IL184715A - Process for the preparation of intermediates - Google Patents

Process for the preparation of intermediates

Info

Publication number: IL184715A
Authority: IL; Israel
Prior art keywords: substituted; formula; process according; compound; nitrite
Prior art date: 2005-02-09

Application number

IL184715A

Other languages

English (en)

Other versions

IL184715A0 (en

Original Assignee

Syngenta Participations Ag

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

2007-07-19

Publication date

2013-03-24

2007-07-19 Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag

2007-12-03 Publication of IL184715A0 publication Critical patent/IL184715A0/en

2013-03-24 Publication of IL184715A publication Critical patent/IL184715A/en

Links

238000000034 method Methods 0.000 title claims description 41
238000002360 preparation method Methods 0.000 title claims description 18
239000000543 intermediate Substances 0.000 title description 5
-1 CrC5alkoxyalkyl Chemical group 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
238000010533 azeotropic distillation Methods 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
229910052802 copper Inorganic materials 0.000 claims description 9
239000010949 copper Substances 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
150000004820 halides Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
238000005292 vacuum distillation Methods 0.000 claims description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
150000001555 benzenes Chemical class 0.000 claims description 6
239000006227 byproduct Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
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
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 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
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 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
125000001072 heteroaryl group Chemical group 0.000 claims 6
125000003282 alkyl amino group Chemical group 0.000 claims 4
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 4
125000005130 alkyl carbonyl thio group Chemical group 0.000 claims 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
125000004001 thioalkyl group Chemical group 0.000 claims 4
150000007529 inorganic bases Chemical class 0.000 claims 3
238000006386 neutralization reaction Methods 0.000 claims 3
238000005191 phase separation Methods 0.000 claims 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 2
125000005241 heteroarylamino group Chemical group 0.000 claims 2
125000005553 heteroaryloxy group Chemical group 0.000 claims 2
125000005368 heteroarylthio group Chemical group 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
125000005240 diheteroarylamino group Chemical group 0.000 claims 1
229940078552 o-xylene Drugs 0.000 claims 1
238000004064 recycling Methods 0.000 claims 1
125000006413 ring segment Chemical group 0.000 claims 1
125000003003 spiro group Chemical group 0.000 claims 1
125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000000297 Sandmeyer reaction Methods 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
239000011260 aqueous acid Substances 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
QWIITRRSNVBPDK-UHFFFAOYSA-N 2-bromo-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Br QWIITRRSNVBPDK-UHFFFAOYSA-N 0.000 description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
238000003556 assay Methods 0.000 description 5
239000012954 diazonium Substances 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
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
238000006193 diazotization reaction Methods 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000000197 pyrolysis Methods 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
CQKJMEVQJREFRF-UHFFFAOYSA-N 2-chloro-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Cl CQKJMEVQJREFRF-UHFFFAOYSA-N 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 2
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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003302 alkenyloxy 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
125000004438 haloalkoxy group Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 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
125000001624 naphthyl group Chemical group 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000003396 thiol group Chemical class [H]S* 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
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
125000006552 (C3-C8) cycloalkyl 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
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 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
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 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
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
125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003518 caustics Substances 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
239000002131 composite material Substances 0.000 description 1
238000005859 coupling reaction 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 group [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
229940117389 dichlorobenzene Drugs 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000003438 dodecyl group Chemical group [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
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
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000005291 haloalkenyloxy group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [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
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 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 group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([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
FEVKBWGLRAAJCR-UHFFFAOYSA-N n,2-diethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1CC FEVKBWGLRAAJCR-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
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 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 group [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 group [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
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 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
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 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
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
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
150000003254 radicals Chemical class 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
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
125000001425 triazolyl group Chemical group 0.000 description 1
125000002948 undecyl group Chemical group [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
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

Landscapes

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

IL184715A 2005-02-09 2007-07-19 Process for the preparation of intermediates IL184715A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US65117505P	2005-02-09	2005-02-09
PCT/EP2006/001068 WO2006084663A1 (en)	2005-02-09	2006-02-07	Process for the preparation of intermediates

Publications (2)

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IL184715A0 IL184715A0 (en)	2007-12-03
IL184715A true IL184715A (en)	2013-03-24

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US (1)	US8030529B2 (2)
EP (1)	EP1848678B1 (2)
JP (2)	JP5254625B2 (2)
KR (1)	KR101355873B1 (2)
CN (2)	CN101115704B (2)
AR (1)	AR053123A1 (2)
AU (1)	AU2006212397B2 (2)
BR (1)	BRPI0606976B1 (2)
CA (1)	CA2596590C (2)
DK (1)	DK1848678T3 (2)
EA (1)	EA013842B1 (2)
ES (1)	ES2546960T3 (2)
HU (1)	HUE027652T2 (2)
IL (1)	IL184715A (2)
MX (1)	MX2007009341A (2)
PL (1)	PL1848678T3 (2)
PT (1)	PT1848678E (2)
TW (1)	TWI360533B (2)
UA (1)	UA89218C2 (2)
WO (1)	WO2006084663A1 (2)
ZA (1)	ZA200705880B (2)

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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

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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
CA2368827A1 (en) *	1999-06-16	2000-12-28	Syngenta Participations Ag	New intermediates
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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
- 2006-02-07 CN CN2006800044338A patent/CN101115704B/zh not_active Expired - Lifetime
- 2006-02-07 MX MX2007009341A patent/MX2007009341A/es active IP Right Grant
- 2006-02-07 DK DK06704443.8T patent/DK1848678T3/en active
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- 2006-02-07 CN CN2012100205799A patent/CN102603444A/zh active Pending
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- 2006-02-07 US US11/815,458 patent/US8030529B2/en active Active
- 2006-02-07 PL PL06704443T patent/PL1848678T3/pl unknown
- 2006-02-07 UA UAA200709950A patent/UA89218C2/ru unknown
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2007
- 2007-07-18 ZA ZA200705880A patent/ZA200705880B/xx unknown
- 2007-07-19 IL IL184715A patent/IL184715A/en active IP Right Grant
2012
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Also Published As

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
EA013842B1 (ru)	2010-08-30
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
UA89218C2 (ru)	2010-01-11
PT1848678E (pt)	2015-10-12
IL184715A0 (en)	2007-12-03
WO2006084663A1 (en)	2006-08-17

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