CH271560A - Process for the preparation of a chlorobenzoic acid amide. - Google Patents
Process for the preparation of a chlorobenzoic acid amide.Info
- Publication number
- CH271560A CH271560A CH271560DA CH271560A CH 271560 A CH271560 A CH 271560A CH 271560D A CH271560D A CH 271560DA CH 271560 A CH271560 A CH 271560A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid amide
- chlorobenzoic acid
- diethylamine
- acid
- Prior art date
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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 Chlorbenzoesäureamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Chlorbenzoe- säureamides. Das Verfahren ist dadurch ge kennzeichnet, dass man eine Verbindung der Formel
EMI0001.0004
mit einer Verbindung der Formel
EMI0001.0005
wobei F und V' sieh bei der Reaktion abspal tende Reste bedeuten, umsetzt.
Die erhaltene, neue Verbindung, das 2,4- Dichlor-benzoesäure-diäthylamid, stellt ein farbloses Öl vom Siedepunkt 176 bis 178'' unter 13 mm Druck dar und kristallisiert in Prismen vom Schmelzpunkt 63 bis 64 . Sie soll als insektenvergrämendes Mittel dienen. <I>Beispiel 1:</I> 21.
Teile 2,4-Diclilor-benzoylehlorid, herge stellt aus 2,4-Dichlor-benzoesäure und Thionyl- chlorid, werden unter Kühlung langsam zu einer Lösung von<B>150</B> Teilen abs. Benzol. und 14 Teilen Diä thylamin gegeben. Nach 1 Stunde Rühren bei Raumtemperatur wird vom aus i geschiedenen Diäthylaminehlorhydrat abge saugt, mit. wenig Benzol nachgewaschen und das Benzol abgedampft.
Der Rückstand lie- fert bei der Destillation ein farbloses, leicht viscoses Öl, das bald erstarrt. Durch Umkri- stallisieren aus Petroläther (Kp. 40 bis 700<B>)</B> kann das 2,4-Diehlor-benzoesäure-diäthylamid in farblosen Prismen vom Schmelzpunkt 63 bis 64 gewonnen werden.
<I>Beispiel</I> ?: 102 Teile 2,4-Dichlor-benzoesäure-methyl- ester, 37 Teile Diäthylamin 100% und 200 Teile trockenes Benzol werden zusammen in einem Stahlautoklaven während 6 Stunden auf 100 bis 110 erhitzt. Das flüssige Reak tionsprodukt wird nacheinander mit 2n-Salz- säure, 2n-Natronlauge und Wasser gewaschen, das Benzol abgedampft und der Rückstand im Vakuum destilliert.
Nach dem Abtrennen von wenig unverändertem Ester wird bei Kp"176 bis 178 das 2,4-Dichlor-benzoesäure-diäthyl- amid erhalten. <I>Beispiel 3:</I> In einem mit Schliff kühler werden 106 Teile 2,4-dichlorbenzoe- saures Natrium mit 73 Teilen Diäthyl-carb- aminsäureehlorid vermischt und in einem Öl bad langsam erhitzt. Bei etwa 150 findet Re aktion statt unter Entweichen von Kohlen dioxyd.
Nachdem die Temperatur noch wei tere 3 Stunden bei 150 bis 160 gehalten wurde, wird die -Masse mit. Nasser verdünnt und das Reaktionsprodukt durch Ausäthern gewonnen. Nach der üblichen Reinigung der ätherischen Lösung mit verdünnter Salzsäure und verdünnter Natronlauge wird die ätheri sche Lösung getrocknet und der Äther abge dampft. Die Destillation des Rückstandes er gibt das 2,4-Dichlorbenzoesäure-diäthylamid.
Process for the preparation of a chlorobenzoic acid amide. The present patent relates to a process for the preparation of a chlorobenzoic acid amide. The process is characterized in that a compound of the formula
EMI0001.0004
with a compound of the formula
EMI0001.0005
where F and V 'see radicals which split off during the reaction are converted.
The new compound obtained, the 2,4-dichlorobenzoic acid diethylamide, is a colorless oil with a boiling point of 176 to 178 '' under 13 mm pressure and crystallizes in prisms with a melting point of 63 to 64. It should serve as an insect repellent. <I> Example 1: </I> 21.
Parts of 2,4-diclorobenzoylechloride, made from 2,4-dichlorobenzoic acid and thionyl chloride, are slowly converted into a solution of 150 parts of abs. Benzene. and 14 parts diethylamine given. After stirring for 1 hour at room temperature, the separated diethylamine chlorohydrate is filtered off with. washed a little benzene and evaporated the benzene.
Upon distillation, the residue yields a colorless, slightly viscous oil that soon solidifies. The 2,4-diehlorobenzoic acid diethylamide can be obtained in colorless prisms with a melting point of 63 to 64 by recrystallizing from petroleum ether (bp 40 to 700).
<I> Example </I>?: 102 parts of 2,4-dichlorobenzoic acid methyl ester, 37 parts of diethylamine 100% and 200 parts of dry benzene are heated together in a steel autoclave to 100 to 110 for 6 hours. The liquid reaction product is washed successively with 2N hydrochloric acid, 2N sodium hydroxide solution and water, the benzene is evaporated and the residue is distilled in vacuo.
After separating off the little unchanged ester, the 2,4-dichlorobenzoic acid diethylamide is obtained at bp "176 to 178. <I> Example 3: </I> In a cooler with a ground joint, 106 parts of 2,4- Sodium dichlorobenzoic acid is mixed with 73 parts of diethylcarbamic acid chloride and slowly heated in an oil bath.
After the temperature has been held at 150 to 160 for a further 3 hours, the mass becomes with. Nasser diluted and the reaction product obtained by etherification. After the usual cleaning of the ethereal solution with dilute hydrochloric acid and dilute sodium hydroxide solution, the ethereal solution is dried and the ether evaporated. The distillation of the residue he gives the 2,4-dichlorobenzoic acid diethylamide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH268783T | 1948-04-09 | ||
| CH271560T | 1948-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH271560A true CH271560A (en) | 1950-10-31 |
Family
ID=25731028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH271560D CH271560A (en) | 1948-04-09 | 1948-04-09 | Process for the preparation of a chlorobenzoic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH271560A (en) |
-
1948
- 1948-04-09 CH CH271560D patent/CH271560A/en unknown
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