DE79814C - - Google Patents
Info
- Publication number
- DE79814C DE79814C DENDAT79814D DE79814DA DE79814C DE 79814 C DE79814 C DE 79814C DE NDAT79814 D DENDAT79814 D DE NDAT79814D DE 79814D A DE79814D A DE 79814DA DE 79814 C DE79814 C DE 79814C
- Authority
- DE
- Germany
- Prior art keywords
- phenetidine
- salicylaldehyde
- alcohol
- anisidine
- bodies
- 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
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 10
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 claims description 5
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JVWYCUBGJVOEIZ-UHFFFAOYSA-N 4-ethoxyaniline;hydron;chloride Chemical compound Cl.CCOC1=CC=C(N)C=C1 JVWYCUBGJVOEIZ-UHFFFAOYSA-N 0.000 description 1
- -1 aromatic compounds Aldehyde Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Nach dem Patent Nr. 68176 und dessen Zusatz Nr. 74691 ist bereits erwiesen, dafs durch Condensation von substituirten Phenylhydrazinen mit hydroxylirten oder nitrirten aromatischen Aldehyden Körper erhalten werden, welche besondere therapeutische Eigenschaften besitzen.According to patent no. 68176 and its addition no. 74691 it has already been proven that by Condensation of substituted phenylhydrazines with hydroxylated or nitrated aromatic compounds Aldehyde bodies are obtained which have special therapeutic properties.
Körper mit ähnlichen Eigenschaften können nach dem vorliegenden Verfahren auch durch Condensation von p-Phenetidin und p-Anisidin mit Salicylaldehyd hergestellt werden.Bodies with similar properties can according to the present process also by condensation of p-phenetidine and p-anisidine made with salicylaldehyde.
Das Verfahren besteht darin, dafs man gleiche Molecule von p-Anisidin oder p-Phenetidin und Salicylaldehyd auf einander einwirken läfst, und zwar entweder direct oder in einem Lösungsmittel, wie Methylalkohol, Aethylalkohol oder dergleichen. Will man beispielsweise das Condensationsproduct des p-Phenetidins mit Salicylaldehyd hersfeilen, so vereinigt man beide Körper entweder direct oder aber in Lösung (z. B. in Alkohol gelöst). Die Reaction geht schon ohne aufsere Wärmezufuhr vor sich, und es tritt unter stärkerer Wärmeentwickelung 1 Molecül Wasser nach folgender Gleichung aus:The procedure consists in making identical molecules of p-anisidine or p-phenetidine and salicylaldehyde act on one another, either directly or in one Solvents such as methyl alcohol, ethyl alcohol or the like. If you want, for example file the condensation product of p-phenetidine with salicylaldehyde, so combined both bodies either directly or in solution (e.g. dissolved in alcohol). the Reaction takes place without any additional supply of heat, and it occurs under stronger conditions Heat development of 1 molecule of water according to the following equation:
C2H6OC6H4NH2 + CnH4(OHJCOH=H2 O + C6 H1 OHCHiNC6H4 OC2H5. C 2 H 6 OC 6 H 4 NH 2 + C n H 4 (OHJCOH = H 2 O + C 6 H 1 OHCHiNC 6 H 4 OC 2 H 5 .
Nach dem Erkalten bildet sich ein gut krystallisirtes Reactionsproduct, das als SaIicyliden-p-Phenetidin bezeichnet werden kann. Durch Umkrystallisiren aus Alkohol ,erhält man den neuen Körper in reinem Zustande. Er bildet hellgelbe Krystalle vom Scbmp. 940C, ist in Wasser unlöslich, in Ligroin schwer, dagegen in Alkohol, Aether, Benzol u. s. w. leicht löslich. Beim Kochen mit- Salzsäure' ;wird~er zersetzt in Salicylaldehyd und salzsaures Phenetidin. ■...'■ ■■■:..·: ■ After cooling, a well-crystallized reaction product is formed, which can be called salicylidene-p-phenetidine. By recrystallizing from alcohol, the new body is obtained in a pure state. It forms pale yellow crystals from the Scbmp. 94 0 C, is insoluble in water, difficult in ligroin, on the other hand easily soluble in alcohol, ether, benzene, etc. When cooking with hydrochloric acid ; it is decomposed into salicylaldehyde and hydrochloric acid phenetidine. ■ ... '■ ■■■: .. ·: ■
Eine analoge Verbindung erhält man, wenn man p-Phenetidin durch p-Anisidin ersetzt.An analogous compound is obtained when p-phenetidine is replaced by p-anisidine.
Die neuen Verbindungen dienen zu therapeutischen Zwecken. The new compounds are used for therapeutic purposes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE79814C true DE79814C (en) |
Family
ID=352424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT79814D Active DE79814C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE79814C (en) |
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0
- DE DENDAT79814D patent/DE79814C/de active Active
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