SU553933A3 - Способ получени 4-амино-1,2,4триазин-5-онов - Google Patents
Способ получени 4-амино-1,2,4триазин-5-оновInfo
- Publication number
- SU553933A3 SU553933A3 SU2086134A SU2086134A SU553933A3 SU 553933 A3 SU553933 A3 SU 553933A3 SU 2086134 A SU2086134 A SU 2086134A SU 2086134 A SU2086134 A SU 2086134A SU 553933 A3 SU553933 A3 SU 553933A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- hydrazide
- amino
- general formula
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- GAIDCDVTAJLEAE-UHFFFAOYSA-N 4-amino-1,2,4-triazin-5-one Chemical class NN1C=NN=CC1=O GAIDCDVTAJLEAE-UHFFFAOYSA-N 0.000 title 1
- -1 glyoxylic acid ester Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- QGYZSBFOYRXLGR-UHFFFAOYSA-N 2-oxoacetohydrazide Chemical compound NNC(=O)C=O QGYZSBFOYRXLGR-UHFFFAOYSA-N 0.000 claims description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 5
- DSTXUOOLKJPQLP-UHFFFAOYSA-N 2-oxo-2-phenylacetohydrazide Chemical compound NNC(=O)C(=O)C1=CC=CC=C1 DSTXUOOLKJPQLP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PNQBNCDICGXLDB-UHFFFAOYSA-N 2-oxo-2-(6-sulfonylcyclohexa-2,4-dien-1-yl)acetic acid Chemical compound S(=O)(=O)=C1C(C=CC=C1)C(C(=O)O)=O PNQBNCDICGXLDB-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2364474A DE2364474C3 (de) | 1973-12-24 | 1973-12-24 | Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU553933A3 true SU553933A3 (ru) | 1977-04-05 |
Family
ID=5901917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2086134A SU553933A3 (ru) | 1973-12-24 | 1974-12-20 | Способ получени 4-амино-1,2,4триазин-5-онов |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3959372A (en]) |
| JP (1) | JPS5747907B2 (en]) |
| AT (1) | AT337707B (en]) |
| BE (1) | BE823760A (en]) |
| BR (1) | BR7410769D0 (en]) |
| CH (2) | CH615428A5 (en]) |
| CS (1) | CS179931B2 (en]) |
| DD (1) | DD118645A5 (en]) |
| DE (1) | DE2364474C3 (en]) |
| DK (1) | DK137726C (en]) |
| FR (1) | FR2256163B1 (en]) |
| GB (1) | GB1447337A (en]) |
| HU (1) | HU172753B (en]) |
| IE (1) | IE40343B1 (en]) |
| IL (1) | IL46298A (en]) |
| IT (1) | IT1027955B (en]) |
| LU (1) | LU71540A1 (en]) |
| NL (1) | NL186513C (en]) |
| PL (1) | PL92416B1 (en]) |
| SU (1) | SU553933A3 (en]) |
| YU (1) | YU341974A (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0167905U (en]) * | 1987-10-28 | 1989-05-01 | ||
| CN103254146B (zh) * | 2013-05-31 | 2015-08-12 | 江苏省农用激素工程技术研究中心有限公司 | 苯嗪草酮的制备方法 |
| CN113896689B (zh) * | 2020-06-22 | 2024-02-27 | 北京颖泰嘉和生物科技股份有限公司 | 苯嗪草酮的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH375369A (de) * | 1958-09-23 | 1964-02-29 | Hoffmann La Roche | Verfahren zur Herstellung substituierter Aminosäurehydrazide |
| US3886211A (en) * | 1968-12-10 | 1975-05-27 | Ciba Geigy Corp | Carboxylic acid hydrazide derivatives |
-
1973
- 1973-12-24 DE DE2364474A patent/DE2364474C3/de not_active Expired
-
1974
- 1974-12-11 US US05/531,637 patent/US3959372A/en not_active Expired - Lifetime
- 1974-12-20 IT IT30909/74A patent/IT1027955B/it active
- 1974-12-20 LU LU71540A patent/LU71540A1/xx unknown
- 1974-12-20 DD DD183284A patent/DD118645A5/xx unknown
- 1974-12-20 IL IL46298A patent/IL46298A/xx unknown
- 1974-12-20 CH CH1709074A patent/CH615428A5/de not_active IP Right Cessation
- 1974-12-20 SU SU2086134A patent/SU553933A3/ru active
- 1974-12-23 AT AT1029074A patent/AT337707B/de not_active IP Right Cessation
- 1974-12-23 YU YU03419/74A patent/YU341974A/xx unknown
- 1974-12-23 HU HU74BA00003181A patent/HU172753B/hu unknown
- 1974-12-23 PL PL1974176819A patent/PL92416B1/pl unknown
- 1974-12-23 BR BR10769/74A patent/BR7410769D0/pt unknown
- 1974-12-23 GB GB5538574A patent/GB1447337A/en not_active Expired
- 1974-12-23 IE IE2656/74A patent/IE40343B1/xx unknown
- 1974-12-23 BE BE151855A patent/BE823760A/xx not_active IP Right Cessation
- 1974-12-23 DK DK677174A patent/DK137726C/da not_active IP Right Cessation
- 1974-12-23 CS CS7400008974A patent/CS179931B2/cs unknown
- 1974-12-23 NL NLAANVRAGE7416797,A patent/NL186513C/xx not_active IP Right Cessation
- 1974-12-24 JP JP49147710A patent/JPS5747907B2/ja not_active Expired
- 1974-12-24 FR FR7442657A patent/FR2256163B1/fr not_active Expired
-
1979
- 1979-04-17 CH CH360379A patent/CH617669A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH615428A5 (en]) | 1980-01-31 |
| IL46298A (en) | 1978-01-31 |
| PL92416B1 (en]) | 1977-04-30 |
| DE2364474C3 (de) | 1979-10-11 |
| GB1447337A (en) | 1976-08-25 |
| NL7416797A (nl) | 1975-06-26 |
| IE40343L (en) | 1975-06-24 |
| IL46298A0 (en) | 1975-03-13 |
| NL186513C (nl) | 1990-12-17 |
| CS179931B2 (en) | 1977-12-30 |
| DK137726B (da) | 1978-04-24 |
| DD118645A5 (en]) | 1976-03-12 |
| DK677174A (en]) | 1975-08-25 |
| BR7410769D0 (pt) | 1975-09-02 |
| DE2364474B2 (de) | 1979-02-15 |
| CH617669A5 (en]) | 1980-06-13 |
| DK137726C (da) | 1978-10-02 |
| HU172753B (hu) | 1978-12-28 |
| IT1027955B (it) | 1978-12-20 |
| AT337707B (de) | 1977-07-11 |
| JPS5095222A (en]) | 1975-07-29 |
| FR2256163A1 (en]) | 1975-07-25 |
| ATA1029074A (de) | 1976-11-15 |
| DE2364474A1 (de) | 1975-06-26 |
| FR2256163B1 (en]) | 1978-07-21 |
| US3959372A (en) | 1976-05-25 |
| JPS5747907B2 (en]) | 1982-10-13 |
| LU71540A1 (en]) | 1975-08-20 |
| IE40343B1 (en) | 1979-05-09 |
| YU341974A (en) | 1982-02-28 |
| BE823760A (fr) | 1975-06-23 |
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