DE2225071A1 - Verfahren zur Herstellung von heterocyclischen Verbindungen und deren Verwendung - Google Patents
Verfahren zur Herstellung von heterocyclischen Verbindungen und deren VerwendungInfo
- Publication number
- DE2225071A1 DE2225071A1 DE19722225071 DE2225071A DE2225071A1 DE 2225071 A1 DE2225071 A1 DE 2225071A1 DE 19722225071 DE19722225071 DE 19722225071 DE 2225071 A DE2225071 A DE 2225071A DE 2225071 A1 DE2225071 A1 DE 2225071A1
- Authority
- DE
- Germany
- Prior art keywords
- isothiocyano
- group
- alkyl
- substituents
- amino groups
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- -1 isothiocyano group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000001555 benzenes Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- KJCGUQFSJWDPTH-UHFFFAOYSA-N 2-isothiocyanato-1h-indole Chemical compound C1=CC=C2NC(N=C=S)=CC2=C1 KJCGUQFSJWDPTH-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 229940124339 anthelmintic agent Drugs 0.000 claims description 2
- 239000000921 anthelmintic agent Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 230000000507 anthelmentic effect Effects 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000287828 Gallus gallus Species 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 235000013330 chicken meat Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000242711 Fasciola hepatica Species 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000204725 Ascaridia galli Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 208000006275 fascioliasis Diseases 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RPNKHQXCPDETKW-UHFFFAOYSA-N 2-(4-isothiocyanatophenoxy)-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1OC1=CC=C(N=C=S)C=C1 RPNKHQXCPDETKW-UHFFFAOYSA-N 0.000 description 2
- POQFDUCYJMJNIE-UHFFFAOYSA-N 2-n-(4-aminophenyl)-1,3-benzoxazole-2,6-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC2=CC=C(N)C=C2O1 POQFDUCYJMJNIE-UHFFFAOYSA-N 0.000 description 2
- LSCUQWNTJJYLJN-UHFFFAOYSA-N 3-(1-methylbenzimidazol-2-yl)oxyaniline Chemical compound N=1C2=CC=CC=C2N(C)C=1OC1=CC=CC(N)=C1 LSCUQWNTJJYLJN-UHFFFAOYSA-N 0.000 description 2
- HQULYFAKUZDRPB-UHFFFAOYSA-N 6-bromo-2-[4-(trifluoromethoxy)phenoxy]-1,3-benzothiazole Chemical compound BrC1=CC2=C(N=C(S2)OC2=CC=C(C=C2)OC(F)(F)F)C=C1 HQULYFAKUZDRPB-UHFFFAOYSA-N 0.000 description 2
- KDURUOCLFKFUDF-UHFFFAOYSA-N 6-isothiocyanato-2-phenoxy-1,3-benzothiazole Chemical compound S1C2=CC(N=C=S)=CC=C2N=C1OC1=CC=CC=C1 KDURUOCLFKFUDF-UHFFFAOYSA-N 0.000 description 2
- KGBLRQYBXOHHHK-UHFFFAOYSA-N 6-nitro-n-(4-nitrophenyl)-1,3-benzoxazol-2-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=NC2=CC=C([N+]([O-])=O)C=C2O1 KGBLRQYBXOHHHK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241001464384 Hymenolepis nana Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 241000869417 Trematodes Species 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEKMJKMSTPFHQD-UHFFFAOYSA-N 1h-benzimidazole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=NC2=C1 VEKMJKMSTPFHQD-UHFFFAOYSA-N 0.000 description 1
- MWJFZHDYJNCTAP-UHFFFAOYSA-N 2-(2-fluorophenoxy)-1,3-benzothiazol-6-amine Chemical compound S1C2=CC(N)=CC=C2N=C1OC1=CC=CC=C1F MWJFZHDYJNCTAP-UHFFFAOYSA-N 0.000 description 1
- GJRBUNBNZGDXMU-UHFFFAOYSA-N 2-(2-fluorophenoxy)-6-nitro-1,3-benzothiazole Chemical compound S1C2=CC([N+](=O)[O-])=CC=C2N=C1OC1=CC=CC=C1F GJRBUNBNZGDXMU-UHFFFAOYSA-N 0.000 description 1
- LHFNLPVDIWFTJA-UHFFFAOYSA-N 2-(3-chlorophenoxy)-6-isothiocyanato-1,3-benzothiazole Chemical compound ClC1=CC=CC(OC=2SC3=CC(=CC=C3N=2)N=C=S)=C1 LHFNLPVDIWFTJA-UHFFFAOYSA-N 0.000 description 1
- XHDYQJOGAMQPSV-UHFFFAOYSA-N 2-(3-isothiocyanatophenoxy)-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1OC1=CC=CC(N=C=S)=C1 XHDYQJOGAMQPSV-UHFFFAOYSA-N 0.000 description 1
- AISOTHGLHJARLS-UHFFFAOYSA-N 2-(3-isothiocyanatophenoxy)-1-methylbenzimidazole;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2N(C)C=1OC1=CC=CC(N=C=S)=C1 AISOTHGLHJARLS-UHFFFAOYSA-N 0.000 description 1
- JAVNSZLHRMEZBZ-UHFFFAOYSA-N 2-(4-fluorophenoxy)-1,3-benzothiazol-6-amine Chemical compound S1C2=CC(N)=CC=C2N=C1OC1=CC=C(F)C=C1 JAVNSZLHRMEZBZ-UHFFFAOYSA-N 0.000 description 1
- XWNDZCGAYSBTFU-UHFFFAOYSA-M 2-(4-isothiocyanatophenoxy)-1,3-dimethylbenzimidazol-3-ium;iodide Chemical compound [I-].C[N+]=1C2=CC=CC=C2N(C)C=1OC1=CC=C(N=C=S)C=C1 XWNDZCGAYSBTFU-UHFFFAOYSA-M 0.000 description 1
