CS214843B2 - Method of making the pure 4-amino-5-chlor-1-phenyl-6-pyridazone - Google Patents
Method of making the pure 4-amino-5-chlor-1-phenyl-6-pyridazone Download PDFInfo
- Publication number
- CS214843B2 CS214843B2 CS806192A CS619280A CS214843B2 CS 214843 B2 CS214843 B2 CS 214843B2 CS 806192 A CS806192 A CS 806192A CS 619280 A CS619280 A CS 619280A CS 214843 B2 CS214843 B2 CS 214843B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- pyridazone
- reaction
- amino
- sulfonic acid
- Prior art date
Links
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 19
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000013543 active substance Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BFOMTEBFEFQJHY-UHFFFAOYSA-N 2-phenylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=CC=C1 BFOMTEBFEFQJHY-UHFFFAOYSA-N 0.000 description 1
- HAKJEHJYRKVCIU-UHFFFAOYSA-N 4-amino-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(N)=C(Cl)C=NN1C1=CC=CC=C1 HAKJEHJYRKVCIU-UHFFFAOYSA-N 0.000 description 1
- MITYOFHEBMHYOJ-UHFFFAOYSA-N 4-pentylpyrrolidin-2-one Chemical class CCCCCC1CNC(=O)C1 MITYOFHEBMHYOJ-UHFFFAOYSA-N 0.000 description 1
- NXSHBXZGGDVKOL-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=NNC1=O NXSHBXZGGDVKOL-UHFFFAOYSA-N 0.000 description 1
- XGZIUJAUPPHEGB-UHFFFAOYSA-N 6-amino-4-chloro-2-phenylpyridazin-3-one Chemical compound NC1=NN(C(C(=C1)Cl)=O)C1=CC=CC=C1 XGZIUJAUPPHEGB-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- -1 phenol-4-sulfonic acid ammonium salt Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792937421 DE2937421A1 (de) | 1979-09-15 | 1979-09-15 | Verfahren zur herstellung von 4-amino-5-chlor-1-phenylpyridazon-(6) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214843B2 true CS214843B2 (en) | 1982-06-25 |
Family
ID=6081005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS806192A CS214843B2 (en) | 1979-09-15 | 1980-09-11 | Method of making the pure 4-amino-5-chlor-1-phenyl-6-pyridazone |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4297493A (da) |
| EP (1) | EP0026847B1 (da) |
| AT (1) | ATE1239T1 (da) |
| BG (1) | BG33282A3 (da) |
| CS (1) | CS214843B2 (da) |
| DD (1) | DD153119A5 (da) |
| DE (2) | DE2937421A1 (da) |
| DK (1) | DK146181C (da) |
| HU (1) | HU184826B (da) |
| IL (1) | IL61014A (da) |
| NL (1) | NL971002I1 (da) |
| PL (1) | PL121912B2 (da) |
| RO (1) | RO80196A (da) |
| SU (1) | SU940648A3 (da) |
| UA (1) | UA7014A1 (da) |
| YU (1) | YU43223B (da) |
| ZA (1) | ZA805664B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981001288A1 (en) * | 1979-10-31 | 1981-05-14 | Koege Kemisk Vaerk | Method for producing 4-chloro-5-amino-2-phenyl-3(2h)-pyridazinone from 4,5-dichloro-2-phenyl-3(2h)-pyridazinone and ammonia |
| DE3926905A1 (de) * | 1989-08-16 | 1991-02-21 | Basf Ag | Verfahren zur abtrennung und wiederverwertung von reststoffen aus dem abwasser der synthese von 5-amino-4-chlor-2-phenyl-3(2h)-pyridazinon |
