CH267575A - Process for the preparation of an α, B-unsaturated carboxamide. - Google Patents
Process for the preparation of an α, B-unsaturated carboxamide.Info
- Publication number
- CH267575A CH267575A CH267575DA CH267575A CH 267575 A CH267575 A CH 267575A CH 267575D A CH267575D A CH 267575DA CH 267575 A CH267575 A CH 267575A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- acid
- formula
- preparation
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RUSPWDWPGXKTFO-UHFFFAOYSA-N n-ethyl-2-methoxyaniline Chemical compound CCNC1=CC=CC=C1OC RUSPWDWPGXKTFO-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines a,19-ungesättigten Carhonsäureamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines a,ss-ungesät- tigten Carbonsäureamides. Das Verfahren ist dadurch gekennzeichnet, dass man ein N-Allv1- arylamin der Formel
EMI0001.0008
mit einer Verbindung der Formel
EMI0001.0009
umsetzt, wobei 1 und 5.' bei der Reaktion sich abspaltende Reste bedeuten.
Als N-Alky 1-aryl- amine der Formel
EMI0001.0016
kommen das freie Amin bzw. seine Salze, Me tallverbindungen oder reaktionsfähigen Deri vate und als Verbindungen der Formel
EMI0001.0017
die freie Säure bzw. ihre reaktionsfähigen funktionellen Derivate, wie z.
B. Halogenide, Anhydride, Ester, Amide oder Salze, in Be- traelit. Eine spezielle Variante, die ebenfalls nach obigem Reaktionsschema verläuft., ist die Umsetzung von Salzen der fl,ss-Diinethyl-acryl- säure mit reaktionsfähigen Derivaten der N- _@th@-1-N-o-anisy 1-carbaminsäure.
Die erhaltene neue Verbindung, das Di- nietliy1acrylsäure-N-äthyl-o-anisidid, stellt, ein schwach gelbliches Öl dar, das unter 0,2 mm Druelz bei<B>1.26</B> bis 1300 siedet, fungizid wirkt und als Mittel zur Insektenvergrämung dienen soll.
<I>Beispiel 1:</I> 11,9 Teile ss,f-Dimethyl-acrylsäurechlorid werden unter Rühren so zu 30 Teilen N-Äthyl- o-anisidin getropft, dass die Temperatur auf 130 bis 140e steigt. Nach dem Erkalten wird das Reaktionsprodukt in Äther oder einem andern mit Wasser nicht mischbaren Lösungs- mittel gelöst und die Lösung nacheinander mit Salzsäure, Lauge und Wasser gewaschen. Nach Abdestillieren des Lösungsmittels wird der Rückstand im Vakuum destilliert.
Das Di- methylacrylsäure-N-äthyl-o-anisidid siedet un ter 0,2 mm Druck bei 126 bis 1300 und stellt, ein schwach gelbliches Öl dar.
Statt in Gegenwart eines übersehusses an N-Äthyl-o-anisidin kann die Reaktion auch in Gegenwart eines säurebindenden Mittels, z. B. von Pottasche, durchgeführt werden, wobei zweckmässig in einem Lösungsmittel, wie z. B. Aceton, gearbeitet wird.
<I>Beispiel 2:</I> Das trockene Natriumsalz der fl,f'-Dimethyl- acryisäure wird zusammen mit der berechne- ten Menge Chlorameisensäure-N-äthyl-o-anisi- did in einem geräumigen Kolben auf etwa 1800 erhitzt, bis die unter starkem Schäumen ver laufende Kohlendioxydentwicklung beendet ist. Man lässt auf etwa 1000 abkühlen, setzt heisses Wasser zu und kocht kurze Zeit auf.
Nach Erkalten nimmt man das Produkt in Äther auf, wäscht die Lösung nacheinander mit verdünnter Säure, Wasser, verdünnter Lauge und hierauf wieder mit. Wasser. Nach Trocknen mit Natriumsulfat wird der Äther abdestilliert. Hierauf wird das als Rückstand erhaltene Dimethylacrylsäure-N-äthyl-o-anisi- did durch Destillieren im Vakuum gereinigt. Es siedet unter 0,2 mm Druck bei 126 bis 130.
Process for the preparation of an α, 19-unsaturated carboxylic acid amide. The present patent relates to a process for the preparation of an α, β-unsaturated carboxamide. The process is characterized in that an N-Allv1-arylamine of the formula
EMI0001.0008
with a compound of the formula
EMI0001.0009
implements, where 1 and 5. ' mean residues which split off during the reaction.
As N-alkyl 1-aryl amines of the formula
EMI0001.0016
come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula
EMI0001.0017
the free acid or its reactive functional derivatives, such as.
B. halides, anhydrides, esters, amides or salts, in beraelite. A special variant, which also proceeds according to the above reaction scheme., Is the reaction of salts of fl, ss-diinethyl-acrylic acid with reactive derivatives of N- _ @ th @ -1-N-o-anisy 1-carbamic acid.
The new compound obtained, the di-nietliy1acrylic acid-N-ethyl-o-anisidide, is a pale yellowish oil that boils at <B> 1.26 </B> up to 1300 under 0.2 mm pressure, has a fungicidal effect and Means to deter insects.
Example 1: 11.9 parts of ss, f-dimethyl-acrylic acid chloride are added dropwise to 30 parts of N-ethyl-o-anisidine with stirring in such a way that the temperature rises to 130 to 140 °. After cooling, the reaction product is dissolved in ether or another water-immiscible solvent and the solution is washed successively with hydrochloric acid, alkali and water. After the solvent has been distilled off, the residue is distilled in vacuo.
The dimethyl acrylic acid-N-ethyl-o-anisidide boils under 0.2 mm pressure at 126 to 1300 and is a pale yellowish oil.
Instead of in the presence of an excess of N-ethyl-o-anisidine, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. of potash, be carried out, advantageously in a solvent such. B. acetone, is worked.
<I> Example 2: </I> The dry sodium salt of fl, f'-dimethyl-acryic acid is heated together with the calculated amount of chloroformic acid-N-ethyl-o-aniside in a spacious flask to about 1800, until the evolution of carbon dioxide, which continues with strong foaming, has ended. Allow to cool to about 1000, add hot water and boil for a short time.
After cooling, the product is taken up in ether, the solution is washed successively with dilute acid, water, dilute alkali and then again with it. Water. After drying with sodium sulfate, the ether is distilled off. The dimethylacrylic acid-N-ethyl-o-aniside obtained as a residue is then purified by distillation in vacuo. It boils under 0.2mm pressure at 126 to 130.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267575T | 1946-06-28 | ||
| CH257648T | 1946-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267575A true CH267575A (en) | 1950-03-31 |
Family
ID=25730096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267575D CH267575A (en) | 1946-06-28 | 1946-06-28 | Process for the preparation of an α, B-unsaturated carboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267575A (en) |
-
1946
- 1946-06-28 CH CH267575D patent/CH267575A/en unknown
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