CH210478A - Process for the preparation of a quaternary aminoacetic acid amide derivative. - Google Patents
Process for the preparation of a quaternary aminoacetic acid amide derivative.Info
- Publication number
- CH210478A CH210478A CH210478DA CH210478A CH 210478 A CH210478 A CH 210478A CH 210478D A CH210478D A CH 210478DA CH 210478 A CH210478 A CH 210478A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary
- preparation
- amide derivative
- acid amide
- aminoacetic acid
- Prior art date
Links
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- ZFLRKAMKGYNFPH-UHFFFAOYSA-N 1,3-dichloro-5-(chloromethyl)benzene Chemical compound ClCC1=CC(Cl)=CC(Cl)=C1 ZFLRKAMKGYNFPH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000000417 fungicide Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- ZRTPLHDJASYNPE-UHFFFAOYSA-N 2-chloro-n-(3,5-dichlorophenyl)acetamide Chemical compound ClCC(=O)NC1=CC(Cl)=CC(Cl)=C1 ZRTPLHDJASYNPE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- -1 dimethylaminoacetic acid-3,5-dichloroanilide Chemical compound 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid 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 Darstellung eines quaternären Aminoessigsäureamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines quater- nären Aminoessigsäureamidderivates, dadurch gekennzeichnet, dass man Chloressigsäure- 3,5-dichloranilid mit Dimethylamin umsetzt und das erhaltene Dimethylaminoessigsäure- 3,5-dichloranilid mit 3,5-Dichlorbenzylchlorid in die quaternäre Verbindung der Formel
EMI0001.0013
überführt.
Die neue Verbindung, ein weisses Pulver, ist in Wasser klar löslich und eignet sich zum Schützen von Pelzwerk, Federn, Haaren, Leder, fibrösen Materialien und der gleichen vor Mottenraupen und andern Frass schädlingen und als fungicides und bacte- ricides Mittel. <I>Beispiel:</I> <B>162</B> Teile 3,5-Dichloranilin werden in 500 Teilen Benzol gelöst und bei<B>500</B> unter Rühren mit 135 Teilen Chloracetylchlorid versetzt. Es fällt ein dicker Brei aus, der sich allmählich unter HCl-Entwicklung löst.
Nach 12stündigem Rühren bei 50 wird noch eine Stunde zum Sieden erhitzt, filtriert und nach dem Erkalten das Chloressigsäure-3,5- dichloranilid abgesaugt und getrocknet.
23,8 Teile dieser Verbindung werden bei Zimmertemperatur in 55 Teile -20o/oige Di- methylaminlösung eingerührt und das Ganze nach einer Stunde auf<B>50'</B> aufgeheizt. Die Reaktion ist beendet, wenn eine Probe der inhomogenen Mischung in verdünnter Salz säure klar löslich ist. Nach dem Abkühlen wird das sich in eine halbfeste und eine wässrige Schicht scheidende Reaktionsgemisch getrennt und die nicht wässrige Schicht mit Wasser gewaschen. Sie erstarrt meist spontan oder aber nach dem Animpfen.
24,7 Teile Dimethylaminoessigsäure-3,5- dichloranilid und 22 Teile 3,5-Dichlorbenzyl- chlorid werden in 200 Teilen Toluol über Nacht gekocht. Es fällt ein weisses Pulver aus, welches abgesaugt, mit Toluol gewaschen und im Vakuum getrocknet wird.
Process for the preparation of a quaternary aminoacetic acid amide derivative. The present patent relates to a process for the preparation of a quaternary aminoacetic acid amide derivative, characterized in that 3,5-dichloroanilide chloroacetic acid is reacted with dimethylamine and the resulting 3,5-dichloroacetic acid dimethylaminoacetic acid is converted into the quaternary compound with 3,5-dichlorobenzyl chloride the formula
EMI0001.0013
convicted.
The new compound, a white powder, is clearly soluble in water and is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like from pests of moths and other feeding stuff and as a fungicidal and bactericidal agent. <I> Example: </I> <B> 162 </B> parts of 3,5-dichloroaniline are dissolved in 500 parts of benzene and at <B> 500 </B> 135 parts of chloroacetyl chloride are added while stirring. A thick paste precipitates out which gradually dissolves with evolution of HCl.
After stirring for 12 hours at 50, the mixture is heated to boiling for a further hour, filtered and, after cooling, the 3,5-dichloroacetic acid is suctioned off and dried.
23.8 parts of this compound are stirred into 55 parts of 20% dimethylamine solution at room temperature and the whole is heated to 50% after one hour. The reaction is over when a sample of the inhomogeneous mixture is clearly soluble in dilute hydrochloric acid. After cooling, the reaction mixture, which separates into a semi-solid and an aqueous layer, is separated and the non-aqueous layer is washed with water. It usually solidifies spontaneously or after inoculation.
24.7 parts of dimethylaminoacetic acid-3,5-dichloroanilide and 22 parts of 3,5-dichlorobenzyl chloride are boiled in 200 parts of toluene overnight. A white powder precipitates out, which is filtered off with suction, washed with toluene and dried in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198052X | 1935-12-23 | ||
| CH210478T | 1938-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210478A true CH210478A (en) | 1940-07-15 |
Family
ID=25724892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210478D CH210478A (en) | 1935-12-23 | 1938-07-11 | Process for the preparation of a quaternary aminoacetic acid amide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210478A (en) |
-
1938
- 1938-07-11 CH CH210478D patent/CH210478A/en unknown
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