CH212060A - Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. - Google Patents
Verfahren zur Darstellung eines Derivates des 2-Aminopyridins.Info
- Publication number
- CH212060A CH212060A CH212060DA CH212060A CH 212060 A CH212060 A CH 212060A CH 212060D A CH212060D A CH 212060DA CH 212060 A CH212060 A CH 212060A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminopyridine
- derivative
- preparation
- alcohol
- sparingly soluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000003930 2-aminopyridines Chemical class 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 150000003927 aminopyridines Chemical class 0.000 claims 1
- BCGPJHIZFZQJRS-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=NC=CC=C1N BCGPJHIZFZQJRS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IQIXOVZKIWONBZ-UHFFFAOYSA-N 4-aminobenzenesulfonamide;sodium Chemical compound [Na].NC1=CC=C(S(N)(=O)=O)C=C1 IQIXOVZKIWONBZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. Die Erfindung betrifft ein Verfahren zur Darstellung eines Derivates des 2-Aniiriopy- ridins, welches sich dadurch auszeichnet, dass man 2-Brompyridin mit einem Alkalisalz des p- Aminobenzolsulfonamids zur Reaktion bringt.
Das dabei unter Austritt von Alkalibromid sich bildende 2 - (p - Aminobenzolsulfonyl -) aminopyridin soll therapeutisch verwendet werden, da es sich als zur Bekämpfung von Kokkeninfektion wertvoll erwiesen hat.
Die Darstellung dieser Verbindung erfolgt beispielsweise folgendermassen 15,8 g 2-Brompyridin und 19,4 g p-Amino- benzolsulfonamid-Nati,ium werden mit wenig Xylol während 2 Stunden am Rückflusskühler erhitzt. Hierauf wird das vom Xylol getrennte Reaktionsgemisch mit Wasser behandelt und das zurückbleibende 2 - (p - Aminobenzolsul- fonyl-)aminopyridin aus heissem Alkohol um kristallisiert.
Das Verfahrensprodukt bildet farblose Prismen (aus Alkohol), die bei<B>189-1911</B> C schmelzen. Es ist leicht löslich in verdünnten Säuren und Alkalien, wenig löslich in Alko hol, Azeton und Äther, sehr schwer löslich in kaltem und warmem Wasser.
Claims (1)
- PATENTANSPRUCH: Verfahren zur Darstellung eines Derivates des 2-Aminopyridins, dadurch gekennzeichnet, dass man 2-Brompyridin mit einem Alkali salz des p-Aminobenzolsulfonamids zur Reak tion bringt, wobei unter Austritt von Alkali bromid 2-(p-Amiiiobenzolsulforiyl-) amino- pyridin gebildet wird. Das Verfahrensprodukt soll therapeutisch, insbesondere gegen Kokkeninfektion Verwen dung finden. Es bildet farblose Prismen (aus Alkohol), die bei 189-191 C schmelzen.Es ist leicht löslich in verdünnten Säuren und Alkalien, wenig löslich in Alkohol, Aze- ton und Äther, sehr schwer löslich in kaltem und warmem Wasser.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212060T | 1938-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212060A true CH212060A (de) | 1940-10-31 |
Family
ID=4447629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212060D CH212060A (de) | 1938-08-30 | 1939-05-20 | Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH212060A (de) |
-
1939
- 1939-05-20 CH CH212060D patent/CH212060A/de unknown
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