CS219728B1 - Method of making the cyanacetylhydrazones of the 2-formylchinoxaline-1,4-dioxides - Google Patents
Method of making the cyanacetylhydrazones of the 2-formylchinoxaline-1,4-dioxides Download PDFInfo
- Publication number
- CS219728B1 CS219728B1 CS81125A CS12581A CS219728B1 CS 219728 B1 CS219728 B1 CS 219728B1 CS 81125 A CS81125 A CS 81125A CS 12581 A CS12581 A CS 12581A CS 219728 B1 CS219728 B1 CS 219728B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxide
- formula
- benzofurazan
- reaction mixture
- reaction
- Prior art date
Links
- JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical class C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 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 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000001256 steam distillation Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- -1 2-formylquinoxaline-1,4-dioxan Chemical compound 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 description 2
- 239000003049 inorganic solvent Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
- DWJDEJZHYRTMRR-UHFFFAOYSA-N 2,2-dimethoxypropanal Chemical compound COC(C)(OC)C=O DWJDEJZHYRTMRR-UHFFFAOYSA-N 0.000 description 1
- MBCZYLSVSCJJJQ-UHFFFAOYSA-N 2-cyano-N-[(1,4-dioxidoquinoxaline-1,4-diium-2-yl)methylideneamino]acetamide Chemical compound C1=CC=C2[N+]([O-])=CC(C=NNC(=O)CC#N)=[N+]([O-])C2=C1 MBCZYLSVSCJJJQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical compound C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS81125A CS219728B1 (en) | 1981-01-07 | 1981-01-07 | Method of making the cyanacetylhydrazones of the 2-formylchinoxaline-1,4-dioxides |
| IL64565A IL64565A (en) | 1981-01-07 | 1981-12-17 | Process for producing cyanoacetyl hydrazones of 2-formylquinoxaline-1,4-dioxides |
| PT74170A PT74170B (en) | 1981-01-07 | 1981-12-21 | Process for producing cyanoacetyl hydrazones of 2-formylquino- xaline-1,4-dioxides |
| NL8105930A NL8105930A (nl) | 1981-01-07 | 1981-12-31 | Werkwijze ter bereiding van cyaanacetylhydrazonen van 2-formylguinoxaline-1,4-dioxiden. |
| IT25953/81A IT1142648B (it) | 1981-01-07 | 1981-12-31 | Processo per la produzione di cianoacetilidrazoni di 2-formilchinossalin-1-4-diossidi |
| BE0/206976A BE891675A (fr) | 1981-01-07 | 1982-01-04 | Procede de preparation de cyanacetyl-hydrazones de 2-formyl-quinoxaline-1,4-dioxydes |
| ES508553A ES8300324A1 (es) | 1981-01-07 | 1982-01-07 | "procedimiento de producir cianoacetilhidrazonas de 2-formilquinoxalina-1,4-dioxidos". |
| DK3082A DK3082A (da) | 1981-01-07 | 1982-01-07 | Fremgangsmaade til fremstilling af cyanoacetylhydrazoner af 2-formylquinoxalin-1,4-dioxider |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS81125A CS219728B1 (en) | 1981-01-07 | 1981-01-07 | Method of making the cyanacetylhydrazones of the 2-formylchinoxaline-1,4-dioxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS219728B1 true CS219728B1 (en) | 1983-03-25 |
Family
ID=5332843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS81125A CS219728B1 (en) | 1981-01-07 | 1981-01-07 | Method of making the cyanacetylhydrazones of the 2-formylchinoxaline-1,4-dioxides |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE891675A (pt) |
| CS (1) | CS219728B1 (pt) |
| DK (1) | DK3082A (pt) |
| ES (1) | ES8300324A1 (pt) |
| IL (1) | IL64565A (pt) |
| IT (1) | IT1142648B (pt) |
| NL (1) | NL8105930A (pt) |
| PT (1) | PT74170B (pt) |
-
1981
- 1981-01-07 CS CS81125A patent/CS219728B1/cs unknown
- 1981-12-17 IL IL64565A patent/IL64565A/xx unknown
- 1981-12-21 PT PT74170A patent/PT74170B/pt unknown
- 1981-12-31 IT IT25953/81A patent/IT1142648B/it active
- 1981-12-31 NL NL8105930A patent/NL8105930A/nl not_active Application Discontinuation
-
1982
- 1982-01-04 BE BE0/206976A patent/BE891675A/fr unknown
- 1982-01-07 DK DK3082A patent/DK3082A/da not_active Application Discontinuation
- 1982-01-07 ES ES508553A patent/ES8300324A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE891675A (fr) | 1982-04-30 |
| IT8125953A0 (it) | 1981-12-31 |
| IL64565A (en) | 1984-12-31 |
| PT74170B (en) | 1983-05-18 |
| IL64565A0 (en) | 1982-03-31 |
| NL8105930A (nl) | 1982-08-02 |
| ES508553A0 (es) | 1982-11-01 |
| DK3082A (da) | 1982-07-08 |
| ES8300324A1 (es) | 1982-11-01 |
| PT74170A (en) | 1982-01-01 |
| IT1142648B (it) | 1986-10-08 |
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