CH264132A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH264132A CH264132A CH264132DA CH264132A CH 264132 A CH264132 A CH 264132A CH 264132D A CH264132D A CH 264132DA CH 264132 A CH264132 A CH 264132A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- radical
- urea derivative
- reduction
- converted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003672 ureas Chemical class 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- -1 4-amino-benzene sulfone Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines Harnstoffderivates. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harnstoff derivates. Das Verfahren ist dadurch gekenn- zeichnet, dass man einen Isoharnstoffäther der Formel worin A einen aliphatisch gebundenen orga nischen Rest und R einen durch Reduktion in die NHZ-Gruppe überführbaren Rest be deuten, verseift und den Rest R durch Reduk tion in die Aminogruppe überführt. Die ent standene neue Verbindung, der N-(4-Amino- benzolsulfon)-N'-benzyl-harnstoff, kristalli siert in feinen Nadeln vom Schmelzpunkt 217 bis 2180.
Sie soll therapeutische Verwendung finden.
Beispiel: 27,8 Teile Benzylisoharnstoff-0-methyl- äther-methylsulfat werden in 200 Teilen Ace ton gelöst und bei<B>00</B> 8,0 Teile trockenes Cal ciumhydroxyd, aufgeschlämmt in 20 Teilen Wasser, zugefügt. Hierauf werden bei 0 bis 50 portionenweise 22 Teile 4-Nitro-benzolsulfo- chlorid eingetragen und alsdann die Tempera tur innert 2 Stunden auf 200 gesteigert. Die Reaktionslösung soll nach dieser Zeit noch alkalisch auf Lackmus reagieren.
Nach dem Verdünnen mit warmem Wasser wird mit Salzsäure angesäuert und abfiltriert. Das gut abgepresste Produkt wird in 400 Teilen 10 % iger Salzsäure 3 Stunden unter Rück fluss erhitzt. Der entstandene 4-Nitro-benzol- sulfon-benzylharnstoff wird nach dem Erkal ten abfiltriert und durch Umfällen aus ver dünntem Ammoniak gereinigt und zeigt dann einen Schmelzpunkt von 228 bis 2320. Durch Reduktion, z.
B. nach Bechamp, wird daraus der N-(4-Amino-benzolsulfon)-N'-benzyl-harn- stoff vom Schmelzpunkt 217 bis 2180 erhalten.
Process for the production of a urea derivative. The present patent is a process for the production of a urea derivative. The process is characterized in that an isourea ether of the formula in which A is an aliphatically bound organic radical and R is a radical which can be converted into the NHZ group by reduction is saponified and the radical R is converted into the amino group by reduction. The resulting new compound, N- (4-aminobenzenesulfone) -N'-benzylurea, crystallizes in fine needles with a melting point of 217 to 2180.
It should find therapeutic use.
Example: 27.8 parts of benzyl isourea-0-methyl-ether-methyl sulfate are dissolved in 200 parts of acetone and, at 00, 8.0 parts of dry calcium hydroxide, suspended in 20 parts of water, are added. 22 parts of 4-nitrobenzenesulfochloride are then added in portions at from 0 to 50 and the temperature is then increased to 200 within 2 hours. After this time, the reaction solution should still react alkaline to litmus.
After dilution with warm water, it is acidified with hydrochloric acid and filtered off. The well pressed product is heated under reflux in 400 parts of 10% hydrochloric acid for 3 hours. The resulting 4-nitro-benzene-sulfone-benzylurea is filtered off after cooling and purified by reprecipitation from dilute ammonia and then shows a melting point of 228 to 2320. By reduction, eg.
B. according to Bechamp, the N- (4-amino-benzenesulfone) -N'-benzyl urea with a melting point of 217 to 2180 is obtained therefrom.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH264132T | 1944-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264132A true CH264132A (en) | 1949-09-30 |
Family
ID=4475148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264132D CH264132A (en) | 1944-12-28 | 1944-12-28 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264132A (en) |
-
1944
- 1944-12-28 CH CH264132D patent/CH264132A/en unknown
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