SK14799A3 - Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-(perfluoroalkylmethyl)arylimidoyl chloride compounds - Google Patents

Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-(perfluoroalkylmethyl)arylimidoyl chloride compounds Download PDF

Info

Publication number: SK14799A3
Authority: SK; Slovakia
Prior art keywords: atom; formula; group; compound; carbon atoms
Prior art date: 1998-02-09

Application number

SK147-99A

Other languages

English (en)

Slovak (sk)

Inventor

Venkataraman Kameswaran

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.)

1998-02-09

Filing date

1999-02-05

Publication date

2000-02-14

1999-02-05 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

2000-02-14 Publication of SK14799A3 publication Critical patent/SK14799A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 28
150000001805 chlorine compounds Chemical class 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 48
150000001875 compounds Chemical class 0.000 claims abstract description 53
-1 OCF2O Chemical group 0.000 claims abstract description 20
239000002904 solvent Substances 0.000 claims abstract description 14
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
229910052740 iodine Inorganic materials 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 20
239000002585 base Substances 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
150000002366 halogen compounds Chemical class 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 abstract description 5
125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 4
229910020587 CmF2m+1 Inorganic materials 0.000 abstract 1
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000004995 haloalkylthio group Chemical group 0.000 abstract 1
125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
150000003233 pyrroles Chemical class 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 5
238000007059 Strecker synthesis reaction Methods 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
JTXQPKNGMDLCTP-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound FC(F)(F)C=1NC=CC=1C#N JTXQPKNGMDLCTP-UHFFFAOYSA-N 0.000 description 4
NTFBKFBCYPRUNB-UHFFFAOYSA-N 4-chloro-n-(2,2,2-trifluoroethyl)benzamide Chemical compound FC(F)(F)CNC(=O)C1=CC=C(Cl)C=C1 NTFBKFBCYPRUNB-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 3
PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 3
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
125000005010 perfluoroalkyl group Chemical group 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
ZTUJDPKOHPKRMO-UHFFFAOYSA-N hydron;2,2,2-trifluoroethanamine;chloride Chemical compound Cl.NCC(F)(F)F ZTUJDPKOHPKRMO-UHFFFAOYSA-N 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FLXSJBCHYNFRKG-UHFFFAOYSA-N 1,4-diazabicyclo[2.2.2]octane;pyridine Chemical compound C1=CC=NC=C1.C1CN2CCN1CC2 FLXSJBCHYNFRKG-UHFFFAOYSA-N 0.000 description 1
LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 1
PWEQOMAXYSTWDN-UHFFFAOYSA-N 2,2,2-trifluoroethanimidoyl chloride Chemical class FC(F)(F)C(Cl)=N PWEQOMAXYSTWDN-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
IVDHYYCFEMRCDZ-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-pyrrole Chemical class FC(F)(F)C1=CC=CN1 IVDHYYCFEMRCDZ-UHFFFAOYSA-N 0.000 description 1
VMJMHIUECKNSMV-UHFFFAOYSA-N 3,4-dichloro-n-(2,2,2-trifluoroethyl)benzenecarboximidoyl chloride Chemical compound FC(F)(F)CN=C(Cl)C1=CC=C(Cl)C(Cl)=C1 VMJMHIUECKNSMV-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
PRAFKAQJQHJMQG-UHFFFAOYSA-N 3,5-dichloro-n-(2,2,2-trifluoroethyl)benzamide Chemical compound FC(F)(F)CNC(=O)C1=CC(Cl)=CC(Cl)=C1 PRAFKAQJQHJMQG-UHFFFAOYSA-N 0.000 description 1
GGHLXLVPNZMBQR-UHFFFAOYSA-N 3,5-dichlorobenzoyl chloride Chemical group ClC(=O)C1=CC(Cl)=CC(Cl)=C1 GGHLXLVPNZMBQR-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
ZJHQQCDVIVSDMQ-UHFFFAOYSA-N 4-chloro-n-(2,2,2-trifluoroethyl)benzenecarboximidoyl chloride Chemical compound FC(F)(F)CN=C(Cl)C1=CC=C(Cl)C=C1 ZJHQQCDVIVSDMQ-UHFFFAOYSA-N 0.000 description 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000005219 aminonitrile group Chemical group 0.000 description 1
229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000003936 benzamides Chemical class 0.000 description 1
IAHMNSCQDXESII-UHFFFAOYSA-N benzenecarboximidoyl chloride Chemical class ClC(=N)C1=CC=CC=C1 IAHMNSCQDXESII-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method 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
238000006352 cycloaddition reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
NDMHJEXUTLCTLH-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carboxylate Chemical compound C1=C(C(F)(F)F)NC(C=2C=CC(Cl)=CC=2)=C1C(=O)OC NDMHJEXUTLCTLH-UHFFFAOYSA-N 0.000 description 1
AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002699 waste material Substances 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
- 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
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK147-99A 1998-02-09 1999-02-05 Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-(perfluoroalkylmethyl)arylimidoyl chloride compounds SK14799A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US09/020,648 US5817834A (en)	1998-02-09	1998-02-09	Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-(perfluoroalkyl-methyl) arylimidoyl chloride compounds

