CH206906A - 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
- CH206906A CH206906A CH206906DA CH206906A CH 206906 A CH206906 A CH 206906A CH 206906D A CH206906D A CH 206906DA CH 206906 A CH206906 A CH 206906A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acid
- acid amide
- amide derivative
- quaternary amino
- preparation
- Prior art date
Links
- -1 amino fatty acid Chemical class 0.000 title claims description 4
- 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 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 210000003746 feather Anatomy 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 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 Aminofettsäureamidderivates,dadurch gekennzeichnet, dass man Di-(chloraceto)- 4,4'-,diaminobenzoph-enon,darstellbar aus 4,4'- Diaminobenzophenon und CMoraeetylchlorid,
mit Dimethylamin umsetzt und das erhal tene Di-(dimethylaminoaceto)-4,4'-diamino- benzophenon mit Benzylchlorid in die bis quaternäre Verbindung überführt.
Die neue Verbindung, eine bräunliche, in Wasser lösliche Masse, eignet sich zum Schützen von Pelzwerk, Federn, Haaren, Leder, fibrösen Materialien und dergleichen vor Mottenraupen und andern Frassschäd- lingen und als fungicides und bactericides Mittel.
<I>Beispiel:</I> Zu 39 Teilen wässriger Dimethylamin- lösung von 33 % werden 200 Vol.-Teile Alko hol und 22 Teile Di-(chloraceto)-4,4'-,diamino- benzophenon, hergestellt aus 4,4'-Diamino- benzophenon und Cliloracetylchlorid,
zu- gesetzt und. die Mischung während 15 Stun- den bei 40 bis <B>50'</B> .gerührt. Hierauf werden der Alkohol und das überschüssige Dimethyl- amin mit Wasserdampf abgeblasen. Das zu rückbleibende 01 wird mit Chloroform auf genommen, getrocknet und das Lösungs- mittel abdestilliert. Ausbeute: 24 Teile.
12 Teile des so erhaltenen Di-(dimethyl- aminoa@ceto)-4,4'-diaminobenzophenons wer den mit 8 Teilen Benzylchlorid während 2 Stunden auf 70-80'C erwärmt. Beim Abkühlen wird die erhaltene dicke Paste glashart. Die neue bisquaternäre Verbindung bildet eine bräunliche, in Wasser lösliche Masse. Ausbeute: 18 Teile.
Process for the preparation of a quaternary amino fatty acid amide derivative. The subject of the present patent is a process for the preparation of a quaternary amino fatty acid amide derivative, characterized in that di- (chloraceto) 4,4 '-, diaminobenzoph-enone, which can be prepared from 4,4'-diaminobenzophenone and CMoraeetyl chloride,
reacts with dimethylamine and the obtained di- (dimethylaminoaceto) -4,4'-diamino-benzophenone is converted into the quaternary compound with benzyl chloride.
The new compound, a brownish, water-soluble mass, is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like from caterpillars and other feeding pests and as a fungicidal and bactericidal agent.
<I> Example: </I> To 39 parts of aqueous dimethylamine solution of 33%, 200 parts by volume of alcohol and 22 parts of di- (chloraceto) -4,4 '-, diamino-benzophenone, prepared from 4, 4'-diamino benzophenone and chloroacetyl chloride,
added and. the mixture was stirred for 15 hours at 40 to 50 '. The alcohol and the excess dimethylamine are then blown off with steam. The oil that remains is taken up in chloroform, dried and the solvent is distilled off. Yield: 24 parts.
12 parts of the di- (dimethylaminoa @ ceto) -4,4'-diaminobenzophenone obtained in this way are heated to 70-80 ° C. with 8 parts of benzyl chloride for 2 hours. The thick paste obtained becomes as hard as glass on cooling. The new bisquaternary compound forms a brownish mass that is soluble in water. Yield: 18 parts.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198052X | 1935-12-23 | ||
| DE206906X | 1937-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206906A true CH206906A (en) | 1939-08-31 |
Family
ID=25758414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206906D CH206906A (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) | CH206906A (en) |
-
1938
- 1938-02-04 CH CH206906D patent/CH206906A/en unknown
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