CZ286772B6 - Process for preparing arylpyrrole compounds and intermediates for their preparation - Google Patents
Process for preparing arylpyrrole compounds and intermediates for their preparation Download PDFInfo
- Publication number
- CZ286772B6 CZ286772B6 CZ19952887A CZ288795A CZ286772B6 CZ 286772 B6 CZ286772 B6 CZ 286772B6 CZ 19952887 A CZ19952887 A CZ 19952887A CZ 288795 A CZ288795 A CZ 288795A CZ 286772 B6 CZ286772 B6 CZ 286772B6
- Authority
- CZ
- Czechia
- Prior art keywords
- formula
- alkyl
- halogen
- haloalkyl
- carbon atoms
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Chemical group 0.000 abstract description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 6
- ZXLQPJBQKJYNGN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound N1C(C(F)(F)F)=CC(C#N)=C1C1=CC=C(Cl)C=C1 ZXLQPJBQKJYNGN-UHFFFAOYSA-N 0.000 description 5
- 150000003233 pyrroles Chemical class 0.000 description 5
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- LFUMGEZWRAFYQW-UHFFFAOYSA-N n-[(4-chlorophenyl)-cyanomethyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NC(C#N)C1=CC=C(Cl)C=C1 LFUMGEZWRAFYQW-UHFFFAOYSA-N 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001422 N-substituted pyrroles Chemical class 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- QJQGMOIUEXCUOH-UHFFFAOYSA-N 1,3-oxazole;1h-pyrrole Chemical compound C=1C=CNC=1.C1=COC=N1 QJQGMOIUEXCUOH-UHFFFAOYSA-N 0.000 description 1
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 description 1
- RJJDLPQZNANQDQ-UHFFFAOYSA-N 2,3-dichloropropanenitrile Chemical compound ClCC(Cl)C#N RJJDLPQZNANQDQ-UHFFFAOYSA-N 0.000 description 1
- JTXQPKNGMDLCTP-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical class FC(F)(F)C=1NC=CC=1C#N JTXQPKNGMDLCTP-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- DQRFCVHLNUNVPL-UHFFFAOYSA-N 2h-1,3-oxazol-5-one Chemical compound O=C1OCN=C1 DQRFCVHLNUNVPL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001364932 Chrysodeixis Species 0.000 description 1
- 241000255990 Helicoverpa Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000255985 Trichoplusia Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- JXYQFUKJZRPXCZ-UHFFFAOYSA-N ethanol;trifluoroborane Chemical compound CCO.FB(F)F JXYQFUKJZRPXCZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/343,147 US5446170A (en) | 1994-11-22 | 1994-11-22 | Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ288795A3 CZ288795A3 (en) | 1996-06-12 |
| CZ286772B6 true CZ286772B6 (en) | 2000-07-12 |
Family
ID=23344892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19952887A CZ286772B6 (en) | 1994-11-22 | 1995-11-06 | Process for preparing arylpyrrole compounds and intermediates for their preparation |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5446170A (enExample) |
| EP (1) | EP0713868B1 (enExample) |
| JP (1) | JP3781464B2 (enExample) |
| KR (1) | KR960017638A (enExample) |
| CN (1) | CN1133836A (enExample) |
| AR (1) | AR000173A1 (enExample) |
| AT (1) | ATE212012T1 (enExample) |
| AU (1) | AU701087B2 (enExample) |
| BR (1) | BR9505251A (enExample) |
| CA (1) | CA2163327A1 (enExample) |
| CZ (1) | CZ286772B6 (enExample) |
| DE (1) | DE69525021T2 (enExample) |
| ES (1) | ES2170785T3 (enExample) |
| HU (1) | HU217922B (enExample) |
| IL (1) | IL116070A0 (enExample) |
| SK (1) | SK143895A3 (enExample) |
| TW (1) | TW296379B (enExample) |
| ZA (1) | ZA959949B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659046A (en) * | 1993-12-30 | 1997-08-19 | American Cyanamid Company | Method for the preparation of 2-perfluoroalkyl-3-oxazolin-5-one |
| US5750726A (en) * | 1996-06-28 | 1998-05-12 | American Cyanamid Company | Process for the manufacture of 2-aryl-5-perfluoroalkylpyrrole derivatives and intermediates useful therefor |
| TW381087B (en) * | 1996-06-28 | 2000-02-01 | American Cyanamid Co | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles |
| US5925773A (en) * | 1996-06-28 | 1999-07-20 | American Cyanamid Company | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use thereof in the manufacture of insecticidal arylpyrroles |
| US5945538A (en) * | 1996-06-28 | 1999-08-31 | American Cyanamid Company | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles |
| US5777132A (en) * | 1996-06-28 | 1998-07-07 | American Cyanamid Company | Process for the manufacture of 2-aryl-5 perfluoroalkylpyrrole derivatives |
