CA1069130A - Produits anthelminthiques de type ester phenylique de l'acide 2-carbalkoxyamino benzimidazolyl-5(6)sulfonique et procede pour leur fabrication - Google Patents
Produits anthelminthiques de type ester phenylique de l'acide 2-carbalkoxyamino benzimidazolyl-5(6)sulfonique et procede pour leur fabricationInfo
- Publication number
- CA1069130A CA1069130A CA314,151A CA314151A CA1069130A CA 1069130 A CA1069130 A CA 1069130A CA 314151 A CA314151 A CA 314151A CA 1069130 A CA1069130 A CA 1069130A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl ester
- nitro
- diamino
- chloro
- acid
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- -1 3,4-diamino-benzene sulfonic acid 3-trifluoromethyl phenyl ester Chemical class 0.000 claims description 38
- ROVPGRDMDASARO-UHFFFAOYSA-N phenyl 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 ROVPGRDMDASARO-UHFFFAOYSA-N 0.000 claims description 11
- NEZIKMJTIOLUGU-UHFFFAOYSA-N phenyl 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 NEZIKMJTIOLUGU-UHFFFAOYSA-N 0.000 claims description 9
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- OEWUTDOUXOVAGR-UHFFFAOYSA-N (3-cyanophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(C#N)=C1 OEWUTDOUXOVAGR-UHFFFAOYSA-N 0.000 claims description 3
- REDRJDQKXRSTBY-UHFFFAOYSA-N (3-cyanophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(C#N)=C1 REDRJDQKXRSTBY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 241000242711 Fasciola hepatica Species 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 230000000973 chemotherapeutic effect Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000006275 fascioliasis Diseases 0.000 abstract 1
- 244000000013 helminth Species 0.000 abstract 1
- 244000045947 parasite Species 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- DXNLDBASBALMSX-UHFFFAOYSA-N phenyl 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 DXNLDBASBALMSX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000004987 o-phenylenediamines Chemical class 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZLHORUGUHGSRRM-UHFFFAOYSA-N (2,5-dichlorophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC(Cl)=CC=C1Cl ZLHORUGUHGSRRM-UHFFFAOYSA-N 0.000 description 2
- BGKBIDOMOFMKSU-UHFFFAOYSA-N (3,5-dichlorophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC(Cl)=CC(Cl)=C1 BGKBIDOMOFMKSU-UHFFFAOYSA-N 0.000 description 2
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KJOOATXDSQOFPX-UHFFFAOYSA-N [4-(2-methylpropoxy)phenyl] 3,4-diaminobenzenesulfonate Chemical compound C1=CC(OCC(C)C)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 KJOOATXDSQOFPX-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- JXCATYHLVAXVEH-UHFFFAOYSA-N (2,4-dimethylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(C)C=C1C JXCATYHLVAXVEH-UHFFFAOYSA-N 0.000 description 1
- ZHGDCLZGIYJAJM-UHFFFAOYSA-N (2,4-dimethylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 ZHGDCLZGIYJAJM-UHFFFAOYSA-N 0.000 description 1
- AKWIYEVWEOEZTC-UHFFFAOYSA-N (2,4-dimethylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 AKWIYEVWEOEZTC-UHFFFAOYSA-N 0.000 description 1
- PDOHEFDSUYVBHI-UHFFFAOYSA-N (2,5-dichlorophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC(Cl)=CC=C1Cl PDOHEFDSUYVBHI-UHFFFAOYSA-N 0.000 description 1
- AWRFXVUKOIBNMG-UHFFFAOYSA-N (2,5-dichlorophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC(Cl)=CC=C1Cl AWRFXVUKOIBNMG-UHFFFAOYSA-N 0.000 description 1
- NIVCVAITNATGMG-UHFFFAOYSA-N (2,5-dichlorophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C(=CC=C(Cl)C=2)Cl)=C1 NIVCVAITNATGMG-UHFFFAOYSA-N 0.000 description 1
- BQPIDRJNXJZWHZ-UHFFFAOYSA-N (2-bromophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1Br BQPIDRJNXJZWHZ-UHFFFAOYSA-N 0.000 description 1
