CH240158A - Process for the preparation of an amine derivative. - Google Patents
Process for the preparation of an amine derivative.Info
- Publication number
- CH240158A CH240158A CH240158DA CH240158A CH 240158 A CH240158 A CH 240158A CH 240158D A CH240158D A CH 240158DA CH 240158 A CH240158 A CH 240158A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitro
- preparation
- oxamidine
- converted
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 title 1
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 3
- -1 imide chloride Chemical class 0.000 claims description 3
- QTDZPCPIVFIEHW-UHFFFAOYSA-N 2-(diethylamino)-2-oxoacetyl chloride Chemical compound CCN(CC)C(=O)C(Cl)=O QTDZPCPIVFIEHW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- BVHNGWRPAFKGFP-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)sulfonylbenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 BVHNGWRPAFKGFP-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- YLNRJRKDEGYSHE-UHFFFAOYSA-N 4-nitrobenzenesulfonamide;sodium Chemical compound [Na].NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 YLNRJRKDEGYSHE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Amidinderivates. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines Amidinderivates, welches dadurch gekenn zeichnet ist, dass ein Salz des p-Nitrobenzol- sulfonamids mit Diäthyloxamidsäurechlorid umgesetzt, das entstandene p-Nitro-benzol- sulfondiäthylamidoxamid mit PCh ins Imid- chlorid übergeführt,
dieses durch Behandlung mit Ammoniak in das p-Nitro-phenylsulfon- diäthylamido-oxamidin übergeführt und aus diesem durch Reduktion das N-(p-Amino- benzolsulfon)-N'-diäthylamido-oxamidin ge wonnen wird. Die neue Verbindung bildet ein langsam erstarrendes, wasserlösliches Harz; sie besitzt therapeutisch wertvolle Eigen schaften.
<I>Beispiel:</I> 45 Teile p-Nitro-benzolsulfonamidnatrium werden in 110 Vol.-Teilen Nitrobenzol suspen diert, mit 16 Teilen N-Diäthyl-oxamidsäure- chlorid, Kp.14 mm 95-98 , versetzt und wäh rend 4 Stunden gerührt. Die Temperatur steigt auf zirka 40 .
Hierauf wird mit Wasser und verdünnter Natronlauge bis zu lackmus- alkalischer Reaktion versetzt, von ungelöstem p-Nitro-benzolsulfonamid abfiltriert, die wäss- rige Schicht ausgeäthert und dann angesäuert. Dabei scheidet sieh das p-Nitro-benzolsulfon- diäthylamidoxamid als bald erstarrendesHarz ab. Es wird aus Alkohol umkristallisiert. F.167-168 .
16 Teile p-Nitro-benzolsulfondiäthylamid- oxamid und 11 Teile Phosphorpentachlorid werden vermischt und auf dem Wasserbad während einigen Stunden erhitzt. Das gebil dete Phosphoroxychlorid wird im Vakuum abgesaugt, wobei das Imidchlorid des p-Nitro- benzolsulfondiäthylamidoxamids als 01 zu rückbleibt. Die ätherische Lösung wird in der Kälte mit Ammoniakgas gesättigt und der gebildete Niederschlag nach einer Stunde ab gesaugt. Er wird mit Äther und dann mit Wasser gewaschen. Dabei bildet sich ein dickes<B>Öl,</B> das langsam erstarrt.
Der Nitro- körper wird aus Wasser in Gegenwart von Tierkohle umkristallisiert, F. 137 . N : her. 17,1 ö gef. 17.0 o .
Durch katalytische Reduktion mit Nickel und Wasserstoff wird das N-(Amino-benzolsul- fon)-N'-diäthyla-midooxa.midin gebildet. Es bildet ein langsam erstarrendes, wasserlös- liches Harz.
Process for the preparation of an amidine derivative. The subject of the present additional patent is a process for the preparation of an amidine derivative, which is characterized in that a salt of p-nitrobenzenesulfonamide is reacted with diethyloxamic acid chloride, the resulting p-nitrobenzenesulfone diethylamidoxamide is converted into the imide chloride with PCh,
this converted by treatment with ammonia in the p-nitro-phenylsulfon-diethylamido-oxamidine and from this by reduction the N- (p-aminobenzenesulfone) -N'-diethylamido-oxamidine is obtained. The new compound forms a slowly solidifying, water-soluble resin; it has therapeutically valuable properties.
<I> Example: </I> 45 parts of sodium p-nitrobenzenesulfonamide are suspended in 110 parts by volume of nitrobenzene, 16 parts of N-diethyl oxamic acid chloride, bp 14 mm 95-98, are added and the mixture is added during the period Stirred for 4 hours. The temperature rises to around 40.
Then water and dilute sodium hydroxide solution are added until the reaction is litmus alkaline, undissolved p-nitrobenzenesulfonamide is filtered off, the aqueous layer is extracted with ether and then acidified. The p-nitrobenzenesulphone diethylamidoxamide separates out as a resin that soon solidifies. It is recrystallized from alcohol. F.167-168.
16 parts of p-nitro-benzenesulfondiäthylamid- oxamid and 11 parts of phosphorus pentachloride are mixed and heated on a water bath for a few hours. The phosphorus oxychloride formed is suctioned off in vacuo, the imide chloride of p-nitrobenzenesulfone diethylamidoxamide remaining as oil. The ethereal solution is saturated with ammonia gas in the cold and the precipitate formed is sucked off after one hour. It is washed with ether and then with water. A thick <B> oil </B> forms, which slowly solidifies.
The nitro body is recrystallized from water in the presence of animal charcoal, F. 137. N: her. 17.1 ö found. 17.0 o.
Through catalytic reduction with nickel and hydrogen, the N- (amino-benzenesulfon) -N'-diethyla-midooxa.midine is formed. It forms a slowly solidifying, water-soluble resin.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234252T | 1939-12-19 | ||
| CH240158T | 1939-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240158A true CH240158A (en) | 1945-11-30 |
Family
ID=25727848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240158D CH240158A (en) | 1939-12-19 | 1939-12-19 | Process for the preparation of an amine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240158A (en) |
-
1939
- 1939-12-19 CH CH240158D patent/CH240158A/en unknown
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