SU1056904A3 - Способ получени производных 1,4-диазепина - Google Patents
Способ получени производных 1,4-диазепина Download PDFInfo
- Publication number
- SU1056904A3 SU1056904A3 SU802992903A SU2992903A SU1056904A3 SU 1056904 A3 SU1056904 A3 SU 1056904A3 SU 802992903 A SU802992903 A SU 802992903A SU 2992903 A SU2992903 A SU 2992903A SU 1056904 A3 SU1056904 A3 SU 1056904A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- diazepine
- mol
- bromo
- chlorine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 150000004911 1,4-diazepines Chemical class 0.000 title abstract description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 28
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000009835 boiling Methods 0.000 claims abstract description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- DVAZKUDTZUIOQK-UHFFFAOYSA-M 2-bromo-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Br DVAZKUDTZUIOQK-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- -1 meth amine Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004908 diazepines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- FJWLWIRHZOHPIY-UHFFFAOYSA-N potassium;hydroiodide Chemical compound [K].I FJWLWIRHZOHPIY-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/71—Ceramic products containing macroscopic reinforcing agents
- C04B35/78—Ceramic products containing macroscopic reinforcing agents containing non-metallic materials
- C04B35/80—Fibres, filaments, whiskers, platelets, or the like
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792940737 DE2940737A1 (de) | 1979-10-08 | 1979-10-08 | Verfahren zur herstellung von substituierten 6-aryl- 4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1056904A3 true SU1056904A3 (ru) | 1983-11-23 |
Family
ID=6082971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802992903A SU1056904A3 (ru) | 1979-10-08 | 1980-10-03 | Способ получени производных 1,4-диазепина |
Country Status (18)
-
1979
- 1979-10-08 DE DE19792940737 patent/DE2940737A1/de active Granted
-
1980
- 1980-09-24 AT AT0475780A patent/AT371820B/de not_active IP Right Cessation
- 1980-10-03 GR GR63045A patent/GR70773B/el unknown
- 1980-10-03 SU SU802992903A patent/SU1056904A3/ru active
- 1980-10-06 LU LU82825A patent/LU82825A1/de unknown
- 1980-10-06 HU HU802432A patent/HU181744B/hu not_active IP Right Cessation
- 1980-10-06 CH CH745180A patent/CH645114A5/de not_active IP Right Cessation
- 1980-10-06 FI FI803161A patent/FI68837C/fi not_active IP Right Cessation
- 1980-10-06 CS CS806739A patent/CS215141B2/cs unknown
- 1980-10-06 PL PL1980227128A patent/PL125636B1/pl unknown
- 1980-10-06 DD DD80224375A patent/DD153373A5/de unknown
- 1980-10-07 YU YU02571/80A patent/YU257180A/xx unknown
- 1980-10-07 PT PT71884A patent/PT71884B/pt not_active IP Right Cessation
- 1980-10-07 DK DK423280A patent/DK154505C/da not_active IP Right Cessation
- 1980-10-07 SE SE8007021A patent/SE441927B/sv not_active IP Right Cessation
- 1980-10-07 NO NO802987A patent/NO156652C/no unknown
- 1980-10-07 ES ES495689A patent/ES495689A0/es active Granted
- 1980-10-07 JP JP13942480A patent/JPS5661383A/ja active Granted
-
1981
- 1981-07-01 ES ES503584A patent/ES503584A0/es active Granted
Non-Patent Citations (1)
| Title |
|---|
| 1. патент СССР-№. 833160, кл. С 07 В 495/14Д978. 2. Патент СССР № 583758, кл. С 07 D 495/14, 1974 (прототип). * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA475780A (de) | 1982-12-15 |
| AT371820B (de) | 1983-08-10 |
| JPS5661383A (en) | 1981-05-26 |
| NO156652C (no) | 1987-10-28 |
| ES8205807A1 (es) | 1982-06-16 |
| HU181744B (en) | 1983-11-28 |
| SE8007021L (sv) | 1981-04-09 |
| DK154505C (da) | 1989-04-17 |
| PL227128A1 (enrdf_load_stackoverflow) | 1981-06-05 |
| ES8200892A1 (es) | 1981-11-16 |
| SE441927B (sv) | 1985-11-18 |
| YU257180A (en) | 1983-02-28 |
| ES503584A0 (es) | 1982-06-16 |
| NO156652B (no) | 1987-07-20 |
| DE2940737A1 (de) | 1981-04-16 |
| PT71884B (de) | 1982-06-15 |
| CH645114A5 (en) | 1984-09-14 |
| DD153373A5 (de) | 1982-01-06 |
| FI68837B (fi) | 1985-07-31 |
| JPH0219118B2 (enrdf_load_stackoverflow) | 1990-04-27 |
| LU82825A1 (de) | 1981-12-02 |
| DK423280A (da) | 1981-04-09 |
| DE2940737C2 (enrdf_load_stackoverflow) | 1988-12-15 |
| FI803161L (fi) | 1981-04-09 |
| FI68837C (fi) | 1985-11-11 |
| CS215141B2 (en) | 1982-07-30 |
| NO802987L (no) | 1981-04-09 |
| PL125636B1 (en) | 1983-06-30 |
| GR70773B (enrdf_load_stackoverflow) | 1983-03-22 |
| DK154505B (da) | 1988-11-21 |
| ES495689A0 (es) | 1981-11-16 |
| PT71884A (de) | 1980-11-01 |
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