CH253473A - Process for the preparation of an amide of an α, B-unsaturated carboxylic acid. - Google Patents
Process for the preparation of an amide of an α, B-unsaturated carboxylic acid.Info
- Publication number
- CH253473A CH253473A CH253473DA CH253473A CH 253473 A CH253473 A CH 253473A CH 253473D A CH253473D A CH 253473DA CH 253473 A CH253473 A CH 253473A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- amide
- unsaturated carboxylic
- carboxylic acid
- crotonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 239000012021 ethylating agents Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- -1 crotonic acid-N-ethyl-o-toluidine Chemical compound 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Amides einer a"P-ungesättigten Carbonsäure. Es wurde gefunden, dass Amide a,ss-un- gesättigter Carbonsäuren, welche der allge meinen Formel
EMI0001.0009
entsprechen, fungizid wirken und wertvolle Mittel zur Insektenvergrämung darstellen.
In obiger Formel bedeuten: R1 und R, Wasserstoff oder Methyl, R, Alkyl, R, Wasserstoff oder wie R, Halogen, llethyl oder Methoxy. Amide dieser Art sind bisher nicht bekanntgeworden.
Zu ihrer Herstellung kann man von Ami den der Formel
EMI0001.0022
worin R1, R2, R., und R.5 der eingangs ge gebenen Definition entsprechen, ausgehen und die erhaltenen Amide am Stickstoff a1 kylieren.
Für die Alkylierung können die an sich bekannten Methoden verwendet werden, z. B. können Dialkylsulfate, Alkylhalogenide oder Arylsulfonsäurealkylester als Alkylierungs- mittel benützt werden. Vgl. z. B. J. chem. Soc., London, 79, 391 (1901).
Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines a,ss-ungesät- tigten Carbonsäureamides -. Das Verfahren ist dadurch gekennzeichnet, dass man Croton- säure-o-toluidid mit einem Äthylierungsmit- tel behandelt. Die erhaltene neue Verbin dung, das Crotonsäure-N-äthyl-o-toluidin, stellt ein schwach gelbliches 01 dar, das un ter 13 mm Druck bei 153 bis 155 siedet. fungizid wirkt und als Mittel zur Insekten- vergrämung dienen soll.
<I>Beispiel:</I> 17,6 Teile Crotonsäure-o-toluididin 30 Vo lumenteilen abs. Toluol werden mit 4 Teilen Natriumamid, das unter Toluol fein pulveri siert wurde, versetzt und unter Rühren er wärmt, bis kein Ammoniak mehr entweicht. Das Natriumsalz des. Crotonsäure-o-toluidids scheidet sich hierbei gallertig ab. Bei 50 bis 60 lässt man 16 Teile Diäthyl,sulfat zu fliessen und erhitzt 10 Stunden unter Rück fluss zum Sieden.
Dann verdünnt man mit Wasser, trennt die Schichten im Scheide trichter und wäscht die Toluollösung nach einander mit verdünnter Lauge, Säure und ,Wasser. Nach Abdestillieren des Toluols geht das Crotonsäure-N-äthyl-o-toluidid un ter 12 mm Druck bei 152 bis 155 als schwach gelb gefärbtes 01 über.
Process for the preparation of an amide of an α "P-unsaturated carboxylic acid. It has been found that amides of α, β-unsaturated carboxylic acids which have the general formula
EMI0001.0009
correspond, have a fungicidal effect and are valuable means of deterring insects.
In the above formula: R1 and R, hydrogen or methyl, R, alkyl, R, hydrogen or, like R, halogen, methyl or methoxy. Amides of this type have not yet become known.
For their preparation one can use the formula
EMI0001.0022
where R1, R2, R., and R.5 correspond to the definition given at the beginning, go out and alkylate the amides obtained on nitrogen a1.
The methods known per se can be used for the alkylation, e.g. B. dialkyl sulfates, alkyl halides or aryl sulfonic acid alkyl esters can be used as alkylating agents. See e.g. B. J. chem. Soc., London, 79, 391 (1901).
The present patent is a process for the preparation of an α, ß-unsaturated carboxamide -. The process is characterized in that crotonic acid-o-toluidide is treated with an ethylating agent. The new compound obtained, crotonic acid-N-ethyl-o-toluidine, is a pale yellowish oil that boils at 153 to 155 under 13 mm pressure. has a fungicidal effect and is intended to serve as a means of repelling insects.
<I> Example: </I> 17.6 parts of crotonic acid-o-toluididine 30 parts by volume of abs. Toluene is mixed with 4 parts of sodium amide, which was finely pulverized under toluene, and heated with stirring until ammonia no longer escapes. The sodium salt of crotonic acid o-toluidide separates out in gelatinous form. At 50 to 60, 16 parts of diethyl sulfate are allowed to flow and the mixture is heated to boiling under reflux for 10 hours.
Then it is diluted with water, the layers are separated in the vaginal funnel and the toluene solution is washed successively with dilute lye, acid and water. After the toluene has been distilled off, the crotonic acid-N-ethyl-o-toluidide passes over under pressure of 12 mm at 152 to 155 as a pale yellow oil.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253473T | 1946-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253473A true CH253473A (en) | 1948-03-15 |
Family
ID=4470012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253473D CH253473A (en) | 1946-06-28 | 1946-06-28 | Process for the preparation of an amide of an α, B-unsaturated carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253473A (en) |
-
1946
- 1946-06-28 CH CH253473D patent/CH253473A/en unknown
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