CH203592A - Process for the preparation of an aminoarylsulfone. - Google Patents
Process for the preparation of an aminoarylsulfone.Info
- Publication number
- CH203592A CH203592A CH203592DA CH203592A CH 203592 A CH203592 A CH 203592A CH 203592D A CH203592D A CH 203592DA CH 203592 A CH203592 A CH 203592A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonyl
- parts
- preparation
- stearophenone
- water
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- -1 p-chlorophenyl-sulfonyl Chemical group 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Aminoa.rylsulfons. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung eines Aminoarylsulfons, dadurch gekenn zeichnet, dass man a-(p-Clilorphenylsulfo- nyl)-stearophenon mit Dimethylamin um setzt und das entstandene a-(p-Dimethyl- aminophenyl-sulfonyl)-stearophenon mit Di- methylsulfat in die quaternäre Ammonium- verbindung überführt.
Das Endprodukt, das MethyIsulfat des a-(p-Trimethylammonium- phenyl-sulfonyl)-stearophenons, eine wachs artige wasserlösliche Masse, eignet sich als Netzmittel, Mottenschutzmittel, Abziehmit tel für Naphtol-AS-Färbungen und besitzt bakterizide und fungizide Eigenschaften. <I>Beispiel:</I> a) Darstellung von p-Chlorphenyl-phen- acyl-sulion.
<B>87</B> Teile p-ehlorphenylsulfinsaures Na trium (61,4%ig) entsprechend %# Mol. wer den in möglichst wenig heissem Wasser ge löst (ca. 200 Teile). Nun werden 46 Teile co-Chloracetophenon ('/,.o Mol.) zugefügt und das Gemisch während<B>5</B> Stunden unter Rück- fluss gekocht. Das Kondensationsprodukt scheidet sieh dabei bald als feste Kruste aus. Nun wird abgesaugt und mit Wasser nach gewaschen. Zur Reinigung wird noch aus Alkohol umkristallisiert.
Das Produkt wird so in glänzenden Blättchen vom Smp. <B>135</B> bis<B>136 '</B> erhalten.
<B>b)</B> a-(p-Chlorphenylsulfonyl)-stearophe- non.
<B>1,15</B> Teile Natrium werden in<B>100</B> Tei len abs. <B>Alkohol</B> gelöst. Nun werden, 14,75 Teile
EMI0001.0035
zugefügt und bis zur völligen Lösung er wärmt, darauf<B>15</B> Teile Cetylbromicl zuge geben und unter Rückfluss <B>15</B> Stunden ge kocht. Dann versetzt man mit Wasser und schüttelt mit Äther aus. Nach dem Trock nen und Abdestillieren wird der Rückstand mit 80%igem Alkohol angerieben und das erstarrte Produkt abgesaugt. Zur weiteren Reinigung wird aus wenig Alkohol umkri stallisiert.
Fettige -Masse vom Smp. <B>73</B> el <B>e)</B> a-(p-Dimethylaminophenyl-sulfoilyl)- stearophenon.
20 Teile a-(p-Chlorplienvi-siilfoilyl)-stea- rophenon der Formel
EMI0002.0007
werden mit einer Lösung von<B>10</B> Teilen Di- methylamin in<B>2200</B> Teilen Alkohol und einer Spur Kupferpulver im Autoklaven während 20 Stunden auf<B>29-0</B> bis<B>'230'</B> erhitzt. Hier auf wird in Äther aufgenommen, der -Athei mit Wasser -ewaschen, getrocknet, filtriert <B>und</B> abdestilliert. Der Rückstand wird di rekt weiter verarbeitet.
<B>d)</B> a-(p-Trimethylammoniuniphenyl-sul- fonyl)-stearophenon.
Das Reaktionsprodukt von<B>c</B> wird durch Erhitzen mit<B>8</B> Teilen DimethyIsulfat wäh- rend 1/2 Stunde auf<B>130'</B> in die quaternäre Ammoniuniverbindung übergeführt, eine honigartige 31asse, welche in Wasser klar löslich ist. 1)as Endprodukt eignet sieh als Netzmittel, Mottenschutzmittel, Abziehmittel für Naphtol-AS-Färbungen und besitzt bak terizide und fungizide Eigensehaften.
<B>C</B>
Process for the preparation of an Aminoa.ryl sulfone. The subject of the present additional patent is a process for the preparation of an aminoarylsulfone, characterized in that a- (p-clilorphenylsulfonyl) -stearophenone is reacted with dimethylamine and the resulting a- (p-dimethyl-aminophenyl-sulfonyl) -stearophenone converted into the quaternary ammonium compound with dimethyl sulfate.
The end product, the methyl sulfate of a- (p-trimethylammonium-phenyl-sulfonyl) -stearophenone, a waxy, water-soluble mass, is suitable as a wetting agent, moth protection agent, pull-off agent for naphthol-AS dyeings and has bactericidal and fungicidal properties. <I> Example: </I> a) Preparation of p-chlorophenyl-phen-acyl-sulion.
<B> 87 </B> parts of sodium p-phenylsulfinic acid (61.4%) corresponding to% mol are dissolved in as little hot water as possible (approx. 200 parts). Now 46 parts of co-chloroacetophenone (1/2 ,.o mol.) Are added and the mixture is refluxed for <B> 5 </B> hours. The condensation product soon separates out as a solid crust. Now it is suctioned off and washed with water. For purification, it is recrystallized from alcohol.
The product is thus obtained in shiny leaves with a melting point of <B> 135 </B> to <B> 136 '</B>.
<B> b) </B> a- (p-Chlorophenylsulfonyl) -stearophenon.
<B> 1.15 </B> parts of sodium are used in <B> 100 </B> parts of abs. <B> Alcohol </B> dissolved. Now that will be 14.75 parts
EMI0001.0035
added and warmed until completely dissolved, then add <B> 15 </B> parts of cetylbromicl and reflux for <B> 15 </B> hours. Then add water and shake out with ether. After drying and distilling off, the residue is rubbed with 80% alcohol and the solidified product is filtered off with suction. For further purification it is crystallized from a little alcohol.
Fatty mass of melting point <B> 73 </B> el <B> e) </B> a- (p-dimethylaminophenyl-sulfoilyl) -stearophenone.
20 parts of a- (p-Chlorplienvi-siilfoilyl) -stea- rophenon of the formula
EMI0002.0007
with a solution of <B> 10 </B> parts of dimethylamine in <B> 2200 </B> parts of alcohol and a trace of copper powder in an autoclave for 20 hours to <B> 29-0 </B> to < B> '230' </B> heated. Here on it is absorbed in ether, the -Athei is washed with water, dried, filtered <B> and </B> distilled off. The residue is processed further directly.
<B> d) </B> a- (p-Trimethylammoniuniphenyl-sulphonyl) -stearophenone.
The reaction product of <B> c </B> is converted into the quaternary ammonium compound, a honey-like compound, by heating with <B> 8 </B> parts of dimethyl sulfate for 1/2 hour to <B> 130 '</B> 31asse, which is clearly soluble in water. 1) The end product is suitable as a wetting agent, moth repellent, stripping agent for Naphtol-AS dyeings and has bactericidal and fungicidal properties.
<B> C </B>
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH203592T | 1937-07-31 | ||
| CH200667T | 1937-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203592A true CH203592A (en) | 1939-03-15 |
Family
ID=25723540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203592D CH203592A (en) | 1937-07-31 | 1937-07-31 | Process for the preparation of an aminoarylsulfone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203592A (en) |
-
1937
- 1937-07-31 CH CH203592D patent/CH203592A/en unknown
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