- TZLGLOTZWNAURF-UHFFFAOYSA-N (2-bromophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1Br TZLGLOTZWNAURF-UHFFFAOYSA-N 0.000 description 1
- UOZMDIWCYKFGHF-UHFFFAOYSA-N (2-bromophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1Br UOZMDIWCYKFGHF-UHFFFAOYSA-N 0.000 description 1
- VLNPUWGTMAYLQO-UHFFFAOYSA-N (2-bromophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C(=CC=CC=2)Br)=C1 VLNPUWGTMAYLQO-UHFFFAOYSA-N 0.000 description 1
- UXSMWEVRCDPXKV-UHFFFAOYSA-N (2-chloro-4-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(C)C=C1Cl UXSMWEVRCDPXKV-UHFFFAOYSA-N 0.000 description 1
- CQNCDRXCCSJEPB-UHFFFAOYSA-N (2-chloro-4-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound ClC1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 CQNCDRXCCSJEPB-UHFFFAOYSA-N 0.000 description 1
- WMLWEUMLUGTERN-UHFFFAOYSA-N (2-chloro-4-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound ClC1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 WMLWEUMLUGTERN-UHFFFAOYSA-N 0.000 description 1
- HFIUZQSIMIGIOF-UHFFFAOYSA-N (2-chloro-4-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound ClC1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HFIUZQSIMIGIOF-UHFFFAOYSA-N 0.000 description 1
- IGESXLVCVIMMAP-UHFFFAOYSA-N (2-chloro-6-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=C(C)C=CC=C1Cl IGESXLVCVIMMAP-UHFFFAOYSA-N 0.000 description 1
- GVEUYYJRVRFMDS-UHFFFAOYSA-N (2-chloro-6-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=CC=CC(Cl)=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 GVEUYYJRVRFMDS-UHFFFAOYSA-N 0.000 description 1
- QSSHUNNUBJRDLU-UHFFFAOYSA-N (2-chloro-6-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC(Cl)=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 QSSHUNNUBJRDLU-UHFFFAOYSA-N 0.000 description 1
- CSGBFALEAZRNQN-UHFFFAOYSA-N (2-chloro-6-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC(Cl)=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 CSGBFALEAZRNQN-UHFFFAOYSA-N 0.000 description 1
- CWTPUEDXFQHLIR-UHFFFAOYSA-N (2-chlorophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1Cl CWTPUEDXFQHLIR-UHFFFAOYSA-N 0.000 description 1
- VUPOVZXDFUPZCR-UHFFFAOYSA-N (2-chlorophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1Cl VUPOVZXDFUPZCR-UHFFFAOYSA-N 0.000 description 1
- WOJHQNCMZCQOFK-UHFFFAOYSA-N (2-chlorophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1Cl WOJHQNCMZCQOFK-UHFFFAOYSA-N 0.000 description 1
- NXLAPUAKSJCSFS-UHFFFAOYSA-N (2-chlorophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C(=CC=CC=2)Cl)=C1 NXLAPUAKSJCSFS-UHFFFAOYSA-N 0.000 description 1
- SGQSDLBDQUTBCP-UHFFFAOYSA-N (2-methoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound COC1=CC=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 SGQSDLBDQUTBCP-UHFFFAOYSA-N 0.000 description 1
- PFDGYOJWWONJTA-UHFFFAOYSA-N (2-methoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound COC1=CC=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 PFDGYOJWWONJTA-UHFFFAOYSA-N 0.000 description 1
- LHNVCIQKOCIAJD-UHFFFAOYSA-N (2-methoxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound COC1=CC=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 LHNVCIQKOCIAJD-UHFFFAOYSA-N 0.000 description 1
- FOPZCEWBOPEBLS-UHFFFAOYSA-N (2-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=CC=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 FOPZCEWBOPEBLS-UHFFFAOYSA-N 0.000 description 1
- UPDSLTBAXXVCPZ-UHFFFAOYSA-N (2-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 UPDSLTBAXXVCPZ-UHFFFAOYSA-N 0.000 description 1
- TVWLMBSSDIEWJL-UHFFFAOYSA-N (2-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 TVWLMBSSDIEWJL-UHFFFAOYSA-N 0.000 description 1
