JPS5925781B2 - Ｎ−アルキル化アニリン化合物の製造法 - Google Patents

Ｎ−アルキル化アニリン化合物の製造法

Info

Publication number: JPS5925781B2
Authority: JP; Japan
Prior art keywords: alkyl; hydrogen; nitro; butyl; hno
Prior art date: 1973-06-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP49072714A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5052033A (cs

Inventor

デイビツドレビ− ステフエン

ユ−ジンデイ−ルロバ−ト

ヘンリ− ガストロツクウイリアム

ジエ−ムスロスロ−レンス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

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.)

1973-06-25

Filing date

1974-06-25

Publication date

1984-06-21

1974-06-25 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1975-05-09 Publication of JPS5052033A publication Critical patent/JPS5052033A/ja

1984-06-21 Publication of JPS5925781B2 publication Critical patent/JPS5925781B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
-1 N-alkylated aniline compound Chemical class 0.000 title description 28
238000000034 method Methods 0.000 claims description 49
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 47
229910017604 nitric acid Inorganic materials 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
239000011541 reaction mixture Substances 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 19
230000000802 nitrating effect Effects 0.000 claims description 16
ZOTRFGNOTDLOAU-UHFFFAOYSA-N 3,4-dimethyl-n-pentan-3-ylaniline Chemical group CCC(CC)NC1=CC=C(C)C(C)=C1 ZOTRFGNOTDLOAU-UHFFFAOYSA-N 0.000 claims description 15
150000001412 amines Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
150000001448 anilines Chemical class 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 10
229910052721 tungsten Inorganic materials 0.000 claims description 9
229910052720 vanadium Inorganic materials 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
239000006227 byproduct Substances 0.000 claims description 6
125000006682 monohaloalkyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
238000007126 N-alkylation reaction Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
150000002832 nitroso derivatives Chemical class 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 36
238000006396 nitration reaction Methods 0.000 description 33
239000002253 acid Substances 0.000 description 32
239000000047 product Substances 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 27
239000003054 catalyst Substances 0.000 description 25
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 22
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 22
238000002360 preparation method Methods 0.000 description 18
150000002576 ketones Chemical class 0.000 description 17
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000004982 aromatic amines Chemical class 0.000 description 12
239000002243 precursor Substances 0.000 description 12
239000007858 starting material Substances 0.000 description 11
239000010410 layer Substances 0.000 description 10
229910052697 platinum Inorganic materials 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000008096 xylene Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
UYRFXZMCMONWSK-UHFFFAOYSA-N n-butan-2-yl-3,4-dimethylaniline Chemical compound CCC(C)NC1=CC=C(C)C(C)=C1 UYRFXZMCMONWSK-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
239000002689 soil Substances 0.000 description 7
239000013076 target substance Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
229910000510 noble metal Inorganic materials 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
238000005932 reductive alkylation reaction Methods 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000004008 N-nitroso compounds Chemical class 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
238000002156 mixing Methods 0.000 description 4
MIHBNYMMGYGFGX-UHFFFAOYSA-N n-(3,4-dimethyl-2,6-dinitrophenyl)-n-pentan-3-ylnitrous amide Chemical compound CCC(CC)N(N=O)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O MIHBNYMMGYGFGX-UHFFFAOYSA-N 0.000 description 4
NKPDMJBXCFNGSC-UHFFFAOYSA-N n-butan-2-yl-3,4-dimethyl-2,6-dinitroaniline Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O NKPDMJBXCFNGSC-UHFFFAOYSA-N 0.000 description 4
VJAABRFQYRCZNI-UHFFFAOYSA-N n-butan-2-yl-4-tert-butylaniline Chemical compound CCC(C)NC1=CC=C(C(C)(C)C)C=C1 VJAABRFQYRCZNI-UHFFFAOYSA-N 0.000 description 4
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
238000004566 IR spectroscopy Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
OIFSXNKXBJFNNG-UHFFFAOYSA-N n-butan-2-yl-3-chloro-4-methylaniline Chemical compound CCC(C)NC1=CC=C(C)C(Cl)=C1 OIFSXNKXBJFNNG-UHFFFAOYSA-N 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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 2
230000007423 decrease Effects 0.000 description 2
230000003453 denitrosating effect Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000007429 general method Methods 0.000 description 2
