CS212276B2 - Method of making the methyl-3-(2-chinoxalinylmethylene) -carbazate n1,n4-dioxide - Google Patents
Method of making the methyl-3-(2-chinoxalinylmethylene) -carbazate n1,n4-dioxide Download PDFInfo
- Publication number
- CS212276B2 CS212276B2 CS742332A CS233274A CS212276B2 CS 212276 B2 CS212276 B2 CS 212276B2 CS 742332 A CS742332 A CS 742332A CS 233274 A CS233274 A CS 233274A CS 212276 B2 CS212276 B2 CS 212276B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbazate
- methyl
- dioxide
- reaction
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- SOEMFPLGOUBPJQ-UHFFFAOYSA-N methyl n-(quinoxalin-2-ylmethylideneamino)carbamate Chemical compound C1=CC=CC2=NC(C=NNC(=O)OC)=CN=C21 SOEMFPLGOUBPJQ-UHFFFAOYSA-N 0.000 title 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002923 oximes Chemical class 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 3
- -1 methylthiophenyl Chemical group 0.000 claims description 4
- 235000015107 ale Nutrition 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 abstract description 2
- 150000007659 semicarbazones Chemical class 0.000 abstract description 2
- 150000007857 hydrazones Chemical class 0.000 abstract 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 abstract 1
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UJEHWLFUEQHEEZ-UHFFFAOYSA-N quinoxaline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CN=C21 UJEHWLFUEQHEEZ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 description 1
- XBXUDUNJEWEIHM-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)quinoxaline Chemical compound O1CCOC1C1=CN=C(C=CC=C2)C2=N1 XBXUDUNJEWEIHM-UHFFFAOYSA-N 0.000 description 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus 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
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- LEHOGBUBQSGCOK-UHFFFAOYSA-N aminothiourea;hydron;chloride Chemical compound Cl.NNC(N)=S LEHOGBUBQSGCOK-UHFFFAOYSA-N 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- PFPWXPRRGWAESP-UHFFFAOYSA-N benzaldehyde;oxalic acid Chemical compound OC(=O)C(O)=O.O=CC1=CC=CC=C1 PFPWXPRRGWAESP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 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
- OVGGLBAWFMIPPY-UHFFFAOYSA-N methyl N-[(1,4-dioxidoquinoxaline-1,4-diium-2-yl)methylideneamino]carbamate Chemical compound C1=CC=CC2=[N+]([O-])C(C=NNC(=O)OC)=C[N+]([O-])=C21 OVGGLBAWFMIPPY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 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
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34980573A | 1973-04-10 | 1973-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS212276B2 true CS212276B2 (en) | 1982-03-26 |
Family
ID=23374042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS742332A CS212276B2 (en) | 1973-04-10 | 1974-04-01 | Method of making the methyl-3-(2-chinoxalinylmethylene) -carbazate n1,n4-dioxide |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5333596B2 (pm) |
| AR (1) | AR210723A1 (pm) |
| AU (1) | AU477279B2 (pm) |
| CA (1) | CA1018977A (pm) |
| CH (1) | CH603599A5 (pm) |
| CS (1) | CS212276B2 (pm) |
| DD (1) | DD110875A5 (pm) |
| DK (1) | DK140756B (pm) |
| ES (1) | ES424803A1 (pm) |
| FI (1) | FI59405C (pm) |
| FR (1) | FR2225429B1 (pm) |
| GB (1) | GB1462424A (pm) |
| HK (1) | HK48877A (pm) |
| HU (1) | HU170050B (pm) |
| IE (1) | IE39110B1 (pm) |
| IL (1) | IL44434A (pm) |
| IT (1) | IT1056058B (pm) |
| MY (1) | MY7800014A (pm) |
| NL (1) | NL7404044A (pm) |
| NO (1) | NO141851C (pm) |
| PH (1) | PH11135A (pm) |
| PL (1) | PL94963B1 (pm) |