- BYGWCYMTSFEQLM-UHFFFAOYSA-N (3,5-dichlorophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC(Cl)=CC(Cl)=C1 BYGWCYMTSFEQLM-UHFFFAOYSA-N 0.000 description 1
- WOWQQLGSWXREKK-UHFFFAOYSA-N (3,5-dichlorophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC(Cl)=CC(Cl)=C1 WOWQQLGSWXREKK-UHFFFAOYSA-N 0.000 description 1
- BMKAZDKKRQRUDH-UHFFFAOYSA-N (3,5-dichlorophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=C(Cl)C=C(Cl)C=2)=C1 BMKAZDKKRQRUDH-UHFFFAOYSA-N 0.000 description 1
- NXOKKXACBQESEI-UHFFFAOYSA-N (3-bromophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC(Br)=C1 NXOKKXACBQESEI-UHFFFAOYSA-N 0.000 description 1
- CGWGGQHTSYXUDD-UHFFFAOYSA-N (3-bromophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(Br)=C1 CGWGGQHTSYXUDD-UHFFFAOYSA-N 0.000 description 1
- SUVVFPGNNBUFED-UHFFFAOYSA-N (3-bromophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(Br)=C1 SUVVFPGNNBUFED-UHFFFAOYSA-N 0.000 description 1
- BTQROPWNFKTNSO-UHFFFAOYSA-N (3-bromophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=C(Br)C=CC=2)=C1 BTQROPWNFKTNSO-UHFFFAOYSA-N 0.000 description 1
- UFWGRYUVACXAGJ-UHFFFAOYSA-N (3-chloro-4-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(C)C(Cl)=C1 UFWGRYUVACXAGJ-UHFFFAOYSA-N 0.000 description 1
- XQYMPPULLSLTTH-UHFFFAOYSA-N (3-chloro-4-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(Cl)C(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 XQYMPPULLSLTTH-UHFFFAOYSA-N 0.000 description 1
- ZAXZIPLTAJSUOK-UHFFFAOYSA-N (3-chloro-4-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 ZAXZIPLTAJSUOK-UHFFFAOYSA-N 0.000 description 1
- ZSVWAAJTTRORET-UHFFFAOYSA-N (3-chloro-4-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C(C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZSVWAAJTTRORET-UHFFFAOYSA-N 0.000 description 1
- ZKHUTBZCEQOSDR-UHFFFAOYSA-N (3-chlorophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(Cl)=C1 ZKHUTBZCEQOSDR-UHFFFAOYSA-N 0.000 description 1
- MVWMIZKBHIIUJW-UHFFFAOYSA-N (3-chlorophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(Cl)=C1 MVWMIZKBHIIUJW-UHFFFAOYSA-N 0.000 description 1
- NPPCVICNVNTDDO-UHFFFAOYSA-N (3-chlorophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=C(Cl)C=CC=2)=C1 NPPCVICNVNTDDO-UHFFFAOYSA-N 0.000 description 1
- UMRIXOOKYJPSSR-UHFFFAOYSA-N (3-ethoxyphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound CCOC1=CC=CC(OS(=O)(=O)C=2C=C3NC(NC(=O)OC)=NC3=CC=2)=C1 UMRIXOOKYJPSSR-UHFFFAOYSA-N 0.000 description 1
- BVDJGIMOJFTONF-UHFFFAOYSA-N (3-ethoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound CCOC1=CC=CC(OS(=O)(=O)C=2C=C(N)C(N)=CC=2)=C1 BVDJGIMOJFTONF-UHFFFAOYSA-N 0.000 description 1
- KRCUXSWQRHFAKL-UHFFFAOYSA-N (3-ethoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CCOC1=CC=CC(OS(=O)(=O)C=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 KRCUXSWQRHFAKL-UHFFFAOYSA-N 0.000 description 1
- ORCRRODNPXBNEA-UHFFFAOYSA-N (3-ethoxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CCOC1=CC=CC(OS(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 ORCRRODNPXBNEA-UHFFFAOYSA-N 0.000 description 1
- MHCALCDTVWGUHT-UHFFFAOYSA-N (3-methoxyphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC(OC)=C1 MHCALCDTVWGUHT-UHFFFAOYSA-N 0.000 description 1
- KKQNCKWAALXEKI-UHFFFAOYSA-N (3-methoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound COC1=CC=CC(OS(=O)(=O)C=2C=C(N)C(N)=CC=2)=C1 KKQNCKWAALXEKI-UHFFFAOYSA-N 0.000 description 1
- GUSLKHUEMKHWEG-UHFFFAOYSA-N (3-methoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound COC1=CC=CC(OS(=O)(=O)C=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 GUSLKHUEMKHWEG-UHFFFAOYSA-N 0.000 description 1
