DE856297C - Process for the production of 3- (2-oxy-phenyl) -pyrazole or its substitution products - Google Patents
Process for the production of 3- (2-oxy-phenyl) -pyrazole or its substitution productsInfo
- Publication number
- DE856297C DE856297C DEK8084A DEK0008084A DE856297C DE 856297 C DE856297 C DE 856297C DE K8084 A DEK8084 A DE K8084A DE K0008084 A DEK0008084 A DE K0008084A DE 856297 C DE856297 C DE 856297C
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- pyrazole
- phenyl
- production
- water
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000006467 substitution reaction Methods 0.000 title description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 3-(2-Oxy-phenyl)-pyrazol bzw. dessen
Substitutionsprodukten
Zur Cberfi-ihrung der Base in das Hydrochlorid werden 5 g Base in 5o ccm Äther gelöst und durch Einleiten von Salzsäuregas das Hydrochlorid zunächst ölig ausgefällt. Nach kurzer Zeit tritt Kristallisation des Öls ein. F. 158 bis 16.4° (aus Alkoholäther).To convert the base into the hydrochloride, 5 g of base are dissolved in Dissolve 50 cc of ether and, first of all, introduce the hydrochloride by introducing hydrochloric acid gas precipitated oily. After a short time, the oil crystallizes. F. 158 to 16.4 ° (from alcohol ether).
2. 3-(2-Oxy-5-chlor-phenyl)-pyrazol: Zu einer Lösung von t 1, i g 2-Oxy-5-clilor-ol-formylacetopheilon in 5o ccm :Methanol werden 12 ccnl 25o/oige Hydrazinhydratlösung unter Ruhren langsam hinzugegeben. Danach wird noch i Stunde auf dem Dampfbad erwärmt und darauf die Reaktionslösung in 250 ccm Wasser gegossen, wobei 7,5 g rohes 3-(2-Oxy-5-chlor-phenyl)-pyrazol ausfallen. Nach dem Umkristallisieren aus heißem Wasser mit Tierkohlezusatz schmilzt die Base bei 15o bis i52°.2. 3- (2-Oxy-5-chlorophenyl) pyrazole: To a solution of t 1, ig 2-oxy-5-clilor-ol-formylacetopheilone in 50 cc: methanol, 12 ccnl of 25% hydrazine hydrate solution are added Stirring slowly added. The mixture is then heated on the steam bath for a further hour and the reaction solution is then poured into 250 cc of water, 7.5 g of crude 3- (2-oxy-5-chlorophenyl) pyrazole precipitating out. After recrystallization from hot water with the addition of animal charcoal, the base melts at 150 to 150 degrees.
3. 3-(2-Oxy-5-brom-phenyl)-pyrazol: 15 g 2-Oxy-5-brom-co-formylacetophenon, hergestellt durch Kondensation von 2-Oxy-5-brom-acetophenon mit Ameisensäureäthylester in Gegenwart von Natrium, werden in 5o ccm Methanol gelöst und mit 13 ccm 25o/oiger Hydrazinhydratlösung 2 Stunden am Rückflußkühler gekocht. Beim Verdünnen mit Wasser fallen 14 g 3-(2-Oxy-5-brom-phenyl)-pyrazol vom .F. 157 bis 15g° (aus Trichloräthylen) aus.3. 3- (2-Oxy-5-bromo-phenyl) -pyrazole: 15 g of 2-oxy-5-bromo-co-formylacetophenone, produced by condensation of 2-oxy-5-bromo-acetophenone with ethyl formate in the presence of sodium, are dissolved in 5o ccm methanol and with 13 ccm 25o / oiger Hydrazine hydrate solution boiled for 2 hours on the reflux condenser. When diluting with water fall 14 g of 3- (2-oxy-5-bromophenyl) pyrazole from the .F. 157 to 15g ° (from trichlorethylene) the end.
