CA1248138A - Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique - Google Patents

Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique

Info

Publication number: CA1248138A
Authority: CA; Canada
Prior art keywords: fluoride; trifluoromethyl; anthraniloyl; reaction; hydrogen fluoride
Prior art date: 1983-06-15
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

CA000549081A

Other languages

English (en)

Inventor

Henry C. Lin

Byron R. Cotter

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.)

Occidental Chemical Corp

Original Assignee

Occidental Chemical Corp

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.)

1983-06-15

Filing date

1987-10-09

Publication date

1989-01-03

1983-06-15 Priority claimed from US06/504,637 external-priority patent/US4481370A/en

1983-06-15 Priority claimed from US06/504,636 external-priority patent/US4466927A/en

1984-06-01 Priority claimed from CA000455705A external-priority patent/CA1232286A/fr

1987-10-09 Application filed by Occidental Chemical Corp filed Critical Occidental Chemical Corp

1987-10-09 Priority to CA000549081A priority Critical patent/CA1248138A/fr

1989-01-03 Application granted granted Critical

1989-01-03 Publication of CA1248138A publication Critical patent/CA1248138A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 31
238000000034 method Methods 0.000 title claims abstract description 30
MWAVGMOUEMRXSM-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]carbamoyl fluoride Chemical compound FC(=O)NC1=CC=CC=C1C(F)(F)F MWAVGMOUEMRXSM-UHFFFAOYSA-N 0.000 title claims abstract description 24
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 71
229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 60
XGLYAMHQMRUXBK-UHFFFAOYSA-N 2-(trifluoromethylamino)benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1NC(F)(F)F XGLYAMHQMRUXBK-UHFFFAOYSA-N 0.000 claims abstract description 24
238000006243 chemical reaction Methods 0.000 claims description 62
-1 phenyl- Chemical group 0.000 claims description 40
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 12
238000006317 isomerization reaction Methods 0.000 claims description 12
VAKRHEJOLWOBBZ-UHFFFAOYSA-N 1-isocyanato-2-(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1N=C=O VAKRHEJOLWOBBZ-UHFFFAOYSA-N 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 26
DZXAINSCQJRLEG-UHFFFAOYSA-N n-phenylcarbamoyl fluoride Chemical class FC(=O)NC1=CC=CC=C1 DZXAINSCQJRLEG-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical class NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 10
239000007795 chemical reaction product Substances 0.000 description 10
239000007789 gas Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000000376 reactant Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000012948 isocyanate Substances 0.000 description 8
239000007791 liquid phase Substances 0.000 description 8
230000008569 process Effects 0.000 description 8
239000000047 product Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000007788 liquid Substances 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
239000012808 vapor phase Substances 0.000 description 7
238000013019 agitation Methods 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000011065 in-situ storage Methods 0.000 description 6
YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 6
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 6
150000004982 aromatic amines Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
229940058401 polytetrafluoroethylene Drugs 0.000 description 5
229920001343 polytetrafluoroethylene Polymers 0.000 description 5
239000004810 polytetrafluoroethylene Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 4
CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000006053 organic reaction Methods 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000000926 separation method Methods 0.000 description 3
AQYMFHBGGLTMEN-UHFFFAOYSA-N 2-(trifluoromethyl)aniline;hydrofluoride Chemical compound F.NC1=CC=CC=C1C(F)(F)F AQYMFHBGGLTMEN-UHFFFAOYSA-N 0.000 description 2
NSPRKIATGBHBRE-UHFFFAOYSA-N 2-aminobenzoyl fluoride Chemical compound NC1=CC=CC=C1C(F)=O NSPRKIATGBHBRE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000011968 lewis acid catalyst Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
