CH222732A - Process for the preparation of a derivative of para-amino-benzene-sulfonamide. - Google Patents
Process for the preparation of a derivative of para-amino-benzene-sulfonamide.Info
- Publication number
- CH222732A CH222732A CH222732DA CH222732A CH 222732 A CH222732 A CH 222732A CH 222732D A CH222732D A CH 222732DA CH 222732 A CH222732 A CH 222732A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzene
- amino
- para
- derivative
- preparation
- Prior art date
Links
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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/64—X and Y being nitrogen atoms, e.g. N-sulfonylguanidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Procédé de préparation d'un dérivé de la para-amino-benzène-sulfamide. La présente invention a pour objet un procédé de préparation d'un dérivé de la para- amino-benzéne-sulfamide, ayant la formule
EMI0001.0004
Ce composé connu, qui forme une poudre blanche et qui fond â 201-2021 C, est sus ceptible d'application thérapeutique.
Selon la présente invention, le composé mentionné ci-dessus est préparé comme suit: On condense du 2-amino-thiazol avec un p-nitro-benzène-halogénure de soufre, ayant pour formule
EMI0001.0007
Ce dernier composé est facile â préparer d'après Zincke A. 400 9.
Le produit de la condensation mentionnée a pour formule
EMI0001.0009
Ce dernier composé est oxydé, par exem ple par le permanganate de potasse ou des oxydants équivalents, en 2(para-nitro-benzène- sulfa.mido)-thiazol. On réduit ensuite le groupe nitro en amino, par exemple avec du fer et de l'acide acétique â 95-100" selon la mé thode bien connue de Béchamp (A. ch. [3] 42 190), et on obtient du 2(para-amino-benzène- sulfamido)-thiazol.
Voici des exemples d'exécution du procédé de l'invention .Exemple <I>1:</I> On dissout 10 gr de 2-amino-thiazol dans 50 cm' d'éther sec et on ajoute 6 gr de car bonate de sodium anhydre. En refroidissant â 10--15 , on ajoute alors lentement une solution de 14 gr de p-nitro-benzène-chlorure
EMI0001.0023
de <SEP> soufre
<tb> <B><I>(02N- < D-SCI)</I></B> dans 100 cm' d'éther séché, en agitant bien le mélange. Un précipité résineux est formé. Après une heure, on ajoute 100 cm3 d'eau en agitant et ensuite on sépare le précipité de l'eau et de l'éther.
Ce composé a la formule
EMI0002.0001
La réaction peut aussi être mise en oeuvre en solution benzénique.
Pour l'oxydation de ce dernier composé en dérivé sulfamido, 1 gr de la matière brute est dissous dans 15 cm" de dioxane et cette solution est diluée par 5 cm3 d'eau. Cette solution étant refroidie à 10-150, on l'agite tout en ajoutant lentement du permanganate de potasse pulvérisé jusqu'à ce qu'un petit excès de cet oxydant soit présent et que la solution reste rouge. Le mélange est ensuite versé dans 100 cm' d'acide sulfurique 10 0;'o et décoloré par un peu de bisulfite de sodium. Le précipité est séparé par filtration.
Il con siste en 2(para-nitro-benzène-sulfamido)-thia- zol.
10 gr de ce composé nitré brut sont ver sés dans un mélange bien agité de 100 gr de limaille de fer et de 300 cm' d'acide acé tique à une température de 95-100 0. Après une heure d'agitation à 95 0, le mélange est refroidi à 20 " et rendu alcalin avec une solu tion de soude caustique. Le mélange est filtré et le filtrat acidifié à l'acide acétique. Le pré cipité est filtré. Il consiste en 2(para-amino- benzène-sulfamido)-thiazol et fond à 201 à 2020. <I>Exemple 2:</I> 5 gr de 2-aniino-thiazol sont dissous dans 30 cm' de pyridine sèche.
On ajoute à cette solution en refroidissant à 10-15 0 et agitant, 9,5 gr de p-iiitro-benzèrie-chlorure de soufre
EMI0002.0019
Après une heure de repos à 20 0, la solution jaune est versée dans 500 emg d'eau. Le pré cipité est filtré et séché. Après recristallisa- tion à l'alcool ou au benzène, le composé obtenu est oxydé à la manière suivante: 1 gr du composé obtenu ainsi est dissous dans 50 cm' d'acétone. La solution est diluée par 10 cm' d'eau. En agitant, on ajoute len tement à 10-15 0 un petit excès de perman ganate de potasse.
Le mélange est alors versé dans 100 cm' d'acide sulfurique 10'1/o et déco loré à l'aide de bisulfite de sodium. Le pré cipité est filtré. Par réduction selon l'exemple 1, on obtient du 2(para-amino-benzéne-sulf- amido)-thiazol.
Process for the preparation of a derivative of para-amino-benzene-sulfonamide. The present invention relates to a process for the preparation of a derivative of para-amino-benzenesulfonamide, having the formula
EMI0001.0004
This known compound, which forms a white powder and which melts at 201-2021 C, is susceptible to therapeutic application.
According to the present invention, the above-mentioned compound is prepared as follows: 2-amino-thiazol is condensed with a p-nitro-benzene-sulfur halide, having the formula
EMI0001.0007
The latter compound is easy to prepare according to Zincke A. 400 9.
