CH615902A5 - Process for the preparation of substituted anilines - Google Patents
Process for the preparation of substituted anilines Download PDFInfo
- Publication number
- CH615902A5 CH615902A5 CH99076A CH99076A CH615902A5 CH 615902 A5 CH615902 A5 CH 615902A5 CH 99076 A CH99076 A CH 99076A CH 99076 A CH99076 A CH 99076A CH 615902 A5 CH615902 A5 CH 615902A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- pentafluoroethyl
- nitro
- aniline
- compounds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 238000000034 method Methods 0.000 title description 20
- 150000001448 anilines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 238000006396 nitration reaction Methods 0.000 abstract description 3
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 abstract description 3
- 230000021736 acetylation Effects 0.000 abstract description 2
- 238000006640 acetylation reaction Methods 0.000 abstract description 2
- 230000031709 bromination Effects 0.000 abstract description 2
- 238000005893 bromination reaction Methods 0.000 abstract description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010932 ethanolysis reaction Methods 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract description 2
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- DHBQQUHYERQIMY-UHFFFAOYSA-N 4-(1,1,2,2,2-pentafluoroethyl)aniline Chemical class NC1=CC=C(C(F)(F)C(F)(F)F)C=C1 DHBQQUHYERQIMY-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- NWBQMKBXBNAKQN-UHFFFAOYSA-N 1-nitro-4-(1,1,2,2,2-pentafluoroethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1 NWBQMKBXBNAKQN-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- OIICZKWDOWBHOS-UHFFFAOYSA-N 1-nitro-2-(1,1,2,2,2-pentafluoroethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C(F)(F)C(F)(F)F OIICZKWDOWBHOS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- CAVBHMKSRANXFK-UHFFFAOYSA-N 4-nitro-2-(1,1,2,2,2-pentafluoroethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)C(F)(F)F CAVBHMKSRANXFK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 pentafluorethyl group Chemical group 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- FFQPDUGBEKSZFP-UHFFFAOYSA-N 2-bromo-4-nitro-6-(1,1,2,2,2-pentafluoroethyl)aniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C(F)(F)C(F)(F)F FFQPDUGBEKSZFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- DSSICQPAVDRLMY-UHFFFAOYSA-N n-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(F)(F)C(F)(F)F)C=C1 DSSICQPAVDRLMY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- IFMXZOQJOVKHRX-UHFFFAOYSA-N 2,6-dinitro-4-(1,1,2,2,2-pentafluoroethyl)aniline Chemical compound [N+](=O)([O-])C1=C(N)C(=CC(=C1)C(C(F)(F)F)(F)F)[N+](=O)[O-] IFMXZOQJOVKHRX-UHFFFAOYSA-N 0.000 description 1
- JPKZRAFDDPJCJT-UHFFFAOYSA-N 2-(1,1,2,2,2-pentafluoroethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)C(F)(F)F JPKZRAFDDPJCJT-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NSDADRWXGNPBNW-UHFFFAOYSA-N 2-nitro-4-(1,1,2,2,2-pentafluoroethyl)aniline Chemical compound NC1=CC=C(C(F)(F)C(F)(F)F)C=C1[N+]([O-])=O NSDADRWXGNPBNW-UHFFFAOYSA-N 0.000 description 1
- KIWAQODFYXPPHZ-UHFFFAOYSA-N 4-amino-3-(1,1,2,2,2-pentafluoroethyl)benzenesulfonic acid Chemical compound S(=O)(=O)(O)C1=CC(=C(N)C=C1)C(C(F)(F)F)(F)F KIWAQODFYXPPHZ-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical class NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- ASSTYWZHGPZAHH-UHFFFAOYSA-N n-[2-(1,1,2,2,2-pentafluoroethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(F)(F)C(F)(F)F ASSTYWZHGPZAHH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7505410A FR2301511A1 (fr) | 1975-02-21 | 1975-02-21 | Pentafluorsethylarylamines et leurs procedes de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615902A5 true CH615902A5 (en) | 1980-02-29 |
Family
ID=9151527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH99076A CH615902A5 (en) | 1975-02-21 | 1976-01-27 | Process for the preparation of substituted anilines |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS51110525A (it) |
| BE (1) | BE838809A (it) |
| BR (1) | BR7601069A (it) |
| CH (1) | CH615902A5 (it) |
| DE (1) | DE2606982A1 (it) |
| FR (1) | FR2301511A1 (it) |
| GB (1) | GB1535234A (it) |
| IT (1) | IT1070239B (it) |
| NL (1) | NL7601722A (it) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058907B2 (ja) * | 1979-06-06 | 1985-12-23 | 財団法人相模中央化学研究所 | ペルフルオロアルキル化合物及びその製造方法 |
| DE3669709D1 (de) * | 1985-05-22 | 1990-04-26 | Rhone Poulenc Chimie | Verfahren zur perfluoralkylierung von aromatischen derivaten. |
| FR2582301B1 (fr) * | 1985-05-22 | 1987-07-10 | Rhone Poulenc Spec Chim | Procede de preparation de (perfluoroalkylaryl)amines |
| US6362369B2 (en) | 1997-11-25 | 2002-03-26 | Nihon Nohyaku Co., Ltd. | Phthalic acid diamide derivatives fluorine-containing aniline compounds as starting material, agricultural and horticultural insecticides, and a method for application of the insecticides |
| DE69916512T2 (de) * | 1998-02-17 | 2004-08-19 | Nihon Nohyaku Co., Ltd. | Fluor enthaltende Anilin-Verbindungen |
| AU731777B2 (en) | 1998-11-30 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Aniline derivative and process for producing the same |
| KR100891599B1 (ko) | 2003-08-29 | 2009-04-08 | 미쓰이 가가쿠 가부시키가이샤 | 농업용 또는 원예용 살충제 및 그의 이용 방법 |
| JP5895454B2 (ja) * | 2011-11-09 | 2016-03-30 | ユニマテック株式会社 | ω−ヨードパーフルオロアルキル置換アニリン誘導体およびその製造法 |
-
1975
- 1975-02-21 FR FR7505410A patent/FR2301511A1/fr active Granted
-
1976
- 1976-01-27 CH CH99076A patent/CH615902A5/fr not_active IP Right Cessation
- 1976-02-20 DE DE19762606982 patent/DE2606982A1/de active Pending
- 1976-02-20 GB GB673976A patent/GB1535234A/en not_active Expired
- 1976-02-20 NL NL7601722A patent/NL7601722A/xx not_active Application Discontinuation
- 1976-02-20 IT IT6739476A patent/IT1070239B/it active
- 1976-02-20 BR BR7601069A patent/BR7601069A/pt unknown
- 1976-02-20 BE BE164527A patent/BE838809A/xx unknown
- 1976-02-20 JP JP1783276A patent/JPS51110525A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR7601069A (pt) | 1976-09-14 |
| FR2301511B1 (it) | 1978-09-22 |
| IT1070239B (it) | 1985-03-29 |
| GB1535234A (en) | 1978-12-13 |
| JPS51110525A (ja) | 1976-09-30 |
| FR2301511A1 (fr) | 1976-09-17 |
| NL7601722A (nl) | 1976-08-24 |
| BE838809A (fr) | 1976-08-20 |
| DE2606982A1 (de) | 1976-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |