DE189333C - - Google Patents
Info
- Publication number
- DE189333C DE189333C DENDAT189333D DE189333DA DE189333C DE 189333 C DE189333 C DE 189333C DE NDAT189333 D DENDAT189333 D DE NDAT189333D DE 189333D A DE189333D A DE 189333DA DE 189333 C DE189333 C DE 189333C
- Authority
- DE
- Germany
- Prior art keywords
- percent
- parts
- eugenol
- aminobenzoyleugenol
- 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.)
- Active
Links
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical class COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 12
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-Aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 claims 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N o-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 claims 1
- -1 p-aminobenzoyleugenol Chemical compound 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000005770 Eugenol Substances 0.000 description 4
- 229960002217 Eugenol Drugs 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N Tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000003444 anaesthetic Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 229940035674 ANESTHETICS Drugs 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- 229960005015 Local anesthetics Drugs 0.000 description 1
- 229940083877 Local anesthetics for treatment of hemorrhoids and anal fissures for topical use Drugs 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical compound O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940064003 local anesthetic throat preparations Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002459 sustained Effects 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE189333C true DE189333C (fr) |
Family
ID=452892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT189333D Active DE189333C (fr) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE189333C (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466458A1 (fr) * | 1979-09-27 | 1981-04-10 | Mathieu Andre | Nouveaux medicaments derives de l'eugenol |
-
0
- DE DENDAT189333D patent/DE189333C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466458A1 (fr) * | 1979-09-27 | 1981-04-10 | Mathieu Andre | Nouveaux medicaments derives de l'eugenol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE189333C (fr) | ||
| DE2130919B2 (de) | Substituierte diphenylaether, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE1020641B (de) | Verfahren zur Herstellung von Derivaten der 3-Oxythiophen-2-carbonsaeure | |
| DE44002C (de) | Verfahren zur Darstellung von Farbstoffen aus der Gruppe des Metaam dophenol-Phtaleins | |
| DE491225C (de) | Verfahren zur Einfuehrung von Rhodangruppen in organische Verbindungen | |
| DE3216281A1 (de) | Fluessig-kristalline biphenyl- oder terphenyl-derivate, verfahren zu deren herstellung sowie zusammensetzungen, welche diese derivate enthalten | |
| DE2046904A1 (de) | Indohzinessigsauren und Verfahren zu ihrer Herstellung | |
| DE62533C (de) | Verfahren zur Darstellung von Salicylsäureacetylamidophenylester | |
| DE2252323C3 (de) | 3,6-Dialkyl-23-dihydro-2,9-dioxo-6H,9H-thiazolo [5,4-fj chinolin-e-carbonyl- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Bakterizide | |
| DE523358C (de) | Verfahren zur Herstellung von 1-Oxynaphthalin-3-carbonsaeure und ihren Derivaten undSubstitutionsprodukten | |
| DE440008C (de) | Verfahren zur Darstellung von Chinolinderivaten | |
| DE544087C (de) | Verfahren zur Darstellung aromatischer N-Dialkylaminoalkylaminoaldehyde und ihrer Derivate | |
| DE679986C (de) | Verfahren zur Herstellung unsymmetrischer, eine bzw. drei Methingruppen enthaltender Methinfarbstoffe der Pyridinreihe | |
| DE689713C (de) | Verfahren zur Darstellung von 1-Oxypyrenen | |
| DE190799C (fr) | ||
| DE2728248A1 (de) | Nitroxolinderivate | |
| DE702064C (de) | Verfahren zur Herstellung von Aminoalkylsulfonen | |
| DE1135478B (de) | Verfahren zur Herstellung von 3, 5-Dioxo-1, 2, 4-triazolidinen | |
| DE67923C (de) | Verfahren zur Darstellung der p-Amidobenzoesäureester des Guajacols und Eugenols, sowie der Acetylderivate dieser Ester | |
| DE919291C (de) | Verfahren zur Herstellung von 2-Styrylfuranen | |
| DE594168C (de) | Verfahren zur Darstellung von Kondensationsprodukten der Anthrachinonreihe | |
| DE964861C (de) | Verfahren zur Herstellung von (Bz)-Oxy-chinolonen-(4) | |
| DE158089C (fr) | ||
| DE210644C (fr) | ||
| DE603622C (de) | Verfahren zur Herstellung von Kondensationsprodukten der aromatischen Reihe |