CH224855A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH224855A CH224855A CH224855DA CH224855A CH 224855 A CH224855 A CH 224855A CH 224855D A CH224855D A CH 224855DA CH 224855 A CH224855 A CH 224855A
- Authority
- CH
- Switzerland
- Prior art keywords
- arylsulfonamide
- acylated
- preparation
- chloride
- thick
- 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 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 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
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 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
- 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
- 239000003795 chemical substances by application 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 aeylierten Arylsulfonamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylier- ten Arylsulfonamids, welches dadurch ge kennzeichnet ist, dass 3,4 - Dichlorbenzol- sulfonäthylamid oder ein Salz desselben mit einem Butyrylierungsmittel behandelt wird. Die neue Verbindung ist ein dickes 01. Sie dient zur Bekämpfung von Schädlingen der Lisektenklasse und der Kleinlebewelt.
Beispiel: 20 Teile 3,4-Dichlorbenzolsulfon-äthyl- amid werden in 100 Volumteilen Chlorbenzol gelöst, mit 15 Teilen n-Butyrylchlorid und 1 Teil Kupferpulver versetzt und 24 Stun den auf l10-120 erwärmt. Nach dem Ver jagen des Chlorbenzols mit Wasserdampf wird nach dem Erkalten das in Wasser un- lösliebe 3,4-Dichlorbenzolsulfonäthyl-buty- ryla.mid ausgeäthert, die Lösung mit stark verdünnter Natronlauge, anschliessend mit Wasser gewaschen und vom Äther befreit.
Nach dem Verjagen. des Äthers hinterbleibt das 3,4 - Dichlorbenzolsulfonäthyl - butyryl- amid als dickes 01.
Durch Zusatz von Katalysatoren oder säurebindenden Mitteln kann bei der Acylie- rung des freien Sulfonamids mit Butyryl- 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 vorteilhaft zum Beispiel dessen Natriumsalz verwenden.
Process for the preparation of an arylated aryl sulfonamide. The subject of the present patent is a process for the production of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonethylamide or a salt thereof is treated with a butyrylating agent. The new connection is a thick 01. It is used to control pests of the Lisektenklasse and the small world of life.
Example: 20 parts of 3,4-dichlorobenzenesulphonethylamide are dissolved in 100 parts by volume of chlorobenzene, 15 parts of n-butyryl chloride and 1 part of copper powder are added and the mixture is heated to 110-120 for 24 hours. After the chlorobenzene has been chased away with steam, the 3,4-dichlorobenzenesulfonethyl-butyla.mid, which is insoluble in water, is extracted with ether after cooling, the solution is washed with very dilute sodium hydroxide solution, then with water and freed from ether.
After being chased away. of the ether remains the 3,4 - dichlorobenzenesulfonethyl - butyryl amide as thick 01.
By adding catalysts or acid-binding agents, the yield can be significantly improved in the acylation of the free sulfonamide with butyryl 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 advantageously be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220746T | 1940-02-02 | ||
| CH224855T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224855A true CH224855A (en) | 1942-12-15 |
Family
ID=25726491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224855D CH224855A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224855A (en) |
-
1940
- 1940-02-02 CH CH224855D patent/CH224855A/en unknown
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