CH220746A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH220746A CH220746A CH220746DA CH220746A CH 220746 A CH220746 A CH 220746A CH 220746D A CH220746D A CH 220746DA CH 220746 A CH220746 A CH 220746A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- acylated
- arylsulfonamide
- preparation
- treated
- 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
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 claims 1
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ILLSOONBCBUBOD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 ILLSOONBCBUBOD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 239000012345 acetylating agent Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001627 beryllium chloride Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides 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 Arylsnlfonamides. Es wurde gefunden, dass man neue, für die Bekämpfung von Schädlingen der Insek- i.enklasse und der Kleinlebewelt sehr gut geeignete Verbindungen erhält, wenn man Arylsulfonsäureamide mit beliebigen Acylie- rungsmitteln aus der Reihe der Carbonsäuren behandelt.
Die neuen Arylsulfonsäureamide sind in den in der Technik verwendeten Lii- sungsmitteln gut löslich, sie können aber auch in wässriger Lösung bezw. Aufschlärrr- mung und auch in Kombination mit an dern bekannten Schädlingsbekämpfungsmit teln verwendet werden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylier- ten Arylsulfonamids, welches dadurch ge kennzeichnet ist, dass man 3,4-Dichlorbenzol- sulfonamid oder ein Salz desselben mit einem Acetylierungsmittel behandelt. Die neue Ver bindung ist ein farbloses Kristallpulver vom F. 140 .
Beispiel: 113 Teile 3.4-Dichlorbenzolsulfamid wer den mit der berechneten Menge Natronlauge in Lösung gebracht und das Natriumsalz 2s durch Eindampfen und Trocknen im Va kuum gewonnen. Dieses wird in 500 Volum- teilen Chlorbenzol suspendiert, mit 42 Teilen Acetylchlorid versetzt und 5 Stunden am Rückfluss gekocht.
Nach dem Verjagen des leo Chlorbenzols mit Wasserdampf wird nach dem Erkalten das in Wasser unlösliche 3,4 Dichlorbenzolsulfonacetamid abfiltriert. Es zeigt nach dem Umkristallisieren aus wässri- gem Alkohol einen Schmelzpunkt von 140' s5 und besitzt folgende Konstitution:
EMI0001.0038
Durch Zusatz von Katalysatoren oder säurebindenden Mitteln kann bei der Acety- lierung des freien Sulfonamids mit Acetyl- chlorid die Ausbeute wesentlich verbessert werden; es können Verwendung finden:
Kupferpulver, Zinntetrachlorid, Aluminium chlorid, Eisenchlorid, Berylliumghlorid oder
EMI0002.0001
cale. <SEP> Soda, <SEP> Caleiumca.rbonat, <SEP> Pyridin, <SEP> Di methylanilin <SEP> etc.
Process for the preparation of an acylated aryl sulfonamide. It has been found that new compounds which are very suitable for combating pests of the insect class and small organisms are obtained if arylsulfonic acid amides are treated with any acylating agents from the range of carboxylic acids.
The new arylsulfonic acid amides are readily soluble in the solvents used in industry, but they can also be or in aqueous solution. Aufschlärrr- mung and can also be used in combination with other known pest control agents.
The present patent relates to a process for the preparation of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonamide or a salt thereof is treated with an acetylating agent. The new compound is a colorless crystal powder from F. 140.
Example: 113 parts of 3,4-dichlorobenzenesulfamide are brought into solution with the calculated amount of sodium hydroxide solution and the sodium salt is obtained by evaporation and drying in vacuo for 2 seconds. This is suspended in 500 parts by volume of chlorobenzene, mixed with 42 parts of acetyl chloride and refluxed for 5 hours.
After chasing away the leo chlorobenzene with steam, the 3,4 dichlorobenzenesulfonacetamide, which is insoluble in water, is filtered off after cooling. After recrystallization from aqueous alcohol, it has a melting point of 140 's5 and has the following constitution:
EMI0001.0038
By adding catalysts or acid-binding agents, the yield can be significantly improved in the acetylation of the free sulfonamide with acetyl chloride; it can be used:
Copper powder, tin tetrachloride, aluminum chloride, ferric chloride, beryllium chloride or
EMI0002.0001
cale. <SEP> soda, <SEP> Caleiumca carbonate, <SEP> pyridine, <SEP> dimethylaniline <SEP> etc.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220746T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220746A true CH220746A (en) | 1942-04-30 |
Family
ID=4451815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220746D CH220746A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220746A (en) |
-
1940
- 1940-02-02 CH CH220746D patent/CH220746A/en unknown
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