DK1858858T3 - Fremgangmsåde til fremstilling af alkylanilider - Google Patents
Fremgangmsåde til fremstilling af alkylanilider Download PDFInfo
- Publication number
- DK1858858T3 DK1858858T3 DK06723163.9T DK06723163T DK1858858T3 DK 1858858 T3 DK1858858 T3 DK 1858858T3 DK 06723163 T DK06723163 T DK 06723163T DK 1858858 T3 DK1858858 T3 DK 1858858T3
- Authority
- DK
- Denmark
- Prior art keywords
- alkyl
- haloalkyl
- halogen
- formula
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 19
- 238000002360 preparation method Methods 0.000 title description 4
- 239000001257 hydrogen Substances 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 104
- 150000002431 hydrogen Chemical class 0.000 claims description 93
- -1 C1-C4-alkylthio Chemical group 0.000 claims description 77
- 125000005843 halogen group Chemical group 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 32
- 125000001246 bromo group Chemical group Br* 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 150000005130 benzoxazines Chemical class 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 21
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 98
- 229910052801 chlorine Inorganic materials 0.000 description 98
- 239000000460 chlorine Substances 0.000 description 98
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 97
- 229910052731 fluorine Chemical group 0.000 description 97
- 239000011737 fluorine Chemical group 0.000 description 97
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 66
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 66
- 229910052794 bromium Inorganic materials 0.000 description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 64
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 57
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 55
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 41
- 150000003254 radicals Chemical class 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007818 Grignard reagent Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- LQOHZKCEEGDSAA-UHFFFAOYSA-N n-(2-acetylphenyl)-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC(=O)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C LQOHZKCEEGDSAA-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- JKSOKTDAASTKIR-UHFFFAOYSA-N 5-fluoro-1,3-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=NN(C)C(F)=C1C(Cl)=O JKSOKTDAASTKIR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- UIIJZQVROQHLAP-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane;sodium Chemical compound [Na].CCC(C)(C)OC(C)(C)CC UIIJZQVROQHLAP-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 1
- WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 description 1
- FSLWXANTEMFPRQ-UHFFFAOYSA-N 5-fluoro-1,3-dimethylpyrazole-4-carbonyl fluoride Chemical compound CC1=NN(C)C(F)=C1C(F)=O FSLWXANTEMFPRQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 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
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (1)
1. Benzoxaziner med formel
hvor R1 står for hydrogen eller fluor, R2 står for hydrogen, halogen, Ci-C4_alkyl eller C1-C4-halogenalkyl med 1 til 9 fluor-, chlor- og/eller bromatomer, A står for gruppen med formel (Al)
(Al) hvor R3 står for hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, C1-C4-alkoxy, Ci-C4-alkylthio, C3-C6-cycloalkyl, Ci-C4-halogenalkyl, Ci-C4-halogenalkoxy eller Ci-C4-halogenalkylthio med hver især 1 til 5 halogenatomer, aminocarbonyl eller aminocarbonyl-Ci-C4-alkyl, R4 står for hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4~alkoxy eller Ci~C4-alkylthio, R5 står for hydrogen, Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C2-C6- alkenyl, C3-C6-cycloalkyl, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4-alkoxy-Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-halogenalkylthio-Ci-C4-alkyl, Ci-C4-halogenalkoxy-Ci-C4-alkyl med hver især 1 til 5 halogenatomer, eller phenyl, eller A står for en gruppe med formel (A2)
(A2): hvor R6 og R7 uafhængigt af hinanden står for hydrogen, halogen, Ci-C4~alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R8 står for halogen, cyano eller Ci-C4-alkyl eller C1-C4- halogenalkyl eller Ci-C4-halogenalkoxy med hver især 1 til 5 halogenatomer, eller A står for gruppen med formel (A3)
(A3) hvor R9 og R10 uafhængigt af hinanden står for hydrogen, halogen, Ci-C4~alkyl eller Ci~C4-halogenalkyl med 1 til 5 halogenatomer, R11 står for hydrogen, halogen, Ci-C4_alkyl eller C1-C4- halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A4)
