DE2364474C3 - Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onen - Google Patents
Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onenInfo
- Publication number
- DE2364474C3 DE2364474C3 DE2364474A DE2364474A DE2364474C3 DE 2364474 C3 DE2364474 C3 DE 2364474C3 DE 2364474 A DE2364474 A DE 2364474A DE 2364474 A DE2364474 A DE 2364474A DE 2364474 C3 DE2364474 C3 DE 2364474C3
- Authority
- DE
- Germany
- Prior art keywords
- ethanol
- triazin
- melting point
- ones
- stirring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 23
- GAIDCDVTAJLEAE-UHFFFAOYSA-N 4-amino-1,2,4-triazin-5-one Chemical class NN1C=NN=CC1=O GAIDCDVTAJLEAE-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000003495 polar organic solvent Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- -1 preferably Älha nol Chemical compound 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- GMMXCUJVWPKZDL-UHFFFAOYSA-N n-[(2-hydrazinyl-2-oxo-1-phenylethylidene)amino]acetamide Chemical compound CC(=O)NN=C(C(=O)NN)C1=CC=CC=C1 GMMXCUJVWPKZDL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HNOCCACIRSAHQC-UHFFFAOYSA-N 2-(4-chloro-2-ethylphenyl)-2-oxoacetic acid Chemical compound CCC1=CC(Cl)=CC=C1C(=O)C(O)=O HNOCCACIRSAHQC-UHFFFAOYSA-N 0.000 description 1
- OXOYOSITARWPAX-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-2-oxoacetic acid Chemical compound CS(=O)(=O)C1=CC=C(C(=O)C(O)=O)C=C1 OXOYOSITARWPAX-UHFFFAOYSA-N 0.000 description 1
- XNIHZNNZJHYHLC-UHFFFAOYSA-N 2-oxohexanoic acid Chemical group CCCCC(=O)C(O)=O XNIHZNNZJHYHLC-UHFFFAOYSA-N 0.000 description 1
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RJHIOLHVEOFXJQ-UHFFFAOYSA-N COC(C=C1)=CC=C1C(C(NN)=O)=O Chemical compound COC(C=C1)=CC=C1C(C(NN)=O)=O RJHIOLHVEOFXJQ-UHFFFAOYSA-N 0.000 description 1
- UIJIURMCSZGQFJ-UHFFFAOYSA-N CSC(C=C1)=CC=C1C(C(NN)=O)=O Chemical compound CSC(C=C1)=CC=C1C(C(NN)=O)=O UIJIURMCSZGQFJ-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
- 241000243251 Hydra Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- ITAQSHHUJHREGB-UHFFFAOYSA-N N-[[1-(4-chlorophenyl)-2-hydrazinyl-2-oxoethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=C(Cl)C=C1 ITAQSHHUJHREGB-UHFFFAOYSA-N 0.000 description 1
- YGDOUCSVPKYYIC-UHFFFAOYSA-N N-[[2-hydrazinyl-2-oxo-1-[4-(trifluoromethoxy)phenyl]ethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=C(OC(F)(F)F)C=C1 YGDOUCSVPKYYIC-UHFFFAOYSA-N 0.000 description 1
- PAIDMJGUVMIHEW-UHFFFAOYSA-N NNC(C(C1=CC(C(F)(F)F)=CC=C1)=O)=O Chemical compound NNC(C(C1=CC(C(F)(F)F)=CC=C1)=O)=O PAIDMJGUVMIHEW-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-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
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005598 acylhydrazone group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate 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
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001411 amidrazones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LRDJLICCIZGMSB-UHFFFAOYSA-N ethenyldiazene Chemical compound C=CN=N LRDJLICCIZGMSB-UHFFFAOYSA-N 0.000 description 1