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
230000036244 malformation Effects 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000007034 nitrosation reaction Methods 0.000 description 2
125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
238000010534 nucleophilic substitution reaction Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000000523 sample Substances 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
APNSUHRNUVUCIP-UHFFFAOYSA-N 1-chloropentan-3-one Chemical compound CCC(=O)CCCl APNSUHRNUVUCIP-UHFFFAOYSA-N 0.000 description 1
IYHKHKUEGSVBMS-UHFFFAOYSA-N 1-methoxypentan-3-one Chemical compound CCC(=O)CCOC IYHKHKUEGSVBMS-UHFFFAOYSA-N 0.000 description 1
CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
RSCSQMIRKUSCQT-UHFFFAOYSA-N 3,4-diethyl-2,6-dinitro-n-propan-2-ylaniline Chemical compound CCC1=CC([N+]([O-])=O)=C(NC(C)C)C([N+]([O-])=O)=C1CC RSCSQMIRKUSCQT-UHFFFAOYSA-N 0.000 description 1
NYWYVPJGXSWDEQ-UHFFFAOYSA-N 3,4-dimethyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O NYWYVPJGXSWDEQ-UHFFFAOYSA-N 0.000 description 1
OYUBPCNMZPYCJP-UHFFFAOYSA-N 3,4-dimethyl-2,6-dinitro-n-propan-2-ylaniline Chemical compound CC(C)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O OYUBPCNMZPYCJP-UHFFFAOYSA-N 0.000 description 1
LXAFKQMKKXFYRJ-UHFFFAOYSA-N 3,4-dimethyl-2-nitro-n-pentan-3-ylaniline Chemical group CCC(CC)NC1=CC=C(C)C(C)=C1[N+]([O-])=O LXAFKQMKKXFYRJ-UHFFFAOYSA-N 0.000 description 1
OQAIEKNGRUJACL-UHFFFAOYSA-N 3,4-dimethyl-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=C(C)C(C)=C1 OQAIEKNGRUJACL-UHFFFAOYSA-N 0.000 description 1
NYPUAFUSYNRJNA-UHFFFAOYSA-N 3-(methoxymethyl)-4-methyl-n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=CC=C(C)C(COC)=C1 NYPUAFUSYNRJNA-UHFFFAOYSA-N 0.000 description 1
HJGXZLXQQPSCMQ-UHFFFAOYSA-N 3-(methoxymethyl)-n-pentan-3-yl-4-(trifluoromethyl)aniline Chemical compound CCC(CC)NC1=CC=C(C(F)(F)F)C(COC)=C1 HJGXZLXQQPSCMQ-UHFFFAOYSA-N 0.000 description 1
XWCKVTPDJIKDEG-UHFFFAOYSA-N 3-chloro-4-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C(Cl)=C1[N+]([O-])=O XWCKVTPDJIKDEG-UHFFFAOYSA-N 0.000 description 1
CDCVNHLJWCXJQH-UHFFFAOYSA-N 3-chloro-n,n-diethyl-4-methyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C)C(Cl)=C1[N+]([O-])=O CDCVNHLJWCXJQH-UHFFFAOYSA-N 0.000 description 1
RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
RCHMRIXFRMRATD-UHFFFAOYSA-N 3-ethoxy-4-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C(OCC)=C1[N+]([O-])=O RCHMRIXFRMRATD-UHFFFAOYSA-N 0.000 description 1
AGNZPDAMQVAENC-UHFFFAOYSA-N 3-ethoxy-4-methyl-n-pentan-2-ylaniline Chemical compound CCCC(C)NC1=CC=C(C)C(OCC)=C1 AGNZPDAMQVAENC-UHFFFAOYSA-N 0.000 description 1
HHAPSLUXHAXDLY-UHFFFAOYSA-N 3-ethyl-2,6-dinitro-n-propan-2-yl-4-(trifluoromethyl)aniline Chemical compound CCC1=C(C(F)(F)F)C=C([N+]([O-])=O)C(NC(C)C)=C1[N+]([O-])=O HHAPSLUXHAXDLY-UHFFFAOYSA-N 0.000 description 1
PAPZOIOWDRYNEN-UHFFFAOYSA-N 3-methyl-2,6-dinitro-n-pentan-3-yl-4-(trifluoromethyl)aniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(C)=C1[N+]([O-])=O PAPZOIOWDRYNEN-UHFFFAOYSA-N 0.000 description 1
HUEIVFRAOUXWGI-UHFFFAOYSA-N 3-methyl-2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical compound CCCNC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(C)=C1[N+]([O-])=O HUEIVFRAOUXWGI-UHFFFAOYSA-N 0.000 description 1
JYTFVCIATXQTHK-UHFFFAOYSA-N 3-methyl-n-pentan-3-yl-4-(trifluoromethyl)aniline Chemical compound CCC(CC)NC1=CC=C(C(F)(F)F)C(C)=C1 JYTFVCIATXQTHK-UHFFFAOYSA-N 0.000 description 1
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DBEGABZQNNHBEW-UHFFFAOYSA-N 4-chloro-3-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(Cl)C(C)=C1[N+]([O-])=O DBEGABZQNNHBEW-UHFFFAOYSA-N 0.000 description 1
MMEQFVOJSGPEFA-UHFFFAOYSA-N 4-chloro-3-methyl-n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=CC=C(Cl)C(C)=C1 MMEQFVOJSGPEFA-UHFFFAOYSA-N 0.000 description 1
GTBGLCILSXEPOQ-UHFFFAOYSA-N 4-chloro-n,n,3-trimethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(Cl)C(C)=C1[N+]([O-])=O GTBGLCILSXEPOQ-UHFFFAOYSA-N 0.000 description 1
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BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 1
MOOOPNRPJGZXPE-UHFFFAOYSA-N 4-methyl-2,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=C(N)C([N+]([O-])=O)=C1 MOOOPNRPJGZXPE-UHFFFAOYSA-N 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
235000014750 Brassica kaber Nutrition 0.000 description 1
244000024671 Brassica kaber Species 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 1
235000009344 Chenopodium album Nutrition 0.000 description 1
240000006122 Chenopodium album Species 0.000 description 1
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244000068988 Glycine max Species 0.000 description 1
235000009432 Gossypium hirsutum Nutrition 0.000 description 1
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239000004472 Lysine Substances 0.000 description 1