- QCCQKSLEMRUDGL-UHFFFAOYSA-N (3-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC(C)=C1 QCCQKSLEMRUDGL-UHFFFAOYSA-N 0.000 description 1
- XFMINSQCONUQCO-UHFFFAOYSA-N (3-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=CC=CC(OS(=O)(=O)C=2C=C(N)C(N)=CC=2)=C1 XFMINSQCONUQCO-UHFFFAOYSA-N 0.000 description 1
- HMEHAKJPTXFDAV-UHFFFAOYSA-N (3-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC(OS(=O)(=O)C=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 HMEHAKJPTXFDAV-UHFFFAOYSA-N 0.000 description 1
- AGSDJTRUYDYOKC-UHFFFAOYSA-N (3-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=CC=CC(OS(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 AGSDJTRUYDYOKC-UHFFFAOYSA-N 0.000 description 1
- WBFISFJOSLSQET-UHFFFAOYSA-N (4-bromophenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(Br)C=C1 WBFISFJOSLSQET-UHFFFAOYSA-N 0.000 description 1
- IDECGGBOCHQSGR-UHFFFAOYSA-N (4-bromophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=C(Br)C=C1 IDECGGBOCHQSGR-UHFFFAOYSA-N 0.000 description 1
- SVNOIDOQRCXHJT-UHFFFAOYSA-N (4-bromophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=CC(Br)=CC=2)=C1 SVNOIDOQRCXHJT-UHFFFAOYSA-N 0.000 description 1
- HZLRYBRIYTWVJI-UHFFFAOYSA-N (4-butoxyphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=CC(OCCCC)=CC=C1OS(=O)(=O)C1=CC=C(N=C(NC(=O)OC)N2)C2=C1 HZLRYBRIYTWVJI-UHFFFAOYSA-N 0.000 description 1
- UBQZRGHBKMEVEX-UHFFFAOYSA-N (4-butoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=CC(OCCCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 UBQZRGHBKMEVEX-UHFFFAOYSA-N 0.000 description 1
- GKOBHQPNYFCMJB-UHFFFAOYSA-N (4-butoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(OCCCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 GKOBHQPNYFCMJB-UHFFFAOYSA-N 0.000 description 1
- UIIWKMJBGFSXLA-UHFFFAOYSA-N (4-butoxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(OCCCC)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 UIIWKMJBGFSXLA-UHFFFAOYSA-N 0.000 description 1
- XUMBWVTXGBAVHY-UHFFFAOYSA-N (4-chloro-2-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(Cl)C=C1C XUMBWVTXGBAVHY-UHFFFAOYSA-N 0.000 description 1
- WSVZNWBBCBGZLW-UHFFFAOYSA-N (4-chloro-2-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 WSVZNWBBCBGZLW-UHFFFAOYSA-N 0.000 description 1
- MWPLAFPYVHBZOY-UHFFFAOYSA-N (4-chloro-2-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 MWPLAFPYVHBZOY-UHFFFAOYSA-N 0.000 description 1
- VOPRPWUYSNRGEP-UHFFFAOYSA-N (4-chloro-2-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VOPRPWUYSNRGEP-UHFFFAOYSA-N 0.000 description 1
- BHRFFHMJAHRLEX-UHFFFAOYSA-N (4-chloro-3,5-dimethylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC(C)=C(Cl)C(C)=C1 BHRFFHMJAHRLEX-UHFFFAOYSA-N 0.000 description 1
- HFMMTBBMICTONS-UHFFFAOYSA-N (4-chloro-3,5-dimethylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=C(N)C(N)=CC=2)=C1 HFMMTBBMICTONS-UHFFFAOYSA-N 0.000 description 1
- FIOWISRTPJTJGI-UHFFFAOYSA-N (4-chloro-3,5-dimethylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 FIOWISRTPJTJGI-UHFFFAOYSA-N 0.000 description 1
- IYNUFNUTBFRYRP-UHFFFAOYSA-N (4-chloro-3,5-dimethylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound CC1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 IYNUFNUTBFRYRP-UHFFFAOYSA-N 0.000 description 1
- JHKXGBVWAIEDJW-UHFFFAOYSA-N (4-chloro-3-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(Cl)C(C)=C1 JHKXGBVWAIEDJW-UHFFFAOYSA-N 0.000 description 1
- ZDDCKEGFMIZQEA-UHFFFAOYSA-N (4-chloro-3-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 ZDDCKEGFMIZQEA-UHFFFAOYSA-N 0.000 description 1
- UIAHQKITDVGGAX-UHFFFAOYSA-N (4-chloro-3-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C(C)=CC(OS(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 UIAHQKITDVGGAX-UHFFFAOYSA-N 0.000 description 1