<A4); hvor R12 står for hydrogen, halogen, hydroxy, cyano, Ci-C6_alkyl, Ci-C4~halogenalkyl, Ci-C4-halogenalkoxy eller C1-C4- halogenalkylthio med hver især 1 til 5 halogenatomer, eller A står for gruppen med formel (A5)
(A5) hvor R13 står for halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-halogenalkyl, Ci-C4-halogenalkylthio eller Ci-C4-halogenalkoxy med hver især 1 til 5 halogenatomer, R14 står for hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-halogenalkyl, Ci-C4-halogenalkoxy med hver især 1 til 5 halogenatomer, Ci-C4-alkylsulphinyl eller Ci-C4-alkylsulphonyl, eller A står for gruppen med formel (A6)
(A6) hvor R15 står for Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R16 står for Ci_C4-alkyl, Q1 står for S (svovl), 0 (oxygen), SO, S02 eller CH2, p står for 0, 1 eller 2, idet R16 står for identiske eller forskellige grupper, hvis p står for 2, eller A står for gruppen med formel (A7)
(A7) hvor R17 står for Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A8)
(A8) hvor R18 står for Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A9)
(A9) hvor R19 og R20 uafhængigt af hinanden står for hydrogen, halogen, amino, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R21 står for hydrogen, halogen, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A10)
(A10) hvor R22 og R23 uafhængigt af hinanden står for hydrogen, halogen, amino, nitro, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R24 står for hydrogen, halogen, Ci-C4-alkyl eller Ci-C4- halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (All)
(All) hvor R25 står for hydrogen, halogen, amino, Ci-C4-alkylamino, di-(Ci — C4-alkyl)amino, cyano, Ci-C4-alkyl eller C4-C4-halogenalkyl med 1 til 5 halogenatomer, R26 står for halogen, C4-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer eller A står for gruppen med formel (A12)
(Al 2) hvor R27 står for hydrogen, halogen, amino, Ci-C4-alkylamino, di-(C4-C4-alkyl)amino, cyano, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R28 står for halogen, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A13)
(Al 3) hvor R29 står for halogen, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A14)
(A14) hvor R30 står for hydrogen eller Ci-C4-alkyl, R31 står for halogen eller Ci-C4-alkyl, eller A står for gruppen med formel (A15)
(Al 5) hvor R32 står for Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A16)
(A16) : hvor R33 står for hydrogen, halogen, Ci-C4-alkyl eller Ci-C4- halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A17)
(Al 7) hvor R34 står for halogen, hydroxy, Ci-C4-alkyl, Ci-C4-alkoxy, C4-C4-alkylthio, Ci-C4-halogenalkyl, Ci-C4-halogenalkylthio eller C4-C4-halogenalkoxy med hver især 1 til 5 halogenatomer, eller A står for gruppen med formel (A18)
(Al 8) hvor R35 står for hydrogen, cyano, Ci-C4-alkyl, Ci-C4-halogenalkyl med 1 til 5 halogenatomer, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-C4-C4-alkyl, Ci-C4-alkylsulfonyl, di (Ci~C4-alkyl) aminosulfonyl, C4-C6_alkylcarbonyl eller hver især i givet fald substitueret phenylsulfonyl eller benzoyl, R36 står for hydrogen, halogen, Ci-C4-alkyl eller Ci-C4-halogenalkyl med 1 til 5 halogenatomer, R37 står for hydrogen, halogen, cyano, Ci-C4-alkyl eller C1-C4-halogenalkyl med 1 til 5 halogenatomer, R38 står for hydrogen, halogen, Ci-C4-alkyl eller C1-C4- halogenalkyl med 1 til 5 halogenatomer, eller A står for gruppen med formel (A19)
(Al 9): hvor R39 står for Ci-C4-alkyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005009457A DE102005009457A1 (de) | 2005-03-02 | 2005-03-02 | Verfahren zum Herstellen von Alkylaniliden |
| PCT/EP2006/001871 WO2006092291A2 (de) | 2005-03-02 | 2006-03-01 | Verfahren zum herstellen von alkylaniliden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1858858T3 true DK1858858T3 (da) | 2015-07-27 |
Family
ID=36754120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK06723163.9T DK1858858T3 (da) | 2005-03-02 | 2006-03-01 | Fremgangmsåde til fremstilling af alkylanilider |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8053572B2 (da) |
| EP (1) | EP1858858B1 (da) |
| JP (1) | JP5173443B2 (da) |
| CN (1) | CN101166728B (da) |
| DE (1) | DE102005009457A1 (da) |
| DK (1) | DK1858858T3 (da) |
| ES (1) | ES2542710T3 (da) |
| IL (1) | IL185627A (da) |
| TW (1) | TWI372145B (da) |
| WO (1) | WO2006092291A2 (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004005787A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
| DE102004005786A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
