CH255624A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents
Process for the preparation of an aromatic acylsulfonamide.Info
- Publication number
- CH255624A CH255624A CH255624DA CH255624A CH 255624 A CH255624 A CH 255624A CH 255624D A CH255624D A CH 255624DA CH 255624 A CH255624 A CH 255624A
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- aromatic
- act
- compound
- dependent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 125000003118 aryl group Chemical group 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 3
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- -1 ß-naphthoic acid halide Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines aromatischen Acylsulfonamids. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines aromatischen Aevlsulfonamids. Das Verfahren ist dadurch gekennzeichnet, da.ss man eine Verbindung der Formel
EMI0001.0008
# au f eine Verbindung der Formel
EMI0001.0016
worin X und Y zwei reaktionsfähige,
bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe sich ab- paltende Reste bedeuten, einwirken lässt.
Die entstandene neue Verbindung, das N - (f '- Naphthoyl) - p - toluolsulf onamid, schmilzt bei 166--168 und soll als Desinfek tionsmittel', z. B. für Gebrauchsgegenstände, V < ,rwendung finden.
Beispiel r: 17,1 Teile p-Toluolsulfonamid werden in 100 Teilen Nitrobenzol suspendiert und mit 19 Teilen Aluminiumchlorid und 19 Teilen ss-Nnphthoesä,urechlorid versetzt. Das Ge misch wird 2 Stunden auf 50 erwärmt und hierauf das Lösungsmittel mit Wasserdampf abdestilliert. Der Rückstand wird in Soda lösung aufgenommen, mit Tierkohle behan delt und filtriert. Aus dem Filtrat wird das N - (f3 - Naphthoyl) - p - toluolsulfonamid mit.
Essigsäure ausgefällt und durch Umkristal- lisieren aus Alkohol gereinigt.
Statt unter Zuhilfenahme eines Konden- sationsmittels kann die Reaktion auch in Gegenwart eines säurebindenden Mittels, wie z. B. von Pyridin oder Dimethylanilin, oder in Gegenwart eines Katalysators, wie z. B. von Kupferpulver, ausgeführt werden.
An Stelle eines, Halogenids kann auch die freie ss-Naphthoesäure in Gegenwart eines Kondensationsmittels, wie Phospharpentogyd oder Phosphorpentachlorid, verwendet werden. <I>Beispiel 2:</I> 28,6 Teile ss-Naphthoesäureamid werden in 200 Teilen absolutem Xylol gelöst. Dann fügt man 8 Teile Natriumamid hinzu und erwärmt bis zum Aufhören der Ammoniak entwicklung.
Nach dem Abkühlen gibt man 38 Teile p-To.luolsulfochlorid in<B>100</B> Teilen Xylol zu und erhitzt mehrere Stunden unter Rückfloss. Nach beendeter Reaktion wird das Xylol im Vakuum abdestilliert. Der Rück stand wird in Bikarbona,tlösung aufgenom men, mit Tierkohle behandelt, filtriert und durch Ansäuern ausgefällt. Das N-(ss-Naph- thGyl)-p-toluol'sulf onamid wird aus verdünn tem Alkohol umkristallisiert und so völlig rein erhalten.
Process for the preparation of an aromatic acylsulfonamide. The present patent relates to a process for the preparation of an aromatic sulfonamide. The process is characterized in that a compound of the formula
EMI0001.0008
# to a compound of the formula
EMI0001.0016
where X and Y are two reactive,
in the reaction, with the exception of an NH group contained in one of them, means splitting off radicals, can act.
The resulting new compound, the N - (f '- naphthoyl) - p - toluenesulfonamide, melts at 166-168 and is said to be used as a disinfectant', e.g. B. for everyday objects, V <, find application.
Example r: 17.1 parts of p-toluenesulfonamide are suspended in 100 parts of nitrobenzene, and 19 parts of aluminum chloride and 19 parts of ß-Nnphthoic acid chloride are added. The mixture is heated to 50 for 2 hours and the solvent is then distilled off with steam. The residue is taken up in soda solution, treated with animal charcoal and filtered. The N - (f3 - naphthoyl) - p - toluenesulfonamide is formed from the filtrate.
Acetic acid precipitated and purified by recrystallization from alcohol.
Instead of using a condensation agent, the reaction can also be carried out in the presence of an acid-binding agent, such as B. of pyridine or dimethylaniline, or in the presence of a catalyst, such as. B. of copper powder.
Instead of a halide, it is also possible to use the free β-naphthoic acid in the presence of a condensing agent such as phospharpentogide or phosphorus pentachloride. Example 2: 28.6 parts of β-naphthoic acid amide are dissolved in 200 parts of absolute xylene. Then 8 parts of sodium amide are added and the mixture is heated until the evolution of ammonia ceases.
After cooling, 38 parts of p-To.luolsulfochlorid in 100 parts of xylene are added and the mixture is heated under reflux for several hours. After the reaction has ended, the xylene is distilled off in vacuo. The residue is taken up in bicarbonate solution, treated with animal charcoal, filtered and precipitated by acidification. The N- (ss-NaphthGyl) -p-toluene sulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH255624T | 1944-10-25 | ||
| CH249867T | 1944-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH255624A true CH255624A (en) | 1948-06-30 |
Family
ID=25729400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH255624D CH255624A (en) | 1944-10-25 | 1944-10-25 | Process for the preparation of an aromatic acylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH255624A (en) |
-
1944
- 1944-10-25 CH CH255624D patent/CH255624A/en unknown
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