- SWXAXGYVTNHQPF-UHFFFAOYSA-N (4-chlorophenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=C(Cl)C=C1 SWXAXGYVTNHQPF-UHFFFAOYSA-N 0.000 description 1
- VOJGRWFRPRCNEI-UHFFFAOYSA-N (4-chlorophenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=C(Cl)C=C1 VOJGRWFRPRCNEI-UHFFFAOYSA-N 0.000 description 1
- ZROLXLXBAHGRFM-UHFFFAOYSA-N (4-chlorophenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=CC(Cl)=CC=2)=C1 ZROLXLXBAHGRFM-UHFFFAOYSA-N 0.000 description 1
- XSFRDQWLPLGEPZ-UHFFFAOYSA-N (4-methoxyphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(OC)C=C1 XSFRDQWLPLGEPZ-UHFFFAOYSA-N 0.000 description 1
- PMVPZZFOLSZEBG-UHFFFAOYSA-N (4-methoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=CC(OC)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 PMVPZZFOLSZEBG-UHFFFAOYSA-N 0.000 description 1
- WNCWVTRWQJIRLO-UHFFFAOYSA-N (4-methoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(OC)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 WNCWVTRWQJIRLO-UHFFFAOYSA-N 0.000 description 1
- ZWEXWSDQKSCGJA-UHFFFAOYSA-N (4-methoxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(OC)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZWEXWSDQKSCGJA-UHFFFAOYSA-N 0.000 description 1
- JJIXFYOIJWXMEQ-UHFFFAOYSA-N (4-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 JJIXFYOIJWXMEQ-UHFFFAOYSA-N 0.000 description 1
- QTBFCLOPCUGTCG-UHFFFAOYSA-N (4-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 QTBFCLOPCUGTCG-UHFFFAOYSA-N 0.000 description 1
- SDPFJPNTJUILAT-UHFFFAOYSA-N (4-methylphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 SDPFJPNTJUILAT-UHFFFAOYSA-N 0.000 description 1
- FXOSNEJPMIYUAG-UHFFFAOYSA-N (4-propan-2-yloxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(OC(C)C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 FXOSNEJPMIYUAG-UHFFFAOYSA-N 0.000 description 1
- ZKSNEZQDTZWKLS-UHFFFAOYSA-N (4-propan-2-yloxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(OC(C)C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZKSNEZQDTZWKLS-UHFFFAOYSA-N 0.000 description 1
- SKPPEFZOZSCEKW-UHFFFAOYSA-N (4-propoxyphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=CC(OCCC)=CC=C1OS(=O)(=O)C1=CC=C(N=C(NC(=O)OC)N2)C2=C1 SKPPEFZOZSCEKW-UHFFFAOYSA-N 0.000 description 1
- PRBTULNBUPMFAB-UHFFFAOYSA-N (4-propoxyphenyl) 3,4-diaminobenzenesulfonate Chemical compound C1=CC(OCCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 PRBTULNBUPMFAB-UHFFFAOYSA-N 0.000 description 1
- NHXNXUMBZYJLLG-UHFFFAOYSA-N (4-propoxyphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(OCCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 NHXNXUMBZYJLLG-UHFFFAOYSA-N 0.000 description 1
- YVUHNROMLBDQEV-UHFFFAOYSA-N (4-propoxyphenyl) 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(OCCC)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 YVUHNROMLBDQEV-UHFFFAOYSA-N 0.000 description 1
- UGCJSPQIFWNLLQ-UHFFFAOYSA-N (5-chloro-2-methylphenyl) 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC(Cl)=CC=C1C UGCJSPQIFWNLLQ-UHFFFAOYSA-N 0.000 description 1
- BRUHGWKEMUAJNB-UHFFFAOYSA-N (5-chloro-2-methylphenyl) 3,4-diaminobenzenesulfonate Chemical compound CC1=CC=C(Cl)C=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 BRUHGWKEMUAJNB-UHFFFAOYSA-N 0.000 description 1
- YBTLISXPQPVFSN-UHFFFAOYSA-N (5-chloro-2-methylphenyl) 4-amino-3-nitrobenzenesulfonate Chemical compound CC1=CC=C(Cl)C=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 YBTLISXPQPVFSN-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FKSRSWQTEJTBMI-UHFFFAOYSA-N 3,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1N FKSRSWQTEJTBMI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVZKTUHIRRBENN-UHFFFAOYSA-N [4-(2-methylpropoxy)phenyl] 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=C(OCC(C)C)C=C1 AVZKTUHIRRBENN-UHFFFAOYSA-N 0.000 description 1
