CS198248B2 - Způsob výroby l-fenyl-4-amino-5-halogen-pyridazon-6-onů - Google Patents
Způsob výroby l-fenyl-4-amino-5-halogen-pyridazon-6-onů Download PDFInfo
- Publication number
- CS198248B2 CS198248B2 CS457577A CS457577A CS198248B2 CS 198248 B2 CS198248 B2 CS 198248B2 CS 457577 A CS457577 A CS 457577A CS 457577 A CS457577 A CS 457577A CS 198248 B2 CS198248 B2 CS 198248B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- toluene
- formula
- water
- mixture
- phenyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 150000001253 acrylic acids Chemical class 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000009435 amidation Effects 0.000 description 5
- 238000007112 amidation reaction Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- LUMLZKVIXLWTCI-UHFFFAOYSA-N 2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(Cl)=C(Cl)C=O LUMLZKVIXLWTCI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- XGQFEGPWMVWRQE-UHFFFAOYSA-N 2-bromo-3-chloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(Br)=C(Cl)C=O XGQFEGPWMVWRQE-UHFFFAOYSA-N 0.000 description 1
- VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 1
- ODNZLRLWXRXPOH-UHFFFAOYSA-N 5-amino-4-bromo-2-phenylpyridazin-3-one Chemical compound O=C1C(Br)=C(N)C=NN1C1=CC=CC=C1 ODNZLRLWXRXPOH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001516614 Exema Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JSPXPZKDILSYNN-UHFFFAOYSA-N but-1-yne-1,4-diol Chemical compound OCCC#CO JSPXPZKDILSYNN-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001712 | 1976-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS198248B2 true CS198248B2 (cs) | 1980-05-30 |
Family
ID=10994636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS457577A CS198248B2 (cs) | 1976-12-30 | 1977-07-08 | Způsob výroby l-fenyl-4-amino-5-halogen-pyridazon-6-onů |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT356659B (de) |
| CS (1) | CS198248B2 (de) |
| DD (1) | DD131172A5 (de) |
| SU (1) | SU845782A3 (de) |
| YU (1) | YU167077A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937421A1 (de) | 1979-09-15 | 1981-04-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-amino-5-chlor-1-phenylpyridazon-(6) |
-
1977
- 1977-06-28 AT AT456077A patent/AT356659B/de not_active IP Right Cessation
- 1977-07-05 YU YU167077A patent/YU167077A/xx unknown
- 1977-07-07 SU SU772499563A patent/SU845782A3/ru active
- 1977-07-08 CS CS457577A patent/CS198248B2/cs unknown
- 1977-07-14 DD DD20006677A patent/DD131172A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU845782A3 (ru) | 1981-07-07 |
| DD131172A5 (de) | 1978-06-07 |
| ATA456077A (de) | 1979-10-15 |
| AT356659B (de) | 1980-05-12 |
| YU167077A (en) | 1982-06-30 |
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