SU486510A3 - Способ получени производных бензо/в/тиофена или их солей - Google Patents
Способ получени производных бензо/в/тиофена или их солейInfo
- Publication number
- SU486510A3 SU486510A3 SU721959344A SU1959344A SU486510A3 SU 486510 A3 SU486510 A3 SU 486510A3 SU 721959344 A SU721959344 A SU 721959344A SU 1959344 A SU1959344 A SU 1959344A SU 486510 A3 SU486510 A3 SU 486510A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzo
- thiophene
- ethyl
- solution
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 title claims description 6
- 125000005605 benzo group Chemical group 0.000 title claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title description 10
- 229930192474 thiophene Natural products 0.000 title description 5
- -1 alkali metal salt Chemical class 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- JOTPBWHXUWXGQL-UHFFFAOYSA-N 3-chloro-n,n-dipropylpropan-1-amine;hydrochloride Chemical compound Cl.CCCN(CCC)CCCCl JOTPBWHXUWXGQL-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KQDJZZWCYTXUDE-UHFFFAOYSA-N hydron;thiophene;chloride Chemical compound Cl.C=1C=CSC=1 KQDJZZWCYTXUDE-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RPMMPCOYPKRVPC-UHFFFAOYSA-N (3,5-dichloro-4-hydroxyphenyl)-(2-ethyl-1-benzothiophen-3-yl)methanone Chemical compound C(C)C=1SC2=C(C1C(C1=CC(=C(C(=C1)Cl)O)Cl)=O)C=CC=C2 RPMMPCOYPKRVPC-UHFFFAOYSA-N 0.000 description 1
- IDJOCJAIQSKSOP-UHFFFAOYSA-N 2,2-dichloroethanol Chemical compound OCC(Cl)Cl IDJOCJAIQSKSOP-UHFFFAOYSA-N 0.000 description 1
- RYEFACFVBYVPSP-UHFFFAOYSA-N 3-(dimethylamino)propyl 4-methylbenzenesulfonate hydrochloride Chemical compound Cl.CN(C)CCCOS(=O)(=O)C1=CC=C(C)C=C1 RYEFACFVBYVPSP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- QYFZCTDKWGVUIO-UHFFFAOYSA-N [Cl].[Sn] Chemical compound [Cl].[Sn] QYFZCTDKWGVUIO-UHFFFAOYSA-N 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- PNNHIYBDBMMXSU-UHFFFAOYSA-N n-(2-chloroethyl)-n-propylpropan-1-amine;hydrochloride Chemical compound [Cl-].CCC[NH+](CCC)CCCl PNNHIYBDBMMXSU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3003271A GB1357212A (en) | 1971-06-25 | 1971-06-25 | Benzothiophene derivatives and process for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU486510A3 true SU486510A3 (ru) | 1975-09-30 |
Family
ID=10301169
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU721959344A SU486510A3 (ru) | 1971-06-25 | 1972-06-23 | Способ получени производных бензо/в/тиофена или их солей |
| SU1800666A SU453844A3 (enrdf_load_stackoverflow) | 1971-06-25 | 1972-06-23 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1800666A SU453844A3 (enrdf_load_stackoverflow) | 1971-06-25 | 1972-06-23 |
Country Status (18)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947470A (en) * | 1974-06-20 | 1976-03-30 | Smithkline Corporation | Substituted benzofurans and benzothiophenes |
| JPS5973579A (ja) * | 1982-10-19 | 1984-04-25 | Kotobuki Seiyaku Kk | ベンゾフラン又はベンゾチオフェン誘導体，この化合物を有効成分とする尿酸排泄剤及びその製造方法 |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| CA2145614A1 (en) * | 1994-03-31 | 1995-10-01 | Jeffrey A. Dodge | Intermediates and processes for preparing benzothiophene compounds |
| CA2231013A1 (en) * | 1997-04-30 | 1998-10-30 | Eli Lilly And Company | Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceuticals |
-
1971
- 1971-06-25 GB GB3003271A patent/GB1357212A/en not_active Expired
-
1972
- 1972-06-01 BE BE784260A patent/BE784260A/xx unknown
- 1972-06-05 FI FI1578/72A patent/FI54477C/fi active
- 1972-06-06 ZA ZA723868A patent/ZA723868B/xx unknown
- 1972-06-07 IE IE790/72A patent/IE36485B1/xx unknown
- 1972-06-13 AU AU43338/72A patent/AU462617B2/en not_active Expired
- 1972-06-13 HU HULA799A patent/HU166255B/hu unknown
- 1972-06-21 SE SE7208187A patent/SE385482B/xx unknown
- 1972-06-21 CH CH930272A patent/CH549042A/fr not_active IP Right Cessation
- 1972-06-21 CH CH1795273A patent/CH548409A/fr not_active IP Right Cessation
- 1972-06-22 FR FR7222480A patent/FR2143250B1/fr not_active Expired
- 1972-06-23 CA CA145,600A patent/CA959492A/en not_active Expired
- 1972-06-23 DE DE19722230669 patent/DE2230669A1/de active Pending
- 1972-06-23 NL NL7208703A patent/NL7208703A/xx not_active Application Discontinuation
- 1972-06-23 SU SU721959344A patent/SU486510A3/ru active
- 1972-06-23 SU SU1800666A patent/SU453844A3/ru active
- 1972-06-24 JP JP47063621A patent/JPS4844248A/ja active Pending
- 1972-06-24 ES ES404252A patent/ES404252A1/es not_active Expired
- 1972-06-26 OA OA54619A patent/OA04117A/xx unknown
- 1972-06-26 AT AT545972A patent/AT312597B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE784260A (fr) | 1972-12-01 |
| DE2230669A1 (de) | 1972-12-28 |
| FR2143250B1 (enrdf_load_stackoverflow) | 1975-06-20 |
| OA04117A (fr) | 1979-11-30 |
| AU4333872A (en) | 1973-12-20 |
| IE36485B1 (en) | 1976-11-10 |
| ES404252A1 (es) | 1975-06-01 |
| FI54477B (fi) | 1978-08-31 |
| NL7208703A (enrdf_load_stackoverflow) | 1972-12-28 |
| FI54477C (fi) | 1978-12-11 |
| AT312597B (de) | 1974-01-10 |
| CA959492A (en) | 1974-12-17 |
| CH549042A (fr) | 1974-05-15 |
| HU166255B (enrdf_load_stackoverflow) | 1975-02-28 |
| FR2143250A1 (enrdf_load_stackoverflow) | 1973-02-02 |
| IE36485L (en) | 1972-12-25 |
| ZA723868B (en) | 1973-03-28 |
| JPS4844248A (enrdf_load_stackoverflow) | 1973-06-26 |
| SE385482B (sv) | 1976-07-05 |
| SU453844A3 (enrdf_load_stackoverflow) | 1974-12-15 |
| CH548409A (fr) | 1974-04-30 |
| GB1357212A (en) | 1974-06-19 |
| AU462617B2 (en) | 1975-06-10 |
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