CH200480A - Process for the preparation of a derivative of 2-chloro-pyridine-5-sulfonic acid amide. - Google Patents
Process for the preparation of a derivative of 2-chloro-pyridine-5-sulfonic acid amide.Info
- Publication number
- CH200480A CH200480A CH200480DA CH200480A CH 200480 A CH200480 A CH 200480A CH 200480D A CH200480D A CH 200480DA CH 200480 A CH200480 A CH 200480A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid amide
- sulfonic acid
- pyridine
- chloro
- derivative
- Prior art date
Links
- HIBWOQXTHBAGDY-UHFFFAOYSA-N 6-chloropyridine-3-sulfonamide Chemical class NS(=O)(=O)C1=CC=C(Cl)N=C1 HIBWOQXTHBAGDY-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 210000002229 urogenital system Anatomy 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- VXPQZDZQAWMEHT-UHFFFAOYSA-N 6-aminopyridine-3-sulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=N1 VXPQZDZQAWMEHT-UHFFFAOYSA-N 0.000 description 1
- YXFLGKSXYWHALA-UHFFFAOYSA-N 6-aminopyridine-3-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=N1 YXFLGKSXYWHALA-UHFFFAOYSA-N 0.000 description 1
- QXZKKHONVQGXAK-UHFFFAOYSA-N 6-chloropyridine-3-sulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=N1 QXZKKHONVQGXAK-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivates des 2-Chlor-pyridin-5-sulfonsäureamids. Die Erfindung betrifft ein Verfahren zur Darstellung eines Derivates des 2- Chlor-pyridin-5-sulfonsäureamides. Das Ver fahren zeichnet sich dadurch aus, dass man 2-Chlor-pyridin-5-sulfonsäureamid mit Am moniak erhitzt, wobei unter Ersatz des Chloratoms durch die Aminogruppe 2-Amino- pyridin-5-sulfonsäureamid entsteht.
Die neue Verbindung eignet sich als sol che oder in Form ihrer Salze zur Bekämp fung septischer Erkrankungen und der In fektionen des Urogenitalsystems. Ausführungsbeispiel: 50 g 2-Chlor-pyridin-5-sulfonsäureamid werden mit 300 cm' konzentriertem Ammo niak unter Zusatz von 2 g Kupfersulfat wäh rend $ Stunden auf 160 C erhitzt. Sodann wird die Lösung eingeengt, worauf das 2 Amino-pyridin-5-sulfonsäureamid beim Er kalten auskristallisiert. Das Verfahrens produkt wird zweckmässig aus Wasser um kristallisiert.
Die neue Verbindung bildet farblose Pris men (aus Wasser), schmilzt bei 175 bis 176 C und löst sich zu 2 Prozent in Wasser von 20' C, leichter in heissem Wasser, in Säuren, Alkalien und Alkohol, nur wenig in gohlenwasserstoffen.
In gleicher Weise kann die neue Verbin dung dadurch erhalten werden, dass in obigem Ausführungsbeispiel an Stelle des 2-Chlor- pyridin-5-sulfonsäureamids 2-Chlor-pyridin- 5-sulfonsäurechlorid verwendet wird.
Die Re aktion verläuft dann in zwei Phasen:
EMI0001.0023
In der ersten wird das an die Sulfogruppe gebundene Chloratom gegen die Amino- gruppe ausgetauscht, so dass sich zunächst 2-Chlor-pyridin-5-sulfonsäureamid, der Aus gangsstoff des Verfahrens nach der Erfin dung, bildet, während in der zweiten Phase auch das Chloratom des Kernes durch die Aminogruppe ersetzt wird.
Es hat sich näm lich gezeigt, dass sich bei tieferen Tempera turen nur die erste Phase vollzieht, was be weist, dass das an der Sulfogruppe haftende Chloratom leichter austauschbar ist als das Kern-Chloratom.
Process for the preparation of a derivative of 2-chloro-pyridine-5-sulfonic acid amide. The invention relates to a method for preparing a derivative of 2-chloro-pyridine-5-sulfonic acid amide. The process is characterized in that 2-chloro-pyridine-5-sulphonic acid amide is heated with ammonia, 2-aminopyridine-5-sulphonic acid amide being formed while the chlorine atom is replaced by the amino group.
The new compound is suitable as such or in the form of its salts for combating septic diseases and infections of the urogenital system. Exemplary embodiment: 50 g of 2-chloro-pyridine-5-sulfonic acid amide are heated to 160 ° C. with 300 cm 'of concentrated ammonia with the addition of 2 g of copper sulfate for $ hours. The solution is then concentrated, whereupon the 2 aminopyridine-5-sulfonic acid amide crystallizes out when it is cold. The process product is expediently crystallized from water.
The new compound forms colorless prisms (from water), melts at 175 to 176 C and dissolves 2 percent in water at 20 C, more easily in hot water, in acids, alkalis and alcohol, but only slightly in hydrocarbons.
In the same way, the new compound can be obtained by using 2-chloro-pyridine-5-sulfonic acid chloride instead of the 2-chloropyridine-5-sulfonic acid amide in the above exemplary embodiment.
The reaction then takes place in two phases:
EMI0001.0023
In the first, the chlorine atom bonded to the sulfo group is exchanged for the amino group, so that 2-chloro-pyridine-5-sulfonic acid amide, the starting material of the process according to the invention, is initially formed, while in the second phase the The chlorine atom of the nucleus is replaced by the amino group.
It has been shown that at lower temperatures only the first phase takes place, which proves that the chlorine atom attached to the sulfo group is easier to replace than the core chlorine atom.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH200480T | 1937-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200480A true CH200480A (en) | 1938-10-15 |
Family
ID=4442334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200480D CH200480A (en) | 1937-11-24 | 1937-11-24 | Process for the preparation of a derivative of 2-chloro-pyridine-5-sulfonic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200480A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362734A (en) * | 1981-08-26 | 1982-12-07 | Sterling Drug Inc. | 2-(Substituted-amino)-5-(pyridinyl-nicotinonitriles, and their cardiotonic use |
-
1937
- 1937-11-24 CH CH200480D patent/CH200480A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362734A (en) * | 1981-08-26 | 1982-12-07 | Sterling Drug Inc. | 2-(Substituted-amino)-5-(pyridinyl-nicotinonitriles, and their cardiotonic use |
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