CH304975A - Process for the preparation of a new aralkylated acetoacetic acid amide. - Google Patents
Process for the preparation of a new aralkylated acetoacetic acid amide.Info
- Publication number
- CH304975A CH304975A CH304975DA CH304975A CH 304975 A CH304975 A CH 304975A CH 304975D A CH304975D A CH 304975DA CH 304975 A CH304975 A CH 304975A
- Authority
- CH
- Switzerland
- Prior art keywords
- acetoacetic acid
- aralkylated
- new
- preparation
- acid amide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 claims description 6
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 claims description 3
- NTMXFHGYWJIAAE-UHFFFAOYSA-N n,n-diethyl-3-oxobutanamide Chemical compound CCN(CC)C(=O)CC(C)=O NTMXFHGYWJIAAE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000077 insect repellent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000009965 odorless effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen aralkylierten Acetessigsäureamids. Gegenstand der Erfindung ist ein Ver fahren zur Herstellung eines neuen aralkylier- ten Acetessigsäureamids, nämlich des a-(p- Chlorbenzyl)-acetessigsäurediäthylamids. Es zeichnet sieh dadurch aus, dass man einen reaktiven Ester des p-Clilorbenzyla.lkohols auf Acetessigsäurediäthylamid einwirken lässt.
Als reaktive Ester des p-Chlorbenzylalkohols eignen sich vor allem die Halo-genwasserstoff- säureester. Der Umsatz erfolgt vorzugsweise in Anwesenheit eines Basisehen Kondensations- mittels, wie zum Beispiel Alkalihydroxyden, Alkalialkoholaten, Alkalicarbonaten usw., so wie in Anwesenheit eines Lösungs- bzw. Ver dünnungsmittels; beispielsweise in Methanol, ithanol oder Propanol.
Das auf diese Weise erhaltene a-(p-Chlor- benzy 1) - acetessigsäurediäthylamid ist ein viskoses Öl, welches unter 0,1 mm bei 157 bis 158 siedet. Es zeigt sehr starke insektenver- grämende Wirkung und soll daher zur Ab haltung von Insekten dienen.
<I>Beispiel:</I> 20 g Acetessigsäurediäthylamid und 20 g p-Chlorbenzylchlorid werden in einer Lösung von 3 g Natrium in 300 cms abs. Äthanol 7 Tage bei 20 stehengelassen. Anschliessend wird das gebildete Kochsalz abfiltriert, die Lösung eingedampft und der ölige Rückstand in 100 eri13 Isopropyläther gelöst. Nach dem Waschen mit Wasser wird mit Natriumsulfat getrocknet und eingedampft. Der Rückstand wird im Feinvakuum destilliert.
Man erhält so 20 g a-(p-Chlorbenzyl)-acetessigsäurediäthyl- aniid als ein viskoses Öl, das unter 0,1 mm bei <B>157-1.58o</B> siedet.
Process for the preparation of a new aralkylated acetoacetic acid amide. The invention relates to a process for the production of a new aralkylated acetoacetic acid amide, namely a- (p-chlorobenzyl) -acetoacetic acid diethyl amide. It is characterized by the fact that a reactive ester of p-Clilorbenzyla.lkohols is allowed to act on acetoacetic acid diethylamide.
Particularly suitable reactive esters of p-chlorobenzyl alcohol are the hydrogen halide esters. The conversion is preferably carried out in the presence of a basic condensation agent, such as, for example, alkali metal hydroxides, alkali metal alcoholates, alkali metal carbonates, etc., as well as in the presence of a solvent or diluent; for example in methanol, ithanol or propanol.
The a- (p-chlorobenzy 1) acetic acid diethylamide obtained in this way is a viscous oil which boils at 157 to 158 below 0.1 mm. It has a very strong insect repellant effect and should therefore serve to deter insects.
<I> Example: </I> 20 g of acetoacetic acid diethylamide and 20 g of p-chlorobenzyl chloride are dissolved in a solution of 3 g of sodium in 300 cms of abs. Ethanol left to stand at 20 for 7 days. The common salt formed is then filtered off, the solution is evaporated and the oily residue is dissolved in 100 ml of isopropyl ether. After washing with water, it is dried with sodium sulfate and evaporated. The residue is distilled in a fine vacuum.
This gives 20 g of a- (p-chlorobenzyl) -acetoacetic acid diethyl aniide as a viscous oil which boils below 0.1 mm at 157-1.58o.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH304975T | 1951-03-30 | ||
| CH302082T | 1951-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304975A true CH304975A (en) | 1955-01-31 |
Family
ID=25734455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304975D CH304975A (en) | 1951-03-30 | 1951-03-30 | Process for the preparation of a new aralkylated acetoacetic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304975A (en) |
-
1951
- 1951-03-30 CH CH304975D patent/CH304975A/en unknown
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