- VEGMDECTEDZPRA-UHFFFAOYSA-N [4-(2-methylpropoxy)phenyl] 4-amino-3-nitrobenzenesulfonate Chemical compound C1=CC(OCC(C)C)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 VEGMDECTEDZPRA-UHFFFAOYSA-N 0.000 description 1
- CUDIMFTVMLHAPR-UHFFFAOYSA-N [4-(2-methylpropoxy)phenyl] 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=CC(OCC(C)C)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 CUDIMFTVMLHAPR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BTLAMBOZGAZYLW-UHFFFAOYSA-N ethyl 2-chloro-4-(3,4-diaminophenyl)sulfonyloxybenzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C(N)=C1 BTLAMBOZGAZYLW-UHFFFAOYSA-N 0.000 description 1
- XIMRNNFPWCYGHU-UHFFFAOYSA-N ethyl 2-chloro-4-(4-chloro-3-nitrophenyl)sulfonyloxybenzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 XIMRNNFPWCYGHU-UHFFFAOYSA-N 0.000 description 1
- MIAISPAAIYBOBH-UHFFFAOYSA-N ethyl 2-chloro-4-[[2-(methoxycarbonylamino)-3h-benzimidazol-5-yl]sulfonyloxy]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1OS(=O)(=O)C1=CC=C(N=C(NC(=O)OC)N2)C2=C1 MIAISPAAIYBOBH-UHFFFAOYSA-N 0.000 description 1
- RJGOUJDYLYFROB-UHFFFAOYSA-N ethyl 4-(4-amino-3-nitrophenyl)sulfonyloxy-2-chlorobenzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1OS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 RJGOUJDYLYFROB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FNKPQMSVJJSRBP-UHFFFAOYSA-N phenyl 2-(butoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OCCCC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 FNKPQMSVJJSRBP-UHFFFAOYSA-N 0.000 description 1
- YVPYMPMYOGQFIW-UHFFFAOYSA-N phenyl 2-(ethoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 YVPYMPMYOGQFIW-UHFFFAOYSA-N 0.000 description 1
- BWJKYQSSWVHQEG-UHFFFAOYSA-N phenyl 2-(propan-2-yloxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC(C)C)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 BWJKYQSSWVHQEG-UHFFFAOYSA-N 0.000 description 1
- ZHGXTLXTHYOYDW-UHFFFAOYSA-N phenyl 2-(propoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OCCC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 ZHGXTLXTHYOYDW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA314,151A CA1069130A (fr) | 1974-08-28 | 1978-10-24 | Produits anthelminthiques de type ester phenylique de l'acide 2-carbalkoxyamino benzimidazolyl-5(6)sulfonique et procede pour leur fabrication |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2441202A DE2441202C2 (de) | 1974-08-28 | 1974-08-28 | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| CA234,273A CA1059136A (fr) | 1974-08-28 | 1975-08-27 | Derives anthelminthiques d'esters phenyliques de l'acide 2-carbalkoxyaminobenzimidazolyl-5 (6) sulfonique et procede pour leur fabrication |
| CA314,151A CA1069130A (fr) | 1974-08-28 | 1978-10-24 | Produits anthelminthiques de type ester phenylique de l'acide 2-carbalkoxyamino benzimidazolyl-5(6)sulfonique et procede pour leur fabrication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069130A true CA1069130A (fr) | 1980-01-01 |
Family
ID=27164086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA314,151A Expired CA1069130A (fr) | 1974-08-28 | 1978-10-24 | Produits anthelminthiques de type ester phenylique de l'acide 2-carbalkoxyamino benzimidazolyl-5(6)sulfonique et procede pour leur fabrication |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1069130A (fr) |
-
1978
- 1978-10-24 CA CA314,151A patent/CA1069130A/fr not_active Expired
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