CH197497A - Process for preparing para- [para-oxybenzyl] aminobenzenesulfamide. - Google Patents
Process for preparing para- [para-oxybenzyl] aminobenzenesulfamide.Info
- Publication number
- CH197497A CH197497A CH197497DA CH197497A CH 197497 A CH197497 A CH 197497A CH 197497D A CH197497D A CH 197497DA CH 197497 A CH197497 A CH 197497A
- Authority
- CH
- Switzerland
- Prior art keywords
- para
- aminobenzenesulfamide
- soluble
- preparing
- oxybenzyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- -1 especially in hot Chemical compound 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de la para- [para-ogybenzyl]aminobenzènesulfamide. On a constaté que les dérivés de la p- aminobenzénesulfamide, substitués sur le grou pement amino par un reste aralcoyl, ont des propriétés bactéricides. Le reste aralcoyl peut renfermer dans son noyau des substi- tuants divers, comme, par exemple, des grou pements hydroxy ou sulfo; dans ce dernier cas, on a des composés solubles dans l'eau.
Cette substitution sur le groupement animé de la p-aminobenzénesulfamide augmente con sidérablement l'activité bactéricide de la p- aminobenzénesulfamide et permet d'obtenir des composés stables ayant de bonnes pro priétés thérapeutiques, ils sont particulière ment actifs sur les streptocoques.
On a trouvé que l'on pouvait préparer ces nouveaux composés en hydrogénant par les méthodes connues, comme. par exemple, en présence de catalyseurs appropriés, les bases de Schiff résultant de la condensation de la p-aminobenzènesulfamide avec une aldéhyde aromatique. La présente invention a pour objet un procédé de préparation de la para-(para-oxy- benzyl]aminobenzènesulfamide.
Ce procédé est caractérisé en ce que l'on condense de la para-aminobenzènesulfamide avec de l'aldéhyde para-oxybenzoïque, de manière à, obtenir de la para- [para-oxyben- zylidène]aminobenzénesulfamide, puis en ce que l'on hydrogénise ce dernier corps en présence d'un catalyseur d'hydrogénation.
Voici, à, titre d'exemple, comment le pro cédé de l'invention peut être exécuté en pratique En chauffant quelques heures â l'ébulli tion 17,2 gr de p-aminobenzènesulfamide dissous dans 100 cc d'alcool, en présence de 12,2 gr d'aldéhyde para-oxybenzoïque, il pré cipite par refroidissement la para-[para-oxyben- zylidène]aminobenzènesulfamide.
13,8 gr de p-[p-oxybenzylidène]aminoben- zènesulfamide sont dissous dans 300 cc de dioxane et hydrogénés en présence de nickel actif à température ordinaire. Après absorp tion de la quantité théorique d'hydrogène, on sépare le catalyseur par filtration. Le filtrat est évaporé à sec et le résidu est recristallisé dans l'acétone.
On obtient ainsi avec un rendement pres que théorique la p-(p-oxybenzyl]aminobenzène- sulfamide sous forme de cristaux incolores fondant à 206 . Ce produit est très peu soluble dans l'eau froide, plus soluble dans l'eau bouillante, soluble dans l'alcool, surtout à chaud, l'acétone, l'acide acétique chaud. Du fait qu'il est insoluble dans l'eau, ce produit s'emploie par ingestion.
Process for the preparation of para- [para-ogybenzyl] aminobenzenesulfamide. It has been found that the p-aminobenzenesulfamide derivatives, substituted on the amino group by an aralkyl residue, have bactericidal properties. The aralkyl residue can contain in its nucleus various substituents, such as, for example, hydroxy or sulfo groups; in the latter case, there are compounds soluble in water.
This substitution on the animate group of p-aminobenzenesulfamide considerably increases the bactericidal activity of p-aminobenzénesulfamide and makes it possible to obtain stable compounds having good therapeutic properties; they are particularly active on streptococci.
It has been found that these new compounds can be prepared by hydrogenating by known methods, such as. for example, in the presence of suitable catalysts, Schiff's bases resulting from the condensation of p-aminobenzenesulfamide with an aromatic aldehyde. The present invention relates to a process for the preparation of para- (para-oxybenzyl] aminobenzenesulfamide.
