CH224847A - Process for the preparation of an acylated arylsulfonamide. - Google Patents
Process for the preparation of an acylated arylsulfonamide.Info
- Publication number
- CH224847A CH224847A CH224847DA CH224847A CH 224847 A CH224847 A CH 224847A CH 224847D A CH224847D A CH 224847DA CH 224847 A CH224847 A CH 224847A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- arylsulfonamide
- preparation
- fatty acid
- palm kernel
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 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
- 238000001816 cooling Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 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 aeylierten Arylsulfonamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines acy- lierten Arylsulfonamids, welches dadurch gekennzeichnet ist, dass 3,4-Dichlorbenzol- sulfonmethylamid oder ein Salz desselben mit Palmkernfettsäurechlorid umgesetzt wird. Die neue Verbindung ist eine weisse, kristallisierte Masse. Sie dient zur Bekämp fung von Schädlingen der Insektenklasse und der Kleinlebewelt.
<I>Beispiel:</I> 120 Teile 3,4-Dichlorbenzolsulfonmethyl- amid werden in 300 Volumteilen Benzol ge löst, mit<B>125</B> Teilen PalmL-ernfettsäurechlo- rid und 5 Teilen Kupferpulver versetzt und 8 Stunden am Rückfluss gekocht.
Nach dem Verjagen des Benzols mit Wasserdampf wird nach dem Erkalten das in Wasser unlös liche 3,4-Dichlorbenzolsulfonpalmkernfett- säuremethylamid abfiltriert. Das Rohpro dukt wird in Äther aufgenommen, mit ver dünnter Natronlauge geschüttelt und mit Wasser ausgewasehen. Nach dem Trocknen und Verdampfen des Äthers hinterbleibt eine weisse kristallisierte Masse. F. 45 bis 48 .
Durch Zusatz von Katalysatoren oder säure bindenden Mitteln kann bei der Acylierung des freien Sulfonamids mit Palmkernfett- säurechlorid die Ausbeute wesentlich verbes sert werden; es können Verwendung finden: Kupferpulver, Zinntetrachlorid, Aluminium chlorid, Eisenchlorid, Berylliumchlorid oder calc. Soda, Calciumcarbonat, Pyridin, Dimethylanilin etc. Statt des freien Sul fonamids kann man mit Vorteil zum Bei spiel das Natriumsalz verwenden.
Process for the preparation of an arylated aryl sulfonamide. The subject matter of the present patent is a process for the production of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonemethylamide or a salt thereof is reacted with palm kernel fatty acid chloride. The new connection is a white, crystallized mass. It is used to control pests of the insect class and small organisms.
<I> Example: </I> 120 parts of 3,4-dichlorobenzenesulfonmethyl amide are dissolved in 300 parts by volume of benzene, and <B> 125 </B> parts of palm oil and 5 parts of copper powder are added and 8 hours on Boiled under reflux.
After the benzene has been chased off with steam, the water-insoluble 3,4-dichlorobenzenesulfone palm kernel fatty acid methylamide is filtered off after cooling. The raw product is taken up in ether, shaken with dilute sodium hydroxide solution and washed out with water. After the ether has dried and evaporated, a white crystallized mass remains. F. 45 to 48.
By adding catalysts or acid-binding agents, the yield can be significantly improved in the acylation of the free sulfonamide with palm kernel fatty acid 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 sulphonamide, it is advantageous to use the sodium salt, for example.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH224847T | 1940-02-02 | ||
| CH220746T | 1940-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224847A true CH224847A (en) | 1942-12-15 |
Family
ID=25726483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224847D CH224847A (en) | 1940-02-02 | 1940-02-02 | Process for the preparation of an acylated arylsulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224847A (en) |
-
1940
- 1940-02-02 CH CH224847D patent/CH224847A/en unknown
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