CH224856A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH224856A CH224856A CH224856DA CH224856A CH 224856 A CH224856 A CH 224856A CH 224856D A CH224856D A CH 224856DA CH 224856 A CH224856 A CH 224856A
- Authority
- CH
- Switzerland
- Prior art keywords
- arylsulfonamide
- acylated
- preparation
- parts
- salt
- Prior art date
Links
- 125000004421 aryl sulphonamide group Chemical group 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 241000238631 Hexapoda Species 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- -1 3,4-dichlorobenzene-methylbenzoylsulfonamide Chemical compound 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
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910001627 beryllium chloride Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines acylierten Arylsulfonamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylier- ten Arylsulfonamids, welches dadurch ge kennzeichnet ist, dass man 3,4-Dichlorbenzol- sulfonmethylamid oder ein Salz desselben mit einem Benzoylierungsmittel behandelt. Die neue Verbindung ist ein farbloses Kri stallpulver vom F. 110 . Sie dient zur Be kämpfung von Schädlingen der Insekten klasse und der Kleinlebewelt.
<I>Beispiel:</I> 60 Teile 3,4-Dichlorbenzolsulfonmethyl- amid werden in 180 Volumteilen Chlorbenzol gelöst, mit 36 Teilen Benzoylchlorid und \?,5 Teilen Kupferpulver versetzt und 1 \3 Stunden am Rückfluss gekocht.
Nach dem Verjagen des Chlorbenzols mit Wasserdampf wird der Rückstand in Äther aufgenommen, die so erhaltene Lösung mit verdünnter Na tronlauge und anschliessend mit Wasser ge- ivaschen. Nach dem Verjagen des Äthers hinterbleibt das 3,4-Dichlorbenzolmethyl- benzoylsulfonamid. Es zeigt nach dem Um- kristallisieren aus Berizol-Petroläther einen Schmelzpunkt von<B>110'.</B>
Durch Zusatz von Katalysatoren oder säurebindenden Mitteln kann bei der Acylie- rung des freien Sulfonamids mit Benzoyl- chlorid die Ausbeute wesentlich verbessert werden; es können Verwendung finden: Kupferpulver, Zinntetrachlorid, Aluminium chlorid, Eisenchlorid, Berylliumchlorid, oder calc. Soda, Calciumcarbonat, Pyridin, Di- methylanilin etc. Anstatt des freien Sulfon amids kann man auch zum Beispiel sein Na triumsalz verwenden.
Process for the preparation of an acylated arylsulfonamide. The subject of the present patent is a process for the preparation of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonmethylamide or a salt thereof is treated with a benzoylating agent. The new compound is a colorless crystal powder from F. 110. It is used to control pests of the insect class and small organisms.
<I> Example: </I> 60 parts of 3,4-dichlorobenzenesulfonmethylamide are dissolved in 180 parts by volume of chlorobenzene, 36 parts of benzoyl chloride and 5 parts of copper powder are added and the mixture is refluxed for 1 \ 3 hours.
After the chlorobenzene has been chased off with steam, the residue is taken up in ether, and the solution thus obtained is washed with dilute sodium hydroxide solution and then with water. After the ether has been driven off, the 3,4-dichlorobenzene-methylbenzoylsulfonamide remains. After recrystallization from Berizol petroleum ether, it has a melting point of <B> 110 '. </B>
The addition of catalysts or acid-binding agents can significantly improve the yield in the acylation of the free sulfonamide with benzoyl chloride; it can be used: copper powder, tin tetrachloride, aluminum chloride, iron chloride, beryllium chloride, or calc. Soda, calcium carbonate, pyridine, dimethylaniline, etc. Instead of the free sulfonamide, you can also use your sodium salt, for example.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220746T | 1940-02-02 | ||
| CH224856T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224856A true CH224856A (en) | 1942-12-15 |
Family
ID=25726492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224856D CH224856A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224856A (en) |
-
1940
- 1940-02-02 CH CH224856D patent/CH224856A/en unknown
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