DE1620186A1 - Verfahren zur Gewinnung von reinem 5-Amino-4-chlor-2-phenylpyridazin-3-on - Google Patents
Verfahren zur Gewinnung von reinem 5-Amino-4-chlor-2-phenylpyridazin-3-onInfo
- Publication number
- DE1620186A1 DE1620186A1 DE19661620186 DE1620186A DE1620186A1 DE 1620186 A1 DE1620186 A1 DE 1620186A1 DE 19661620186 DE19661620186 DE 19661620186 DE 1620186 A DE1620186 A DE 1620186A DE 1620186 A1 DE1620186 A1 DE 1620186A1
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- phenylpyridazin
- technical
- extraction
- amino
- 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 4
- 238000002360 preparation method Methods 0.000 title description 2
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 title 1
- 238000000605 extraction Methods 0.000 claims description 11
- 238000005576 amination reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- CQZSJSRTGSYXPX-UHFFFAOYSA-N 4,5-dichloro-2-phenyl-1H-pyridazine Chemical compound ClC1=CN(NC=C1Cl)C1=CC=CC=C1 CQZSJSRTGSYXPX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
- BFOMTEBFEFQJHY-UHFFFAOYSA-N 2-phenylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=CC=C1 BFOMTEBFEFQJHY-UHFFFAOYSA-N 0.000 description 1
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical compound C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS341665 | 1965-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620186A1 true DE1620186A1 (de) | 1970-02-12 |
Family
ID=5374142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620186 Pending DE1620186A1 (de) | 1965-05-26 | 1966-03-09 | Verfahren zur Gewinnung von reinem 5-Amino-4-chlor-2-phenylpyridazin-3-on |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT260943B (enExample) |
| BE (1) | BE678857A (enExample) |
| DE (1) | DE1620186A1 (enExample) |
| GB (1) | GB1124398A (enExample) |
| NL (1) | NL6603960A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2100685A1 (en) * | 1971-01-08 | 1972-07-20 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Pure 4-amino-5-halo-6-pyridazones sepn - from isomers by extraction with halohydrocarbons, alkanols or ethers |
| DE2925110A1 (de) * | 1978-06-22 | 1980-01-10 | Oxon Italia Spa | Selektives unkrautvertilgungsmittel 5-amino-4-chlor-2-phenyl-3(2h)-pyridazinon, das frei von 5-chlor-4-amino-2-phenyl- 3(2h)-pyridazinon ist |
| EP0026847A1 (de) * | 1979-09-15 | 1981-04-15 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-5-chlor-1-phenyl-pyridazon-(6) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1165520T3 (da) | 1999-03-31 | 2009-08-24 | Basf Se | Fremgangsmåde til fremstilling af 4-amino-5-chlor-1-phenylpyridazinon |
-
1966
- 1966-03-07 AT AT211666A patent/AT260943B/de active
- 1966-03-09 DE DE19661620186 patent/DE1620186A1/de active Pending
- 1966-03-25 NL NL6603960A patent/NL6603960A/xx unknown
- 1966-04-01 BE BE678857D patent/BE678857A/xx unknown
- 1966-04-21 GB GB1742566A patent/GB1124398A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2100685A1 (en) * | 1971-01-08 | 1972-07-20 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Pure 4-amino-5-halo-6-pyridazones sepn - from isomers by extraction with halohydrocarbons, alkanols or ethers |
| DE2925110A1 (de) * | 1978-06-22 | 1980-01-10 | Oxon Italia Spa | Selektives unkrautvertilgungsmittel 5-amino-4-chlor-2-phenyl-3(2h)-pyridazinon, das frei von 5-chlor-4-amino-2-phenyl- 3(2h)-pyridazinon ist |
| EP0026847A1 (de) * | 1979-09-15 | 1981-04-15 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-5-chlor-1-phenyl-pyridazon-(6) |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1124398A (en) | 1968-08-21 |
| BE678857A (enExample) | 1966-09-16 |
| AT260943B (de) | 1968-03-25 |
| NL6603960A (enExample) | 1966-11-28 |
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