DE262476C - - Google Patents
Info
- Publication number
- DE262476C DE262476C DENDAT262476D DE262476DA DE262476C DE 262476 C DE262476 C DE 262476C DE NDAT262476 D DENDAT262476 D DE NDAT262476D DE 262476D A DE262476D A DE 262476DA DE 262476 C DE262476 C DE 262476C
- Authority
- DE
- Germany
- Prior art keywords
- aminoazotoluene
- diazotized
- ethyl
- alkyl esters
- acid alkyl
- 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
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003444 anaesthetic Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N Benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 diazoamino Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 229940035674 ANESTHETICS Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N Ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N Scarlet Red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 262476 KLASSE 22«. GRUPPE- M 262476 CLASS 22 «. GROUP
RUPPERT JULIUS ZINK in DRESDEN.RUPPERT JULIUS ZINK in DRESDEN.
Wird diazotiertes Aminoazotoluol mit p-Aminobenzoesäurealkylestern oder p-Oxybenzoesäurealkylestern umgesetzt, so erhält man therapeutisch wichtige Verbindungen, welche in der Wund- und Hautbehandlung Anwendung finden sollen.Is diazotized aminoazotoluene with p-aminobenzoic acid alkyl esters or p-oxybenzoic acid alkyl esters reacted, therapeutically important compounds are obtained, which to be used in wound and skin treatment.
p-Aminobenzoesäureester führen hierbei zu Diazoaminokörpern, Verbindungen, welche bislang eine therapeutische Verwendung nichtp-aminobenzoic acid esters lead to diazoamino bodies, compounds that have hitherto been used no therapeutic use
ίο gefunden haben. Die nach untenstehendem Beispiel I erhaltene Verbindung aus diazotiertem Aminoazotoluol mit p-Aminobenzoesäureäthylester besitzt als ein in der Aminogruppe substituiertes Anästhesin noch wahrnehmbare anästhesierende Eigenschaften. Der neue Arzneikörper erzeugt auf der Zunge bei längerer Berührung ein stumpfes Gefühl der Unempfindlichkeit.ίο have found. The below Example I compound obtained from diazotized aminoazotoluene with ethyl p-aminobenzoate possesses an anesthetic that is substituted in the amino group, which is still perceptible anesthetic properties. The new medicinal body produces on the tongue at prolonged touch a dull feeling of insensitivity.
Mit p-Oxybenzoesäureestern führt diazotiertes Aminoazotoluol zu Azofarbstoffen, Verbindungen, welche ihrer Konstitution nach als in der Aminogruppe substituierte Orthoforme, und zwar m-Amino-p-oxybenzoesäureester aufzufassen sind. Sie besitzen ebenfalls anästhesierende Eigenschaften. Der nach Beispiel II erhaltene Farbstoff aus ρ - Oxybenzoesäureäthylester hat einen zunächst schwach brennenden Geschmack und ruft alsdann auf der Zunge ein etwas stumpfes Gefühl hervor.. Vor dem bisher gebräuchlichen Scharlachrot R medicinale (Aminoazotoluolazo-ß-naphtol) zeichnen sich demnach die vorgenannten neuen Verbindungen durch diese anästhesierenden Eigenschaften, welche sich zu den bekannten epithelisierenden Wirkungen zugesellen, vorteilhaft aus. .With p-oxybenzoic acid esters, diazotized aminoazotoluene leads to azo dyes, compounds, which according to their constitution as orthoforms substituted in the amino group, and although m-amino-p-oxybenzoic acid esters are to be understood. They also have anesthetics Properties. The dye obtained according to Example II from ρ - ethyl oxybenzoate has an initially weakly burning taste and then produces a somewhat dull feeling on the tongue the previously common scarlet red R medicinale (Aminoazotoluolazo-ß-naphtol) draw Accordingly, the aforementioned new compounds are characterized by these anesthetic properties, which are associated with the known epithelializing effects, advantageous the end. .
22,5 g Aminoazotoluol, in bekannter Weise diazotiert, werden einer wässerigen Anreibung oder alkoholischen Lösung von 16,5 g p-Aminobenzoesäureäthylester zugegeben und die Umsetzung durch allmählichen Zusatz von Natriumacetatlösung oder Natriumbicarbonat bis zur schwach sauren oder neutralen Reaktion gefördert. Nach beendeter Umsetzung wird schwach alkalisch gemacht, der Niederschlag abgesaugt, gewaschen und bei niedriger Temperatur getrocknet.22.5 g of aminoazotoluene, diazotized in a known manner, are an aqueous grind or alcoholic solution of 16.5 g of ethyl p-aminobenzoate was added and the reaction by gradually adding sodium acetate solution or sodium bicarbonate up to promoted to a weakly acidic or neutral reaction. After implementation is complete Made weakly alkaline, the precipitate filtered off with suction, washed and kept at low temperature dried.
Die so erhaltene Diazoaminoverbindung aus Aminoazotoluol und p-Aminobenzoesäureäthylester ist ein schwarzbraunes Pulver, unlöslich in Wasser, dagegen mit gelbbrauner Farbe löslich in Alkohol, Äther und fetten ölen.The diazoamino compound thus obtained from aminoazotoluene and ethyl p-aminobenzoate is a black-brown powder, insoluble in water, but with a yellow-brown color soluble in alcohol, ether and fats oils.
-N = N--N = N-
CHx CH x
-N=N-NH--N = N-NH-
CH,CH,
22,5 g Aminoazotoluol werden in bekannter Weise diazotiert, die Diazoverbindung einer -COOC9H.. 22.5 g of aminoazotoluene are diazotized in a known manner, the diazo compound of a -COOC 9 H ..
Lösung von 16,6 g p-Oxybenzoesäureäthylester und 35 g Natriumcarbonat in 500 g Wasser unter Rühren zugegeben. Innerhalb kurzer Zeit ist die Farbstoffbildung beendet, woraufA solution of 16.6 g of ethyl p-oxybenzoate and 35 g of sodium carbonate in 500 g of water was added with stirring. The dye formation is complete within a short time, whereupon
abfiltriert, der Niederschlag gewaschen und bei niedriger Temperatur getrocknet wird. Der so erhaltene Aminoazotoluolazo-p-oxybenzoesäureäthylester ist ein rostbraunes Pulver, unlöslich in Wasser, mit gelbbrauner Farbe löslich in Alkohol, Äther und fetten Ölen.filtered off, the precipitate is washed and dried at low temperature. The aminoazotoluene-azo-p-oxybenzoic acid ethyl ester thus obtained is a rust-brown powder, insoluble in water, with a yellow-brown color soluble in alcohol, ether and fatty oils.
-N =N~-N = N ~
-N ~ N--N ~ N-
COOC9H,COOC 9 H,
- O H. - O H.
CFLCFL
CH3 CH 3
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE262476C true DE262476C (en) |
Family
ID=519936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT262476D Active DE262476C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE262476C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098847A (en) * | 1959-12-15 | 1963-07-23 | Acna | Disazo dyes |
-
0
- DE DENDAT262476D patent/DE262476C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098847A (en) * | 1959-12-15 | 1963-07-23 | Acna | Disazo dyes |
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