DE945446C - Process for the preparation of a halogenated salicylic acid arylamide - Google Patents
Process for the preparation of a halogenated salicylic acid arylamideInfo
- Publication number
- DE945446C DE945446C DEK14168A DEK0014168A DE945446C DE 945446 C DE945446 C DE 945446C DE K14168 A DEK14168 A DE K14168A DE K0014168 A DEK0014168 A DE K0014168A DE 945446 C DE945446 C DE 945446C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- salicylic acid
- halogenated
- acid arylamide
- thionyl chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000011872 intimate mixture Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- -1 hydrogen halides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XBECFEJUQZXMFE-UHFFFAOYSA-N n-(4-aminobutyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCCCN XBECFEJUQZXMFE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines halogenierten Salicylsäurearylamids Es ist bekannt, daß Oxybenzoesäureanilide gegen Hautpilzerkrankungen wirksam sind.Process for the preparation of a halogenated salicylic acid arylamide It is known that oxybenzoic acid anilides are effective against fungal skin diseases.
Im. 5-Bromsalicyl-4#-chloranilid wurde nun eine Verbindung gefunden, bei der die baktericide und fungicide Wirkung von bekannten Oxybenzoesäurearylamiden auf ein Vielfaches gesteigert ist und die sich insbesondere bei der Behandlung von Hautpilzen aller Art am Menschen ausgezeichnet bewährt.A compound has now been found in 5-bromosalicyl-4 # -chloranilide in which the bactericidal and fungicidal action of known oxybenzoic acid arylamides is increased many times over and which is particularly useful in the treatment of All kinds of skin fungi have proven their worth on humans.
Die neue Verbindung wird dadurch hergestellt, daß man äquiniolekulare Mengen der Komponenten 5-B#romsalicylsäure und 4#-Chloranillin, in feinpulverisierter Form innig mischt und auf die Mischung, gegebenenfalls in Gegenwart eines Suspensionsmittels, Thionylchlorid, zweckmäßig unter Zusatz eines halogenwasserstoffbindenden Mittels einwirken läßt. Anstatt der innigen Mischung der Ausgangskomponenten kann auch ein durch Zusammenschmelzen der Komponenten und anschließendes Pulverisieren der Schmelze erhaltenes Pulver angewendet werden. Hierbei kann man auch so. vorgehen, daß man die mit der tertiären Base versetzte Suspension der innig gemischten Reaktionskomponenten in einem inerten Verdünnungsmittel portionsweise in das Thionylchlorid einträgt, das gegebenenfalls mit einem inerten Mittel verdünnt ist.The new connection is made by using equiniolecular Quantities of the components 5-B # romsalicylic acid and 4 # -chloranillin, in finely powdered form Mix intimately and on the mixture, optionally in the presence of a suspending agent, Thionyl chloride, expediently with the addition of an agent which binds hydrogen halide can act. Instead of the intimate mixture of the starting components, a by melting the components together and then pulverizing the melt obtained powder can be applied. You can do this too. proceed that one the suspension of the intimately mixed reaction components mixed with the tertiary base added in portions to the thionyl chloride in an inert diluent, which is optionally diluted with an inert agent.
Zur Halogenwasserstoffbindung sind tertiäre Basen, wie Dimethylanilin, Pyridin oder Chinolin, geeignet. Als Suspensionsmittel sind Kohlenwasserstoffe, wie Benzol, Toluol, odex haloglenlierte Kohlenwasserstoffe, wie TetrachlK>rkdhl--n.stoff, verwendbar. Beispiel i 7m einer feinpulverisierten, innligen Mischutig von :2:2 g 5-Bromsalicylsäure (hergestellt durch Einwirkung von Brom auf eine Lösung von Salicylsäure in bromwasserstoffhaltigem Äthylenbrc;mid) und 13 g' p-Chloranilin, die zusammen mit 12 g Dimethylanilin und 30 ccm trockenem Benzol zu einer homogenen Masse verrührt ist, werden i o ccm Thionylchlorid zugetropft und die Reaktio - nsmischung noch etwa 30 Minuten auf dem Wasserbad unter Rückfluß erwärmt. Nach Verdampfen des Benzols und des Thionylchloridüberschusses im Vakuum wird der Rückstand zur Entfernung nicht umgesetzter Stoffe mit verdünnter Salzsäure und darauf mit Natri#mbicarbc>nat behandelt. Es hinterbleiben 32,8 9 5-Bromsalir-yl-p-chloranilid vom F. = 239 bis 2400 (aus Alkohol oder Butanol). An Stelle von Dimethylanilin kann auch Pyridin als chlorwasserstoffbindendes Mittel angewendet werden. - Tertiary bases such as dimethylaniline, pyridine or quinoline are suitable for binding hydrogen halides. Hydrocarbons such as benzene, toluene, or halogenated hydrocarbons such as carbon dioxide can be used as suspending agents. Example i 7m of a finely powdered, intimate mixture of: 2: 2 g of 5-bromosalicylic acid (produced by the action of bromine on a solution of salicylic acid in ethylene bromide containing hydrogen) and 13 g of p-chloroaniline, which together with 12 g of dimethylaniline and 30 cc dry benzene is stirred into a homogeneous mass, io cc of thionyl chloride are added dropwise and the Reaktio - nsmischung about 30 minutes in the water bath heated to reflux. After the benzene and the excess thionyl chloride have evaporated in vacuo, the residue is treated with dilute hydrochloric acid and then with sodium bicarbonate to remove unreacted substances. There remain 32.8 9 5-bromosalir-yl-p-chloroanilide from F. = 239 to 2400 (from alcohol or butanol). Instead of dimethylaniline, pyridine can also be used as an agent that binds hydrogen chloride. -
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK14168A DE945446C (en) | 1952-05-11 | 1952-05-11 | Process for the preparation of a halogenated salicylic acid arylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK14168A DE945446C (en) | 1952-05-11 | 1952-05-11 | Process for the preparation of a halogenated salicylic acid arylamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE945446C true DE945446C (en) | 1956-07-12 |
Family
ID=7214240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK14168A Expired DE945446C (en) | 1952-05-11 | 1952-05-11 | Process for the preparation of a halogenated salicylic acid arylamide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE945446C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB375883A (en) * | 1931-04-07 | 1932-07-07 | Ici Ltd | Improved manufacture of carboxylic acid amides |
| US1955802A (en) * | 1931-10-10 | 1934-04-24 | Ici Ltd | Manufacture of aromatic arylides |
-
1952
- 1952-05-11 DE DEK14168A patent/DE945446C/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB375883A (en) * | 1931-04-07 | 1932-07-07 | Ici Ltd | Improved manufacture of carboxylic acid amides |
| US1955802A (en) * | 1931-10-10 | 1934-04-24 | Ici Ltd | Manufacture of aromatic arylides |
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