IL125997A - Process for the preparation of unsymmetrical 4, 6-bis (aryloxy) pyrimidine compounds - Google Patents
Process for the preparation of unsymmetrical 4, 6-bis (aryloxy) pyrimidine compoundsInfo
- Publication number
- IL125997A IL125997A IL12599798A IL12599798A IL125997A IL 125997 A IL125997 A IL 125997A IL 12599798 A IL12599798 A IL 12599798A IL 12599798 A IL12599798 A IL 12599798A IL 125997 A IL125997 A IL 125997A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- c4alkyl
- independently hydrogen
- hydrogen
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 65
- 125000004104 aryloxy group Chemical group 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 150000003230 pyrimidines Chemical class 0.000 title description 9
- -1 haloalkylsufinyl Chemical group 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 40
- 239000000203 mixture Chemical class 0.000 claims abstract description 34
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 229910052736 halogen Chemical group 0.000 claims abstract description 24
- 150000002367 halogens Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 238000011065 in-situ storage Methods 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002585 base Substances 0.000 claims description 21
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 8
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 4
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 13
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 229940093956 potassium carbonate Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- DHPCRFYUUWAGAH-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)phenol Chemical compound OC1=CC=C(F)C(C(F)(F)F)=C1 DHPCRFYUUWAGAH-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- MCLDVUCSDZGNRR-UHFFFAOYSA-N 4,6-difluoropyrimidine Chemical compound FC1=CC(F)=NC=N1 MCLDVUCSDZGNRR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010961 commercial manufacture process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 101100028325 Streptomyces rimosus oxyT gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/929,293 US5849910A (en) | 1997-09-05 | 1997-09-05 | Process for the preparation of unsymmetrical 4,6-bis aryloxy-pyrimidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL125997A0 IL125997A0 (en) | 1999-04-11 |
| IL125997A true IL125997A (en) | 2002-09-12 |
Family
ID=25457617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12599798A IL125997A (en) | 1997-09-05 | 1998-08-31 | Process for the preparation of unsymmetrical 4, 6-bis (aryloxy) pyrimidine compounds |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5849910A (es) |
| EP (1) | EP0902020B1 (es) |
| JP (1) | JPH11147879A (es) |
| KR (1) | KR100555053B1 (es) |
| CN (1) | CN1139577C (es) |
| AR (1) | AR015431A3 (es) |
| AT (1) | ATE209636T1 (es) |
| AU (1) | AU735102B2 (es) |
| BR (1) | BR9803388A (es) |
| CA (1) | CA2246588A1 (es) |
| CZ (1) | CZ291587B6 (es) |
| DE (1) | DE69802636T2 (es) |
| ES (1) | ES2169480T3 (es) |
| HU (1) | HU226270B1 (es) |
| IL (1) | IL125997A (es) |
| MX (1) | MXPA98007127A (es) |
| NZ (1) | NZ331701A (es) |
| PT (1) | PT902020E (es) |
| SK (1) | SK285101B6 (es) |
| TW (1) | TW505638B (es) |
| ZA (1) | ZA988032B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6087498A (en) * | 1998-05-12 | 2000-07-11 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds |
| DE10014607A1 (de) * | 2000-03-24 | 2001-09-27 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen 4,6-Bis(aryloxy pyrimidin-Derivaten |
| TWI621614B (zh) * | 2013-05-28 | 2018-04-21 | 科麥農股份有限公司 | 4,6-雙(芳氧基)嘧啶衍生物的製備方法 |
| CN109721548B (zh) * | 2017-10-31 | 2020-11-13 | 南通泰禾化工股份有限公司 | 一种嘧菌酯的制备方法 |