Publications (1)

Publication Number	Publication Date
SK14799A3 true SK14799A3 (en)	2000-02-14

Family

ID=21799807

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK147-99A SK14799A3 (en)	1998-02-09	1999-02-05	Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-(perfluoroalkylmethyl)arylimidoyl chloride compounds

Country Status (19)

Country	Link
US (1)	US5817834A (cs)
EP (1)	EP0934930B1 (cs)
JP (1)	JP4451938B2 (cs)
KR (1)	KR19990072455A (cs)
CN (1)	CN1230539A (cs)
AR (1)	AR016449A1 (cs)
AT (1)	ATE421950T1 (cs)
AU (1)	AU1548099A (cs)
BR (1)	BR9900544A (cs)
CA (1)	CA2260699A1 (cs)
CZ (1)	CZ35899A3 (cs)
DE (1)	DE69940362D1 (cs)
DK (1)	DK0934930T3 (cs)
ES (1)	ES2318883T3 (cs)
HU (1)	HUP9900273A1 (cs)
IL (1)	IL128342A0 (cs)
PT (1)	PT934930E (cs)
SK (1)	SK14799A3 (cs)
ZA (1)	ZA99939B (cs)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
ZA200001195B (en) *	1999-03-09	2000-10-18	American Cyanamid Co	Process for the preparation of 2-Aryl-5-(Perfluoro-Alkyl) Pyrrole Compounds from N-[1-Chloro-1-(Perfluoroalkyl) Methyl] 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
US6805940B2 (en) *	2001-09-10	2004-10-19	3M Innovative Properties Company	Method for making conductive circuits using powdered metals
US7102522B2 (en) *	2002-12-24	2006-09-05	3M Innovative Properties Company	Tamper-indicating radio frequency identification antenna and sticker, a radio frequency identification antenna, and methods of using the same
US6816125B2 (en) *	2003-03-01	2004-11-09	3M Innovative Properties Company	Forming electromagnetic communication circuit components using densified metal powder
EP1661886B1 (en)	2003-08-29	2016-08-10	Mitsui Chemicals Agro, Inc.	Insecticide for agricultural or horticultural use and method of use thereof
US20070218258A1 (en) *	2006-03-20	2007-09-20	3M Innovative Properties Company	Articles and methods including patterned substrates formed from densified, adhered metal powders
US20080143519A1 (en) *	2006-12-19	2008-06-19	3M Innovative Properties Company	Tamper-indicating radio frequency identification tag and methods of indicating tampering of a radio frequency identification tag
BR112014004945A2 (pt) *	2011-09-01	2017-03-21	Biotelliga Holdings Ltd	agentes lipídicos de inseticida isolados de fugos entomopatogênicos e usos dos mesmos

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5010098A (en) *	1987-07-29	1991-04-23	American Cyanamid Company	Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
US5068390A (en) *	1990-07-31	1991-11-26	American Cyanamid Company	1,1,1-trifluoro-2-propene compounds
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
US5449789A (en) *	1992-11-30	1995-09-12	American Cyanamid Company	Debrominative chlorination of pyrroles
US5359090A (en) *	1993-12-29	1994-10-25	American Cyanamid Company	Alkoxymethylation of pyrroles
US5426225A (en) *	1993-12-30	1995-06-20	American Cyanamid Company	Perfluoroalkanoyl aminonitriles
US5446170A (en) *	1994-11-22	1995-08-29	American Cyanamid Company	Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates

