SU685153A3 - Способ получени производных 4,5,6,7-тетрагидро-7-оксо(окси) бензо(в)тиофен-4-амина - Google Patents
Способ получени производных 4,5,6,7-тетрагидро-7-оксо(окси) бензо(в)тиофен-4-аминаInfo
- Publication number
- SU685153A3 SU685153A3 SU762416551A SU2416551A SU685153A3 SU 685153 A3 SU685153 A3 SU 685153A3 SU 762416551 A SU762416551 A SU 762416551A SU 2416551 A SU2416551 A SU 2416551A SU 685153 A3 SU685153 A3 SU 685153A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiophen
- amine
- acetic acid
- tetrahydro
- formyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- IRMXPESEXLQKHG-UHFFFAOYSA-N 1-benzothiophen-4-amine Chemical compound NC1=CC=CC2=C1C=CS2 IRMXPESEXLQKHG-UHFFFAOYSA-N 0.000 title 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 8
- 239000007864 aqueous solution Substances 0.000 claims 7
- 239000000284 extract Substances 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- HKVFISRIUUGTIB-UHFFFAOYSA-O azanium;cerium;nitrate Chemical compound [NH4+].[Ce].[O-][N+]([O-])=O HKVFISRIUUGTIB-UHFFFAOYSA-O 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000012267 brine Substances 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000007800 oxidant agent Substances 0.000 claims 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 4
- 229940117975 chromium trioxide Drugs 0.000 claims 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229960001701 chloroform Drugs 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000011630 iodine Chemical group 0.000 claims 2
- 229910052740 iodine Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- 125000005544 phthalimido group Chemical group 0.000 claims 2
- 229910001923 silver oxide Inorganic materials 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 238000001665 trituration Methods 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- LVUYUDNBONPETF-UHFFFAOYSA-N ClCCl.N1=CC=CC=C1.[O-2].[O-2].[O-2].[Cr+6] Chemical compound ClCCl.N1=CC=CC=C1.[O-2].[O-2].[O-2].[Cr+6] LVUYUDNBONPETF-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 235000014676 Phragmites communis Nutrition 0.000 claims 1
- RUKCJUBTRDGPCC-UHFFFAOYSA-N acetic acid;acetyl acetate Chemical compound CC(O)=O.CC(=O)OC(C)=O RUKCJUBTRDGPCC-UHFFFAOYSA-N 0.000 claims 1
- IRAKVRJJLPZVGE-UHFFFAOYSA-L acetic acid;dihydroxy(dioxo)chromium Chemical compound CC(O)=O.O[Cr](O)(=O)=O IRAKVRJJLPZVGE-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 1
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium nitrate Inorganic materials [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims 1
- MMXSKTNPRXHINM-UHFFFAOYSA-N cerium(3+);trisulfide Chemical compound [S-2].[S-2].[S-2].[Ce+3].[Ce+3] MMXSKTNPRXHINM-UHFFFAOYSA-N 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- -1 dimetoksiztana Chemical compound 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 239000012286 potassium permanganate Substances 0.000 claims 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver nitrate Substances [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims 1
- 229910001961 silver nitrate Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002576 ketones Chemical class 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62871675A | 1975-11-04 | 1975-11-04 | |
| US05/628,714 US3994924A (en) | 1975-11-04 | 1975-11-04 | 4,5,6,7-Tetra hydro-7-oxobenzo(B)thien-4-yl isocyanate and isothiocyanate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU685153A3 true SU685153A3 (ru) | 1979-09-05 |
Family
ID=27090779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762416551A SU685153A3 (ru) | 1975-11-04 | 1976-11-03 | Способ получени производных 4,5,6,7-тетрагидро-7-оксо(окси) бензо(в)тиофен-4-амина |
Country Status (13)
-
1976
- 1976-10-13 NZ NZ18232476A patent/NZ182324A/xx unknown
- 1976-10-15 IL IL5068376A patent/IL50683A/xx unknown
- 1976-10-20 AR AR26515676A patent/AR229075A1/es active
- 1976-10-20 IN IN1914/CAL/1976A patent/IN144699B/en unknown
- 1976-10-28 IE IE238676A patent/IE44846B1/en unknown
- 1976-11-02 YU YU268576A patent/YU40654B/xx unknown
- 1976-11-03 PL PL19343776A patent/PL112081B1/pl unknown
- 1976-11-03 SU SU762416551A patent/SU685153A3/ru active
- 1976-11-03 DD DD19557676A patent/DD128921A6/xx unknown
- 1976-11-03 DK DK497676A patent/DK497676A/da not_active Application Discontinuation
- 1976-11-03 IT IT5202776A patent/IT1066301B/it active
- 1976-11-04 CU CU34625A patent/CU34625A/es unknown
- 1976-11-04 ES ES452988A patent/ES452988A2/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1066301B (it) | 1985-03-04 |
| DK497676A (da) | 1977-05-05 |
| IN144699B (enrdf_load_stackoverflow) | 1978-06-17 |
| ES452988A2 (es) | 1978-07-16 |
| IE44846L (en) | 1977-05-04 |
| IE44846B1 (en) | 1982-04-21 |
| YU40654B (en) | 1986-04-30 |
| CU34625A (es) | 1979-09-08 |
| IL50683A (en) | 1981-10-30 |
| AR229075A1 (es) | 1983-06-15 |
| PL112081B1 (en) | 1980-09-30 |
| YU268576A (en) | 1982-06-30 |
| DD128921A6 (de) | 1977-12-21 |
| PL193437A1 (pl) | 1978-09-11 |
| NZ182324A (en) | 1979-03-28 |
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