NO790155L - V nye anilinderivater og fremgangsmaate for fremstilling dera - Google Patents
V nye anilinderivater og fremgangsmaate for fremstilling deraInfo
- Publication number
- NO790155L NO790155L NO790155A NO790155A NO790155L NO 790155 L NO790155 L NO 790155L NO 790155 A NO790155 A NO 790155A NO 790155 A NO790155 A NO 790155A NO 790155 L NO790155 L NO 790155L
- Authority
- NO
- Norway
- Prior art keywords
- stated
- formyl
- formula
- dinitrobenzotrifluoride
- formanilido
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 230000006324 decarbonylation Effects 0.000 claims description 11
- 238000006606 decarbonylation reaction Methods 0.000 claims description 11
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 9
- -1 aromatic halide Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002516 radical scavenger Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- RLXKADBMLQPLDV-UHFFFAOYSA-N 2-chloro-1,5-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C(C(F)(F)F)=C1 RLXKADBMLQPLDV-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- JGHUUZYDRJTNOX-UHFFFAOYSA-N (4-chloro-2-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 JGHUUZYDRJTNOX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- XYJJSLMPHYYITA-UHFFFAOYSA-N 1-chloro-2-methylsulfonyl-4-nitrobenzene Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl XYJJSLMPHYYITA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 description 1
- BPPMIQPXQVIZNJ-UHFFFAOYSA-N 2-chloro-1,3-dinitrobenzene Chemical class [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1Cl BPPMIQPXQVIZNJ-UHFFFAOYSA-N 0.000 description 1
- SAHBOHJNDBWWBP-UHFFFAOYSA-N 2-chloro-1-methylsulfonyl-3,5-dinitrobenzene Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1Cl SAHBOHJNDBWWBP-UHFFFAOYSA-N 0.000 description 1
- ZGILLTVEEBNDOB-UHFFFAOYSA-N 2-chloro-5-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C#N)=C1 ZGILLTVEEBNDOB-UHFFFAOYSA-N 0.000 description 1
- DNWNOXLEJIRYFP-UHFFFAOYSA-N 3,5-dichloro-2-fluoro-6-methoxy-4-(3-methoxy-2,5-dinitroanilino)-2h-pyridine-1-carbaldehyde Chemical compound FC1N(C=O)C(OC)=C(Cl)C(NC=2C(=C(OC)C=C(C=2)[N+]([O-])=O)[N+]([O-])=O)=C1Cl DNWNOXLEJIRYFP-UHFFFAOYSA-N 0.000 description 1
- KIQMNTKYGMEHKS-UHFFFAOYSA-N 3,5-dichloro-4-(2,5-dinitroanilino)-2,6-difluoro-2,4-dihydropyrimidine-1-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C(NC2C(=C(F)N(C=O)C(F)N2Cl)Cl)=C1 KIQMNTKYGMEHKS-UHFFFAOYSA-N 0.000 description 1
- VWPJXEYDYJQMBC-UHFFFAOYSA-N 3-methylsulfonylbenzonitrile Chemical compound CS(=O)(=O)C1=CC=CC(C#N)=C1 VWPJXEYDYJQMBC-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates 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
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VCYWZLGOWNCJNJ-UHFFFAOYSA-N methyl 2-chloro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl VCYWZLGOWNCJNJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- POOAXOGRBVEUFA-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)formamide Chemical compound O=CNC1=NC=CS1 POOAXOGRBVEUFA-UHFFFAOYSA-N 0.000 description 1
- KHHXWNMNFNRSRW-UHFFFAOYSA-N n-(1-phenylpyrazol-3-yl)formamide Chemical compound N1=C(NC=O)C=CN1C1=CC=CC=C1 KHHXWNMNFNRSRW-UHFFFAOYSA-N 0.000 description 1
- REWYPKAXVAFTLU-UHFFFAOYSA-N n-(1h-pyrazol-5-yl)formamide Chemical compound O=CNC=1C=CNN=1 REWYPKAXVAFTLU-UHFFFAOYSA-N 0.000 description 1
- WBRIYBDNSINRPS-UHFFFAOYSA-N n-(2,4-dichloronaphthalen-1-yl)-n-(2,6-dinitrophenyl)formamide Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1N(C=O)C1=C(Cl)C=C(Cl)C2=CC=CC=C12 WBRIYBDNSINRPS-UHFFFAOYSA-N 0.000 description 1
- ODFPSNVGBDOZST-UHFFFAOYSA-N n-(2,4-dinitrophenyl)-n-(2-methylfuran-3-yl)formamide Chemical compound O1C=CC(N(C=O)C=2C(=CC(=CC=2)[N+]([O-])=O)[N+]([O-])=O)=C1C ODFPSNVGBDOZST-UHFFFAOYSA-N 0.000 description 1
- CMRLEIHOFQKMCW-UHFFFAOYSA-N n-(2,6-dichlorophenyl)formamide Chemical compound ClC1=CC=CC(Cl)=C1NC=O CMRLEIHOFQKMCW-UHFFFAOYSA-N 0.000 description 1
- PYHXNHQAVPSOKT-UHFFFAOYSA-N n-(4-bromophenyl)formamide Chemical class BrC1=CC=C(NC=O)C=C1 PYHXNHQAVPSOKT-UHFFFAOYSA-N 0.000 description 1
- LMLFHXMNNHGRRO-UHFFFAOYSA-N n-(4-chlorophenyl)formamide Chemical class ClC1=CC=C(NC=O)C=C1 LMLFHXMNNHGRRO-UHFFFAOYSA-N 0.000 description 1
- KXCSOTXPAIQFPU-UHFFFAOYSA-N n-(4-cyano-5-methyl-2-nitrophenyl)-n-(4,8-dichloronaphthalen-1-yl)formamide Chemical compound C1=C(C#N)C(C)=CC(N(C=O)C=2C3=C(Cl)C=CC=C3C(Cl)=CC=2)=C1[N+]([O-])=O KXCSOTXPAIQFPU-UHFFFAOYSA-N 0.000 description 1
- RIXSUSUNXMNVNN-UHFFFAOYSA-N n-(4-cyanophenyl)formamide Chemical class O=CNC1=CC=C(C#N)C=C1 RIXSUSUNXMNVNN-UHFFFAOYSA-N 0.000 description 1
- GRVKDWHXLFEVBP-UHFFFAOYSA-N n-(4-methylphenyl)formamide Chemical class CC1=CC=C(NC=O)C=C1 GRVKDWHXLFEVBP-UHFFFAOYSA-N 0.000 description 1
- ZTCQFVRINYOPOH-UHFFFAOYSA-N n-(4-nitrophenyl)formamide Chemical class [O-][N+](=O)C1=CC=C(NC=O)C=C1 ZTCQFVRINYOPOH-UHFFFAOYSA-N 0.000 description 1
- FSFWVKBVSJJIML-UHFFFAOYSA-N n-(5-methylpyrimidin-4-yl)formamide Chemical compound CC1=CN=CN=C1NC=O FSFWVKBVSJJIML-UHFFFAOYSA-N 0.000 description 1
- ODLJCVGAFRZOOB-UHFFFAOYSA-N n-(5-nitro-1,3-thiazol-2-yl)formamide Chemical compound [O-][N+](=O)C1=CN=C(NC=O)S1 ODLJCVGAFRZOOB-UHFFFAOYSA-N 0.000 description 1
- AKUOIQRCSTTZPX-UHFFFAOYSA-N n-[2-nitro-4-(trifluoromethyl)phenyl]-n-thiophen-3-ylformamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N(C=O)C1=CSC=C1 AKUOIQRCSTTZPX-UHFFFAOYSA-N 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- CBKFHSNATJJWQK-UHFFFAOYSA-N n-pyridin-3-ylformamide Chemical compound O=CNC1=CC=CN=C1 CBKFHSNATJJWQK-UHFFFAOYSA-N 0.000 description 1
- OMFCKPHCFZLGSQ-UHFFFAOYSA-N n-quinolin-3-ylformamide Chemical compound C1=CC=CC2=CC(NC=O)=CN=C21 OMFCKPHCFZLGSQ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB199178 | 1978-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO790155L true NO790155L (no) | 1979-07-19 |
Family