4. 3-(2 - Oxy - 5 - brom-phenyl)-5-methyl-pyrazol 5,1 g 2-Oxy-5-brombenzoylaceton, hergestellt durch Kondensation von 2-Oxy-5-bromacetophenon mit Essigester in Gegenwart von Natrium, werden in einer Mischung von 2o ccm Alkohol, to ccm Wasser und 5 ccm Eisessig gelöst und nach Zugabe von 2,3 g Semicarbazidhydrochlorid 2 Stunden auf dem Dampfbad erwärmt. Beim Verdünnen der Reaktionslösung mit Wasser fallen 3,5 g 3-(2-Oxy-5 - brom - phenyl) - 5 - methyl - pyrazol aus. F. 158 bis 159° (aus Trichloräthylen).4. 3- (2 - oxy - 5 - bromophenyl) -5-methyl-pyrazole 5.1 g of 2-oxy-5-bromobenzoylacetone, produced by condensation of 2-oxy-5-bromoacetophenone with ethyl acetate in the presence of sodium, are in a mixture of 20 cc of alcohol, to cc of water and 5 cc Dissolved glacial acetic acid and after adding 2.3 g of semicarbazide hydrochloride for 2 hours heated in the steam bath. When the reaction solution is diluted with water, 3.5 g fall 3- (2-Oxy-5 - bromo - phenyl) - 5 - methyl - pyrazole from. F. 158 to 159 ° (from trichlorethylene).
5. 3-(2-OxY-5-brom-phenyl)-5-methyl-pyrazol: 5,1 g 2-Oxy-5-brom-benzoylaceton, gelöst in 45 ccm Methanol, werden zusammen mit 4 ccm 25o/oiger Hydrazinhydratlösung auf dem Dampfbad erwärmt. Beim Verdünnen mit Wasser fallen 5 g 3-(2-OxY-5-brom-phenyl)-5-methyl-pyrazol aus. F. 158 bis 15g'° aus Trichloräthylen.5. 3- (2-OxY-5-bromo-phenyl) -5-methyl-pyrazole: 5.1 g of 2-oxy-5-bromo-benzoylacetone, dissolved in 45 cc of methanol, together with 4 cc of 25% hydrazine hydrate solution warmed up on the steam bath. On dilution with water, 5 g of 3- (2-OxY-5-bromo-phenyl) -5-methyl-pyrazole fall the end. F. 158 to 15g '° from trichlorethylene.
6. 3 -(2 - Oxy - 5 - chlor-phenyl)-5-methyl-pyrazol 5 g 2-Oxy-5-chlor-benzoylaceton, gelöst in 4o ccm Methanol, werden mit 5 g 25o/oiger Hydrazinhydratlösung versetzt und 1 Stunde auf dem Dampfbad erwärmt. Beim Verdünnen mit Wasser fallen 4,5 g 3 - (2-Oxy-5-chlor-phenyl) - 5 - methylpyrazol aus. F. 16o bis 161° (aus Trichloräthylen).6. 3 - (2 - oxy - 5 - chlorophenyl) -5-methyl-pyrazole 5 g of 2-oxy-5-chlorobenzoylacetone, dissolved in 40 cc of methanol, 5 g of 25% hydrazine hydrate solution are added and heated on the steam bath for 1 hour. When diluting with water, 4.5 g of 3 fall - (2-Oxy-5-chlorophenyl) - 5 - methylpyrazole from. F. 16o to 161 ° (made of trichlorethylene).
