CH227919A - Process for the preparation of benzenesulfonylurea. - Google Patents
Process for the preparation of benzenesulfonylurea.Info
- Publication number
- CH227919A CH227919A CH227919DA CH227919A CH 227919 A CH227919 A CH 227919A CH 227919D A CH227919D A CH 227919DA CH 227919 A CH227919 A CH 227919A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzenesulfonylurea
- salt
- cyanic acid
- preparation
- production
- Prior art date
Links
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- XCSGUMXBOFCZJC-UHFFFAOYSA-N n-[4-(carbamoylsulfamoyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 XCSGUMXBOFCZJC-UHFFFAOYSA-N 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Benzolsulfonylharnstoff. Im Hauptpatent ist ein Verfahren zur Her stellung von p-Acetylaminobenzolsulfonylharn- stoff beschrieben, gemäss welchem man auf Ace- ty1sulfanilamid oder ein Salz desselben Cyan- säure oder ein Salz derselben einwirken lässt.
Es wurde nun gefunden, dass man in ana loger Weise zum Benzolsulfonylharnstoff ge langt, wenn man auf Benzolsulfonamid oder ein Salz desselben Cyansäure oder ein Salz derselben einwirken lässt.
Es kann auch Cyansäure zur Einwirkung gebracht werden, die aus einer Cyansäure liefernden Verbindung, wie Harnstoff, Nitro- harnstoff oder Urethan im gleichen Arbeits gang mit der Herstellung des Benzolsulfonyl- harnstoffes gebildet wurde.
<I>Beispiel:</I> 50 g Benzolsulfonamid und 28 g Kalium- cyanat werden in 80-90%igem Alkohol so lange zum Sieden erhitzt, bis eine Probe fast völlig wasserlöslich geworden ist.
Es hat sich<B>dann</B> das Kaliumsalz des Benzol sulfonylharnstoffes gebildet, das man als sol ches aus Wasser, eventuell unter Zusatz von Kaliumcarbonat, zur Herabsetzung der Lös lichkeit umkristallisieren kann. In Wasser gelöst und mit Eisessig angesäuert fällt der freie Harnstoff aus, der nach dem Trocknen den F. 170-1710 hat. Ausbeute etwa 90 0/0.
Process for the preparation of benzenesulfonylurea. The main patent describes a process for the preparation of p-acetylaminobenzenesulfonylurea, according to which acetylsulfanilamide or a salt thereof is allowed to act on cyanoic acid or a salt thereof.
It has now been found that the benzenesulfonylurea is obtained in an analogous manner if benzenesulfonamide or a salt thereof is allowed to act on cyanic acid or a salt thereof.
Cyanic acid can also be brought into action, which was formed from a compound which yields cyanic acid, such as urea, nitrourea or urethane, in the same process as the production of the benzenesulfonyl urea.
<I> Example: </I> 50 g benzenesulfonamide and 28 g potassium cyanate are heated to the boil in 80-90% alcohol until a sample has become almost completely water-soluble.
The potassium salt of benzene sulfonylurea has then formed, which can be recrystallized as such from water, possibly with the addition of potassium carbonate, to reduce solubility. Dissolved in water and acidified with glacial acetic acid, the free urea precipitates, which after drying has the F. 170-1710. Yield about 90%.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE227919X | 1939-12-15 | ||
| CH224638T | 1940-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH227919A true CH227919A (en) | 1943-07-15 |
Family
ID=25726788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH227919D CH227919A (en) | 1939-12-15 | 1940-12-14 | Process for the preparation of benzenesulfonylurea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH227919A (en) |
-
1940
- 1940-12-14 CH CH227919D patent/CH227919A/en unknown
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