DE65393C - Process for the preparation of the amide of eugenolacetic acid - Google Patents
Process for the preparation of the amide of eugenolacetic acidInfo
- Publication number
- DE65393C DE65393C DENDAT65393D DE65393DA DE65393C DE 65393 C DE65393 C DE 65393C DE NDAT65393 D DENDAT65393 D DE NDAT65393D DE 65393D A DE65393D A DE 65393DA DE 65393 C DE65393 C DE 65393C
- Authority
- DE
- Germany
- Prior art keywords
- amide
- acid
- eugenolacetic
- preparation
- eugenol
- 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
- 150000001408 amides Chemical class 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000005770 Eugenol Substances 0.000 description 7
- 229960002217 Eugenol Drugs 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 210000004400 Mucous Membrane Anatomy 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 230000002421 anti-septic Effects 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- ZPUCINDJVBIVPJ-BARDWOONSA-N cocaine Natural products O([C@@H]1C[C@H]2CC[C@H](N2C)[C@@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-BARDWOONSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 231100000078 corrosive Toxicity 0.000 description 1
- 231100001010 corrosive Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Eugenolessigsäure, erhalten aus Eugenolnatrium mit Monochloressigsäure (s. Sa ar bach, J. p. Ch. (2.) 21, 158) läfst sich leicht durch Behandlung mit Alkohol und Schwefelsäure oder Salzsäuregas in Eugenolessigsäureätbyläther überführen.Eugenol acetic acid, obtained from eugenol sodium with monochloroacetic acid (see Sa ar bach, J. p. Ch. (2.) 21, 158) runs through easily Treatment with alcohol and sulfuric acid or hydrochloric acid gas in eugenol acetic acid ethyl ether convict.
Der Eugenolessigäther bildet eine im Wasser unlösliche, in Alkohol leicht lösliche, in reinem Zustande farblose ölartige Flüssigkeit.The Eugenolessigäther forms an insoluble in water, easily soluble in alcohol, in pure Forms a colorless, oily liquid.
Zur Darstellung des Amids aus Eugenolessigester verfährt man wie folgt:To prepare the amide from eugenol acetic ester, proceed as follows:
Eugenolessigsäureäther wird mit starker alkoholischer Ammoniaklösung gemischt oder mit starkem wässerigem Ammoniak geschüttelt. Nach längerem Stehen scheiden sich im ersten Falle schön ausgebildete Kristalle, im zweiten glänzende Blättchen des Amids aus, die abfiltrirt und durch Umkrystallisiren gereinigt werden. Es krystallisirt aus Wasser in glänzenden Blättchen, aus Alkohol in feinen Nadeln vom Schmelzpunkt 1100C.Eugenol acetic acid ether is mixed with strong alcoholic ammonia solution or shaken with strong aqueous ammonia. After standing for a long time, nicely formed crystals separate in the first case, and shiny flakes of the amide in the second, which are filtered off and purified by recrystallization. It crystallizes from water in shiny leaves, from alcohol in fine needles with a melting point of 110 ° C.
Diese Verbindung besitzt besonders in der Form eines feinen Pulvers die Eigenthümlichkeit, auf der Schleimhaut der Zunge an der Applicationsstelle eine je nach der angewendeten Menge kürzer oder länger andauernde Gefühllosigkeit ähnlich der des Cocaine hervorzurufen, ohne jedoch die ätzende Wirkung des Eugenols zu zeigen. Diese und die stark antiseptische Eigenschaft der Eugenolessigsäure dürften das Amid sehr geeignet zur Anwendung in der Wundbehandlung machen.This compound, especially in the form of a fine powder, has the peculiarity on the mucous membrane of the tongue at the application site one depending on the one used Cause a lot of short or long lasting numbness similar to that of cocaine, but without showing the corrosive effects of eugenol. This and the strong antiseptic properties of eugenol acetic acid should make the amide very suitable for use in wound treatment.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE65393C true DE65393C (en) |
Family
ID=339193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT65393D Expired - Lifetime DE65393C (en) | Process for the preparation of the amide of eugenolacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE65393C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2811507A (en) * | 1954-10-20 | 1957-10-29 | Koppers Co Inc | Alkenylaryloxyacetamides |
| US2850482A (en) * | 1954-10-20 | 1958-09-02 | Koppers Co Inc | Allylaryloxyacetamides and polymers therefrom |
| US2911440A (en) * | 1955-06-14 | 1959-11-03 | Geigy Chem Corp | Eugenol glycolic acid and isoeugenol glycolic acid amides |
-
0
- DE DENDAT65393D patent/DE65393C/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2811507A (en) * | 1954-10-20 | 1957-10-29 | Koppers Co Inc | Alkenylaryloxyacetamides |
| US2850482A (en) * | 1954-10-20 | 1958-09-02 | Koppers Co Inc | Allylaryloxyacetamides and polymers therefrom |
| US2911440A (en) * | 1955-06-14 | 1959-11-03 | Geigy Chem Corp | Eugenol glycolic acid and isoeugenol glycolic acid amides |
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