CH236174A - Process for the preparation of a sulfonamide. - Google Patents
Process for the preparation of a sulfonamide.Info
- Publication number
- CH236174A CH236174A CH236174DA CH236174A CH 236174 A CH236174 A CH 236174A CH 236174D A CH236174D A CH 236174DA CH 236174 A CH236174 A CH 236174A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- aminobenzene
- pyrimidine
- marked
- sulfonylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940124530 sulfonamide Drugs 0.000 title claims description 4
- 150000003456 sulfonamides Chemical class 0.000 title claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- -1 p-aminobenzene-sulfonylamino- Chemical class 0.000 claims description 5
- BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Sulfonamides. Gegenstand der Erfindung ist ein eigen artiges Verfahren zur Darstellung eines Sul fonamides, nämlich des bekannten 2-(p- Aminobenzol=sulfonylamino-)pyrimidins, wel ches weisse Kristalle vom Schmelzpunkt 255 bis 256 bildet und als Heilmittel gegen In fektionen verwendbar ist.
Das Verfahren ist dadurch gekennzeich net, dass man p-Aminobenzol-sulfonyl-guani- din mit Malonsäure zum 2-(p-Aminobenzol- sulfonyla-mino-) 4,6-diogy-pyrimidin konden siert, letzteres mittels eines Halogenierungs- mittels in das 2-(p-Aminobenzolsulfonyl- a.mino-) 4,6 - dihalogen - pyrimidin überführt und dieses zum 2-(p-Aminobenzol-sulfon@-1- amino-)pyrimidin reduziert.
Ausführungsbeispiel: 10,7 g p-Aminobenzol-sulfonyl-guanidin werden in 100 cm' auf 0 abgekühlte rau chende Schwefelsäure eingetragen. Zu diesem Gemisch werden unter Rühren 5,2 g Malon- säure gegeben, wobei die Temperatur 0 nicht übersteigen darf. Hierauf lässt man einige Stunden bei Zimmertemperatur stehen und erwärmt dann unter Rühren 1 Stunde auf 50-60 .
Das erkaltete Reaktionsgemisch wird auf Eis gegeben und bei 0 mit konzen triertem Ammoniak neutralisiert, worauf sich 2 - (p-Aminobenzol-sulfonylamino-) 4,6-dioxy- pyrimidin ausscheidet. Ausbeute: 11,8 g oder 8.3,1 % d. Th.
10 g der letzteren Verbindung werden mit 60 cm' Phosphorogychlorid am Rückflussküh- ler gekocht. Nach Entfernung des überschüs sigen Phosphorogychlorids wird das Reak tionsgemisch auf Eis gegossen und mit Am moniak unter Kühlung neutralisiert. Der da bei entstehende farblose Niederschlag von 2-(p-Aminobenzol-sulfonylamino-)4,6-dichlor- pyrimidin wird mit Wasser gewaschen und bei 40-50 im Vakuum getrocknet. Aus beute: 10,8 g oder 92,8 % d. Th.
10 g dieser Chlorverbindung werden in alkoholischer Lösung mit katalytisch ange regtem Wasserstoff reduziert. Nach dem Ab dampfen des Alkohols erhält man das 2-(p- Aminobenzol-sulfonylamino-)pyrimidin in einer Menge von 7,58 g oder 96,5 % d. Th. Es zeigt, in Übereinstimmung mit dem Schrift- tum, einen Schmelzpunkt von 255-256 .
Die Kondensation von p-Aminobenzol- sulfonyl-guanidin mit der Malonsäure kann statt mit rauchender Schwefelsäure auch in Gegenwart anderer wasserentziehender Mittel ausgeführt werden.
Process for the preparation of a sulfonamide. The invention relates to a peculiar method for the preparation of a Sul fonamides, namely the well-known 2- (p-aminobenzene = sulfonylamino) pyrimidine, wel Ches white crystals from melting point 255 to 256 forms and can be used as a remedy against infections.
The process is characterized in that p-aminobenzene-sulfonyl-guanidine is condensed with malonic acid to form 2- (p-aminobenzene-sulfonyla-mino-) 4,6-diogy-pyrimidine, the latter using a halogenating agent in the 2- (p-aminobenzene-sulfonyl- a.mino-) 4,6-dihalo-pyrimidine is converted and this is reduced to 2- (p-aminobenzene-sulfon @ -1-amino-) pyrimidine.
Exemplary embodiment: 10.7 g of p-aminobenzene-sulfonyl-guanidine are introduced into 100 cm ′ of fuming sulfuric acid cooled to 0. 5.2 g of malonic acid are added to this mixture with stirring, the temperature not being allowed to exceed 0. This is left to stand for a few hours at room temperature and then heated to 50-60 for 1 hour while stirring.
The cooled reaction mixture is poured onto ice and neutralized at 0 with concentrated ammonia, whereupon 2 - (p-aminobenzene-sulfonylamino) 4,6-dioxy-pyrimidine precipitates. Yield: 11.8 g or 8.3.1% of theory. Th.
10 g of the latter compound are refluxed with 60 cm 'of phosphorogychloride. After removal of the excess phosphorogychloride, the reaction mixture is poured onto ice and neutralized with ammonia while cooling. The colorless precipitate of 2- (p-aminobenzene-sulfonylamino-) 4,6-dichloropyrimidine that is formed is washed with water and dried at 40-50 in a vacuum. From booty: 10.8 g or 92.8% d. Th.
10 g of this chlorine compound are reduced in an alcoholic solution with catalytically excited hydrogen. After the alcohol has been evaporated, the 2- (p-aminobenzene-sulfonylamino) pyrimidine is obtained in an amount of 7.58 g or 96.5% of theory. Th. It shows, in accordance with the literature, a melting point of 255-256.
The condensation of p-aminobenzenesulfonylguanidine with the malonic acid can be carried out in the presence of other dehydrating agents instead of using fuming sulfuric acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH236174T | 1942-02-19 | ||
| CH226118T | 1943-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236174A true CH236174A (en) | 1945-01-15 |
Family
ID=25726965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236174D CH236174A (en) | 1942-02-19 | 1942-02-19 | Process for the preparation of a sulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236174A (en) |
-
1942
- 1942-02-19 CH CH236174D patent/CH236174A/en unknown
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