CH246983A - Process for the preparation of a 4-chloro-benzenesulfonamide. - Google Patents
Process for the preparation of a 4-chloro-benzenesulfonamide.Info
- Publication number
- CH246983A CH246983A CH246983DA CH246983A CH 246983 A CH246983 A CH 246983A CH 246983D A CH246983D A CH 246983DA CH 246983 A CH246983 A CH 246983A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- preparation
- benzenesulfonamide
- amide
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003071 parasitic effect Effects 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 4-Chlor-benzolsulfonamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines 4-Chlor- benzolsulfonamides. Das Verfahren ist da durch gekennzeichnet, dass man 4-Amino- benzolsulfon-N-dimethyl-amid diazotiert und die Diazogruppe mit Kupfer(I)-chlorid und Salzsäure durch Chlor ersetzt.
Die entstan dene neue Verbindung, das 4-Chlor-benzol- sulfon-N-dimethyl-amid, bildet farblose Kri- stalle vom Schmelzpunkt 80 und siedet unter einem Druck von 0,05 mm bei 140 . Sie soll als Milbenbekämpfungsmittel (sowohl für freilebende als auch für parasitisch lebende Milben) Verwendung finden.
Beispiel: 20 Teile 4-Amino-benzolsulfon-N-di- methyl-amid werden in salzsaurer Lösung in üblicher Weise diazotiert und die Diazo- lösung portionenweise bei Raumtemperatur zu 10 Teilen Kupfer(I)-chlorid in 30 Volum- teile konzentrierte Salzsäure gegeben.
Nach beendeter Zugabe wird noch i/4 Stunde auf 50-60 erwärmt, dann erkalten gelassen und das 4-Chlor-benzolsulfon-N-dimethyl- amid' mit Äther ausgezogen. Nach Ab dampfen des Äthers verbleibt ein braunes 01, das im Hochvakuum unter einem Druck von 0,05 mm bei 140 destilliert und in der gälte erstarrt. Es bildet farblose Kristalle vom Schmelzpunkt 80 .
Process for the preparation of a 4-chloro-benzenesulfonamide. The present patent is a process for the preparation of a 4-chlorobenzenesulfonamide. The process is characterized in that 4-aminobenzenesulfone-N-dimethyl-amide is diazotized and the diazo group is replaced with copper (I) chloride and hydrochloric acid by chlorine.
The resulting new compound, 4-chloro-benzenesulfone-N-dimethyl-amide, forms colorless crystals with a melting point of 80 and boils at 140 under a pressure of 0.05 mm. It should be used as a mite control agent (for both free-living and parasitic mites).
Example: 20 parts of 4-amino-benzenesulfon-N-dimethyl-amide are diazotized in a hydrochloric acid solution in the usual way and the diazo solution is added in portions at room temperature to 10 parts of copper (I) chloride in 30 parts by volume of concentrated hydrochloric acid .
When the addition is complete, the mixture is heated to 50-60 for a further 1/4 hour, then allowed to cool and the 4-chloro-benzenesulfone-N-dimethylamide is extracted with ether. After the ether has evaporated, a brown oil remains, which distills in a high vacuum under a pressure of 0.05 mm at 140 and solidifies in the cold. It forms colorless crystals with a melting point of 80.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH246983T | 1945-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH246983A true CH246983A (en) | 1947-02-15 |
Family
ID=4465914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH246983D CH246983A (en) | 1945-06-28 | 1945-06-28 | Process for the preparation of a 4-chloro-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH246983A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005090296A3 (en) * | 2004-03-11 | 2005-11-24 | Elan Pharm Inc | N-substituted benzene sulfonamides |
-
1945
- 1945-06-28 CH CH246983D patent/CH246983A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005090296A3 (en) * | 2004-03-11 | 2005-11-24 | Elan Pharm Inc | N-substituted benzene sulfonamides |
| US8193389B2 (en) | 2004-03-11 | 2012-06-05 | Elan Pharmaceuticals, Inc. | N-substituted benzene sulfonamides |
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