1998
- 1998-02-09 US US09/020,648 patent/US5817834A/en not_active Expired - Lifetime
1999
- 1999-02-02 IL IL12834299A patent/IL128342A0/xx unknown
- 1999-02-03 DE DE69940362T patent/DE69940362D1/de not_active Expired - Lifetime
- 1999-02-03 CZ CZ99358A patent/CZ35899A3/cs unknown
- 1999-02-03 PT PT99300810T patent/PT934930E/pt unknown
- 1999-02-03 DK DK99300810T patent/DK0934930T3/da active
- 1999-02-03 ES ES99300810T patent/ES2318883T3/es not_active Expired - Lifetime
- 1999-02-03 AT AT99300810T patent/ATE421950T1/de active
- 1999-02-03 EP EP99300810A patent/EP0934930B1/en not_active Expired - Lifetime
- 1999-02-05 ZA ZA9900939A patent/ZA99939B/xx unknown
- 1999-02-05 AU AU15480/99A patent/AU1548099A/en not_active Abandoned
- 1999-02-05 CA CA002260699A patent/CA2260699A1/en not_active Abandoned
- 1999-02-05 SK SK147-99A patent/SK14799A3/sk unknown
- 1999-02-05 KR KR1019990003969A patent/KR19990072455A/ko not_active Withdrawn
- 1999-02-08 BR BR9900544-1A patent/BR9900544A/pt not_active Application Discontinuation
- 1999-02-08 AR ARP990100535A patent/AR016449A1/es unknown
- 1999-02-08 HU HU9900273A patent/HUP9900273A1/hu unknown
- 1999-02-09 JP JP03142899A patent/JP4451938B2/ja not_active Expired - Fee Related
- 1999-02-09 CN CN99102354A patent/CN1230539A/zh active Pending

Also Published As

Publication number	Publication date
EP0934930A1 (en)	1999-08-11
AR016449A1 (es)	2001-07-04
IL128342A0 (en)	2000-01-31
ATE421950T1 (de)	2009-02-15
ES2318883T3 (es)	2009-05-01
JPH11286480A (ja)	1999-10-19
CZ35899A3 (cs)	1999-09-15
AU1548099A (en)	1999-08-26
CA2260699A1 (en)	1999-08-09
ZA99939B (en)	2000-08-07
HUP9900273A1 (hu)	2000-03-28
DK0934930T3 (da)	2009-05-04
BR9900544A (pt)	2000-05-09
CN1230539A (zh)	1999-10-06
JP4451938B2 (ja)	2010-04-14
US5817834A (en)	1998-10-06
DE69940362D1 (de)	2009-03-19
HU9900273D0 (en)	1999-04-28
PT934930E (pt)	2009-02-11
EP0934930B1 (en)	2009-01-28
KR19990072455A (ko)	1999-09-27

Publication	Publication Date	Title
SK14799A3 (en)	2000-02-14	Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-(perfluoroalkylmethyl)arylimidoyl chloride compounds
KR100236237B1 (ko)	2001-11-22	2-아릴-3-치환-5-(트리플루오로메틸)피롤화합물의제조방법
US5574175A (en)	1996-11-12	Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates
US6011161A (en)	2000-01-04	Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoro-alkylmethyl)arylimidoyl chloride compounds
EP0934929B1 (en)	2003-09-17	Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds
US6133455A (en)	2000-10-17	Process for the preparation of 2-aryl-5(perfluoro-alkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds
US5965773A (en)	1999-10-12	Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(perfluoroalkylmethyl) arylimidoyl chloride compounds
US6320059B1 (en)	2001-11-20	Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds
EP1035113B1 (en)	2004-10-06	Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds
US5631379A (en)	1997-05-20	Oxazole amines as intermediates in the manufacture of insecticidal pyrroles
MXPA99001252A (en)	2000-10-01	Process for the preparation of compounds of 2-aril-5- (perfluoroalquil) pirrol from n-perfluroalquilmetil chloride compounds) arilimide
CZ2000753A3 (cs)	2001-03-14	Způsob přípravy 2-aryl-5- (perfluoroalkyl)pyrrolových sloučenin z N-[lchloro-1- (perfluoroalkyl)methyl]arylimidoylchloridových sloučenin
MXPA00002257A (en)	2002-06-05	Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from n-[1-chloro-1-(perfluoroalkyl) methyl]arylimidoyl chloride compounds
MXPA99001261A (en)	2000-10-01	Process for the preparation of compounds of 2-aril-5- (perfluoroalquil) pirrol from compounds n- (arilmetilen) -1-chlorine-1- (perfluoroalquil) metilam
JPH1072435A (ja)	1998-03-17	２−アリール−５−パーフルオロアルキルピロール誘導体及びその有用な中間体の製造方法