| WO2000059891A1 (de) | 1999-03-31 | 2000-10-12 | Basf Aktiengesellschaft | Verfahren zur herstellung von 4-amino-5-chlor-1-phenylpyridazinon-(6) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL245646A (da) * | 1960-03-19 | |||
| AT260943B (de) * | 1965-05-26 | 1968-03-25 | Pavel Dipl Ing Rapos | Verfahren zur Gewinnung von reinem 5-Amino-4-chlor-2-phenylpyridazin-3-on |
| HU169505B (da) * | 1974-05-22 | 1976-12-28 | ||
| DD124918A1 (da) * | 1976-02-27 | 1977-03-23 | ||
| IT1096594B (it) * | 1978-06-22 | 1985-08-26 | Oxon Italia Spa | Procedimento per ottenere 5-amino-4-cloro-2-fenil-3(2h)-pirid azinone esente da 5-cloro-4amino-2-fenil-3(2h)-pirida zionone da miscele dei due isomeri ed applicazione quale erbicida selettivo del prodotto ottenuto |
| IT1107509B (it) * | 1978-07-28 | 1985-11-25 | Oxon Italia Spa | Procedimento per ottenere 4,5-dicloro-2-fenil-3(2h)-piridazinone a partire da 5-cloro-4-ammino-2-fenil-3(2h)-piridazinone |
-
1979
- 1979-09-15 DE DE19792937421 patent/DE2937421A1/de not_active Withdrawn
-
1980
- 1980-09-04 DE DE8080105271T patent/DE3060595D1/de not_active Expired
- 1980-09-04 EP EP80105271A patent/EP0026847B1/de not_active Expired
- 1980-09-04 AT AT80105271T patent/ATE1239T1/de active
- 1980-09-08 US US06/185,403 patent/US4297493A/en not_active Expired - Lifetime
- 1980-09-10 IL IL61014A patent/IL61014A/xx not_active IP Right Cessation
- 1980-09-11 BG BG8049035A patent/BG33282A3/xx unknown
- 1980-09-11 CS CS806192A patent/CS214843B2/cs unknown
- 1980-09-12 ZA ZA00805664A patent/ZA805664B/xx unknown
- 1980-09-12 DD DD80223875A patent/DD153119A5/de not_active IP Right Cessation
- 1980-09-12 DK DK388980A patent/DK146181C/da active
- 1980-09-12 UA UA2980754A patent/UA7014A1/uk unknown
- 1980-09-12 SU SU802980754A patent/SU940648A3/ru active
- 1980-09-13 PL PL1980226744A patent/PL121912B2/xx unknown
- 1980-09-15 YU YU2342/80A patent/YU43223B/xx unknown
- 1980-09-15 HU HU802273A patent/HU184826B/hu unknown
- 1980-09-15 RO RO80102159A patent/RO80196A/ro unknown
-
1997
- 1997-03-03 NL NL971002C patent/NL971002I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK146181B (da) | 1983-07-18 |
| UA7014A1 (uk) | 1995-03-31 |
| DK388980A (da) | 1981-03-16 |
| RO80196A (ro) | 1982-12-06 |
| DE3060595D1 (en) | 1982-08-12 |
| ATE1239T1 (de) | 1982-07-15 |
| ZA805664B (en) | 1981-09-30 |
| PL226744A2 (da) | 1981-06-19 |
| YU234280A (en) | 1983-09-30 |
| IL61014A (en) | 1984-03-30 |
| IL61014A0 (en) | 1980-11-30 |
| DD153119A5 (de) | 1981-12-23 |
| YU43223B (en) | 1989-06-30 |
| EP0026847A1 (de) | 1981-04-15 |
| NL971002I1 (nl) | 1997-06-02 |
| PL121912B2 (en) | 1982-06-30 |
| SU940648A3 (ru) | 1982-06-30 |
| DK146181C (da) | 1983-12-12 |
| EP0026847B1 (de) | 1982-06-23 |
| BG33282A3 (en) | 1983-01-14 |
| HU184826B (en) | 1984-10-29 |
| DE2937421A1 (de) | 1981-04-09 |
| US4297493A (en) | 1981-10-27 |
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