This process is characterized in that one condenses para-aminobenzenesulfamide with para-oxybenzoic aldehyde, so as to obtain para- [para-oxybenzylidene] aminobenzenesulfamide, then in that one hydrogenates the latter body in the presence of a hydrogenation catalyst.
Here is, by way of example, how the process of the invention can be carried out in practice by heating for a few hours at boiling 17.2 g of p-aminobenzenesulfamide dissolved in 100 cc of alcohol, in the presence of 12.2 g of para-oxybenzoic aldehyde, it precipitates by cooling the para- [para-oxybenzylidene] aminobenzenesulfamide.
13.8 g of p- [p-oxybenzylidene] aminobenzenesulfamide are dissolved in 300 cc of dioxane and hydrogenated in the presence of active nickel at room temperature. After absorption of the theoretical quantity of hydrogen, the catalyst is separated by filtration. The filtrate is evaporated to dryness and the residue is recrystallized from acetone.
In this way, p- (p-oxybenzyl] aminobenzenesulphamide is obtained with an almost theoretical yield in the form of colorless crystals, melting at 206. This product is very slightly soluble in cold water, more soluble in boiling water, soluble. in alcohol, especially hot, acetone, hot acetic acid As it is insoluble in water, this product can be used by ingestion.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB197497X | 1936-02-18 | ||
| CH192700T | 1937-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH197497A true CH197497A (en) | 1938-04-30 |
Family
ID=25722320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH197497D CH197497A (en) | 1936-02-18 | 1937-02-01 | Process for preparing para- [para-oxybenzyl] aminobenzenesulfamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH197497A (en) |
-
1937
- 1937-02-01 CH CH197497D patent/CH197497A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0074903B1 (en) | Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene, their preparation and their therapeutic use | |
| CH197497A (en) | Process for preparing para- [para-oxybenzyl] aminobenzenesulfamide. | |
| Borrows et al. | S 42. The synthesis of thyroxine and related substances. Part I. The preparation of tyrosine and some of its derivatives, and a new route to thyroxine | |
| Jones et al. | The synthesis of some analogs of histamine and histidine containing the thiazole nucleus | |
| CH197496A (en) | Process for preparing para-ºrtho-oxybenzyl] aminobenzenesulfamide. | |
| CH192700A (en) | Process for the preparation of parabenzylaminobenzenesulfamide. | |
| CH197498A (en) | A process for preparing the sodium salt of para-[meta-sulfobenzyl] aminobenzenesulfamide. | |
| Borrows et al. | S 44. The synthesis of thyroxine and related substances. Part III. The synthesis of thyroxine from 2: 6-dinitrodiphenyl ethers | |
| Saunders et al. | Some Derivatives of 6, 8-Dichloroquinoline1 | |
| CH314548A (en) | Process for preparing a 1-p-nitrophenyl-2-acylamido-propanediol-1,3 | |
| DE425739C (en) | Process for the preparation of 6-nitro-3, 4-dimethoxy-1-methylbenzene (6-nitrohomoveratrol) | |
| CH402842A (en) | Process for the preparation of new heparin derivatives | |
| KLINGI et al. | VOL. oxvm. i. hh | |
| CH192699A (en) | Process for the preparation of parabenzylaminobenzenesulfamide. | |
| CH293430A (en) | Process for the preparation of a new oxazoline derivative. | |
| CH275969A (en) | A process for preparing a substituted sulfanilamido-quinoxaline. | |
| CH201764A (en) | Process for the preparation of sodium benzyl para-aminobenzenesulfamide-w-sulfonate. | |
| BE513351A (en) | ||
| BE542106A (en) | ||
| Deulofeu | CCXXIV.—Formation of l-threose | |
| CH310415A (en) | Process for preparing a 1-p-nitrophenyl-2-acylamido-propanediol-1,3. | |
| BE474887A (en) | ||
| CH288985A (en) | Process for preparing an aromatic acylamidodiol, nitrated in the nucleus. | |
| CH394204A (en) | Procédé de preparation de dérivés de la phenoxazine | |
| BE551920A (en) |