IL43505A - Process for bromination of nitrogen-containing heterocyclic compounds - Google Patents
Process for bromination of nitrogen-containing heterocyclic compoundsInfo
- Publication number
- IL43505A IL43505A IL43505A IL4350573A IL43505A IL 43505 A IL43505 A IL 43505A IL 43505 A IL43505 A IL 43505A IL 4350573 A IL4350573 A IL 4350573A IL 43505 A IL43505 A IL 43505A
- Authority
- IL
- Israel
- Prior art keywords
- nitrogen
- pyrimidine
- hydrochloride
- solvent
- containing heterocyclic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 title claims description 23
- 238000005893 bromination reaction Methods 0.000 title claims description 6
- 230000031709 bromination Effects 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 25
- 239000012433 hydrogen halide Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
- SDPYFZLDWYNXJF-UHFFFAOYSA-N 5-bromo-4-phenylpyrimidine Chemical compound BrC1=CN=CN=C1C1=CC=CC=C1 SDPYFZLDWYNXJF-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical group Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 claims description 5
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 claims description 4
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 claims description 4
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 4
- ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 claims description 4
- SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 claims description 4
- MKLQPIYLZMLAER-UHFFFAOYSA-N 4-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=CC=NC=N1 MKLQPIYLZMLAER-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- GOZNZGWCQSNZFX-UHFFFAOYSA-N 1,6-naphthyridine;hydrochloride Chemical compound Cl.C1=CN=CC2=CC=CN=C21 GOZNZGWCQSNZFX-UHFFFAOYSA-N 0.000 claims description 3
- DCHUYAXTJQCCRX-UHFFFAOYSA-N 4-phenylpyrimidine;hydrochloride Chemical compound Cl.C1=CC=CC=C1C1=CC=NC=N1 DCHUYAXTJQCCRX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000011874 heated mixture Substances 0.000 claims description 3
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims description 3
- IEJBHGRSGHMNTB-UHFFFAOYSA-N 4-phenylpyrimidine hydrobromide Chemical compound Br.C1(=CC=CC=C1)C1=NC=NC=C1 IEJBHGRSGHMNTB-UHFFFAOYSA-N 0.000 claims description 2
- UGSBNWMMAHCMON-UHFFFAOYSA-N 4-phenylpyrimidine hydroiodide Chemical compound I.C1(=CC=CC=C1)C1=NC=NC=C1 UGSBNWMMAHCMON-UHFFFAOYSA-N 0.000 claims description 2
- FXMQMXNRMSLCKG-UHFFFAOYSA-N [I-].c1c[nH+]c2ccncc2c1 Chemical compound [I-].c1c[nH+]c2ccncc2c1 FXMQMXNRMSLCKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- BATMYWDOUUWCJE-UHFFFAOYSA-N pyrimidin-1-ium;bromide Chemical compound Br.C1=CN=CN=C1 BATMYWDOUUWCJE-UHFFFAOYSA-N 0.000 claims description 2
- ZSIALBZCWCLSOG-UHFFFAOYSA-N pyrimidine;hydroiodide Chemical compound I.C1=CN=CN=C1 ZSIALBZCWCLSOG-UHFFFAOYSA-N 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- SHLPPXXKRFINFY-UHFFFAOYSA-N isoquinolin-2-ium;bromide Chemical compound Br.C1=NC=CC2=CC=CC=C21 SHLPPXXKRFINFY-UHFFFAOYSA-N 0.000 claims 1
- GHESMRYCQSFSSF-UHFFFAOYSA-N isoquinolin-2-ium;iodide Chemical compound [I-].C1=[NH+]C=CC2=CC=CC=C21 GHESMRYCQSFSSF-UHFFFAOYSA-N 0.000 claims 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000003822 preparative gas chromatography Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- YKPXUVTWLVHJBM-UHFFFAOYSA-N 1,1,1,3-tetraethoxypropane Chemical compound CCOCCC(OCC)(OCC)OCC YKPXUVTWLVHJBM-UHFFFAOYSA-N 0.000 description 2
- WGDHEJVNOWBUCH-UHFFFAOYSA-N 5-bromopyrimidine;hydrobromide Chemical compound Br.BrC1=CN=CN=C1 WGDHEJVNOWBUCH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
- FFPZTTQEXPMQBS-UHFFFAOYSA-N 4-amino-n-isoquinolin-1-ylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC2=CC=CC=C12 FFPZTTQEXPMQBS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- GDKWFLJNGDCPDY-UHFFFAOYSA-N [Br-].c1cnc2cc[nH+]cc2c1 Chemical compound [Br-].c1cnc2cc[nH+]cc2c1 GDKWFLJNGDCPDY-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000000935 anti-streptococcal effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000013489 large scale run Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- TYRDEZUMAVRTEO-UHFFFAOYSA-N pyrimidin-5-ylmethanol Chemical class OCC1=CN=CN=C1 TYRDEZUMAVRTEO-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000008096 xylene Substances 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
