CH214344A - Process for the preparation of 2- (para-amino-benzenesulfamido) -6-methyl-pyridine. - Google Patents
Process for the preparation of 2- (para-amino-benzenesulfamido) -6-methyl-pyridine.Info
- Publication number
- CH214344A CH214344A CH214344DA CH214344A CH 214344 A CH214344 A CH 214344A CH 214344D A CH214344D A CH 214344DA CH 214344 A CH214344 A CH 214344A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- pyridine
- methyl
- para
- hydrolysis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Procédé de préparation de la 2-(para-amino-benzène-sulfamido)-6-méthyl-pyridine. La présente invention a pour objet un procédé de préparation de la 2-(para-amino- benzène-sulfamido)-6-méthyl-pyridine, ayant pour formule
EMI0001.0004
Ce composé fond à 219 C; il est peu soluble à froid dans l'eau, l'acétone, l'alcool; il présente des propriétés bactéricides mar quantes et il est susceptible d'applications thérapeutiques.
Le procédé selon l'invention est caracté risé en ce que l'on fait réagir de la 2-amino- 6-méthyl-pyridine avec un halogénure de para- acyle-amino-benzène-sulfonyle, de manière à former, en éliminant de l'halogénure d'hydro gène, de la 2-(para-acyle-amino-benzène-sulf- amido)-6-méthyl-pyridine, puis en ce que l'on <I>soumet ce</I> dernier corps à une hydrolyse pour en éliminer le groupe acyle et obtenir la 2 (p ara-amino-benzène - sulfamido)
-6-méthyl- py- ridine. De préférence, on fait réagir de la 2 amino-6-méthylpyridine avec du chlorure de para-acétyl-amino-benzène-sulfonyle. L'hydro lyse de la 2-(para-acyle-amino-benzène-sulf- amido)-6-méthyl-pyridine peut être réalisée en milieu alcalin.
Voici un exemple d'exécution du procédé de l'invention 10,8 gr de 2-amino-6-méthyl-pyridine sont mis en suspension dans 20 cm3 de pyridine: on ajoute 23,5 gr de chlorure de p-acétyl- amino-benzène-sulfonyle et le mélange est chauffé au bain-marie pendant 10 minutes.. En diluant à l'eau la 6-méthyl-2-(p-acétyl- amino-benzène-sulfamido)-pyridine brute se sépare, que l'on recueille et qui, après cris tallisation dans l'acide acétique dilué, fond à 215 C.
Elle est traitée à l'ébullition avec 150 cml d'une solution 2 N de soude, filtrée, et on ajoute 150 cm' d'acide acétique 2 N. On obtient ainsi le précipité de 2-(p-amino- benzène-sulfamido)-6-méthyl-pyridine pure cristallisée. Le point de fusion du produit ëst 219 C après recristallisation dans l'acide acétique dilué.
Process for the preparation of 2- (para-amino-benzenesulfamido) -6-methyl-pyridine. The present invention relates to a process for the preparation of 2- (para-amino-benzene-sulfamido) -6-methyl-pyridine, having the formula
EMI0001.0004
This compound melts at 219 C; it is poorly soluble in cold water, acetone, alcohol; it has remarkable bactericidal properties and is capable of therapeutic applications.
The process according to the invention is characterized in that 2-amino-6-methyl-pyridine is reacted with a para-acyl-amino-benzene-sulfonyl halide, so as to form, while eliminating hydrogen halide, 2- (para-acyl-amino-benzene-sulf-amido) -6-methyl-pyridine, then in that we <I> subject this </I> last body hydrolysis to remove the acyl group and obtain 2 (p ara-amino-benzene - sulfamido)
-6-methyl-pyridine. Preferably, 2 amino-6-methylpyridine is reacted with para-acetyl-amino-benzenesulfonyl chloride. The hydrolysis of 2- (para-acyl-amino-benzene-sulf-amido) -6-methyl-pyridine can be carried out in an alkaline medium.
Here is an example of execution of the process of the invention 10.8 g of 2-amino-6-methyl-pyridine are suspended in 20 cm3 of pyridine: 23.5 g of p-acetyl-amino chloride are added -benzene-sulfonyl and the mixture is heated in a water bath for 10 minutes. By diluting with water the crude 6-methyl-2- (p-acetyl-amino-benzene-sulfamido) -pyridine separates, that the 'is collected and which, after crystallization in dilute acetic acid, melts at 215 ° C.
It is treated at the boiling point with 150 cml of a 2N sodium hydroxide solution, filtered, and 150 cml of 2N acetic acid are added. The precipitate of 2- (p-amino-benzene-sulfamido ) -6-methyl-pyridine pure crystalline. The melting point of the product is 219 C after recrystallization from dilute acetic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205678T | 1937-07-14 | ||
| GB214344X | 1937-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214344A true CH214344A (en) | 1941-04-15 |
Family
ID=25724207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214344D CH214344A (en) | 1937-07-14 | 1938-11-15 | Process for the preparation of 2- (para-amino-benzenesulfamido) -6-methyl-pyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214344A (en) |
-
1938
- 1938-11-15 CH CH214344D patent/CH214344A/en unknown
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