CH201765A - Process for the preparation of parabenzylaminobenzenesulfamide. - Google Patents
Process for the preparation of parabenzylaminobenzenesulfamide.Info
- Publication number
- CH201765A CH201765A CH201765DA CH201765A CH 201765 A CH201765 A CH 201765A CH 201765D A CH201765D A CH 201765DA CH 201765 A CH201765 A CH 201765A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- para
- acetylbenzylaniline
- ammonia
- parabenzylaminobenzenesulfamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- BISSQVWYQNHTIH-UHFFFAOYSA-N n-benzyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C(=O)C)CC1=CC=CC=C1 BISSQVWYQNHTIH-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- 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
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de la parabenzylaminobenzènesulfamide. On sait que les. dérivés de la. p-aminoben- zènesulfamide, substitués sur le groupe amino par un reste aralcoyl, ont des proprié tés bactéricides, en particulier sur les strepto coques; parmi ces dérivés on peut citer la para-benzylaminobenzènesulf amide.
On a décrit dans les brevets suisses nos 192699 et 192700 deux procédés de prépa ration de la para-benzylaminobenzènesulfa- mide.
Poursuivant ses recherches, la demande- resse a trouvé qu'on peut facilement préparer la para-benzylaminobenzènesulfamide, ainsi que d'autres p-aminobenzènesulfamides N- aralkylées (par exemple la para-phénylpro- pylaminobenzènesulfamide) en faisant réa gir sur l'acétylbenzylaniline ou ses homo logues correspondants, la chlorhydrine sulfu rique et en traitant le sulfoehlorure formé par l'ammoniaque.
La formule ci-après donne une représentation schématique des réactions de cette préparation:
EMI0001.0028
La présente invention a donc pour objet un procédé de préparation de la para-benzyl- aminobenzènesulfamide. Ce procédé -est caractérisé en ce que l'on fait réagir de l'acétylbenzylaniline avec de la chlorhydrine sulfurique, de manière à for- mer le para-sulfochlorure correspondant, puis en ce que l'on traite ce dernier par l'am moniaque et l'eau.
Voici, à titre d'exemple, comment le pro cédé de l'invention peut être réalisé en pra tique: On ajoute à 145 gr de chlorhydrine sul furique, en heure, en agitant et en main tenant la température au-dessus de 20 C. 55 gr d'acétylbenzylaniline. On porte alors la température à 65 et on maintient le chauffage et l'agitation pendant ? h. On re froidit et l'on coule peu à peu sur 400 gr de glace pilée. On reprend par ?00 cm' de ben zène qui dissout le sulfochlorRZre brut préci pité.
On coule, en refroidissant et en agitant la solution décantée dans 200 emd d'ammonia que à. 22 Bé. On filtre le précipité solide après quelques minutes de repos et on le re- cristallise dans l'alcool ou l'acétone à. 50 . Le produit fond à 175 , comme celui obtenu par les procédés des brevets suisses nos 193699 et 19\3700.
Process for the preparation of parabenzylaminobenzenesulfamide. We know that the. derived from the. p-aminobenzenesulfamide, substituted on the amino group by an aralkyl residue, have bactericidal properties, in particular on streptococci; among these derivatives, mention may be made of para-benzylaminobenzenesulf amide.
Two processes for the preparation of para-benzylaminobenzenesulfamide have been described in Swiss Patents Nos. 192699 and 192700.
Continuing her research, the applicant has found that para-benzylaminobenzenesulfamide, as well as other N-aralkylated p-aminobenzenesulfonamides (for example para-phenylpropylaminobenzenesulfamide) can easily be prepared by reacting on acetylbenzylaniline. or its corresponding counterparts, sulfuric chlorohydrin and by treating the sulfohloride formed by ammonia.
The formula below gives a schematic representation of the reactions of this preparation:
EMI0001.0028
A subject of the present invention is therefore a process for the preparation of para-benzylaminobenzenesulfamide. This process -is characterized in that one reacts acetylbenzylaniline with sulfuric chlorohydrin, so as to form the corresponding para-sulfochloride, then in that the latter is treated with ammonia. and water.
Here is, by way of example, how the process of the invention can be carried out in practice: 145 g of sulfuric chlorohydrin are added to 145 g, in the hour, while stirring and keeping the temperature above 20 ° C. 55 gr of acetylbenzylaniline. The temperature is then brought to 65 and the heating and stirring are maintained for? h. Cool down again and gradually pour over 400 g of crushed ice. It is taken up in 00 cm 'of ben zene which dissolves the abovementioned crude sulfochlorRZre.
Poured, cooling and stirring the solution decanted in 200 emd of ammonia as. 22 Bé. The solid precipitate is filtered off after standing for a few minutes and recrystallized from alcohol or acetone. 50. The product melts at 175, like that obtained by the methods of Swiss Patent Nos. 193699 and 19 \ 3700.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201765X | 1937-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201765A true CH201765A (en) | 1938-12-15 |
Family
ID=10141651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201765D CH201765A (en) | 1937-03-19 | 1938-03-17 | Process for the preparation of parabenzylaminobenzenesulfamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201765A (en) |
-
1938
- 1938-03-17 CH CH201765D patent/CH201765A/en unknown
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