| RO (1) | RO71311A (pm) |
| SE (1) | SE407219B (pm) |
| SU (1) | SU730302A3 (pm) |
| YU (1) | YU39151B (pm) |
| ZA (1) | ZA742052B (pm) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5135625Y2 (pm) * | 1971-03-30 | 1976-09-02 | ||
| JPS4984830U (pm) * | 1972-11-09 | 1974-07-23 | ||
| JPS49100338U (pm) * | 1972-12-20 | 1974-08-29 | ||
| IT1078991B (it) * | 1977-05-26 | 1985-05-08 | Erregierre Ind Chim Spa | Processo per la preparazione del carbometossi idrazone,della 2-formilchinossalina-1,4-di-n-ossido |
| JPS5487994U (pm) * | 1977-12-02 | 1979-06-21 | ||
| DK141708B (da) * | 1978-04-20 | 1980-05-27 | Rasmussen Holding As V Kann | Manøvrerings- og låsegreb til vinduer. |
-
1974
- 1974-03-11 SE SE7403236A patent/SE407219B/xx not_active IP Right Cessation
- 1974-03-15 GB GB1170674A patent/GB1462424A/en not_active Expired
- 1974-03-18 IL IL44434A patent/IL44434A/en unknown
- 1974-03-19 AU AU66828/74A patent/AU477279B2/en not_active Expired
- 1974-03-26 YU YU00834/74A patent/YU39151B/xx unknown
- 1974-03-26 NL NL7404044A patent/NL7404044A/xx unknown
- 1974-03-27 IT IT49751/74A patent/IT1056058B/it active
- 1974-03-28 JP JP3402874A patent/JPS5333596B2/ja not_active Expired
- 1974-03-29 CH CH446274A patent/CH603599A5/xx not_active IP Right Cessation
- 1974-03-29 FR FR7411526A patent/FR2225429B1/fr not_active Expired
- 1974-03-29 FI FI978/74A patent/FI59405C/fi active
- 1974-03-29 HU HUPI412A patent/HU170050B/hu unknown
- 1974-03-29 SU SU742013770A patent/SU730302A3/ru active
- 1974-03-29 NO NO741133A patent/NO141851C/no unknown
- 1974-03-29 DK DK174874AA patent/DK140756B/da not_active IP Right Cessation
- 1974-03-29 IE IE00686/74A patent/IE39110B1/xx unknown
- 1974-03-30 ES ES424803A patent/ES424803A1/es not_active Expired
- 1974-03-30 RO RO7478252A patent/RO71311A/ro unknown
- 1974-04-01 PL PL1974170010A patent/PL94963B1/pl unknown
- 1974-04-01 CS CS742332A patent/CS212276B2/cs unknown
- 1974-04-01 ZA ZA00742052A patent/ZA742052B/xx unknown
- 1974-04-01 AR AR253076A patent/AR210723A1/es active
- 1974-04-01 CA CA196,545A patent/CA1018977A/en not_active Expired
- 1974-04-01 DD DD177605A patent/DD110875A5/xx unknown
-
1976
- 1976-03-23 PH PH18245A patent/PH11135A/en unknown
-
1977
- 1977-09-22 HK HK488/77A patent/HK48877A/xx unknown
-
1978
- 1978-12-30 MY MY14/78A patent/MY7800014A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD110875A5 (pm) | 1975-01-12 |
| PH11135A (en) | 1977-10-27 |
| IT1056058B (it) | 1982-01-30 |
| FI59405C (fi) | 1981-08-10 |
| NO141851B (no) | 1980-02-11 |
| NO741133L (no) | 1974-10-11 |
| JPS5030893A (pm) | 1975-03-27 |
| FR2225429A1 (pm) | 1974-11-08 |
| NL7404044A (pm) | 1974-10-14 |
| ES424803A1 (es) | 1976-05-16 |
| ZA742052B (en) | 1975-03-26 |
| YU83474A (en) | 1982-08-31 |
| GB1462424A (en) | 1977-01-26 |
| PL94963B1 (pm) | 1977-09-30 |
| SU730302A3 (ru) | 1980-04-25 |
| YU39151B (en) | 1984-06-30 |
| FI59405B (fi) | 1981-04-30 |
| RO71311A (ro) | 1981-08-30 |
| JPS5333596B2 (pm) | 1978-09-14 |
| IE39110B1 (en) | 1978-08-02 |
| MY7800014A (en) | 1978-12-31 |
| HU170050B (pm) | 1977-03-28 |
| AU477279B2 (en) | 1976-10-21 |
| IE39110L (en) | 1974-10-10 |
| CH603599A5 (pm) | 1978-08-31 |
| NO141851C (no) | 1980-06-04 |
| CA1018977A (en) | 1977-10-11 |
| AU6682874A (en) | 1975-09-25 |
| DK140756C (pm) | 1980-04-14 |
| HK48877A (en) | 1977-09-30 |
| DK140756B (da) | 1979-11-12 |
| SE407219B (sv) | 1979-03-19 |
| IL44434A (en) | 1977-08-31 |
| IL44434A0 (en) | 1974-06-30 |
| AR210723A1 (es) | 1977-09-15 |
| FR2225429B1 (pm) | 1977-06-24 |
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