FI59404C - Foerfarande foer framstaellning av metyl-3-(2-kinoxalinylmetylen)karbazat-n1,n4-dioxid - Google Patents
Foerfarande foer framstaellning av metyl-3-(2-kinoxalinylmetylen)karbazat-n1,n4-dioxid Download PDFInfo
- Publication number
- FI59404C FI59404C FI490/74A FI49074A FI59404C FI 59404 C FI59404 C FI 59404C FI 490/74 A FI490/74 A FI 490/74A FI 49074 A FI49074 A FI 49074A FI 59404 C FI59404 C FI 59404C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- methyl
- carbazate
- oxidizing agent
- dioxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 11
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical group CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- SOEMFPLGOUBPJQ-NTUHNPAUSA-N methyl n-[(e)-quinoxalin-2-ylmethylideneamino]carbamate Chemical compound C1=CC=CC2=NC(/C=N/NC(=O)OC)=CN=C21 SOEMFPLGOUBPJQ-NTUHNPAUSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- -1 2-quinoxalinyl Chemical group 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 235000013594 poultry meat Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002924 anti-infective effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 208000014085 Chronic respiratory disease Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000420100 Morinda lucida Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000282339 Mustela Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000004251 balanced diet Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- UJEHWLFUEQHEEZ-UHFFFAOYSA-N quinoxaline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CN=C21 UJEHWLFUEQHEEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000000083 urinary anti-infective agent Substances 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33890673 | 1973-03-07 | ||
| US338906A US3926991A (en) | 1973-03-07 | 1973-03-07 | Process for producing quinoxaline-di-N-oxides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59404B FI59404B (fi) | 1981-04-30 |
| FI59404C true FI59404C (fi) | 1981-08-10 |
Family
ID=23326639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI490/74A FI59404C (fi) | 1973-03-07 | 1974-02-20 | Foerfarande foer framstaellning av metyl-3-(2-kinoxalinylmetylen)karbazat-n1,n4-dioxid |
Country Status (23)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006142A (en) * | 1973-03-07 | 1977-02-01 | Pfizer Inc. | Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide |
| US4740652A (en) * | 1985-05-23 | 1988-04-26 | Uop Inc. | Process for the oligomerization of olefins |
| US4737479A (en) * | 1986-03-21 | 1988-04-12 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4737480A (en) * | 1986-03-25 | 1988-04-12 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4795851A (en) * | 1987-03-12 | 1989-01-03 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4795852A (en) * | 1987-03-13 | 1989-01-03 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4935575A (en) * | 1988-12-12 | 1990-06-19 | Uop | Process for the oligomerization of olefins and a catalyst thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545786A (en) * | 1951-03-20 | S-methoxyquinoxaline-l | ||
| US2626259A (en) * | 1953-01-20 | Ffiii-ce | ||
| GB1170807A (en) * | 1967-03-21 | 1969-11-19 | Ici Ltd | Quinoxaline Derivatives |
| DE2015676A1 (de) * | 1970-04-02 | 1971-10-21 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Neue Imine der 2-Formyl-chinoxalindi-N-oxidcarbon-säure-(3) und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als antimikrobielle Mittel |
| GB1298268A (en) * | 1970-06-18 | 1972-11-29 | Ici Ltd | Process for the manufacture of quinoxaline dioxides |
| ZA725675B (en) * | 1971-06-21 | 1973-05-30 | Ciba Geigy Ag | New heterocyclic compounds |
-
1973
- 1973-03-07 US US338906A patent/US3926991A/en not_active Expired - Lifetime
-
1974
- 1974-02-04 IE IE197/74A patent/IE39170B1/xx unknown
- 1974-02-05 SE SE7401528A patent/SE420603B/xx not_active IP Right Cessation
- 1974-02-05 ZA ZA740745A patent/ZA74745B/xx unknown
- 1974-02-13 NL NL7401966A patent/NL7401966A/xx unknown
- 1974-02-20 FI FI490/74A patent/FI59404C/fi active
- 1974-02-20 IT IT48504/74A patent/IT1056054B/it active
- 1974-02-20 YU YU00439/74A patent/YU39150B/xx unknown
- 1974-02-21 ES ES423464A patent/ES423464A1/es not_active Expired
- 1974-02-21 JP JP49019992A patent/JPS5024282A/ja active Pending
- 1974-02-21 DK DK92574AA patent/DK138945B/da not_active IP Right Cessation
- 1974-02-22 LU LU69471A patent/LU69471A1/xx unknown
- 1974-02-22 FR FR7406155A patent/FR2220524B1/fr not_active Expired
- 1974-02-22 AR AR252487A patent/AR200516A1/es active
- 1974-02-22 CH CH254874A patent/CH580096A5/xx not_active IP Right Cessation
- 1974-02-28 CS CS7400001493A patent/CS180003B2/cs unknown
- 1974-02-28 HU HUPI408A patent/HU170488B/hu unknown
- 1974-03-01 SU SU2002363A patent/SU539527A3/ru active
- 1974-03-01 PL PL1974169209A patent/PL94858B1/pl unknown
- 1974-03-05 CA CA194,053A patent/CA982584A/en not_active Expired
- 1974-03-06 GB GB1014974A patent/GB1459561A/en not_active Expired
-
1977
- 1977-09-15 HK HK471/77A patent/HK47177A/xx unknown
-
1978
- 1978-12-30 MY MY13/78A patent/MY7800013A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA982584A (en) | 1976-01-27 |
| ZA74745B (en) | 1974-12-24 |
| MY7800013A (en) | 1978-12-31 |
| SE420603B (sv) | 1981-10-19 |
| US3926991A (en) | 1975-12-16 |
| FI59404B (fi) | 1981-04-30 |
| FR2220524B1 (enrdf_load_stackoverflow) | 1977-03-04 |
| DK138945C (enrdf_load_stackoverflow) | 1979-05-07 |
| LU69471A1 (enrdf_load_stackoverflow) | 1974-09-25 |
| ES423464A1 (es) | 1976-05-01 |
| NL7401966A (enrdf_load_stackoverflow) | 1974-09-10 |
| CH580096A5 (enrdf_load_stackoverflow) | 1976-09-30 |
| YU43974A (en) | 1982-06-30 |
| GB1459561A (en) | 1976-12-22 |
| PL94858B1 (enrdf_load_stackoverflow) | 1977-09-30 |
| IE39170B1 (en) | 1978-08-16 |
| IT1056054B (it) | 1982-01-30 |
| FR2220524A1 (enrdf_load_stackoverflow) | 1974-10-04 |
| YU39150B (en) | 1984-06-30 |
| SU539527A3 (ru) | 1976-12-15 |
| HU170488B (enrdf_load_stackoverflow) | 1977-06-28 |
| JPS5024282A (enrdf_load_stackoverflow) | 1975-03-15 |
| CS180003B2 (en) | 1977-12-30 |
| AR200516A1 (es) | 1974-11-15 |
| HK47177A (en) | 1977-09-23 |
| DK138945B (da) | 1978-11-20 |
| IE39170L (en) | 1974-09-07 |
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