DE1212104B - Verfahren zur Herstellung von 2, 5-Di-acylamino-3, 6-diamino-benzochinonen-1, 4 - Google Patents
Verfahren zur Herstellung von 2, 5-Di-acylamino-3, 6-diamino-benzochinonen-1, 4Info
- Publication number
- DE1212104B DE1212104B DEF41704A DEF0041704A DE1212104B DE 1212104 B DE1212104 B DE 1212104B DE F41704 A DEF41704 A DE F41704A DE F0041704 A DEF0041704 A DE F0041704A DE 1212104 B DE1212104 B DE 1212104B
- Authority
- DE
- Germany
- Prior art keywords
- acylamino
- diamino
- benzoquinone
- benzoquinones
- vol
- 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 13
- 230000008569 process Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000725 suspension Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 208000003495 Coccidiosis Diseases 0.000 description 4
- 206010023076 Isosporiasis Diseases 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- OMXMYDUYAUOFRX-UHFFFAOYSA-N n-(3-chloro-1,4-dioxonaphthalen-2-yl)acetamide Chemical compound C1=CC=C2C(=O)C(NC(=O)C)=C(Cl)C(=O)C2=C1 OMXMYDUYAUOFRX-UHFFFAOYSA-N 0.000 description 2
- 210000003250 oocyst Anatomy 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZEFNOZRLAWVAQF-UHFFFAOYSA-N Dinitolmide Chemical compound CC1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZEFNOZRLAWVAQF-UHFFFAOYSA-N 0.000 description 1
- 241000223931 Eimeria acervulina Species 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 238000009835 boiling Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004200 deflagration Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- -1 ethanol 2,5 - diacetylamino - 3,6 - diamino - benzoquinone Chemical compound 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41704A DE1212104B (de) | 1964-01-10 | 1964-01-10 | Verfahren zur Herstellung von 2, 5-Di-acylamino-3, 6-diamino-benzochinonen-1, 4 |
| NL6415174A NL6415174A (enExample) | 1964-01-10 | 1964-12-29 | |
| CH13265A CH453377A (de) | 1964-01-10 | 1965-01-07 | Verfahren zur Herstellung von 2,5-Di-acylamino-3,6-diamino-1,4-benzochinonen |
| AT11165A AT252904B (de) | 1964-01-10 | 1965-01-08 | Verfahren zur Herstellung von 2,5-Di-acylamino-3,6-diamino-1,4-benzochinonen |
| FR1432A FR1434198A (fr) | 1964-01-10 | 1965-01-11 | Nouvelles benzoquinones substituées et leur préparation |
| BE658140A BE658140A (enExample) | 1964-01-10 | 1965-01-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41704A DE1212104B (de) | 1964-01-10 | 1964-01-10 | Verfahren zur Herstellung von 2, 5-Di-acylamino-3, 6-diamino-benzochinonen-1, 4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1212104B true DE1212104B (de) | 1966-03-10 |
Family
ID=7098784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF41704A Pending DE1212104B (de) | 1964-01-10 | 1964-01-10 | Verfahren zur Herstellung von 2, 5-Di-acylamino-3, 6-diamino-benzochinonen-1, 4 |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT252904B (enExample) |
| BE (1) | BE658140A (enExample) |
| CH (1) | CH453377A (enExample) |
| DE (1) | DE1212104B (enExample) |
| FR (1) | FR1434198A (enExample) |
| NL (1) | NL6415174A (enExample) |
-
1964
- 1964-01-10 DE DEF41704A patent/DE1212104B/de active Pending
- 1964-12-29 NL NL6415174A patent/NL6415174A/xx unknown
-
1965
- 1965-01-07 CH CH13265A patent/CH453377A/de unknown
- 1965-01-08 AT AT11165A patent/AT252904B/de active
- 1965-01-11 FR FR1432A patent/FR1434198A/fr not_active Expired
- 1965-01-11 BE BE658140A patent/BE658140A/fr unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH453377A (de) | 1968-06-14 |
| AT252904B (de) | 1967-03-10 |
| FR1434198A (fr) | 1966-04-08 |
| BE658140A (enExample) | 1965-07-12 |
| NL6415174A (enExample) | 1965-07-12 |
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