CH642615A5 - Diphenylaether und verfahren zu deren herstellung. - Google Patents
Diphenylaether und verfahren zu deren herstellung. Download PDFInfo
- Publication number
- CH642615A5 CH642615A5 CH588879A CH588879A CH642615A5 CH 642615 A5 CH642615 A5 CH 642615A5 CH 588879 A CH588879 A CH 588879A CH 588879 A CH588879 A CH 588879A CH 642615 A5 CH642615 A5 CH 642615A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- compound
- trifluoromethylphenyl
- ether
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- XYOIJZIZIQPTOY-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-1-[2-[2-chloro-4-(trifluoromethyl)phenyl]-3-nitrophenoxy]-3-nitrobenzene Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C=1C([N+](=O)[O-])=CC=CC=1OC1=CC=CC([N+]([O-])=O)=C1C1=CC=C(C(F)(F)F)C=C1Cl XYOIJZIZIQPTOY-UHFFFAOYSA-N 0.000 claims description 7
- OIGGYZRCTKUNEY-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-1-[2-[2-chloro-4-(trifluoromethyl)phenyl]-3,4-dinitrophenoxy]-3,4-dinitrobenzene Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C1=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1C1=CC=C(C(F)(F)F)C=C1Cl OIGGYZRCTKUNEY-UHFFFAOYSA-N 0.000 claims description 6
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- -1 4-trifluoromethylphenyl-3-chloro-4-nitro-phenyl ether Chemical compound 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- OACSWVKLYPVBQC-UHFFFAOYSA-N 1-chloro-3-[3-chloro-2-[2-chloro-4-(trifluoromethyl)phenyl]phenoxy]-2-[2-chloro-4-(trifluoromethyl)phenyl]benzene Chemical compound ClC1=CC(C(F)(F)F)=CC=C1C1=C(Cl)C=CC=C1OC1=CC=CC(Cl)=C1C1=CC=C(C(F)(F)F)C=C1Cl OACSWVKLYPVBQC-UHFFFAOYSA-N 0.000 description 2
- GGDYAKVUZMZKRV-UHFFFAOYSA-N 2-fluoroethanol Chemical compound OCCF GGDYAKVUZMZKRV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- HYENCGGZLIWXNP-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-1-[2-[2-chloro-4-(trifluoromethyl)phenyl]-3-(2-fluoroethoxy)-4-nitrophenoxy]-3-(2-fluoroethoxy)-4-nitrobenzene Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C1=C(OCCF)C([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C(OCCF)=C1C1=CC=C(C(F)(F)F)C=C1Cl HYENCGGZLIWXNP-UHFFFAOYSA-N 0.000 description 1
- MPTCHULRGVSVLF-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-1-[2-[2-chloro-4-(trifluoromethyl)phenyl]-3-methylsulfanyl-4-nitrophenoxy]-3-methylsulfanyl-4-nitrobenzene Chemical compound C=1C=C([N+]([O-])=O)C(SC)=C(C=2C(=CC(=CC=2)C(F)(F)F)Cl)C=1OC1=CC=C([N+]([O-])=O)C(SC)=C1C1=CC=C(C(F)(F)F)C=C1Cl MPTCHULRGVSVLF-UHFFFAOYSA-N 0.000 description 1
- DVVTXTPCNPAOLJ-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-3-[2-[2-chloro-4-(trifluoromethyl)phenyl]-3-hydroxy-4-nitrophenoxy]-6-nitrophenol Chemical compound C=1C=C([N+]([O-])=O)C(O)=C(C=2C(=CC(=CC=2)C(F)(F)F)Cl)C=1OC1=CC=C([N+]([O-])=O)C(O)=C1C1=CC=C(C(F)(F)F)C=C1Cl DVVTXTPCNPAOLJ-UHFFFAOYSA-N 0.000 description 1
- NPFLOEPJBAVWDU-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-3-[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-nitro-3-(propylamino)phenoxy]-6-nitro-n-propylaniline Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C=1C(NCCC)=C([N+]([O-])=O)C=CC=1OC1=CC=C([N+]([O-])=O)C(NCCC)=C1C1=CC=C(C(F)(F)F)C=C1Cl NPFLOEPJBAVWDU-UHFFFAOYSA-N 0.000 description 1
- LQCBTSPNQZPYID-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-3-[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-nitro-3-sulfanylphenoxy]-6-nitrobenzenethiol Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C1=C(S)C([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C(S)=C1C1=CC=C(C(F)(F)F)C=C1Cl LQCBTSPNQZPYID-UHFFFAOYSA-N 0.000 description 1
- UNFBXLHCJMSGRQ-UHFFFAOYSA-N 2-chloro-1-[3-[2-chloro-4-(trifluoromethyl)phenoxy]-4-nitrophenoxy]-4-(trifluoromethyl)benzene Chemical compound C1=C(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl UNFBXLHCJMSGRQ-UHFFFAOYSA-N 0.000 description 1
- YNAYWSDJWWDWRR-UHFFFAOYSA-N 2-chloro-1-[3-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]-4-(trifluoromethyl)benzene Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 YNAYWSDJWWDWRR-UHFFFAOYSA-N 0.000 description 1
- YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CEXAQRUPJYFDMZ-UHFFFAOYSA-N 3-chloro-1-[3-chloro-2-[2-chloro-4-(trifluoromethyl)phenyl]-4-nitrophenoxy]-2-[2-chloro-4-(trifluoromethyl)phenyl]-4-nitrobenzene Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C1=C(Cl)C([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1C1=CC=C(C(F)(F)F)C=C1Cl CEXAQRUPJYFDMZ-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- WZUGWKXTWPCGHK-UHFFFAOYSA-N 5-chloro-1-[5-chloro-3-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitrophenoxy]-3-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitrobenzene Chemical compound C1=C(Cl)C=C(C=2C(=CC(=CC=2)C(F)(F)F)Cl)C([N+](=O)[O-])=C1OC(C=1[N+]([O-])=O)=CC(Cl)=CC=1C1=CC=C(C(F)(F)F)C=C1Cl WZUGWKXTWPCGHK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8086078A JPS5513206A (en) | 1978-07-05 | 1978-07-05 | Production of novel diphenyl ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642615A5 true CH642615A5 (de) | 1984-04-30 |
Family
ID=13730084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH588879A CH642615A5 (de) | 1978-07-05 | 1979-06-22 | Diphenylaether und verfahren zu deren herstellung. |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US4277624A (en, 2012) |
| JP (1) | JPS5513206A (en, 2012) |
| CH (1) | CH642615A5 (en, 2012) |
| DE (1) | DE2926829A1 (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR20258A (tr) * | 1978-07-15 | 1980-12-08 | Celamerck Gmbh & Co Kg | 2-klor-6-nitroanilin |
| US4375981A (en) * | 1979-05-14 | 1983-03-08 | Ppg Industries, Inc. | Method for controlling weed growth using herbicidally 5-(2-chloro-4-trifluoromethyl)-, or (4-trifluoromethyl or 2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-substituted carbonyl oxime-O-alkyl ethers |
| DE3300585A1 (de) * | 1983-01-11 | 1984-07-12 | Basf Ag, 6700 Ludwigshafen | Diphenylether, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| US5028732A (en) * | 1983-06-23 | 1991-07-02 | Rohm And Haas Company | Herbicidally active amino diphenyl ethers |
| US4548640A (en) * | 1983-10-21 | 1985-10-22 | Fmc Corporation | Allylthiodiphenyl ether herbicides |
| US4694105A (en) * | 1983-12-20 | 1987-09-15 | Ciba-Geigy Corporation | Herbicidal alkoxyamino- and polyalkoxyaminodiphenyl ethers |
| US4638045A (en) * | 1985-02-19 | 1987-01-20 | Massachusetts Institute Of Technology | Non-peptide polyamino acid bioerodible polymers |
| FR2606944B1 (fr) * | 1986-11-14 | 1989-01-13 | Cables De Lyon Geoffroy Delore | Tete articulee de cable pour liaisons sous-marines |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2988571A (en) * | 1961-06-13 | Dinitrophenoxyethanol process | ||
| US3294847A (en) * | 1962-09-11 | 1966-12-27 | Rohm & Haas | Method for the preparation of ethercontaining chlorides |
| US3376281A (en) * | 1965-09-13 | 1968-04-02 | Union Carbide Corp | Chlorinated hydroxyl-containing compositions and urethane polymers prepared therefrom |
| GB1129175A (en) * | 1966-06-23 | 1968-10-02 | Pfizer Ltd | 4,4'-substituted biphenyls |
| US3849503A (en) * | 1969-10-14 | 1974-11-19 | Ishihara Mining & Chemical Co | Diphenylethers having herbicidal properties |
| US3776961A (en) * | 1971-12-23 | 1973-12-04 | Oil Corp | 3-substituted 4-nitrophenyl halophenyl ethers |
| US3928416A (en) * | 1972-03-14 | 1975-12-23 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
| US4093446A (en) * | 1972-03-14 | 1978-06-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
| US3888932A (en) * | 1972-03-14 | 1975-06-10 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| EG11593A (en) * | 1973-07-03 | 1980-07-31 | Bayer Ag | Halogenated 4-trifluiromethyl-4-cyano-diphenyl-ethers process for their preparation and their use as herbicides |
| JPS5237047B2 (en, 2012) * | 1973-08-28 | 1977-09-20 | ||
| JPS5724761B2 (en, 2012) * | 1973-12-19 | 1982-05-26 | ||
| JPS5735803B2 (en, 2012) * | 1974-12-23 | 1982-07-31 | ||
| EP0014684B1 (de) * | 1979-02-06 | 1982-05-19 | Ciba-Geigy Ag | 2-Substituierte 5-Phenoxy-phenylphosphonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| USRE30361E (en) | 1979-03-09 | 1980-08-05 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US4259510A (en) * | 1979-05-02 | 1981-03-31 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
-
1978
- 1978-07-05 JP JP8086078A patent/JPS5513206A/ja active Granted
-
1979
- 1979-06-22 CH CH588879A patent/CH642615A5/de not_active IP Right Cessation
- 1979-07-03 DE DE19792926829 patent/DE2926829A1/de not_active Ceased
- 1979-07-05 US US06/054,865 patent/US4277624A/en not_active Expired - Lifetime
-
1981
- 1981-01-23 US US06/227,667 patent/US4385189A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4385189A (en) | 1983-05-24 |
| JPS5513206A (en) | 1980-01-30 |
| DE2926829A1 (de) | 1980-01-17 |
| US4277624A (en) | 1981-07-07 |
| JPS6145613B2 (en, 2012) | 1986-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |