CH224848A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH224848A CH224848A CH224848DA CH224848A CH 224848 A CH224848 A CH 224848A CH 224848D A CH224848D A CH 224848DA CH 224848 A CH224848 A CH 224848A
- 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
- 239000012345 acetylating agent 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 4
- 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
- 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 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
- 238000001816 cooling Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
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 acy- lierten Arylsulfonamids, welches dadurch gekennzeichnet ist, dass man 3,4-Dichlorben- zolsulfonmethylamid oder ein Salz desselben mit einem Acetylierungsmittel behandelt. Die neue Verbindung ist ein farbloses Kri stallpulver vom F.<B>98'.</B> Sie dient zur Be kämpfung von Schädlingen der Insekten klasse und der Kleinlebewelt.
<I>Beispiel:</I> 120 Teile 3,4-Dichlorbenzolsulfonmethyl- amid werden in 350 Volumteilen Chlorbenzol suspendiert, mit 40 Teilen Acetylchlorid und 5 Teilen Kupferpulver versetzt und 12 bis 15 Stunden am RückfluB gekocht. Nach dem Verjagen des Chlorbenzols mit Wasser dampf wird nach dem Erkalten das in Wasser unlösliche 3,4-Dichlorbenzolsulfon- methylacetamid abfiltriert. Der Rückstand wird in Äther aufgenommen und mit ver dünnter Natronlauge und anschliessend mit Wasser ausgewaschen.
Nach dem Trocknen und Verjagen des Äthers hinterbleibt ein hellgelbes, zähes 01, das langsam erstarrt.
Durch Zusatz von Katalysatoren oder säurebindenden Mitteln kann bei der Ace- tylierung des freien Sulfonamids mit Ace- tylchlorid die Ausbeute wesentlich verbes sert werden; es können Verwendung finden:
Kupferpulver, Zinntetrachlorid, Aluminium chlorid, Eisenchlorid, Berylliumchlorid, oder calc. Soda, Calciumcarbonat, Pyridin, Dimethylanilin etc. An Stelle des freien Sulfonamids kann mit Vorteil auch zum Beispiel dessen Natriumsalz verwendet wer den.
Process for the preparation of an acylated arylsulfonamide. The present patent relates to a process for the preparation of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonmethylamide or a salt thereof is treated with an acetylating agent. The new compound is a colorless crystal powder from F. <B> 98 '. </B> It is used to combat pests of the insect class and small organisms.
<I> Example: </I> 120 parts of 3,4-dichlorobenzenesulfonmethylamide are suspended in 350 parts by volume of chlorobenzene, 40 parts of acetyl chloride and 5 parts of copper powder are added and the mixture is refluxed for 12 to 15 hours. After the chlorobenzene has been driven off with steam, the 3,4-dichlorobenzenesulfonethylacetamide, which is insoluble in water, is filtered off after cooling. The residue is taken up in ether and washed with dilute sodium hydroxide solution and then with water.
After the ether has dried and chased away, a light yellow, tough oil remains, which slowly solidifies.
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, iron chloride, beryllium chloride, or calc. Soda, calcium carbonate, pyridine, dimethylaniline, etc. Instead of the free sulfonamide, for example, its sodium salt can also be used with advantage.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH224848T | 1940-02-02 | ||
| CH220746T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224848A true CH224848A (en) | 1942-12-15 |
Family
ID=25726484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224848D CH224848A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224848A (en) |
-
1940
- 1940-02-02 CH CH224848D patent/CH224848A/en unknown
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