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230000002159 abnormal effect Effects 0.000 description 1
238000004847 absorption spectroscopy Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
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238000006640 acetylation reaction Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
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238000000889 atomisation Methods 0.000 description 1
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229910052918 calcium silicate Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
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238000005660 chlorination reaction Methods 0.000 description 1
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239000012530 fluid Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
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238000001030 gas--liquid chromatography Methods 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
NRMYUJBWRRMJDZ-UHFFFAOYSA-N n,n,3,4-tetramethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O NRMYUJBWRRMJDZ-UHFFFAOYSA-N 0.000 description 1
DZGNLHAJKBYQLS-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-3,4-dimethyl-2,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=C(N(CCCl)CCCl)C([N+]([O-])=O)=C1C DZGNLHAJKBYQLS-UHFFFAOYSA-N 0.000 description 1
OZOUCVPMAZQVOX-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-3,4-dimethylaniline Chemical compound CC1=CC=C(N(CCCl)CCCl)C=C1C OZOUCVPMAZQVOX-UHFFFAOYSA-N 0.000 description 1
XKUWFOYPQIVFMM-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-methyl-2,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=C(N(CCCl)CCCl)C([N+]([O-])=O)=C1 XKUWFOYPQIVFMM-UHFFFAOYSA-N 0.000 description 1
YSWMVWWXZLNNLF-UHFFFAOYSA-N n,n-dibutyl-3,4-dimethyl-2,6-dinitroaniline Chemical compound CCCCN(CCCC)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O YSWMVWWXZLNNLF-UHFFFAOYSA-N 0.000 description 1
PCYJWAIMNQMEKE-UHFFFAOYSA-N n,n-diethyl-3,4-dimethyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O PCYJWAIMNQMEKE-UHFFFAOYSA-N 0.000 description 1
RSDNOTLHFVGRID-UHFFFAOYSA-N n,n-diethyl-3-methoxy-4-methyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C)C(OC)=C1[N+]([O-])=O RSDNOTLHFVGRID-UHFFFAOYSA-N 0.000 description 1
MERHDLUCOZIMJT-UHFFFAOYSA-N n-(2-chloroethyl)-n,3,4-trimethyl-2,6-dinitroaniline Chemical compound ClCCN(C)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O MERHDLUCOZIMJT-UHFFFAOYSA-N 0.000 description 1
XALJBLCXNVTGMH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-n-nitronitramide Chemical group CC1=CC=C(N([N+]([O-])=O)[N+]([O-])=O)C=C1C XALJBLCXNVTGMH-UHFFFAOYSA-N 0.000 description 1
OSONHUUMLPGWPQ-UHFFFAOYSA-N n-butan-2-yl-3,4-dimethyl-2-nitroaniline Chemical compound CCC(C)NC1=CC=C(C)C(C)=C1[N+]([O-])=O OSONHUUMLPGWPQ-UHFFFAOYSA-N 0.000 description 1
RCDQLHUTVHEJSV-UHFFFAOYSA-N n-butan-2-yl-3-methoxy-4-methyl-2,6-dinitroaniline Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C)C(OC)=C1[N+]([O-])=O RCDQLHUTVHEJSV-UHFFFAOYSA-N 0.000 description 1
JOCIBTOQHZBCTH-UHFFFAOYSA-N n-butan-2-yl-3-methyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(C)=C1[N+]([O-])=O JOCIBTOQHZBCTH-UHFFFAOYSA-N 0.000 description 1
QYNBFLGNBJWLFV-UHFFFAOYSA-N n-butan-2-yl-4-methyl-2,6-dinitro-3-propan-2-ylaniline Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C)C(C(C)C)=C1[N+]([O-])=O QYNBFLGNBJWLFV-UHFFFAOYSA-N 0.000 description 1
NUSCSIGZZCTURT-UHFFFAOYSA-N n-butan-2-yl-4-tert-butyl-3-methylaniline Chemical compound CCC(C)NC1=CC=C(C(C)(C)C)C(C)=C1 NUSCSIGZZCTURT-UHFFFAOYSA-N 0.000 description 1
JPEZSTABLOULFK-UHFFFAOYSA-N n-butan-2-yl-n-(3,4-dimethyl-2,6-dinitrophenyl)nitrous amide Chemical compound CCC(C)N(N=O)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O JPEZSTABLOULFK-UHFFFAOYSA-N 0.000 description 1
PEEYSGCDTNILEF-UHFFFAOYSA-N n-butyl-n-ethyl-3,4-dimethyl-2,6-dinitroaniline Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O PEEYSGCDTNILEF-UHFFFAOYSA-N 0.000 description 1
ABLOYYZKKUMNKF-UHFFFAOYSA-N n-cyclobutyl-3,4-dimethyl-2,6-dinitroaniline Chemical compound [O-][N+](=O)C1=C(C)C(C)=CC([N+]([O-])=O)=C1NC1CCC1 ABLOYYZKKUMNKF-UHFFFAOYSA-N 0.000 description 1
VFOYZPFFJWXAET-UHFFFAOYSA-N n-ethyl-n,3,4-trimethyl-2,6-dinitroaniline Chemical compound CCN(C)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O VFOYZPFFJWXAET-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
229940005654 nitrite ion Drugs 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000004756 silanes Chemical class 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
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
230000000475 sunscreen effect Effects 0.000 description 1
239000000516 sunscreening agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000013077 target material Substances 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups

Landscapes

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

JP49072714A 1973-06-25 1974-06-25 Ｎ−アルキル化アニリン化合物の製造法 Expired JPS5925781B2 (ja)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date
US37307873A	1973-06-25	1973-06-25
US37307973A	1973-06-25	1973-06-25
US37307773A	1973-06-25	1973-06-25
US373077		1973-06-25
US373078		1973-06-25
US373079		1989-06-29

Publications (2)

Publication Number	Publication Date
JPS5052033A JPS5052033A (cs)	1975-05-09
JPS5925781B2 true JPS5925781B2 (ja)	1984-06-21

Family

ID=27409108

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP49072714A Expired JPS5925781B2 (ja)	1973-06-25	1974-06-25	Ｎ−アルキル化アニリン化合物の製造法

Country Status (20)

Country	Link
JP (1)	JPS5925781B2 (cs)
AR (1)	AR214707A1 (cs)
BG (1)	BG25788A3 (cs)
BR (1)	BR7405158D0 (cs)
CH (3)	CH605612A5 (cs)
CS (3)	CS184848B2 (cs)
DD (3)	DD115111A5 (cs)
DE (1)	DE2429958C2 (cs)
DK (1)	DK152751C (cs)
FR (1)	FR2233937A1 (cs)
HU (1)	HU170762B (cs)
IL (1)	IL44927A (cs)
IN (1)	IN139715B (cs)
IT (1)	IT1016118B (cs)
NL (2)	NL183579C (cs)
PL (1)	PL93741B1 (cs)
RO (2)	RO70074A (cs)
SE (1)	SE416198B (cs)
SU (1)	SU897108A3 (cs)
YU (1)	YU39721B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0024503B1 (en) *	1979-08-24	1983-06-15	American Cyanamid Company	N-denitration of n,2,6-trinitroanilines with phase transfer catalysts
CN109320424B (zh) *	2017-07-31	2021-12-21	江苏永安化工有限公司	一种二甲戊灵的纯化方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1207397B (de) *	1963-06-22	1965-12-23	Hoechst Ag	Verfahren zur Herstellung von 4-Chlor- und 4-Methoxy-2, 6-dinitranilin
US3504033A (en) *	1967-09-08	1970-03-31	American Cyanamid Co	Process for preparing n-tertiary-alkylanilines and their hydrohalide salts