- XCGGOUSHHFTILQ-UHFFFAOYSA-N ethyl 2-(acetylhydrazinylidene)-2-phenylacetate Chemical compound CCOC(=O)C(=NNC(C)=O)C1=CC=CC=C1 XCGGOUSHHFTILQ-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- NTPXNEQCDPWJQA-AZDHXYLBSA-N hydia Chemical compound C1[C@@H](O)[C@@](N)(C(O)=O)[C@@H]2[C@@H](C(O)=O)[C@H]12 NTPXNEQCDPWJQA-AZDHXYLBSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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)
Priority Applications (23)
| 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 |
| US05/531,637 US3959372A (en) | 1973-12-24 | 1974-12-11 | Glyoxylic acid hydrazide-2-acylhydrazone compounds |
| IT30909/74A IT1027955B (it) | 1973-12-24 | 1974-12-20 | Procedimento per la preparazione di 4 amini 1.2.4. triazin 5 oni |
| DD183284A DD118645A5 (en]) | 1973-12-24 | 1974-12-20 | |
| LU71540A LU71540A1 (en]) | 1973-12-24 | 1974-12-20 | |
| IL46298A IL46298A (en) | 1973-12-24 | 1974-12-20 | Glyoxylic acid hydrazide-2-acylhydrazones their production and their use for the preparation of 4-amino-1,2,4-triazin-5-ones |
| SU2086134A SU553933A3 (ru) | 1973-12-24 | 1974-12-20 | Способ получени 4-амино-1,2,4триазин-5-онов |
| CH1709074A CH615428A5 (en]) | 1973-12-24 | 1974-12-20 | |
| IE2656/74A IE40343B1 (en) | 1973-12-24 | 1974-12-23 | Glyoxylic acid hydrazide-2-acylhydrazones and their use for the preparation of 4-amino-1,2,4-triazin-5-ones |
| HU74BA00003181A HU172753B (hu) | 1973-12-24 | 1974-12-23 | Sposob poluchenija proizvodnykh 4-amino-1,2,4-triazin-5-ona |
| AT1029074A AT337707B (de) | 1973-12-24 | 1974-12-23 | Verfahren zur herstellung von 4-amino-1,2,4-triazin-5-onen |
| PL1974176819A PL92416B1 (en]) | 1973-12-24 | 1974-12-23 | |
| YU03419/74A YU341974A (en) | 1973-12-24 | 1974-12-23 | Process for preparing 4-amino-1,2,4-triazine-5-ones |
| BR10769/74A BR7410769D0 (pt) | 1973-12-24 | 1974-12-23 | Processo para preparacao de 4-amino-1,2,4-triazino-5onas |
| NLAANVRAGE7416797,A NL186513C (nl) | 1973-12-24 | 1974-12-23 | Werkwijze voor het bereiden van 4-amino 1,2,4-triazine 5-onen. |
| BE151855A BE823760A (fr) | 1973-12-24 | 1974-12-23 | Procede de preparation de 4-amino-1 |
| GB5538574A GB1447337A (en) | 1973-12-24 | 1974-12-23 | Glyoxylic acid hydrazide-2-acylhydrazones and their use for the preparations of 4-amino-1,2,4-triazin-5-ones |
| CS7400008974A CS179931B2 (en) | 1973-12-24 | 1974-12-23 | Method for production of 4-amino-1,2,4-triazine-5-ones |
| DK677174A DK137726C (da) | 1973-12-24 | 1974-12-23 | Fremgangsmaade til fremstilling af 4-amino-1,2,4-triazin-5-oner |
| FR7442657A FR2256163B1 (en]) | 1973-12-24 | 1974-12-24 | |
| JP49147710A JPS5747907B2 (en]) | 1973-12-24 | 1974-12-24 | |
| US05/625,277 US4057546A (en) | 1973-12-24 | 1975-10-23 | 4-Amino-1,2,4-triazin-5-ones |
| CH360379A CH617669A5 (en]) | 1973-12-24 | 1979-04-17 |
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2364474A1 DE2364474A1 (de) | 1975-06-26 |
| DE2364474B2 DE2364474B2 (de) | 1979-02-15 |
| DE2364474C3 true DE2364474C3 (de) | 1979-10-11 |
Family
ID=5901917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2364474A Expired DE2364474C3 (de) | 1973-12-24 | 1973-12-24 | Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onen |
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 |
| 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 |
| SU553933A3 (ru) | 1977-04-05 |
| BE823760A (fr) | 1975-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) |