CH206910A - Process for the preparation of a quaternary amino fatty acid amide derivative. - Google Patents
Process for the preparation of a quaternary amino fatty acid amide derivative.Info
- Publication number
- CH206910A CH206910A CH206910DA CH206910A CH 206910 A CH206910 A CH 206910A CH 206910D A CH206910D A CH 206910DA CH 206910 A CH206910 A CH 206910A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acid
- acid amide
- amide derivative
- preparation
- quaternary amino
- Prior art date
Links
- -1 amino fatty acid Chemical class 0.000 title claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 4
- 229930195729 fatty acid Natural products 0.000 title claims description 4
- 239000000194 fatty acid Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003931 anilides Chemical class 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 210000003746 feather Anatomy 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- YTISFYMPVILQRL-UHFFFAOYSA-N 4-(4-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 YTISFYMPVILQRL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines quaternären Aminofettsäureamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines quater- nären Aminofettsäureamid:
derivates, dadurch gekennzeichnet, dass man Chloressigsäure-4- (4'- chlorphenogy) - anilid, darstellbar aus 4-Amino-4'-chlordiphenyläther und Chlor- acetylchlorid, mit Dimethylamin umsetzt und das erhaltene Dimethylaminoessigsäure-4- (4'-:chlorphenogy)-anilid mit co=Chlor-2,5-,di- chloracetophenon in die quaternäre Verbin dung überführt.
Die neue Verbindung, eine braune, wasserlösliche Masse, eignet sich zum @S@chüt- zen von Pelzwerk, Federn, Haaren, Leder, fibrösen Materialien und (dergleichen vor Mottenraupen und andern Frassschädlingen und als fungicides und bactericides Mittel. <I>Beispiel:</I> Zu 85 'Teilen wässriger Dimethylamin- lösung von 19 % werden 300 Vol.-Teile Alko hol und 43 Teile Chlores:
sigsäure-4-(4'-chlor- phenogy)-anilid, hergestellt aus 4-Amino-4'- ehlordiphenyläther und Chloraoetyl.chlorid, zugesetzt und die Mischung während 20 Stunden bei 40-50' gerührt.
Aus der erhal tenen Lösung werden der Alkohol und das überschüssige Dimethylamin mit Wasser dampf abgeblasen. Das ölige Dimethylamino- essigsäure - 4 - (4' - chlorphenogy) - anilid wird mit Äther aufgenommen, getrocknet und nach dem Abdestillieren des Extraktions- mittels als festes, in verdünnter Salzsäure leicht lösliches Produkt gewonnen.
30 Teile Dimethylaminoessigsäure - 4 - (4'-chlorphenogy)-anilid werden in 100 Vol.- Teilen Toluol gelöst, mit einer Lösung von 20 Teilen co-Chlor-2, 5-dichloracetophenon in 100 Vol.-Teilen T'oluol versetzt und das Ganze während 24 Stunden auf 90-100'C erwärmt.
Hierauf wird das Toluol abdestil- liert, der Rückstand in wenig Aceton ,gelöst und die quaternäre Verbindung mit trocke nem Äther gefällt. Die Fällung wird ab gesaugt, mit Wasser ausgekocht, etwas un löslicher Rückstand .abfiltriert und :die Lö- sung einbedampft. Nach dein Troeknen er hält man eine braune, wasserlösliche Masse.
Process for the preparation of a quaternary amino fatty acid amide derivative. The subject of the present patent is a process for the production of a quaternary amino fatty acid amide:
Derivates, characterized in that chloroacetic acid 4- (4'-chlorophenogy) - anilide, which can be prepared from 4-amino-4'-chlorodiphenyl ether and chloroacetyl chloride, is reacted with dimethylamine and the dimethylaminoacetic acid 4- (4'-: chlorphenogy) anilide with co = chlorine-2,5-, dichloroacetophenone converted into the quaternary compound.
The new compound, a brown, water-soluble compound, is suitable for @protecting fur, feathers, hair, leather, fibrous materials and the like from moth caterpillars and other feeding pests and as a fungicidal and bactericidal agent. <I> Example: </I> To 85 parts of 19% aqueous dimethylamine solution are 300 parts by volume of alcohol and 43 parts of chlorine:
acetic acid 4- (4'-chlorophenogy) anilide, prepared from 4-amino-4'-ehlordiphenyl ether and chloroetyl chloride, was added and the mixture was stirred at 40-50 'for 20 hours.
The alcohol and excess dimethylamine are blown off with water vapor from the solution obtained. The oily dimethylamino acetic acid - 4 - (4 '- chlorphenogy) - anilide is taken up with ether, dried and, after the extraction agent has been distilled off, obtained as a solid product that is easily soluble in dilute hydrochloric acid.
30 parts of dimethylaminoacetic acid 4 - (4'-chlorophenogy) anilide are dissolved in 100 parts by volume of toluene, a solution of 20 parts of co-chloro-2,5-dichloroacetophenone in 100 parts by volume of toluene is added and the whole thing heated to 90-100'C for 24 hours.
The toluene is then distilled off, the residue is dissolved in a little acetone and the quaternary compound is precipitated with dry ether. The precipitate is filtered off with suction, boiled up with water, some insoluble residue is filtered off and: the solution is evaporated. After drying, you get a brown, water-soluble mass.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198052X | 1935-12-23 | ||
| DE206910X | 1937-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206910A true CH206910A (en) | 1939-08-31 |
Family
ID=25758418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206910D CH206910A (en) | 1935-12-23 | 1938-02-04 | Process for the preparation of a quaternary amino fatty acid amide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206910A (en) |
-
1938
- 1938-02-04 CH CH206910D patent/CH206910A/en unknown
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