7. 3-(2-Oxy-phenyl)-5-methyl-pyrazol: to g 2-Oxy-l)enzoy laceton, gelöst in 5o ccm Methanol, werden mit 24 ccm 25o/oiger Hydrazinhydratlösung versetzt und i Stunde auf dem Dampfbad erwärmt. Beim Verdünnen mit Wasser fallen 8,8 g 3-(2-Oxyphenyl)-5-methyl-pyrazol aus. F. 133 bis 134° (aus Dibtityläther). B. 3-(2-Oxy-5-brom-hlietiyl)-5-ätliyl-pyrazol : 2,79 2-Oxy-5-brom-w-propiotivl-acetophenon, hergestellt durch Kondensation von 2-Oxy-5-brom-acetophenon mit Propionsäureäthylester in Gegenwart von Natrium, werden in 2o ccm ZTethanol gelöst und mit 3 CCM 25o/oiger Hvdrazinhydratlösung 2 Stunden am Rückflußkühler gekocht. Beim Verdünnen mit Wasser werden 1,5 g 3-(2-Oxy-5-brom-phenyl)-5-äthyl-pyrazol. vom F. 1223 (aus Methanol) erhalten.7. 3- (2-Oxy-phenyl) -5-methyl-pyrazole: to g of 2-oxy-1) enzoy lacetone, dissolved in 50 cc of methanol, are mixed with 24 cc of 25% hydrazine hydrate solution and put on the steam bath for one hour warmed up. On dilution with water, 8.8 g of 3- (2-oxyphenyl) -5-methyl-pyrazole precipitate. F. 133 to 134 ° (from dibtityl ether). B. 3- (2-Oxy-5-bromo-hlietiyl) -5-ethyl-pyrazole: 2.79 2-Oxy-5-bromo-w-propiotivl-acetophenone, prepared by the condensation of 2-oxy-5-bromo -acetophenone with ethyl propionate in the presence of sodium, are dissolved in 2o ccm of Z-ethanol and refluxed with 3 cc of 25% Hvdrazine hydrate solution for 2 hours. When diluted with water, 1.5 g of 3- (2-oxy-5-bromophenyl) -5-ethyl-pyrazole are obtained. obtained from F. 1223 (from methanol).
9. 3-(2-Oxyphe,nyl)-pyrazol: Eine Lösung von to g Oxy-oo-formylacetol>lienon in too ccm 2n-NaOH wird mit g g Hydrazinsulfat versetzt und 2 Stunden auf dem Dampfbad erhitzt. Darauf wird mit 2n-Salzsäure angesäuert, vom Ungelösten abfiltriert und das Filtrat mit gesättigter Sodalösung neutralisiert, wobei das gebildete 3-(2-Oxyphenyl)-pyrazol ausfällt. Die Fällung wird abgesaugt und mit Wasser gewaschen. Ausbeute: 4,9 g.9. 3- (2-Oxyphe, nyl) -pyrazole: A solution of to g oxy-oo-formylacetole> lienone g g hydrazine sulfate are added to too ccm 2N NaOH and put on the steam bath for 2 hours heated. It is then acidified with 2N hydrochloric acid, the undissolved material is filtered off and the filtrate is neutralized with saturated sodium carbonate solution, the 3- (2-oxyphenyl) pyrazole formed fails. The precipitate is filtered off with suction and washed with water. Yield: 4.9 g.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK8084A DE856297C (en) | 1950-11-19 | 1950-11-19 | Process for the production of 3- (2-oxy-phenyl) -pyrazole or its substitution products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK8084A DE856297C (en) | 1950-11-19 | 1950-11-19 | Process for the production of 3- (2-oxy-phenyl) -pyrazole or its substitution products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE856297C true DE856297C (en) | 1952-11-20 |
Family
ID=7211822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK8084A Expired DE856297C (en) | 1950-11-19 | 1950-11-19 | Process for the production of 3- (2-oxy-phenyl) -pyrazole or its substitution products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE856297C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2926517A1 (en) * | 1979-06-30 | 1981-01-15 | Beiersdorf Ag | SUBSTITUTED 3-ARYL-PYRAZOLE AND 5-ARYL-ISOXAZOLE AND METHOD FOR THE PRODUCTION THEREOF |
-
1950
- 1950-11-19 DE DEK8084A patent/DE856297C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2926517A1 (en) * | 1979-06-30 | 1981-01-15 | Beiersdorf Ag | SUBSTITUTED 3-ARYL-PYRAZOLE AND 5-ARYL-ISOXAZOLE AND METHOD FOR THE PRODUCTION THEREOF |
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