CH224849A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH224849A CH224849A CH224849DA CH224849A CH 224849 A CH224849 A CH 224849A CH 224849D A CH224849D A CH 224849DA CH 224849 A CH224849 A CH 224849A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- arylsulfonamide
- preparation
- parts
- chloride
- 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
- 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
- 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
- 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
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride 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
- 150000001408 amides Chemical class 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
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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 acylier ten Arylsulfonamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylier- ten Arylsulfonamids, welches dadurch ge kennzeichnet ist, dass man 3,4-Dichlorbenzol- sulfonbutylamid oder ein Salz desselben mit einem Acetylierungsmittel behandelt. Die neue Verbindung ist ein hellgelbes, nur lang sam erstarrendes 01. Sie dient zur Bekämp fung vom Schädlingen der Insektenklasse und der Kleinlebewelt.
Beispiel: 70 Teile 3,4-Dichlorbenzolsulfonbutyl- amid werden in 350 Volumteilen Chlorbenzol suspendiert, mit 20 Teilen Aeetylchlorid und 5 Teilen Kupferpulver versetzt und 12 bis 15 Stunden am Rückfluss gekocht. Nach dem Verjagen des Chlorbenzols mit Wasserdampf wird nach dem Erkalten das in Wasser un lösliche 3,4-Dichlorbenzolsulfonbutylacetamid abfiltriert. Der Rückstand wird in Äther aufgenommen und mit verdünnter Natron lauge und anschliessend mit Wasser ausge waschen.
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 Acetyl- chlorid die Ausbeute wesentlich verbessert werden; es können Verwendung finden:
Kupferpulver, Zinntetrachlorid, Aluminium chlorid, Eisenchlorid, Berylliumchlorid, oder cale. Soda, Calciumcarbonat, Pyridin, Di- methylanilin etc. An Stelle des freien Sulfon amids kann mit Vorteil auch zum Beispiel dessen Natriumsalz verwendet werden..
Process for the preparation of an acylated aryl sulfonamide. The present patent relates to a process for the preparation of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonobutylamide or a salt thereof is treated with an acetylating agent. The new compound is a light yellow, only slowly solidifying 01. It is used to control pests of the insect class and the small world.
Example: 70 parts of 3,4-dichlorobenzenesulfonobutyl amide are suspended in 350 parts by volume of chlorobenzene, 20 parts of ethyl chloride and 5 parts of copper powder are added and the mixture is refluxed for 12 to 15 hours. After the chlorobenzene has been chased away with steam, the 3,4-dichlorobenzenesulfonobutylacetamide, which is insoluble in water, is filtered off after cooling. The residue is taken up in ether and washed out 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, ferric chloride, beryllium chloride, or cale. Soda, calcium carbonate, pyridine, dimethylaniline etc. Instead of the free sulfonamide, its sodium salt, for example, can also be used with advantage.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220746T | 1940-02-02 | ||
| CH224849T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224849A true CH224849A (en) | 1942-12-15 |
Family
ID=25726485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224849D CH224849A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224849A (en) |
-
1940
- 1940-02-02 CH CH224849D patent/CH224849A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH224848A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224851A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224855A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224845A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224846A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224850A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224856A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224854A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH224847A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH220746A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| DE932373C (en) | Process for the preparation of coumarin derivatives | |
| DE924450C (en) | Process for the preparation of coumarin derivatives | |
| AT165068B (en) | Process for the preparation of acylated p-aminobenzenesulfonamides | |
| CH283652A (en) | Process for the production of a new isothiocyanate. | |
| AT235853B (en) | Process for the production of new thiobarbituric acids | |
| DE555085C (en) | Process for the preparation of 2-amino-3-oxynaphthalene | |
| CH210784A (en) | Process for the preparation of a benzene sulfamide derivative. | |
| AT71175B (en) | Process for the preparation of salizyloyl theobromine. | |
| CH405274A (en) | Process for the preparation of 4-nitrostilbenes | |
| CH224852A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| DE921204C (en) | Process for the production of clumps of sulfonamides | |
| CH228335A (en) | Process for the preparation of a sulfonamide derivative. | |
| CH269404A (en) | Process for the representation of a basic ether. | |
| CH224853A (en) | Process for the preparation of an acylated arylsulfonamide. | |
| CH548402A (en) | PROCESS FOR THE PREPARATION OF 3-METHOXY-2-SULFANILAMIDOPYRAZINE. |