| DE102005022147A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005028293A1 (de) | 2005-06-18 | 2007-01-04 | Bayer Cropscience Gmbh | Verfahren zum Herstellen von Carboxamiden |
| EP2272345A1 (en) | 2009-07-07 | 2011-01-12 | Bayer CropScience AG | Process for improving seedling growth and/or early emergence of crops |
| EP2535334A1 (de) | 2011-06-17 | 2012-12-19 | Bayer CropScience AG | Kristalline Modifikationen von Penflufen |
| US9656964B2 (en) * | 2012-11-13 | 2017-05-23 | Bayer Cropscience Ag | Method for producing carboxamides |
| WO2014140111A1 (en) | 2013-03-13 | 2014-09-18 | Bayer Cropscience Ag | Lawn growth-promoting agent and method of using same |
| DK3097081T3 (da) * | 2014-01-24 | 2018-01-29 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af 1-alkyl-3-difluormethyl-5-fluor-1h-pyrazol-4-carbaldehyder og 1-alkyl-3-difluormethyl-5-fluor-1h-pyrazol-4-carboxylater |
| MX2016012936A (es) | 2014-04-01 | 2016-12-07 | Bayer Cropscience Ag | Proceso para la preparacion de n-[3-(bencilcarbamoil)fenil]-1h-pir azol-5-carboxamidas. |
| CN110054595B (zh) * | 2019-05-30 | 2020-10-16 | 山东省联合农药工业有限公司 | 一种解草酮的合成工艺 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2072015T3 (es) * | 1990-08-21 | 1995-07-01 | Upjohn Co | Derivados del acido bisfosfonico como agente anti-artritico. |
| US5223526A (en) | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
| DE4231517A1 (de) | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE4231519A1 (de) | 1992-09-21 | 1994-03-24 | Basf Ag | Cyclohex(en)ylcarbonsäureamide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| GB9405347D0 (en) * | 1994-03-18 | 1994-05-04 | Agrevo Uk Ltd | Fungicides |
| US5914344A (en) | 1996-08-15 | 1999-06-22 | Mitsui Chemicals, Inc. | Substituted carboxanilide derivative and plant disease control agent comprising same as active ingredient |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| WO2004103953A1 (de) | 2003-05-21 | 2004-12-02 | Bayer Cropscience Aktiengesellschaft | Difluormethylbenzanilide und deren verwendung zur bekämpfung bon mikroorganismen, sowie zwischen produkte und deren herstellung |
| JP4648324B2 (ja) | 2003-05-21 | 2011-03-09 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ヨードピラゾリルカルボキシアニリド類 |
| DE10325438A1 (de) | 2003-05-21 | 2004-12-09 | Bayer Cropscience Ag | Difluormethylbenzanilide |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102004005785A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004005786A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005787A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
| JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
| DE102005022147A1 (de) | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005035300A1 (de) | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006033090A1 (de) | 2006-07-14 | 2008-01-24 | Bayer Cropscience Ag | Verfahren zum Herstellen von Alkylaniliden aus Halogenbenzolderivaten |
| EP2272345A1 (en) | 2009-07-07 | 2011-01-12 | Bayer CropScience AG | Process for improving seedling growth and/or early emergence of crops |
-
2005
- 2005-03-02 DE DE102005009457A patent/DE102005009457A1/de not_active Withdrawn
-
2006
- 2006-03-01 JP JP2007557418A patent/JP5173443B2/ja not_active Expired - Fee Related
- 2006-03-01 WO PCT/EP2006/001871 patent/WO2006092291A2/de not_active Ceased
- 2006-03-01 ES ES06723163.9T patent/ES2542710T3/es not_active Expired - Lifetime
- 2006-03-01 TW TW095106709A patent/TWI372145B/zh not_active IP Right Cessation
- 2006-03-01 EP EP20060723163 patent/EP1858858B1/de not_active Expired - Lifetime
- 2006-03-01 CN CN2006800139605A patent/CN101166728B/zh not_active Expired - Fee Related
- 2006-03-01 US US11/817,373 patent/US8053572B2/en not_active Expired - Fee Related
- 2006-03-01 DK DK06723163.9T patent/DK1858858T3/da active
-
2007
- 2007-08-30 IL IL185627A patent/IL185627A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2542710T3 (es) | 2015-08-10 |
| US20090209769A1 (en) | 2009-08-20 |
| CN101166728A (zh) | 2008-04-23 |
| IL185627A0 (en) | 2008-01-06 |
| EP1858858A2 (de) | 2007-11-28 |
| JP2008531629A (ja) | 2008-08-14 |
| IL185627A (en) | 2015-10-29 |
| JP5173443B2 (ja) | 2013-04-03 |
| CN101166728B (zh) | 2011-08-31 |
| EP1858858B1 (de) | 2015-04-29 |
| US8053572B2 (en) | 2011-11-08 |
| TW200702331A (en) | 2007-01-16 |
| WO2006092291A2 (de) | 2006-09-08 |
| DE102005009457A1 (de) | 2006-09-07 |
| WO2006092291A3 (de) | 2006-11-30 |
| TWI372145B (en) | 2012-09-11 |
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