The product of the mentioned condensation has the formula
EMI0001.0009
The latter compound is oxidized, for example by potassium permanganate or equivalent oxidants, to 2 (para-nitro-benzene-sulfa.mido) -thiazol. The nitro group is then reduced to amino, for example with iron and 95-100 "acetic acid according to the well-known method of Béchamp (A. ch. [3] 42 190), and 2 (para-amino-benzene-sulfamido) -thiazol.
Here are examples of execution of the process of the invention. Example <I> 1: </I> 10 g of 2-amino-thiazol are dissolved in 50 cm 3 of dry ether and 6 g of car bonate of sodium anhydrous. While cooling to 10--15, a solution of 14 g of p-nitro-benzene-chloride is then slowly added.
EMI0001.0023
of <SEP> sulfur
<tb> <B> <I> (02N- <D-SCI) </I> </B> in 100 cm 'of dried ether, stirring the mixture well. A resinous precipitate is formed. After one hour, 100 cm3 of water are added with stirring and then the precipitate is separated from the water and ether.
This compound has the formula
EMI0002.0001
The reaction can also be carried out in benzene solution.
For the oxidation of the latter compound to a sulfamido derivative, 1 g of the crude material is dissolved in 15 cm 3 of dioxane and this solution is diluted with 5 cm 3 of water. This solution being cooled to 10-150, it is added. stir while slowly adding powdered potassium permanganate until a small excess of this oxidant is present and the solution remains red. The mixture is then poured into 100 cm 3 of sulfuric acid 10% and decolorized with a little sodium bisulphite The precipitate is separated by filtration.
It consists of 2 (para-nitro-benzene-sulfamido) -thia-zol.
10 g of this crude nitrated compound are poured into a well-stirred mixture of 100 g of iron filings and 300 cm 3 of acetic acid at a temperature of 95-100 0. After stirring for one hour at 95 0 , the mixture is cooled to 20 "and made alkaline with caustic soda solution. The mixture is filtered and the filtrate acidified with acetic acid. The precipitate is filtered. It consists of 2 (para-amino-benzene- sulfamido) -thiazol and melts at 201 to 2020. <I> Example 2: </I> 5 g of 2-aniino-thiazol are dissolved in 30 cm 3 of dry pyridine.
Is added to this solution while cooling to 10-15 0 and stirring, 9.5 g of p-iiitro-benzenesulfur chloride
EMI0002.0019
After standing at 20 ° for one hour, the yellow solution is poured into 500 emg of water. The precipitate is filtered and dried. After recrystallization with alcohol or benzene, the compound obtained is oxidized as follows: 1 g of the compound thus obtained is dissolved in 50 cm 3 of acetone. The solution is diluted with 10 cm 3 of water. With stirring, a small excess of potassium hydroxide permanence is added slowly to 10-15 °.
The mixture is then poured into 100 cm 3 of 10'1 / o sulfuric acid and decolorized with sodium bisulphite. The precipitate is filtered. By reduction according to Example 1, 2 (para-amino-benzenesulfamido) -thiazol is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220046T | 1941-08-08 | ||
| CH222732T | 1941-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH222732A true CH222732A (en) | 1942-07-31 |
Family
ID=25726386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH222732D CH222732A (en) | 1941-08-08 | 1941-08-08 | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH222732A (en) |
-
1941
- 1941-08-08 CH CH222732D patent/CH222732A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH398887A (en) | X-ray contrast agent | |
| CH222732A (en) | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. | |
| CH222734A (en) | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. | |
| CH222733A (en) | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. | |
| EP0004257B1 (en) | Benzonitrile derivative, process for its preparation and its application | |
| CH220046A (en) | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. | |
| CH222735A (en) | Process for the preparation of a derivative of para-amino-benzene-sulfonamide. | |
| EP0627403B1 (en) | Method for the production of hydroxyphenylacetic acids | |
| CH297837A (en) | Process for preparing 1-chloro-4-methylthiaxanthone. | |
| CH370093A (en) | Process for the preparation of diamino-caproic acid derivatives | |
| CH237879A (en) | Process for the preparation of -dimethyl-ss-cyclohexylethylamine. | |
| CH268051A (en) | Process for preparing 1-methyl-4-piperazine-N, N-diethyl-carboxamide. | |
| CH396030A (en) | Process for the preparation of N-isopropyl-N-benzyl-hydrazine and its salts | |
| CH326417A (en) | Process for preparing geranyl acetone | |
| CH307324A (en) | A process for preparing amino-2-hydroxy-4- (chloro-4'-phenyl) -5-ethyl-6-pyrimidine. | |
| CH286752A (en) | A process for the preparation of a fully acylated aromatic aminodiol, nitrated in the nucleus. | |
| CH299940A (en) | Process for the preparation of a pyrimidine derivative. | |
| CH329255A (en) | Process for the preparation of aryl-triamino-sulfamic acids and their salts | |
| CH271931A (en) | Process for preparing 2-bromo-2-formyl-ethyl-pyridinium bromide. | |
| CH205679A (en) | Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. | |
| CH207309A (en) | Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. | |
| CH286745A (en) | A process for preparing an aromatic diacylated hydroxy-amino-ketone. | |
| CH377837A (en) | Process for the preparation of unsaturated derivatives of the reserpine series | |
| CH286751A (en) | A process for the preparation of a fully acylated aromatic aminodiol, nitrated in the nucleus. | |
| CH357384A (en) | Process for preparing 5,5'-dinitro-2,2'-dichlorobenzil |