CH220971A - Process for the preparation of a condensation product. - Google Patents
Process for the preparation of a condensation product.Info
- Publication number
- CH220971A CH220971A CH220971DA CH220971A CH 220971 A CH220971 A CH 220971A CH 220971D A CH220971D A CH 220971DA CH 220971 A CH220971 A CH 220971A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- preparation
- nitrobenzenesulfonamide
- reduction
- salt
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UQNAQAROTUILLB-UHFFFAOYSA-N 1-isocyanato-3-methylbutane Chemical compound CC(C)CCN=C=O UQNAQAROTUILLB-UHFFFAOYSA-N 0.000 description 1
- YLNRJRKDEGYSHE-UHFFFAOYSA-N 4-nitrobenzenesulfonamide;sodium Chemical class [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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines Kondensationsproduktes, welches dadurch ge kennzeichnet ist, dass ein Salz des p-Nitro- benzolsulfonamids mit Isoamylisocyansäure- ester kondensiert und der entstandene N-(p- Nitrobenzolsulfon) -N'-monoisoamylharnstoff durch Reduktion in das entsprechende Amino- derivat übergeführt wird.
-Die neue Verbin dung ist ein farbloses Kristallpulver vom F.<B>150</B> bis 152 , und besitzt wertvolle thera peutische Eigenschaften.
<I>Beispiel:</I> 135 Teile trockenes, feinverteiltes p-nitro- benzolsulfonamidsaures Natrium werden in 300 Volumteilen Nitrobenzol suspendiert und unter Rühren mit 35 Teilen Isoamylisocyan- säureester versetzt. Das Reaktionsgemisch wird 15 Stunden auf 50 bis 60 gehalten, dann mit Wasser versetzt, mit Essigsäure phenolphthaleinneutral, jedoch lackmusalka- lisch gestellt und filtriert. Die wässrige Lö sung wird abgetrennt, ausgeäthert und an gesäuert.
Das gefällte Kondensationsprodukt wird mit Wasser gewaschen und aus Alkohol umkristallisiert, F. 155 .
Durch Reduktion mit Wasserstoff und Nickelkatalysator wird der N-(p-Aminoben- zolsulfon)-N'-monoisoamylharnstofF folgender Konstitution
EMI0001.0024
erhalten, F. 150 bis 152 . Mit gleichem Erfolg lässt sich die Reak tion auch mit andern Salzen, beispielsweise dem Kalium- oder Calciumsalz des p-Nitro- benzolsulfonamids, ausführen.
Process for the preparation of a condensation product. The subject of the present additional patent is a process for the preparation of a condensation product, which is characterized in that a salt of p-nitrobenzenesulfonamide condenses with isoamylisocyanoate and the resulting N- (p-nitrobenzenesulfone) -N'-monoisoamylurea by reduction is converted into the corresponding amino derivative.
-The new compound is a colorless crystal powder from F. <B> 150 </B> to 152, and has valuable therapeutic properties.
<I> Example: </I> 135 parts of dry, finely divided sodium p-nitrobenzenesulfonamides are suspended in 300 parts by volume of nitrobenzene, and 35 parts of isoamyl isocyanate are added while stirring. The reaction mixture is kept at 50 to 60 for 15 hours, then treated with water, made phenolphthalein-neutral with acetic acid, but litmus alkaline, and filtered. The aqueous solution is separated off, extracted with ether and acidified.
The precipitated condensation product is washed with water and recrystallized from alcohol, mp 155.
By reduction with hydrogen and a nickel catalyst, the N- (p-aminobenzenesulfone) -N'-monoisoamylurea becomes the following constitution
EMI0001.0024
received, F. 150 to 152. The reaction can also be carried out with other salts, for example the potassium or calcium salt of p-nitrobenzenesulfonamide, with the same success.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215241T | 1939-12-23 | ||
| CH220971T | 1939-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220971A true CH220971A (en) | 1942-04-30 |
Family
ID=25725706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220971D CH220971A (en) | 1939-12-23 | 1939-12-23 | Process for the preparation of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220971A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2977375A (en) * | 1953-02-11 | 1961-03-28 | Boehringer & Soehne Gmbh | Process of manufacturing n-sulphanilyl ureas |
| US3015673A (en) * | 1956-09-28 | 1962-01-02 | Swiss Serum And Vaccine Inst | New urea derivatives and preparation thereof |
-
1939
- 1939-12-23 CH CH220971D patent/CH220971A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2977375A (en) * | 1953-02-11 | 1961-03-28 | Boehringer & Soehne Gmbh | Process of manufacturing n-sulphanilyl ureas |
| US3015673A (en) * | 1956-09-28 | 1962-01-02 | Swiss Serum And Vaccine Inst | New urea derivatives and preparation thereof |
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