DE66705C - Process for the preparation of a chlorine-containing antipyrine derivative - Google Patents
Process for the preparation of a chlorine-containing antipyrine derivativeInfo
- Publication number
- DE66705C DE66705C DENDAT66705D DE66705DA DE66705C DE 66705 C DE66705 C DE 66705C DE NDAT66705 D DENDAT66705 D DE NDAT66705D DE 66705D A DE66705D A DE 66705DA DE 66705 C DE66705 C DE 66705C
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- preparation
- derivative
- antipyrine derivative
- containing antipyrine
- 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 - Lifetime
Links
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims description 4
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052801 chlorine Inorganic materials 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 title claims description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 3
- 239000004571 lime Substances 0.000 claims description 3
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960005222 phenazone Drugs 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 Dichlormethylphenylpyrazolon Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 229950009041 edaravone Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
. Löst man ι ο kg Antipyrin in 1000 1 Wasser und (4 Mol.) Salzsäure und versetzt ,diese auf unter o° abgekühlte Lösung mit Chlorkalklösung, so entsteht ein weifser Niederschlag. Man fährt fort mit Zusatz von Chlorkalk, so lange noch ein Niederschlag entsteht. Derselbe wird abfiltrirt und geprefst. Der Prefskuchen wird aus Alkohol oder Eisessig umkrystallisirt. Man erhält so glänzende Blättchen, die bei 2280 schmelzen, unter Salzsäureabspaltung und Verkohlung. Der Körper ist unlöslich in Wasser, verdünnten Säuren, Chloroform, Aether, Ligroin, löslich in heifsem Alkohol und in heifsem Eisessig und wird aus diesen beiden Lösungsmitteln zweckmäfsig umkrystallisirt. Er ist löslich in Alkalien unter Zersetzung. Die Zusammensetzung des Körpers entspricht der Formel Cn H12 N2 O8 CZ2. Der Körper geht durch die verschiedensten Reactionen, z. B. beim Schmelzen im Chlorstrom, beim Einleiten von Chlor in die Lösung des Körpers in Eisessig, beim Erhitzen mit concentrirter Salzsäure oder mit Alkohol auf 1500 u. s. w. in Dichlormethylphenylpyrazolon über, welches selbst leicht zu Methylphenylpyrazolon reducirt werden kann.. If ι ο kg of antipyrine are dissolved in 1000 l of water and (4 mol.) Hydrochloric acid and this is mixed with chlorinated lime solution, which has cooled to below 0 °, a white precipitate is formed. The addition of chlorinated lime is continued as long as there is still a precipitate. It is filtered off and pressed. The prefecture is recrystallized from alcohol or glacial acetic acid. This gives such brilliant leaflets, melting at 228 0, with hydrochloric acid cleavage and charring. The body is insoluble in water, dilute acids, chloroform, ether, ligroin, soluble in hot alcohol and in hot glacial acetic acid, and is expediently recrystallized from these two solvents. It is soluble in alkalis with decomposition. The composition of the body corresponds to the formula C n H 12 N 2 O 8 CZ 2 . The body goes through the most diverse reactions, e.g. B. the melting in the chlorine stream, while introducing chlorine into the solution of the body in glacial acetic acid by heating with concentrated hydrochloric acid, or with alcohol to 150 0 and so on in Dichlormethylphenylpyrazolon, which itself can be easily reduced to methylphenylpyrazolone.
Der neue Körper soll zu medicinischen Zwecken Verwendung finden.The new body is to be used for medical purposes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE66705C true DE66705C (en) |
Family
ID=340399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT66705D Expired - Lifetime DE66705C (en) | Process for the preparation of a chlorine-containing antipyrine derivative |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE66705C (en) |
-
0
- DE DENDAT66705D patent/DE66705C/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1180372B (en) | Process for the preparation of 2,6-dioxopiperazines | |
| DE66705C (en) | Process for the preparation of a chlorine-containing antipyrine derivative | |
| DE214376C (en) | ||
| DE1263743B (en) | Process for the preparation of substituted acetamides | |
| DE2166270C3 (en) | Nicotinoylaminoethanesulfonyl-2amino-thiazole | |
| DE2011078C3 (en) | Process for purifying hexetidine | |
| DE1543328A1 (en) | Process for the preparation of aminimides | |
| DE235430C (en) | ||
| DE60102325T2 (en) | A process for the preparation of 2,6-dichloropurine | |
| DE69226016T2 (en) | Process for the preparation of 2,4,5-trihalobenzoic acid | |
| DE98760C (en) | ||
| EP0457725A2 (en) | Process for the preparation of 2,3-dibromopropionyl chloride | |
| DE224953C (en) | ||
| DE50835C (en) | Process for the preparation of the carboxylic acids of metaamidophenol and its alkyl derivatives | |
| DE2223128C3 (en) | Process for the preparation of derivatives of hexahydrophthalic acid | |
| DE213713C (en) | ||
| DEF0008777MA (en) | ||
| DE2062679A1 (en) | ||
| DE253226C (en) | ||
| CH305891A (en) | Process for the preparation of isonicotinic acid hydrazide. | |
| EP0397048A2 (en) | Process for the preparation of 2-mercapto-4-methyl-1,3-thiazol-5-yl acetic acid and its esters | |
| DE542421C (en) | Process for the production of the anhydrides of halogenated fatty acids | |
| DE2151565C3 (en) | Process for the simultaneous production of aliphatic bromocarboxylic acids and alkyl bromides | |
| DE1153009B (en) | Process for the production of benzaldehydes | |
| DE77937C (en) | Process for the preparation of a monosulfonic acid of ai a ^ -amidonaphthol |