ID=9731683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790155A NO790155L (no) | 1978-01-18 | 1979-01-17 | V nye anilinderivater og fremgangsmaate for fremstilling dera |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4292446A (de) |
| EP (1) | EP0003259B1 (de) |
| JP (1) | JPS54100328A (de) |
| AU (1) | AU525264B2 (de) |
| BR (1) | BR7900123A (de) |
| CA (1) | CA1133482A (de) |
| DE (1) | DE2861703D1 (de) |
| DK (1) | DK22179A (de) |
| NO (1) | NO790155L (de) |
| NZ (1) | NZ189282A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316988A (en) * | 1976-07-21 | 1982-02-23 | Eli Lilly And Company | N-Alkyldiphenylamines |
| US5571810A (en) * | 1990-06-11 | 1996-11-05 | Fujisawa Pharmaceutical Co., Ltd. | Thiophene derivatives |
| DE69323275T2 (de) * | 1992-11-25 | 1999-07-08 | Rhodia Chimie, Courbevoie | Syntheseweg zu desaktivierten Anilinen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2961465A (en) * | 1954-04-26 | 1960-11-22 | Monsanto Chemicals | Alkali metal derivatives of di-nu-substituted formamides |
| BE577941A (de) * | 1958-04-22 | |||
| US2924620A (en) * | 1959-03-30 | 1960-02-09 | Du Pont | Process for the preparation of diphenylamines |
| GB1218965A (en) * | 1968-09-16 | 1971-01-13 | Nii Farmakologii I Khim | Method of preparing 3-trifluoromethyldiphenylamine |
| US3830842A (en) | 1970-09-10 | 1974-08-20 | Squibb & Sons Inc | Alpha,alpha,alpha,alpha',alpha',alpha'-hexafluorodi-m-tolylamine derivatives |
| GB1383523A (en) * | 1971-08-26 | 1974-02-12 | Ici Ltd | Diphenylamine derivatives and pesticidal compositions thereof |
| US3950377A (en) * | 1972-12-20 | 1976-04-13 | Imperial Chemical Industries Limited | Diphenylamine derivatives |
| GB1405120A (en) | 1972-12-20 | 1975-09-03 | Ici Ltd | Nitrobenzene derivatives |
| GB1430046A (en) | 1974-03-07 | 1976-03-31 | Ici Ltd | Nitrobenzene derivatives |
| GB1455207A (en) * | 1974-11-06 | 1976-11-10 | Ici Ltd | Substituted dinitro-diphenylamines and their pesticidal compositions |
-
1978
- 1978-12-13 EP EP78300812A patent/EP0003259B1/de not_active Expired
- 1978-12-13 DE DE7878300812T patent/DE2861703D1/de not_active Expired
- 1978-12-21 NZ NZ189282A patent/NZ189282A/xx unknown
- 1978-12-28 AU AU42896/78A patent/AU525264B2/en not_active Expired
-
1979
- 1979-01-10 BR BR7900123A patent/BR7900123A/pt unknown
- 1979-01-16 JP JP229779A patent/JPS54100328A/ja active Pending
- 1979-01-17 NO NO790155A patent/NO790155L/no unknown
- 1979-01-18 CA CA319,851A patent/CA1133482A/en not_active Expired
- 1979-01-18 DK DK22179A patent/DK22179A/da not_active Application Discontinuation
-
1980
- 1980-07-14 US US06/168,513 patent/US4292446A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0003259B1 (de) | 1982-03-24 |
| EP0003259A1 (de) | 1979-08-08 |
| DK22179A (da) | 1979-07-19 |
| AU4289678A (en) | 1979-07-26 |
| BR7900123A (pt) | 1979-08-14 |
| US4292446A (en) | 1981-09-29 |
| DE2861703D1 (en) | 1982-04-29 |
| CA1133482A (en) | 1982-10-12 |
| AU525264B2 (en) | 1982-10-28 |
| NZ189282A (en) | 1981-03-16 |
| JPS54100328A (en) | 1979-08-08 |
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