CH214352A - Process for the preparation of a derivative of 2-aminopyridine. - Google Patents
Process for the preparation of a derivative of 2-aminopyridine.Info
- Publication number
- CH214352A CH214352A CH214352DA CH214352A CH 214352 A CH214352 A CH 214352A CH 214352D A CH214352D A CH 214352DA CH 214352 A CH214352 A CH 214352A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminopyridine
- derivative
- preparation
- alcohol
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000003930 2-aminopyridines Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 150000003927 aminopyridines Chemical class 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- -1 p - Butyrylaminobenzolsulfonyl- Chemical group 0.000 claims description 2
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical compound CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SZVWBINNBHRDJG-UHFFFAOYSA-N pyridin-2-amine;sodium Chemical compound [Na].NC1=CC=CC=N1 SZVWBINNBHRDJG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent 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)
Description
Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. Die Erfindung betrifft ein Verfahren zur Damteilung eines Derivates des 2-Amino- pyridins, welches dadurch gekennzeichnet ist,
dass man p-Butyrylaminobenzo1sulfonsäure- cblorid mit dem aus Pyridin und Natriumamid erhältlichen 2-Aminopyridin-Natrium zur Reaktion bringt und das dabei entstehende 2 - (p -Butyrylaminobenzol@sulfonyl-)aminopy- ridin. mit Alkali zum 2-(p-Aminobenzol- sulfonyl-)aminopyridin verseift.
Das Verfahrensprodukt hat sich als wert voll .erwiesen zur Bekämpfung von Kokken infektionen und soll daher therapeutisch ver wendet werden. :Seine Darstellung erfolgt beispielsweise folgendermassen: 26,1g p-Butyrylaminobenzolsulfonsäure- chlorid werden mit 11;
6<B>g</B> des aus Pyridin und Natriumamid in aliphatis,chen Kohlen- waGserstoffei gebildeten 2-Aminopyridin- Natrium zusammengebracht; das Reaktions gemisch wird vom Lösungsmittel getrennt, mit Wasser vom Natriumehlo@rid befreit und das Zurückbleibende durch Erhitzen mit 115prozentiger Natronlauge verseift.
Dass so erhältliche 2-(p-Aminobenzol- sulfonyl-)aminopyridin bildet farblose Pris men (aus Alkohol), die bei 189-1.-91' C schmelzen. Es ist leicht löslich in verdünn- ten Säuren und Alkalien, wenig löslich in Alkohol, Azeton und Äther, sehr schwer lös lich in kaltem und warmem Wasser.
Process for the preparation of a derivative of 2-aminopyridine. The invention relates to a method for the division of a derivative of 2-aminopyridine, which is characterized in
that p-butyrylaminobenzo1sulphonic acid chloride is reacted with the 2-aminopyridine sodium obtainable from pyridine and sodium amide, and the resulting 2 - (p-butyrylaminobenzene @ sulfonyl) aminopyridine. saponified with alkali to give 2- (p-aminobenzenesulfonyl) aminopyridine.
The process product has proven to be valuable for combating cocci infections and should therefore be used therapeutically. : It is represented as follows, for example: 26.1 g of p-butyrylaminobenzenesulfonic acid chloride are mixed with 11;
6 g of the 2-aminopyridine sodium formed from pyridine and sodium amide in aliphatic, small hydrocarbons; the reaction mixture is separated from the solvent, freed from sodium chloride with water and what remains is saponified by heating with 115 percent sodium hydroxide solution.
The 2- (p-aminobenzenesulfonyl) aminopyridine obtainable in this way forms colorless prisms (from alcohol) that melt at 189-1.-91 ° C. It is easily soluble in dilute acids and alkalis, sparingly soluble in alcohol, acetone and ether, very poorly soluble in cold and warm water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212060T | 1938-08-30 | ||
| CH214352T | 1939-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214352A true CH214352A (en) | 1941-04-15 |
Family
ID=25725132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214352D CH214352A (en) | 1938-08-30 | 1939-05-20 | Process for the preparation of a derivative of 2-aminopyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214352A (en) |
-
1939
- 1939-05-20 CH CH214352D patent/CH214352A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH214352A (en) | Process for the preparation of a derivative of 2-aminopyridine. | |
| CH212060A (en) | Process for the preparation of a derivative of 2-aminopyridine. | |
| CH253657A (en) | Process for the preparation of a new derivative of a carboxylic acid. | |
| CH214351A (en) | Process for the preparation of a derivative of 2-aminopyridine. | |
| DE674590C (en) | Process for the preparation of the guaiacol ester of acetylsalicylic acid | |
| SU12141A1 (en) | Method for producing amino-3-chloro-4-hydroxybenzene-1-arsic acid | |
| CH156308A (en) | Process for the preparation of a sulfuric acid ester. | |
| CH222728A (en) | Process for the preparation of a derivative of citrazinic acid. | |
| DE510449C (en) | Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives | |
| DE512233C (en) | Process for the preparation of 1-aminocarbazole and its derivatives | |
| DE487788C (en) | Process for the preparation of the N-oxyaethyl derivatives of nuclear substitution products and homologues of 4-amino-1-oxybenzene | |
| AT227708B (en) | Process for the preparation of new sulfonamides of the pyrimidine series and salts thereof | |
| CH289538A (en) | Process for the preparation of the diethylaminoethyl ester of 4-amino-2-oxy-benzoic acid. | |
| CH221518A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH265664A (en) | Process for the preparation of a new sulfanilamide derivative. | |
| CH207672A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH221516A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH222965A (en) | Process for the preparation of 4-amino-benzenesulfonamido-benzene-3'-sulfonacetylamide. | |
| CH221515A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH239147A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH213815A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH213816A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH222074A (en) | Process for the preparation of a sulfonamide. | |
| CH211294A (en) | Process for the production of a condensation product. | |
| CH294179A (en) | Process for the preparation of pyridyl mercury chloride. |