1974
- 1974-05-30 IL IL44927A patent/IL44927A/xx unknown
- 1974-05-31 IN IN1198/CAL/74A patent/IN139715B/en unknown
- 1974-06-10 AR AR254137A patent/AR214707A1/es active
- 1974-06-20 IT IT51637/74A patent/IT1016118B/it active
- 1974-06-21 YU YU1748/74A patent/YU39721B/xx unknown
- 1974-06-21 DE DE2429958A patent/DE2429958C2/de not_active Expired
- 1974-06-24 BR BR5158/74A patent/BR7405158D0/pt unknown
- 1974-06-24 PL PL1974172146A patent/PL93741B1/pl unknown
- 1974-06-24 HU HU74AE00000418A patent/HU170762B/hu unknown
- 1974-06-24 DK DK338974A patent/DK152751C/da not_active IP Right Cessation
- 1974-06-24 SE SE7408285A patent/SE416198B/xx not_active IP Right Cessation
- 1974-06-24 SU SU742038395A patent/SU897108A3/ru active
- 1974-06-25 RO RO7479298A patent/RO70074A/ro unknown
- 1974-06-25 DD DD179464A patent/DD115111A5/xx unknown
- 1974-06-25 BG BG027074A patent/BG25788A3/xx unknown
- 1974-06-25 DD DD188248A patent/DD120431A5/xx unknown
- 1974-06-25 JP JP49072714A patent/JPS5925781B2/ja not_active Expired
- 1974-06-25 CH CH1229377A patent/CH605612A5/xx not_active IP Right Cessation
- 1974-06-25 NL NLAANVRAGE7408514,A patent/NL183579C/xx not_active IP Right Cessation
- 1974-06-25 CS CS7600006395A patent/CS184848B2/cs unknown
- 1974-06-25 DD DD188247A patent/DD120432A5/xx unknown
- 1974-06-25 CS CS7600006394A patent/CS184847B2/cs unknown
- 1974-06-25 FR FR7422133A patent/FR2233937A1/fr active Granted
- 1974-06-25 CH CH872274A patent/CH605613A5/xx not_active IP Right Cessation
- 1974-06-25 RO RO7488141A patent/RO70150A/ro unknown
- 1974-06-25 CH CH1229277A patent/CH605618A5/xx not_active IP Right Cessation
- 1974-06-25 CS CS7400004463A patent/CS184828B2/cs unknown
1988
- 1988-01-08 NL NL8800037A patent/NL8800037A/nl active Search and Examination

Also Published As

Publication number	Publication date
HU170762B (hu)	1977-09-28
AR214707A1 (es)	1979-07-31
DE2429958A1 (de)	1975-01-16
YU174874A (en)	1982-02-28
CS184828B2 (en)	1978-09-15
NL183579C (nl)	1988-12-01
FR2233937B1 (cs)	1979-02-09
RO70074A (ro)	1980-06-15
DE2429958C2 (de)	1985-04-11
AU6958774A (en)	1975-12-04
NL8800037A (nl)	1988-05-02
SE7408285L (cs)	1975-02-24
FR2233937A1 (en)	1975-01-17
JPS5052033A (cs)	1975-05-09
SE416198B (sv)	1980-12-08
SU897108A3 (ru)	1982-01-07
IL44927A (en)	1979-07-25
YU39721B (en)	1985-04-30
DD120432A5 (cs)	1976-06-12
IT1016118B (it)	1977-05-30
NL183579B (nl)	1988-07-01
CS184848B2 (en)	1978-09-15
DD115111A5 (cs)	1975-09-12
CS184847B2 (en)	1978-09-15
CH605613A5 (cs)	1978-09-29
CH605618A5 (cs)	1978-09-29
DD120431A5 (cs)	1976-06-12
BR7405158D0 (pt)	1975-01-07
IN139715B (cs)	1976-07-24
DK152751B (da)	1988-05-09
NL7408514A (cs)	1974-12-30
CH605612A5 (cs)	1978-09-29
RO70150A (ro)	1981-07-30
BG25788A3 (en)	1978-12-12
DK338974A (cs)	1975-02-24
PL93741B1 (cs)	1977-06-30
IL44927A0 (en)	1974-07-31
DK152751C (da)	1988-10-03

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JPS609706B2 (ja)	1985-03-12	アミノジフェニルエ−テル類の製造法
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