SU512711A3 - Способ получени производных бензо-(4,5)-циклогепта (1,2-в) -тиофена - Google Patents
Способ получени производных бензо-(4,5)-циклогепта (1,2-в) -тиофенаInfo
- Publication number
- SU512711A3 SU512711A3 SU1628614A SU1628614A SU512711A3 SU 512711 A3 SU512711 A3 SU 512711A3 SU 1628614 A SU1628614 A SU 1628614A SU 1628614 A SU1628614 A SU 1628614A SU 512711 A3 SU512711 A3 SU 512711A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzo
- methyl
- residue
- cyclohepta
- chloroform
- Prior art date
Links
- BQYAIXRTUQAHCK-UHFFFAOYSA-N 2h-benzo[1,2]cyclohepta[3,6-b]thiophene Chemical class C1=C2C=CC=CC2=CC2=CCSC2=C1 BQYAIXRTUQAHCK-UHFFFAOYSA-N 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000002585 base Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 28
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 22
- -1 1-methyl-4-piperidylidene Chemical group 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 229930192474 thiophene Natural products 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000012452 mother liquor Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000004452 microanalysis Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000001530 fumaric acid Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100150128 Schizosaccharomyces pombe (strain 972 / ATCC 24843) spo14 gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH359870A CH533639A (de) | 1970-03-11 | 1970-03-11 | Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate |
| CH1159370A CH531000A (de) | 1970-03-11 | 1970-07-31 | Verfahren zur Herstellung neuer Benzocycloheptathiophene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU512711A3 true SU512711A3 (ru) | 1976-04-30 |
Family
ID=25693399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1628614A SU512711A3 (ru) | 1970-03-11 | 1971-03-05 | Способ получени производных бензо-(4,5)-циклогепта (1,2-в) -тиофена |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5217030B1 (https=) |
| BG (1) | BG22398A3 (https=) |
| CS (1) | CS185562B2 (https=) |
| DD (1) | DD100000A5 (https=) |
| DK (1) | DK134404B (https=) |
| ES (2) | ES389044A1 (https=) |
| FI (1) | FI52980C (https=) |
| HU (1) | HU162868B (https=) |
| IE (2) | IE34997B1 (https=) |
| IL (1) | IL36370A (https=) |
| IT (1) | IT7827770A0 (https=) |
| MY (1) | MY8300201A (https=) |
| NO (1) | NO133838C (https=) |
| PL (1) | PL84083B1 (https=) |
| SU (1) | SU512711A3 (https=) |
| YU (2) | YU35019B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ587050A (en) | 2008-01-30 | 2012-08-31 | Nippon Zoki Pharmaceutical Co | Compounds featuring a tricyclic group double bonded to a piperidine group, as an antihistamine |
-
1971
- 1971-03-05 SU SU1628614A patent/SU512711A3/ru active
- 1971-03-09 ES ES389044A patent/ES389044A1/es not_active Expired
- 1971-03-09 PL PL14675171A patent/PL84083B1/pl unknown
- 1971-03-09 HU HUSA002175 patent/HU162868B/hu unknown
- 1971-03-09 FI FI68371A patent/FI52980C/fi active
- 1971-03-09 CS CS171771A patent/CS185562B2/cs unknown
- 1971-03-09 YU YU58671A patent/YU35019B/xx unknown
- 1971-03-09 IL IL36370A patent/IL36370A/xx unknown
- 1971-03-10 DK DK111471A patent/DK134404B/da not_active IP Right Cessation
- 1971-03-10 IE IE29971A patent/IE34997B1/xx unknown
- 1971-03-10 NO NO90171A patent/NO133838C/no unknown
- 1971-03-10 DD DD16465971A patent/DD100000A5/xx unknown
- 1971-03-10 BG BG017004A patent/BG22398A3/xx unknown
- 1971-03-10 JP JP46013021A patent/JPS5217030B1/ja active Pending
-
1973
- 1973-06-30 ES ES416480A patent/ES416480A1/es not_active Expired
-
1974
- 1974-07-15 IE IE149474A patent/IE34998B1/xx unknown
-
1978
- 1978-03-24 YU YU69978A patent/YU35254B/xx unknown
- 1978-09-15 IT IT7827770A patent/IT7827770A0/it unknown
-
1983
- 1983-12-30 MY MY8300201A patent/MY8300201A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU58671A (en) | 1979-12-31 |
| ES416480A1 (es) | 1976-10-16 |
| DK134404B (da) | 1976-11-01 |
| DD100000A5 (https=) | 1973-09-05 |
| IE34997B1 (en) | 1975-10-15 |
| JPS5217030B1 (https=) | 1977-05-12 |
| FI52980B (https=) | 1977-09-30 |
| PL84083B1 (https=) | 1976-02-28 |
| HU162868B (https=) | 1973-04-28 |
| IL36370A (en) | 1974-10-22 |
| NO133838B (https=) | 1976-03-29 |
| IE34998L (en) | 1975-10-15 |
| ES389044A1 (es) | 1974-02-01 |
| YU35019B (en) | 1980-06-30 |
| DK134404C (https=) | 1977-04-04 |
| BG22398A3 (bg) | 1977-02-20 |
| IE34997L (en) | 1971-09-11 |
| NO133838C (https=) | 1976-07-07 |
| IE34998B1 (en) | 1975-10-15 |
| YU69978A (en) | 1980-04-30 |
| IL36370A0 (en) | 1971-05-26 |
| YU35254B (en) | 1980-10-31 |
| FI52980C (https=) | 1978-01-10 |
| IT7827770A0 (it) | 1978-09-15 |
| CS185562B2 (en) | 1978-10-31 |
| MY8300201A (en) | 1983-12-31 |
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