DE129562C - - Google Patents
Info
- Publication number
- DE129562C DE129562C DENDAT129562D DE129562DA DE129562C DE 129562 C DE129562 C DE 129562C DE NDAT129562 D DENDAT129562 D DE NDAT129562D DE 129562D A DE129562D A DE 129562DA DE 129562 C DE129562 C DE 129562C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- cyanomethylanthranilic
- converted
- ester
- bromoethyl
- 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
- 238000002360 preparation method Methods 0.000 claims description 3
- 229940100198 ALKYLATING AGENTS Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 125000005998 bromoethyl group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- -1 nitrile ester Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRTQTOBOLIGMED-UHFFFAOYSA-N 2-(carboxyamino)-2-phenylacetic acid Chemical compound OC(=O)NC(C(O)=O)C1=CC=CC=C1 RRTQTOBOLIGMED-UHFFFAOYSA-N 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229940097275 Indigo Drugs 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 240000007871 Indigofera tinctoria Species 0.000 description 1
- 229940045681 Other alkylating agents in ATC Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
- M 129562 KLASSE 12 #. - M 129562 CLASS 12 #.
In der Patentschrift 117924 ist ein Verfahren zur Darstellung von ω - Cyanmethylanthranilsäure: In the patent specification 117924 a method for the preparation of ω- cyanomethylanthranilic acid is:
r „/NH.CHz'CN ^n^i^COOH r "/NH.CHz'CN ^ n ^ i ^ COOH
beschrieben, welches darin besteht, dafs man Anthranilsäure bei Gegenwart von Wasser oder organischen Lösungsmitteln der gleichzeitigen oder successiven Einwirkung von Blausäure und Formaldehyd unterwirft.described, which consists in the fact that anthranilic acid is used in the presence of water or organic solvents of the simultaneous or successive action of hydrocyanic acid and formaldehyde subjects.
Es hat sich nun gezeigt, dafs man die genannte tu-Cyanmethylanthranilsäure in die zugehörigen Ester (ω - Cyanmethylanthranilsäureester) überführen kann, wenn man ihre Salze mit Alkylirungsmitteln, z. B. Halogenalkylen, behandelt.It has now been shown that the abovementioned tu-cyanomethylanthranilic acid can be converted into the associated Esters (ω - cyanomethylanthranilic acid ester) can be converted if their salts with alkylating agents, e.g. B. haloalkylene treated.
Diese Reaction war nicht mit Sicherheit vorauszusehen, da die angewendete Nitrilsäure eine se.cundäre Icnidgruppe enthält, deren Wasserstoffatom bei der Einwirkung des Halogenalkyls durch den Alkylrest hätte substituirt werden können.This reaction could not be foreseen with certainty, because of the nitrilic acid used contains a secondary Icnidgruppe whose hydrogen atom on the action of the haloalkyl could have been substituted by the alkyl radical.
Die nach vorstehendem Verfahren erhältlichen ω-Cyanmethylanthranilsäureester können leicht in Derivate übergeführt werden, welche wichtige Ausgangsmaterialien für die Darstellung von künstlichem Indigo bilden. So gehen dieselben z. B. durch Kochen mit Salzsäure in die Phenylglycin-o-carbonestersäuren über, welche letztere leicht in Phenylglycin - ο - carbonsäure umgewandelt werden können.The ω-cyanomethylanthranilic acid esters obtainable by the above process can easily are converted into derivatives, which are important starting materials for the preparation of make artificial indigo. So go the same z. B. by boiling with hydrochloric acid in the Phenylglycine-o-carboxylic ester acids over, which latter easily into phenylglycine -o-carboxylic acid can be converted.
17 kg ω-Cyanmethylanthranilsäure werden in 60 1 Sodalösung von iopCt. gelöst oder mit 55 1 Kalkmilch von iopCt. versetzt. Man giebt zur kalten Lösung 60 1 Spiritus und 15 kg Bromäthyl und erhitzt im geschlossenen Gefäfs etwa 12 Stunden im kochenden Wasserbade. Nach dem Erkalten findet sich der gebildete Nitrilester zum gröfsten Theil auskrystallisirt. Er ist zum Unterschied vom Ausgangsmaterial in Soda unlöslich, krystallisirt leicht aus Alkohol und schmilzt bei 890G.17 kg of ω-cyanomethylanthranilic acid are dissolved in 60 l of iopCt. dissolved or with 55 1 lime milk from iopCt. offset. 60 l of spirit and 15 kg of bromoethyl are added to the cold solution and the mixture is heated in a closed vessel for about 12 hours in a boiling water bath. After cooling, most of the nitrile ester formed is found completely crystallized. In contrast to the starting material, it is insoluble in soda, easily crystallizes from alcohol and melts at 89 % .
An Stelle von Bromäthyl können mit gleichem Erfolge andere HalogenalkyIe Anwendung finden. Der analog dargestellte Methylester schmilzt bei io8°. Desgleichen können an Stelle der Halogenalkyle selbstredend auch andere für die Esterificirung von Säuren sonst verwendete Alkylirungsmittel, wie Methylsulfat, Alphylsulfosäureester (Patent 76574), benutzt werden. Bei Anwendung von Methylsulfat z. B. hat man in obigem Beispiel nur die angegebene Menge Bromäthyl durch die gleiche Menge Methylsulfat zu ersetzen und entsprechend weniger hoch, z. B. auf 500, zu erhitzen.Instead of bromoethyl, other haloalkyls can be used with the same success. The methyl ester shown analogously melts at 10 °. Likewise, other alkylating agents otherwise used for the esterification of acids, such as methyl sulfate, alphyl sulfonic acid ester (Patent 76574), can of course also be used in place of the haloalkyls. When using methyl sulfate z. B. in the above example you only have to replace the specified amount of bromoethyl with the same amount of methyl sulfate and accordingly less high, e.g. B. to 50 0 to heat.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE129562C true DE129562C (en) |
Family
ID=398016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT129562D Active DE129562C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE129562C (en) |
-
0
- DE DENDAT129562D patent/DE129562C/de active Active
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