DE68240C - Process for the preparation of p-ethoxyantipyrine - Google Patents
Process for the preparation of p-ethoxyantipyrineInfo
- Publication number
- DE68240C DE68240C DENDAT68240D DE68240DA DE68240C DE 68240 C DE68240 C DE 68240C DE NDAT68240 D DENDAT68240 D DE NDAT68240D DE 68240D A DE68240D A DE 68240DA DE 68240 C DE68240 C DE 68240C
- Authority
- DE
- Germany
- Prior art keywords
- ethoxyantipyrine
- preparation
- acid
- benzene
- ethoxyphenylmethylpyrazolonecarboxylic
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-N Methyl bisulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LPOSDRDCHBRQLT-UHFFFAOYSA-N (4-ethoxyphenyl)hydrazine Chemical compound CCOC1=CC=C(NN)C=C1 LPOSDRDCHBRQLT-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N Acetonedicarboxylic acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- -1 methyl halogens Chemical class 0.000 description 1
- VJWFFRAUKLEPHS-UHFFFAOYSA-N methyl hydrogen sulfate;sodium Chemical compound [Na].COS(O)(=O)=O VJWFFRAUKLEPHS-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT)PATENT OFFICE)
Die p-Aethoxyphenylmethylpyrazoloncarbonsäure, dargestellt durch Condensation von p-Aethoxyphenylhydrazin mit Acetondicarbonsäure, läfst sich durch Behandlung mit Methylhalogenen oder methylschwefelsaurem NatronThe p-ethoxyphenylmethylpyrazolonecarboxylic acid, represented by condensation of p-ethoxyphenylhydrazine with acetone dicarboxylic acid, can be achieved by treatment with methyl halogens or methylsulfuric acid sodium
C2H5OC6H4-N-N / \C 2 H 5 OC 6 H 4 -NN / \
und darauf folgende Abspaltung von Kohlensäure in glatter Weise in Aethoxyantipyrin überführen. Diese Bildungsweise des letzteren läfst sich durch folgende Formeln darstellen:and subsequent splitting off of carbonic acid in a smooth manner into ethoxyantipyrine convict. This method of formation of the latter can be represented by the following formulas:
/ .
CO
\ /. CO
\
C-CH0-COOHC-CH 0 -COOH
+ CHJ+ CHJ
= C2H5 O= C 2 H 5 O
C2H5 OC6H1-N- N- C Hs C 2 H 5 OC 6 H 1 -N- N- CH s
CH2 CH 2
-N-N-CH5 -NN-CH 5 CO C- CH0-C O OHCO C-CH 0 -CO OH
j H.j H.
CHCH
CO C-CH1- C O OHCO C-CH 1 - CO OH CO2 + C2H5 OC6H4-N-N- CH3 CO 2 + C 2 H 5 OC 6 H 4 -NN- CH 3
CO C-CH-CO C-CH-
CHCH
Man verfährt hierbei wie folgt:Proceed as follows:
5,2 g (1 Mol.) ρ - Aethoxyphenylmethylpyrazoloncarbonsäure, 15g Methylalkohol und 2,8 g (1 Mol.) Jodmethyl werden im Einschmelzrohr einen Tag im Wasserbad erhitzt.5.2 g (1 mol.) Ρ - ethoxyphenylmethylpyrazolonecarboxylic acid, 15g methyl alcohol and 2.8 g (1 mol.) Iodomethyl are in the melting tube heated in a water bath for a day.
Dann wird der Methylalkohol abdestillirt, der Rückstand einige Zeit auf 165 bis 1700 erhitzt, bis die Kohlensä'ureentwickelung aufgehört hat. Der harzige Rückstand wird in heifsem Wasser aufgenommen, die Lösung nach dem Erkalten von dem Harz abfiltrirt, mit Natronlauge alkalisch gemacht und ca. 6o° warm mit Benzol ausgeschüttelt. Die Benzollösung' wird getrocknet und filtrirt. Nach dem Verdunsten des Benzols bleibt ein nach einiger Zeit krystallinisch werdender Rückstand, CH Then, the methyl alcohol is distilled off, the residue is heated for some time at 165 to 170 0, stopped until the Kohlensä'ureentwickelung. The resinous residue is taken up in hot water, the solution is filtered off from the resin after cooling, made alkaline with sodium hydroxide solution and shaken out with benzene at a temperature of about 60 °. The benzene solution is dried and filtered. After the benzene has evaporated, there remains a residue that becomes crystalline after a while, CH
welcher nach mehrmaligem Umkrystallisiren aus Essigäther bei 89 bis 90 ° schmilzt. Derselbe ist in Wasser und Alkohol sehr leicht löslich, giebt eine grüne Nitrosoverbindung und in wässeriger Lösung mit Eisenchlorid eine dunkelrothe Färbung.which, after repeated recrystallization from vinegar ether, melts at 89 to 90 °. Same is very easily soluble in water and alcohol, gives a green nitroso compound and a dark red color in an aqueous solution with ferric chloride.
Analyse und Eigenschaften charakterisiren den neuen Körper als p-AethoxyantipyrinAnalysis and properties characterize the new body as p-ethoxyantipyrine
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE68240C true DE68240C (en) |
Family
ID=341797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT68240D Active DE68240C (en) | Process for the preparation of p-ethoxyantipyrine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE68240C (en) |
-
0
- DE DENDAT68240D patent/DE68240C/en active Active
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