CH299568A - Process for the preparation of an ammonium compound containing trifluoromethyl groups. - Google Patents
Process for the preparation of an ammonium compound containing trifluoromethyl groups.Info
- Publication number
- CH299568A CH299568A CH299568DA CH299568A CH 299568 A CH299568 A CH 299568A CH 299568D A CH299568D A CH 299568DA CH 299568 A CH299568 A CH 299568A
- Authority
- CH
- Switzerland
- Prior art keywords
- dichlorobenzyl
- compound
- preparation
- compound containing
- ammonium compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000003868 ammonium compounds Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 4
- -1 (3-trifluoromethyl-phenyl-carbamyl-methyl) - (3,4-dichlorobenzyl) -dimethylammonium chloride Chemical compound 0.000 claims description 3
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 claims description 3
- IYUNVIWIRATEJF-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(Cl)C(Cl)=C1 IYUNVIWIRATEJF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 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
- JULIBQBCWYYRTF-UHFFFAOYSA-N 2-(dimethylamino)-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CN(C)CC(=O)NC1=CC=CC(C(F)(F)F)=C1 JULIBQBCWYYRTF-UHFFFAOYSA-N 0.000 claims description 2
- 241000396431 Anthrenus scrophulariae Species 0.000 claims description 2
- 241000186310 Brevibacterium linens Species 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims description 2
- 241000364037 Mimoschinia rufofascialis Species 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 210000004209 hair Anatomy 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 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
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer trifluormethylgruppenhaltigen Ammoniumverbindung. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer tri- fluormethylgruppenhaltigen Ammoniumver- bindung, dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0009
mit einer Verbindung der Formel
EMI0001.0010
worin das eine Z den Rest
EMI0001.0011
und das andere Chlor bedeutet,
-umsetzt. Man kann beispielsweise Dimethylaminoessigsäure- 3-trifluormethylanilid mit 3,4-Dichlorbenzyl- chlorid zur Reaktion bringen, oder man setzt 3,4-Dichlorbenzyl-dimethyl-amin mit Chlor- aeet-3-trifluormethylanilid um.
Die neue Verbindung, das (3-Trifluor methyl-phenyl-carbamyl-methyl)-(3,4-dichlor- benzyl)-dimethylammoniumchlorid, ein weisses Pulver vom Schmelzpunkt 133,5-136 , ist in heissem-Wasser löslich, hemmt das Bakterien wachstum und schützt damit behandelte Ware, wie z. B. Leinen, Wolle, gegen das Vermor schen durch Pilze. Textilmaterialien, Leder, Pelzwerk, Federn, Haare, die dem Angriff von Schädlingen, wie z. B. Mottenraupen, Teppich käferlarven, ausgesetzt sind, werden durch sie vor Beschädigung und Zerstörung geschützt.
Beispiele: 1. 12,3 Gewichtsteile Dimethylaminoessig- säure-3-triflitormethylanüid und 12 Gewichts teile 3,4-Dichlorbenzylchlorid werden in 31 Volumteilen Essigester aufgenommen und während 14 Stunden unter Rückfluss erhitzt; nach dem Erkalten wird das Kondensations- produkt mit Petroläther ölig ausgeschieden.
Nach einigem Stehen kristallisiert das quater- näre Ammoniumsalz und kann beispielsweise durch Umkristallisation aus o-Dichlorbenzol gereinigt werden. Man erhält so 20 bis 30 Ge wichtsteile (3-Trifluormethyl-phenyl-carbamyl methyl) - (3,4 - dichlorbenzyl) - dimethylammo- niumchlorid als weisses, in heissem Wasser lös liches Pulver vom Schmelzpunkt 133,5-136 .
2. Zu der in Beispiel 1 beschriebenen Am moniumverbindung gelangt man auch, wenn äquivalente Mengen 3,4-Dichlorbenzyl-dime- thylamin und Chloressigsäure-3-trifluorme- thylanilid in Essigester in der oben angege benen Weise umgesetzt werden.
Process for the preparation of an ammonium compound containing trifluoromethyl groups. The present patent relates to a process for the preparation of an ammonium compound containing trifluoromethyl groups, characterized in that a compound of the formula
EMI0001.0009
with a compound of the formula
EMI0001.0010
where one Z is the rest
EMI0001.0011
and the other means chlorine,
-implemented. For example, dimethylaminoacetic acid 3-trifluoromethylanilide can be reacted with 3,4-dichlorobenzyl chloride, or 3,4-dichlorobenzyldimethylamine is reacted with chloroet-3-trifluoromethylanilide.
The new compound, (3-trifluoro methyl-phenyl-carbamyl-methyl) - (3,4-dichlorobenzyl) -dimethylammonium chloride, a white powder with a melting point of 133.5-136, is soluble in hot water, which inhibits this Bacteria grow and protect goods treated with it, such as B. linen, wool, against the Vermor rule by fungi. Textile materials, leather, fur, feathers, hair that are prone to attack by pests such as B. caterpillars, carpet beetle larvae are exposed, are protected from damage and destruction by them.
Examples: 1. 12.3 parts by weight of dimethylaminoacetic acid-3-triflitormethylanide and 12 parts by weight of 3,4-dichlorobenzyl chloride are taken up in 31 parts by volume of ethyl acetate and refluxed for 14 hours; After cooling, the condensation product is oily excreted with petroleum ether.
After standing for a while, the quaternary ammonium salt crystallizes and can be purified, for example, by recrystallization from o-dichlorobenzene. This gives 20 to 30 parts by weight of (3-trifluoromethyl-phenyl-carbamyl-methyl) - (3,4-dichlorobenzyl) -dimethylammonium chloride as a white powder which is soluble in hot water and has a melting point of 133.5-136.
2. The ammonium compound described in Example 1 is also obtained if equivalent amounts of 3,4-dichlorobenzyl-dimethylamine and 3-chloroacetic acid 3-trifluoromethylanilide are reacted in ethyl acetate in the manner indicated above.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292326T | 1950-04-21 | ||
| CH299568T | 1950-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299568A true CH299568A (en) | 1954-06-15 |
Family
ID=25733197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299568D CH299568A (en) | 1950-04-21 | 1950-04-21 | Process for the preparation of an ammonium compound containing trifluoromethyl groups. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299568A (en) |
-
1950
- 1950-04-21 CH CH299568D patent/CH299568A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2133049A1 (en) | Heterocyclic compounds, processes for their preparation and their use | |
| DE1518692C3 (en) | Pesticides containing N- <2-ethyl-4-bromophenyl) -N ', N'-dimethylformamidine | |
| DE1209798B (en) | Insecticidal, acaricidal and fungicidal agents | |
| DE1099530B (en) | Process for the preparation of chlorine-substituted alkylthionophosphonic acid-O-alkyl-O-phenyl esters | |
| CH299587A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299583A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299579A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299582A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299567A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299571A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299569A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299577A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299581A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299580A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299578A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299572A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299575A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299574A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299573A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299588A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299570A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299591A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH299590A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. | |
| CH225104A (en) | Process for producing a quaternary phosphonium compound. | |
| CH299589A (en) | Process for the preparation of an ammonium compound containing trifluoromethyl groups. |