XTYOTPBIDRGAML-UHFFFAOYSA-N 1-(chloromethyl)-2-isocyanatobenzene Chemical class ClCC1=CC=CC=C1N=C=O XTYOTPBIDRGAML-UHFFFAOYSA-N 0.000 description 1
RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 1
NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical class FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
CPLHJFDXCHVSHW-UHFFFAOYSA-N 3,4,5-trifluoro-2-methylaniline Chemical compound CC1=C(N)C=C(F)C(F)=C1F CPLHJFDXCHVSHW-UHFFFAOYSA-N 0.000 description 1
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
ZHLYHEDQTJZYFI-UHFFFAOYSA-N 4-bromo-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1C(F)(F)F ZHLYHEDQTJZYFI-UHFFFAOYSA-N 0.000 description 1
PHXGKHTWEOPCEW-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C=C1C(F)(F)F PHXGKHTWEOPCEW-UHFFFAOYSA-N 0.000 description 1
AZQHXOGNBRYMQJ-UHFFFAOYSA-N 4-chloro-1-isocyanato-2-(trichloromethyl)benzene Chemical compound ClC1=CC=C(N=C=O)C(C(Cl)(Cl)Cl)=C1 AZQHXOGNBRYMQJ-UHFFFAOYSA-N 0.000 description 1
SBDPJLJFODHSFF-UHFFFAOYSA-N 4-chloro-1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1N=C=O SBDPJLJFODHSFF-UHFFFAOYSA-N 0.000 description 1
ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
206010008583 Chloroma Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
241000694408 Isomeris Species 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000193803 Therea Species 0.000 description 1
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
DQPBABKTKYNPMH-UHFFFAOYSA-M amino sulfate Chemical compound NOS([O-])(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-M 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
FMKDDEABMQRAKW-UHFFFAOYSA-N aniline;hydrofluoride Chemical compound F.NC1=CC=CC=C1 FMKDDEABMQRAKW-UHFFFAOYSA-N 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
CDVVDOZZNDHWCP-UHFFFAOYSA-N n-(fluoromethyl)-n-phenylcarbamoyl fluoride Chemical compound FCN(C(F)=O)C1=CC=CC=C1 CDVVDOZZNDHWCP-UHFFFAOYSA-N 0.000 description 1
SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical class FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
JIIIITWUHCLOJY-UHFFFAOYSA-N n-[3-(trifluoromethyl)phenyl]carbamoyl fluoride Chemical compound FC(=O)NC1=CC=CC(C(F)(F)F)=C1 JIIIITWUHCLOJY-UHFFFAOYSA-N 0.000 description 1
YRDSTBRXHALWFY-UHFFFAOYSA-N n-[4-(trifluoromethyl)phenyl]carbamoyl fluoride Chemical compound FC(=O)NC1=CC=C(C(F)(F)F)C=C1 YRDSTBRXHALWFY-UHFFFAOYSA-N 0.000 description 1
KTXKKCFDLCCZDO-UHFFFAOYSA-N n-[4-chloro-2-(trifluoromethyl)phenyl]carbamoyl fluoride Chemical compound FC(=O)NC1=CC=C(Cl)C=C1C(F)(F)F KTXKKCFDLCCZDO-UHFFFAOYSA-N 0.000 description 1
PUFGEEHFTRCGRD-UHFFFAOYSA-N n-phenyl-n-(trifluoromethyl)carbamoyl fluoride Chemical compound FC(=O)N(C(F)(F)F)C1=CC=CC=C1 PUFGEEHFTRCGRD-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000003128 rodenticide Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229940070710 valerate Drugs 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000549081A 1983-06-15 1987-10-09 Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique Expired CA1248138A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000549081A CA1248138A (fr)	1983-06-15	1987-10-09	Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US06/504,637 US4481370A (en)	1983-06-15	1983-06-15	Method for the preparation of benzenamines
US06/504,636 US4466927A (en)	1983-06-15	1983-06-15	Method for the preparation of 2-(trifluoromethyl)phenyl carbamic fluoride
US504,636		1983-06-15
US504,637		1983-06-15
CA000455705A CA1232286A (fr)	1983-06-15	1984-06-01	Preparation de benzenamines
CA000549081A CA1248138A (fr)	1983-06-15	1987-10-09	Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000455705A Division CA1232286A (fr)	1983-06-15	1984-06-01	Preparation de benzenamines

Publications (1)

Publication Number	Publication Date
CA1248138A true CA1248138A (fr)	1989-01-03

Family

ID=27167445

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000549081A Expired CA1248138A (fr)	1983-06-15	1987-10-09	Preparation de fluorure 2-(trifluoro-methyl) phenyl-carbamique

Country Status (1)

Country	Link
CA (1)	CA1248138A (fr)

1987
- 1987-10-09 CA CA000549081A patent/CA1248138A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-01-03	MKEX	Expiry

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