- LBIBWIIVLUCNKP-UHFFFAOYSA-N 2-(4-isothiocyanatophenyl)sulfanyl-1,3-benzothiazole Chemical compound C1=CC(N=C=S)=CC=C1SC1=NC2=CC=CC=C2S1 LBIBWIIVLUCNKP-UHFFFAOYSA-N 0.000 description 1
- JXYUXELMGWBZTD-UHFFFAOYSA-N 2-(4-methylphenoxy)-1,3-benzothiazol-6-amine Chemical compound C1=CC(C)=CC=C1OC1=NC2=CC=C(N)C=C2S1 JXYUXELMGWBZTD-UHFFFAOYSA-N 0.000 description 1
- CFKYGISPRYOSCQ-UHFFFAOYSA-N 2-(4-nitrophenyl)sulfanyl-1,3-benzothiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=NC2=CC=CC=C2S1 CFKYGISPRYOSCQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH754271 | 1971-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2225071A1 true DE2225071A1 (de) | 1972-12-07 |
Family
ID=4326772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722225071 Pending DE2225071A1 (de) | 1971-05-24 | 1972-05-23 | Verfahren zur Herstellung von heterocyclischen Verbindungen und deren Verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3840550A (OSRAM) |
| BE (1) | BE783791A (OSRAM) |
| BR (1) | BR7203298D0 (OSRAM) |
| DD (1) | DD98517A5 (OSRAM) |
| DE (1) | DE2225071A1 (OSRAM) |
| FR (1) | FR2138884A1 (OSRAM) |
| IL (1) | IL39501A0 (OSRAM) |
| NL (1) | NL7206929A (OSRAM) |
| ZA (1) | ZA723514B (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815621A1 (de) * | 1977-04-12 | 1978-10-19 | Ciba Geigy Ag | Anthelmintika |
| US4568674A (en) * | 1984-02-15 | 1986-02-04 | Bayer Aktiengesellschaft | Anti-coccidal agents 1-[4-(benzothia- or -oxazol-2-ylthio- or -2-yloxy)phenyl]-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione derivatives, compositions, and method of use thereof |
| EP0192180A1 (de) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)barbitursäure-derivate als Wirkstoffe für Anthelmintika |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933841A (en) * | 1971-05-24 | 1976-01-20 | Ciba-Geigy Corporation | 2-Phenoxy, -phenylthio-, and -phenyl-amino-benzoxazoles having an isothiocyano substituent |
| US3969351A (en) * | 1974-05-17 | 1976-07-13 | E. R. Squibb & Sons, Inc. | Morpholine containing isothiocyanobenzoxazoles |
| US3915986A (en) * | 1974-06-19 | 1975-10-28 | Smithkline Corp | Methyl 5-propylthio-2-benzimidazolecarbamate |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| DE2913527A1 (de) * | 1979-04-04 | 1980-10-16 | Bayer Ag | Schaedlingsbekaempfungsmittel |
| EP0204215B1 (en) * | 1985-05-24 | 1993-08-11 | G.D. Searle & Co. | 2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-benzenamines |
| AU2002221902B2 (en) * | 2000-12-06 | 2006-11-23 | F. Hoffmann-La Roche Ag | Fused heteroaromatic glucokinase activators |
-
1972
- 1972-05-22 US US00255334A patent/US3840550A/en not_active Expired - Lifetime
- 1972-05-23 IL IL39501A patent/IL39501A0/xx unknown
- 1972-05-23 DD DD163138A patent/DD98517A5/xx unknown
- 1972-05-23 BE BE783791A patent/BE783791A/xx unknown
- 1972-05-23 DE DE19722225071 patent/DE2225071A1/de active Pending
- 1972-05-23 NL NL7206929A patent/NL7206929A/xx unknown
- 1972-05-23 ZA ZA723514A patent/ZA723514B/xx unknown
- 1972-05-23 FR FR7218265A patent/FR2138884A1/fr active Pending
- 1972-05-24 BR BR3298/72A patent/BR7203298D0/pt unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815621A1 (de) * | 1977-04-12 | 1978-10-19 | Ciba Geigy Ag | Anthelmintika |
| US4568674A (en) * | 1984-02-15 | 1986-02-04 | Bayer Aktiengesellschaft | Anti-coccidal agents 1-[4-(benzothia- or -oxazol-2-ylthio- or -2-yloxy)phenyl]-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione derivatives, compositions, and method of use thereof |
| US4611060A (en) * | 1984-02-15 | 1986-09-09 | Bayer Aktiengesellschaft | Intermediate(1,3-benzothiazol-2H-yl or 1,3-benzoxazol-2H-yl)4-oxy-or 4-thio-phenylurea derivatives |
| EP0192180A1 (de) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)barbitursäure-derivate als Wirkstoffe für Anthelmintika |
| US4762830A (en) * | 1985-02-15 | 1988-08-09 | Ciba-Geigy Corporation | 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics |
Also Published As
| Publication number | Publication date |
|---|---|
| BE783791A (fr) | 1972-11-23 |
| ZA723514B (en) | 1973-03-28 |
| US3840550A (en) | 1974-10-08 |
| NL7206929A (OSRAM) | 1972-11-28 |
| DD98517A5 (OSRAM) | 1973-06-20 |
| BR7203298D0 (pt) | 1974-08-29 |
| FR2138884A1 (OSRAM) | 1973-01-05 |
| IL39501A0 (en) | 1972-08-30 |
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