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30838972A | 1972-11-21 | 1972-11-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43505A0 IL43505A0 (en) | 1974-01-14 |
| IL43505A true IL43505A (en) | 1977-04-29 |
Family
ID=23193800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43505A IL43505A (en) | 1972-11-21 | 1973-10-29 | Process for bromination of nitrogen-containing heterocyclic compounds |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS596854B2 (de) |
| BE (1) | BE807525A (de) |
| CH (1) | CH584205A5 (de) |
| DE (1) | DE2356358C2 (de) |
| FR (1) | FR2207100B1 (de) |
| GB (1) | GB1439682A (de) |
| IL (1) | IL43505A (de) |
| IT (1) | IT1001824B (de) |
| NL (1) | NL184058C (de) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2221808C2 (de) * | 1972-05-04 | 1985-06-20 | Sandoz-Patent-GmbH, 7850 Lörrach | Hydrazinopyridazin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und Heilmittel |
-
1973
- 1973-10-29 IL IL43505A patent/IL43505A/en unknown
- 1973-10-30 GB GB5046973A patent/GB1439682A/en not_active Expired
- 1973-11-06 CH CH1558773A patent/CH584205A5/xx not_active IP Right Cessation
- 1973-11-12 DE DE2356358A patent/DE2356358C2/de not_active Expired
- 1973-11-16 NL NLAANVRAGE7315788,A patent/NL184058C/xx not_active IP Right Cessation
- 1973-11-16 IT IT31462/73A patent/IT1001824B/it active
- 1973-11-20 BE BE1005515A patent/BE807525A/xx not_active IP Right Cessation
- 1973-11-21 FR FR7341410A patent/FR2207100B1/fr not_active Expired
- 1973-11-21 JP JP48131177A patent/JPS596854B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL184058B (nl) | 1988-11-01 |
| JPS596854B2 (ja) | 1984-02-15 |
| FR2207100A1 (de) | 1974-06-14 |
| BE807525A (fr) | 1974-05-20 |
| JPS4981375A (de) | 1974-08-06 |
| NL184058C (nl) | 1989-04-03 |
| IL43505A0 (en) | 1974-01-14 |
| CH584205A5 (de) | 1977-01-31 |
| IT1001824B (it) | 1976-04-30 |
| DE2356358C2 (de) | 1984-12-06 |
| DE2356358A1 (de) | 1974-05-30 |
| FR2207100B1 (de) | 1981-06-19 |
| NL7315788A (de) | 1974-05-24 |
| GB1439682A (en) | 1976-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4987232A (en) | Preparation of 2-chloropyridine 3-carboxylic acid esters | |
| US4155909A (en) | 2-Alkyl nicotinoids and processes for their production | |
| JPH0778065B2 (ja) | （６，７―置換―８―アルコキシ―１―シクロプロピル―１，４―ジヒドロ―４―オキソ―３―キノリンカルボン酸―ｏ▲上３▼，ｏ▲上４▼）ビス（アシルオキシ―ｏ）ホウ素化合物及びその塩並びにその製造方法 | |
| US4066665A (en) | 2-Alkylamino-α-phenyl-1-cyclohexene-1-methyleneimine, its salts and preparation | |
| US3956301A (en) | Process for bromination of pyrimidine | |
| EP0052333B1 (de) | 4-Fluor-5-oxypyrazol-Derivate und Verfahren zu ihrer Herstellung | |
| NO166712B (no) | Fremgangsmaate ved fremstilling av pyrrolidonderivater. | |
| IL43505A (en) | Process for bromination of nitrogen-containing heterocyclic compounds | |
| JPS6117826B2 (de) | ||
| US4167638A (en) | Process for production of 8-NHR quinolines | |
| US4894457A (en) | 7-bromo-beta-carboline compound and method for producing same | |
| US4154743A (en) | 3-Oxobenzofuranyl-2-idenyl, haloacetic acids | |
| JP4231556B2 (ja) | １，３−ジ置換２−ニトログアニジンの製造法 | |
| WO1989006230A1 (en) | Cyano-dienes, halopyridines, intermediates and a process for their preparation | |
| US3433802A (en) | 3-(n-lower-alkylanilino)pyrrolidines | |
| US4062891A (en) | N-formyl-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-methylamine | |
| AU2004232454B2 (en) | Method for the production of nicotinaldehydes | |
| NO830877L (no) | Tricykliske derivater av 5,6-dihydro-11h-dibenzo-(b,e)azepin-6-on med farmakologisk aktivitet og fremgangsmaate for deres fremstilling | |
| US2696488A (en) | 2, 4, 6-tris-(1-piperidyl)-5-benzylpyrimidine and process of preparing same | |
| EP0013726B1 (de) | Indanyloxaminsäure-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| Van Heyningen | 3-Benzoyl-4-piperidones | |
| US20040186300A1 (en) | Process for the preparation of zafirlukast | |
| US4727149A (en) | Preparation of nitriles of fused ring pyridine derivatives | |
| KR790001654B1 (ko) | S-트리아졸로[3, 4-b] 벤조티아졸류의 제조방법 | |
| KR790001652B1 (ko) | S-트리아졸로 [3, 4-b] 벤조티아졸류의 제조방법 |