DE1257154B - Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4) - Google Patents
Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4)Info
- Publication number
- DE1257154B DE1257154B DEF45167A DEF0045167A DE1257154B DE 1257154 B DE1257154 B DE 1257154B DE F45167 A DEF45167 A DE F45167A DE F0045167 A DEF0045167 A DE F0045167A DE 1257154 B DE1257154 B DE 1257154B
- Authority
- DE
- Germany
- Prior art keywords
- diacylamino
- diamino
- benzoquinones
- reaction
- benzoquinone
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- -1 propen-1-yl Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- 150000000469 3,5-xylenols Chemical class 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- RYVFSUJSDXQEPY-UHFFFAOYSA-N 4-chlorophenol 3-methylphenol Chemical compound CC1=CC=CC(O)=C1.OC1=CC=C(Cl)C=C1 RYVFSUJSDXQEPY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920006051 Capron® Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- 244000168525 Croton tiglium Species 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides 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
- 235000014121 butter Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002672 m-cresols Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 210000003250 oocyst Anatomy 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF45167A DE1257154B (de) | 1965-02-06 | 1965-02-06 | Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4) |
| DE19661543567 DE1543567A1 (de) | 1965-02-06 | 1966-01-15 | Verfahren zur Herstellung von 2,5-Diacylamino-3,6-diamino-1,4-benzochinonen |
| NL6601262A NL6601262A (enrdf_load_stackoverflow) | 1965-02-06 | 1966-02-01 | |
| AT102666A AT260905B (de) | 1965-02-06 | 1966-02-04 | Verfahren zur Herstellung von 2,5-Diacylamino-3,6-diamino-1,4-benzochinonen |
| GB524266A GB1135804A (en) | 1965-02-06 | 1966-02-07 | Process for preparing 2,5-diacylamino-3,6-diamino-1,4-benzoquinones |
| BE676157D BE676157A (enrdf_load_stackoverflow) | 1965-02-06 | 1966-02-07 | |
| FR48654A FR1467521A (fr) | 1965-02-06 | 1966-02-07 | Procédé de préparation de 2.5-diacylamino-3.6-diamino-1.4-benzoquinones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF45167A DE1257154B (de) | 1965-02-06 | 1965-02-06 | Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4) |
| DEF0048177 | 1966-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1257154B true DE1257154B (de) | 1967-12-28 |
Family
ID=25976613
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF45167A Pending DE1257154B (de) | 1965-02-06 | 1965-02-06 | Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4) |
| DE19661543567 Pending DE1543567A1 (de) | 1965-02-06 | 1966-01-15 | Verfahren zur Herstellung von 2,5-Diacylamino-3,6-diamino-1,4-benzochinonen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543567 Pending DE1543567A1 (de) | 1965-02-06 | 1966-01-15 | Verfahren zur Herstellung von 2,5-Diacylamino-3,6-diamino-1,4-benzochinonen |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT260905B (enrdf_load_stackoverflow) |
| BE (1) | BE676157A (enrdf_load_stackoverflow) |
| DE (2) | DE1257154B (enrdf_load_stackoverflow) |
| GB (1) | GB1135804A (enrdf_load_stackoverflow) |
| NL (1) | NL6601262A (enrdf_load_stackoverflow) |
-
1965
- 1965-02-06 DE DEF45167A patent/DE1257154B/de active Pending
-
1966
- 1966-01-15 DE DE19661543567 patent/DE1543567A1/de active Pending
- 1966-02-01 NL NL6601262A patent/NL6601262A/xx unknown
- 1966-02-04 AT AT102666A patent/AT260905B/de active
- 1966-02-07 GB GB524266A patent/GB1135804A/en not_active Expired
- 1966-02-07 BE BE676157D patent/BE676157A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT260905B (de) | 1968-03-25 |
| GB1135804A (en) | 1968-12-04 |
| DE1543567A1 (de) | 1969-09-25 |
| NL6601262A (enrdf_load_stackoverflow) | 1966-08-08 |
| BE676157A (enrdf_load_stackoverflow) | 1966-08-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1245357B (de) | Verfahren zur Herstellung von basischen AEthern von substituierten Hydroxybenzoesaeureamiden | |
| DE2757506C2 (de) | Verfahren zur Herstellung von Piperonylidencrotonsaureamiden | |
| DE1257154B (de) | Verfahren zur Herstellung von 2, 5-diacylamino-3, 6-diamino-benzochinonen-(1, 4) | |
| DE2319645B2 (de) | Verfahren zur Herstellung von 5-Chlor-2-toluidin | |
| DE1078582B (de) | Verfahren zur Herstellung substituierter Thyropropionsaeuren | |
| DE1545554A1 (de) | Verfahren zur Herstellung von 1,3-Benzoxazin-2,4-dion | |
| DE681850C (de) | Verfahren zur Herstellung quaternaerer Stickstoffverbindungen | |
| EP0688763B1 (de) | Verfahren zur Herstellung von Hydroxycarbonsäureaniliden | |
| DE887198C (de) | Verfahren zur Herstellung von Naphthostyrilen | |
| DE1257152B (de) | Verfahren zur Herstellung substituierter Malonsaeurehydrazide | |
| DE1026301B (de) | Verfahren zur Herstellung von antimykotisch wirksamen 4-Halogensalicylsaeureamiden | |
| DE686243C (de) | Verfahren zur Herstellung von Abkoemmlingen der Pyridin-2, 3-dicarbonsaeure | |
| DE662646C (de) | Verfahren zur Darstellung von Oxyzimtsaeuren | |
| AT234698B (de) | Verfahren zur Herstellung von 4-Sulfanilamido-2,6-di-nieder-alkoxy-pyrimidinen | |
| DE867244C (de) | Verfahren zur Herstellung von Aminoaryloxyessigsaeureamiden | |
| AT226220B (de) | Verfahren zur Herstellung von Phenyläthanolaminderivaten | |
| DE1493893C (de) | 2 (5 Nitrofurfuryliden) crotonsäure meffeylester und Verfahren zu seiner Her stellung | |
| DE750481C (de) | Verfahren zur Herstellung von in waessrigen Loesungen bestaendigen Abkoemmlingen des2-Methyl-4-amino-naphthols-(1) | |
| DE748541C (de) | Verfahren zur Herstellung von chlorierten 3,6-Dinitrocharbazolen | |
| AT295542B (de) | Verfahren zur Herstellung von neuen Diamino-chlor-s-triazinen | |
| AT163640B (de) | Verfahren zur Herstellung eines Salzes einer Chloraryloxyalkylcarbonsäure | |
| DE1222049B (de) | Verfahren zur Herstellung von 1, 2, 5, 6, 9, 10-Hexabromcyclododecan | |
| DE1468344A1 (de) | Ungesaettigte saeuren und verfahren zu ihrer herstellung | |
| AT216511B (de) | Verfahren zur Herstellung von 1,2,4-Benzothiadiazin-1,1-dioxydverbindungen | |
| DE1768787C3 (de) | (o-Carboxy-phenyl)-acetamidine, Verfahren zu deren Herstellung und (o-CarboxyphenyO-acetamidine enthaltende Präparate |