DE2002800C3 - Benzo [b] thiophen-l,l-dioxidverbindungen und Verfahren zu ihrer Herstellung - Google Patents
Benzo [b] thiophen-l,l-dioxidverbindungen und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2002800C3 DE2002800C3 DE2002800A DE2002800A DE2002800C3 DE 2002800 C3 DE2002800 C3 DE 2002800C3 DE 2002800 A DE2002800 A DE 2002800A DE 2002800 A DE2002800 A DE 2002800A DE 2002800 C3 DE2002800 C3 DE 2002800C3
- Authority
- DE
- Germany
- Prior art keywords
- thiophene
- benzo
- dioxide
- preparation
- dioxide compounds
- 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
- 150000001875 compounds Chemical class 0.000 title description 7
- 238000000034 method Methods 0.000 title description 5
- 125000005605 benzo group Chemical group 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- FRJNKYGTHPUSJR-UHFFFAOYSA-N 1-benzothiophene 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)C=CC2=C1 FRJNKYGTHPUSJR-UHFFFAOYSA-N 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NBZLCHKKWFSOKP-UHFFFAOYSA-N 2-phenylsulfanyl-1-benzothiophene 1,1-dioxide Chemical compound C1(=CC=CC=C1)SC=1S(C2=C(C1)C=CC=C2)(=O)=O NBZLCHKKWFSOKP-UHFFFAOYSA-N 0.000 description 1
- NYCQQNBEXVWFED-UHFFFAOYSA-N 3-chloro-2-phenylsulfanyl-2,3-dihydro-1-benzothiophene 1,1-dioxide Chemical compound C1(=CC=CC=C1)SC1C(C2=C(S1(=O)=O)C=CC=C2)Cl NYCQQNBEXVWFED-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- -1 sulphenyl halides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79356169A | 1969-01-23 | 1969-01-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2002800A1 DE2002800A1 (de) | 1970-07-30 |
| DE2002800B2 DE2002800B2 (de) | 1978-11-23 |
| DE2002800C3 true DE2002800C3 (de) | 1979-07-26 |
Family
ID=25160200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2002800A Expired DE2002800C3 (de) | 1969-01-23 | 1970-01-22 | Benzo [b] thiophen-l,l-dioxidverbindungen und Verfahren zu ihrer Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3686216A (enExample) |
| JP (1) | JPS4830052B1 (enExample) |
| AT (1) | AT294073B (enExample) |
| BE (1) | BE744708A (enExample) |
| DE (1) | DE2002800C3 (enExample) |
| ES (1) | ES375812A1 (enExample) |
| GB (1) | GB1295916A (enExample) |
| IT (1) | IT954109B (enExample) |
| SU (1) | SU361569A3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4397850A (en) * | 1981-10-07 | 1983-08-09 | Sandoz, Inc. | Isoxazolyl indolamines |
| WO1999051587A1 (en) | 1998-04-01 | 1999-10-14 | Ono Pharmaceutical Co., Ltd. | Fused thiophene derivatives and drugs containing the same as the active ingredient |
-
1969
- 1969-01-23 US US793561*A patent/US3686216A/en not_active Expired - Lifetime
-
1970
- 1970-01-19 GB GB1295916D patent/GB1295916A/en not_active Expired
- 1970-01-21 BE BE744708D patent/BE744708A/xx unknown
- 1970-01-21 AT AT55870A patent/AT294073B/de not_active IP Right Cessation
- 1970-01-22 IT IT67187/70A patent/IT954109B/it active
- 1970-01-22 DE DE2002800A patent/DE2002800C3/de not_active Expired
- 1970-01-23 JP JP45006226A patent/JPS4830052B1/ja active Pending
- 1970-01-23 SU SU1397698A patent/SU361569A3/ru active
- 1970-01-23 ES ES375812A patent/ES375812A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES375812A1 (es) | 1972-04-16 |
| IT954109B (it) | 1973-08-30 |
| JPS4830052B1 (enExample) | 1973-09-17 |
| DE2002800B2 (de) | 1978-11-23 |
| AT294073B (de) | 1971-11-10 |
| SU361569A3 (enExample) | 1972-12-07 |
| US3686216A (en) | 1972-08-22 |
| BE744708A (fr) | 1970-07-22 |
| GB1295916A (enExample) | 1972-11-08 |
| DE2002800A1 (de) | 1970-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2041771C3 (de) | derivate | |
| DE3026201C2 (enExample) | ||
| DE3141198C2 (enExample) | ||
| DE2510525B2 (de) | Quartaere 2-alkylimidazoliumsalze | |
| DE2500265A1 (de) | Neue mikrobizide | |
| DE2206010A1 (de) | 1-aminosulfonyl-2-amino-benzimidazole, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2206011A1 (de) | 1-acyl-3-aminosulfonyl-2-imino-benzimidazoline, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2002800C3 (de) | Benzo [b] thiophen-l,l-dioxidverbindungen und Verfahren zu ihrer Herstellung | |
| DE1960029A1 (de) | Ureidophenylthioharnstoffe,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2053080A1 (de) | N substituierte Imidazole, Ver fahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE2201062A1 (de) | N-alkoxycarbonyl- bzw. n-alkylthiocarbonyl-2-(2'-thienyl)-benzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE2059949C3 (de) | Thienyl-fettsäurederivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE1060655B (de) | Schaedlingsbekaempfungsmittel | |
| DE2025413A1 (de) | Ureidophenylisothioharnstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2545569B2 (de) | 1,3-dithiacyclopenten-2-ylidenmalonsaeuredialkylester, verfahren zu deren herstellung und diese enthaltende fungizide mittel | |
| DE2454795A1 (de) | Heterocyclische verbindungen und ihre verwendung als schaedlingsbekaempfungsmittel | |
| DE2311983A1 (de) | N-(fluordichlormethylthio)-n-(trifluormethyl)-aminobenzhydroxamsaeuren und deren salze, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2242785A1 (de) | 1-alkylsulfonyl-2-trifluormethylbenzimidazole, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitenmittel | |
| DE2144125A1 (de) | Dithiocarbamidsaure salze von harnstoff-derivaten, verfahren zu ihrer herstellung und ihre fungizide und mikrobizide verwendung | |
| EP0081679A2 (de) | Substituierte Benzylimidazoliumsalze und diese enthaltende Mikrobizide | |
| EP0148442B1 (de) | Halogenierte Sulfide, Verfahren zu ihrer Herstellung und ihre Verwendung in mikrobiziden Mitteln | |
| EP0014887B1 (de) | Spiro-Derivate von 3-(3,5-Dihalogenphenyl)-oxazolidin-2-thion-4-onen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2410184A1 (de) | Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide | |
| DE2160020A1 (de) | Perchlor-imidazo-pyrimidin, verfahren zu seiner herstellung, sowie seine verwendung als fungizid | |
| DE2814453A1 (de) | Carbamoyloxyphenyl-verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BERENDT, T., DIPL.-CHEM. DR. LEYH, H., DIPL.-ING. DR.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |