DE149345C - - Google Patents
Info
- Publication number
- DE149345C DE149345C DENDAT149345D DE149345DA DE149345C DE 149345 C DE149345 C DE 149345C DE NDAT149345 D DENDAT149345 D DE NDAT149345D DE 149345D A DE149345D A DE 149345DA DE 149345 C DE149345 C DE 149345C
- Authority
- DE
- Germany
- Prior art keywords
- water
- percent
- acid
- soluble
- alcohol
- 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
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000008379 phenol ethers Chemical class 0.000 claims description 2
- -1 phenol sulfonic acids Chemical class 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003444 anaesthetic Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QDRCGSIKAHSALR-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzene-1-sulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1O QDRCGSIKAHSALR-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940057818 guaiacolsulfonic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000622 irritating Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
- C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
nqa'.\iiir,i> bo*nqa '. \ iiir, i> bo *
Im Patent 147790 ist die Darstellung von Verbindungen der aromatischen Amidokarbonsäureester mit den Phenolsulfosäuren beschrieben. Es wurde nun gefunden, daß man in ganz gleicher Weise die Amidokarbonsäureester auch mit den Sulfosäuren der Phenoläther kombinieren kann und daß man so zu weiteren wasserlöslichen, durch ihre besonders milde und reizlose Wirkung therapeutisch wichtigen Derivaten gelangt.In the patent 147790 is the representation of compounds of the aromatic amidocarboxylic acid esters described with the phenol sulfonic acids. It has now been found that one in exactly the same way the amidocarboxylic acid esters can also be combined with the sulfonic acids of the phenol ethers and that one so to further water-soluble, therapeutic due to their particularly mild and non-irritating effect important derivatives.
Anisolsulf osäure + p-Amidobenzoesäureäthylester. Anisolsulfonic acid + p-amidobenzoic acid ethyl ester.
Wenn man das durch zweistündiges Erhitzen äquivalenter" Mengen Anisol und Schwefelsäure auf dem Wasserbad erhaltene Sulfierungsgemisch mit dem gleichen Gewichte Wasser verdünnt und dann in die warme Lösung den vierten Teil ihres Gewichtes an p-Amidobenzoesäureäthylester einträgt, so geht zunächst alles in Lösung. Beim Erkalten scheiden sich glänzende Nadeln aus, die aus Alkohol umkristallisiert bei i88° schmelzen. Dieselben sind in kaltem Wasser löslich, leicht löslich in heißem Wasser und Alkohol. Eine halbprozentige wässerige Lösung wirkt stark anästhesierend.If you can do this by heating equivalent "amounts of anisole and Sulfuric acid on the water bath obtained sulfation mixture diluted with the same weight of water and then poured into the warm solution enters the fourth part of its weight of ethyl p-amidobenzoate, so everything goes into solution at first. When it cools, shiny needles separate out, which recrystallize from alcohol at 188 ° melt. The same are soluble in cold water, easily soluble in hot water and Alcohol. A half percent aqueous solution has a strong anesthetic effect.
Berechnet für
/OC Ha r Ty /
\s O3H Cß n* \ Calculated for
/ OC H ar Ty /
\ s O 3 H Cß n * \
2
C O 2
C O
54,39 Proz. C; 5,38 Proz. H; 3,97 Proz. N. 54.39 percent C; 5.38 percent H; 3.97 percent N.
GefundenFound
35 54,53 Proz. C; 5,42 Proz. H; 4,37 Proz.35 54.53 percent C; 5.42 percent H; 4.37 percent
N.N.
Guaj akolsulf osäure + p-Amidobenzoesäureäthylester. Guaj akolsulfonic acid + p-amidobenzoic acid ethyl ester.
Löst man 242 g des in Alkohol schwer löslichen Kaliumsalzes der Guajakolsulfosäure in 600 ecm warmem Wasser und andrerseits in 400 ecm Wasser unter Zufügung der äquivalenten Menge Salzsäure 165 g p-Amidobenzoesäureäthylester und gießt noch warm zusammen, so erstarrt das anfangs klare Gemisch beim Erkalten zu einem Brei nadelförmiger Kristalle vom Schmelzpunkt 1700. Durch Umkristallisieren aus Alkohol erhöht sich der Schmelzpunkt auf 1750. Die stark anästhesierende Substanz ist in kaltem Wasser löslich, leicht löslich in heißem Wasser oder in Alkohol.If 242 g of the potassium salt of guaiacolsulfonic acid, which is sparingly soluble in alcohol, is dissolved in 600 ecm of warm water and, on the other hand, in 400 ecm of water with the addition of the equivalent amount of hydrochloric acid, 165 g of ethyl p-amidobenzoate and poured together while still warm, the initially clear mixture solidifies to one when it cools A paste of needle-shaped crystals with a melting point of 170 ° . Recrystallization from alcohol increases the melting point to 175 ° . The strong anesthetic substance is soluble in cold water, easily soluble in hot water or in alcohol.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE149345C true DE149345C (en) |
Family
ID=416359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT149345D Active DE149345C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE149345C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6390634B1 (en) | 1997-03-20 | 2002-05-21 | Mekra Lang Gmbh & Co. Kg | Assembly for external mirror assembly for commercial vehicles |
-
0
- DE DENDAT149345D patent/DE149345C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6390634B1 (en) | 1997-03-20 | 2002-05-21 | Mekra Lang Gmbh & Co. Kg | Assembly for external mirror assembly for commercial vehicles |
| US6688749B2 (en) | 1997-03-20 | 2004-02-10 | Mekra Lang Gmbh & Co. Kg | External mirror assembly for vehicles and method of assembling same |
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