吡啶基-2-氨基)丙腈及其类似物的制造方法
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