| CN119684236B (zh) * | 2024-12-30 | 2025-07-04 | 常州瑞华化工工程技术股份有限公司 | 一种异丙苯法低能耗生产环氧丙烷的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
| IE74711B1 (en) * | 1990-07-27 | 1997-07-30 | Ici Plc | Fungicides |
| GB9122430D0 (en) * | 1990-11-16 | 1991-12-04 | Ici Plc | Chemical process |
| IL100428A0 (en) * | 1990-12-21 | 1992-09-06 | Ciba Geigy | Pyrimidinyl-and triazinyl-salicylamides,their preparation and their use as herbicides and plant growth regulants |
| TW234077B (es) * | 1992-07-17 | 1994-11-11 | Shell Internat Res Schappej B V | |
| DE4327596A1 (de) * | 1993-08-17 | 1995-02-23 | Bayer Ag | 3-Methoxy-2-phenyl-acrylsäuremethylester |
| DE4340181A1 (de) * | 1993-11-25 | 1995-06-01 | Bayer Ag | 3-Methoxy-2-phenyl-acrylsäuremethylester |
| UA53611C2 (uk) * | 1996-03-07 | 2003-02-17 | Амерікан Ціанамід Компані | Спосіб одержання несиметричних 4,6-біс(арилокси)піримідинових сполук |
-
1997
- 1997-09-05 US US08/929,293 patent/US5849910A/en not_active Expired - Fee Related
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1998
- 1998-08-26 TW TW087114030A patent/TW505638B/zh not_active IP Right Cessation
- 1998-08-28 CZ CZ19982755A patent/CZ291587B6/cs not_active IP Right Cessation
- 1998-08-31 KR KR1019980035505A patent/KR100555053B1/ko not_active Expired - Fee Related
- 1998-08-31 IL IL12599798A patent/IL125997A/en not_active IP Right Cessation
- 1998-08-31 JP JP10259098A patent/JPH11147879A/ja not_active Withdrawn
- 1998-09-01 PT PT98306988T patent/PT902020E/pt unknown
- 1998-09-01 AT AT98306988T patent/ATE209636T1/de not_active IP Right Cessation
- 1998-09-01 EP EP98306988A patent/EP0902020B1/en not_active Expired - Lifetime
- 1998-09-01 ES ES98306988T patent/ES2169480T3/es not_active Expired - Lifetime
- 1998-09-01 DE DE69802636T patent/DE69802636T2/de not_active Expired - Fee Related
- 1998-09-02 ZA ZA9808032A patent/ZA988032B/xx unknown
- 1998-09-02 AU AU83047/98A patent/AU735102B2/en not_active Ceased
- 1998-09-02 MX MXPA98007127A patent/MXPA98007127A/es not_active IP Right Cessation
- 1998-09-02 SK SK1209-98A patent/SK285101B6/sk not_active IP Right Cessation
- 1998-09-03 CA CA002246588A patent/CA2246588A1/en not_active Abandoned
- 1998-09-03 CN CNB981188737A patent/CN1139577C/zh not_active Expired - Fee Related
- 1998-09-03 NZ NZ331701A patent/NZ331701A/xx unknown
- 1998-09-04 AR ARP980104421A patent/AR015431A3/es active IP Right Grant
- 1998-09-04 BR BR9803388A patent/BR9803388A/pt not_active Application Discontinuation
- 1998-09-04 HU HU9802020A patent/HU226270B1/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU8304798A (en) | 1999-03-18 |
| PT902020E (pt) | 2002-05-31 |
| JPH11147879A (ja) | 1999-06-02 |
| TW505638B (en) | 2002-10-11 |
| BR9803388A (pt) | 2000-03-21 |
| CZ275598A3 (cs) | 1999-06-16 |
| ZA988032B (en) | 2000-03-22 |
| MXPA98007127A (es) | 2005-01-25 |
| SK285101B6 (sk) | 2006-06-01 |
| EP0902020B1 (en) | 2001-11-28 |
| HUP9802020A2 (hu) | 1999-05-28 |
| AU735102B2 (en) | 2001-06-28 |
| US5849910A (en) | 1998-12-15 |
| DE69802636T2 (de) | 2002-08-01 |
| HU226270B1 (en) | 2008-07-28 |
| IL125997A0 (en) | 1999-04-11 |
| HUP9802020A3 (en) | 1999-08-30 |
| CZ291587B6 (cs) | 2003-04-16 |
| KR100555053B1 (ko) | 2006-06-13 |
| AR015431A3 (es) | 2001-05-02 |
| CN1139577C (zh) | 2004-02-25 |
| SK120998A3 (en) | 1999-06-11 |
| CN1222515A (zh) | 1999-07-14 |
| DE69802636D1 (de) | 2002-01-10 |
| NZ331701A (en) | 2000-01-28 |
| EP0902020A1 (en) | 1999-03-17 |
| ES2169480T3 (es) | 2002-07-01 |
| KR19990029377A (ko) | 1999-04-26 |
| CA2246588A1 (en) | 1999-03-05 |
| HU9802020D0 (en) | 1998-11-30 |
| ATE209636T1 (de) | 2001-12-15 |
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