| US5817834A (en) * | 1998-02-09 | 1998-10-06 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-(perfluoroalkyl-methyl) arylimidoyl chloride compounds |
| US6133455A (en) * | 1998-02-09 | 2000-10-17 | American Cyanamid Company | Process for the preparation of 2-aryl-5(perfluoro-alkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds |
| US6011161A (en) * | 1998-02-09 | 2000-01-04 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoro-alkylmethyl)arylimidoyl chloride compounds |
| US5965773A (en) * | 1998-02-09 | 1999-10-12 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(perfluoroalkylmethyl) arylimidoyl chloride compounds |
| US6320059B1 (en) | 2000-03-07 | 2001-11-20 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds |
| CN103058946A (zh) * | 2012-12-19 | 2013-04-24 | 浙江工业大学 | 一种2,5-二取代噁唑衍生物的制备方法 |
| JP7260480B2 (ja) | 2017-03-13 | 2023-04-18 | ビーエーエスエフ アグロ ベー．ブイ． | Ｄｉｐｅａ塩基の存在下でのアリールピロール化合物の製造 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030735A (en) * | 1990-07-31 | 1991-07-09 | American Cyanamid Company | Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds |
| US5118816A (en) * | 1990-12-26 | 1992-06-02 | American Cyanamid Company | 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles |
| YU8592A (sh) * | 1991-08-28 | 1994-06-10 | Flumroc Ag. | Postupak i uređaj za izradu ploča od mineralnih vlakana primenjenih kao nosač zidnog premaza |
| US5130328A (en) * | 1991-09-06 | 1992-07-14 | American Cyanamid Company | N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents |
| US5145986A (en) * | 1991-09-09 | 1992-09-08 | American Cyanamid Company | Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds from N-(substituted benzyl)-2,2,2-trifluoro-acetimidoyl chloride compounds |
| CN1074439A (zh) * | 1992-01-17 | 1993-07-21 | 中国科学院上海有机化学研究所 | 一种从三氟甲基唑酮合成三氟甲基吡咯类化合物的方法 |
| US5286743A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-aminoalkylcarbonyloxyalkylpyrrole insecticidal acaricidal and molluscicidal agents |
| US5426225A (en) | 1993-12-30 | 1995-06-20 | American Cyanamid Company | Perfluoroalkanoyl aminonitriles |
-
1994
- 1994-11-22 US US08/343,147 patent/US5446170A/en not_active Expired - Lifetime
-
1995
- 1995-05-16 US US08/442,045 patent/US5574175A/en not_active Expired - Fee Related
- 1995-08-10 TW TW084108310A patent/TW296379B/zh active
- 1995-11-06 CZ CZ19952887A patent/CZ286772B6/cs not_active IP Right Cessation
- 1995-11-16 SK SK1438-95A patent/SK143895A3/sk unknown
- 1995-11-17 JP JP32383695A patent/JP3781464B2/ja not_active Expired - Fee Related
- 1995-11-20 CA CA002163327A patent/CA2163327A1/en not_active Abandoned
- 1995-11-21 DE DE69525021T patent/DE69525021T2/de not_active Expired - Lifetime
- 1995-11-21 BR BR9505251A patent/BR9505251A/pt not_active IP Right Cessation
- 1995-11-21 IL IL11607095A patent/IL116070A0/xx unknown
- 1995-11-21 KR KR1019950042446A patent/KR960017638A/ko not_active Abandoned
- 1995-11-21 AT AT95308298T patent/ATE212012T1/de not_active IP Right Cessation
- 1995-11-21 HU HU9503324A patent/HU217922B/hu not_active IP Right Cessation
- 1995-11-21 EP EP95308298A patent/EP0713868B1/en not_active Expired - Lifetime
- 1995-11-21 ES ES95308298T patent/ES2170785T3/es not_active Expired - Lifetime
- 1995-11-21 AR AR33431495A patent/AR000173A1/es unknown
- 1995-11-22 CN CN95118932A patent/CN1133836A/zh active Pending
- 1995-11-22 ZA ZA959949A patent/ZA959949B/xx unknown
- 1995-11-22 AU AU39017/95A patent/AU701087B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2163327A1 (en) | 1996-05-23 |
| CN1133836A (zh) | 1996-10-23 |
| JPH08225522A (ja) | 1996-09-03 |
| JP3781464B2 (ja) | 2006-05-31 |
| ES2170785T3 (es) | 2002-08-16 |
| HU217922B (hu) | 2000-05-28 |
| EP0713868A1 (en) | 1996-05-29 |
| US5446170A (en) | 1995-08-29 |
| AU3901795A (en) | 1996-05-30 |
| BR9505251A (pt) | 1997-09-16 |
| CZ288795A3 (en) | 1996-06-12 |
| DE69525021T2 (de) | 2002-07-18 |
| ZA959949B (en) | 1997-05-22 |
| IL116070A0 (en) | 1996-01-31 |
| HU9503324D0 (en) | 1996-01-29 |
| AU701087B2 (en) | 1999-01-21 |
| DE69525021D1 (de) | 2002-02-21 |
| EP0713868B1 (en) | 2002-01-16 |
| US5574175A (en) | 1996-11-12 |
| KR960017638A (ko) | 1996-06-17 |
| AR000173A1 (es) | 1997-05-21 |
| ATE212012T1 (de) | 2002-02-15 |
| SK143895A3 (en) | 1996-09-04 |
| TW296379B (enExample) | 1997-01-21 |
| HUT73018A (en) | 1996-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20011106 |