CH203065A - Process for the preparation of an aminobenzenesulfonic acid amide derivative. - Google Patents
Process for the preparation of an aminobenzenesulfonic acid amide derivative.Info
- Publication number
- CH203065A CH203065A CH203065DA CH203065A CH 203065 A CH203065 A CH 203065A CH 203065D A CH203065D A CH 203065DA CH 203065 A CH203065 A CH 203065A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- sodium
- aminobenzenesulfonic acid
- acid amide
- amide derivative
- Prior art date
Links
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- BABGMPQXLCJMSK-UHFFFAOYSA-N 4-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(N)C=C1 BABGMPQXLCJMSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 3
- -1 dimethyl amide - phenylaminoacetic acid sodium Chemical compound 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
Verfahren zur Darstellung eines Aminobenzolsulfonsäureamid-Abkömmlings. Im Patent Nr. 197718 ist angegeben, dass N - Alkylsulfonsäure-, N - Alkylsulfinsäure- und N'- Alkylcarbonsäureverbindungen von Aminobenzolsulfonsäureamiden;
die entweder eine Sulfonsäureamidgruppe in p - Stellung zur Aminogruppe oder mehrere Sulfonsäüre- amidgruppen im Ring enthalten, therapeu tisch wertvolle, gegen bakterielle Infektion nen wirksame Produkte darstellen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Zierstellung eines Amino- benzolsulfonsäureamidabkömmlings, welches dadurch gekennzeichnet ist, dass man 4- Aminobenzolsulfonsäuredimethylamid durch Erhitzen mit einer wässerigen Lösung von Natriumcyanid und Formaldehyd zum 4-sül- fonsäuredimethylamid - phenylaminoessigsau- ren Natrium umsetzt. Der Reaktionsmischung wird zweckmässig noch Alkohol als Lösungs mittel zugegeben.
Das so erhaltene Natrium salz ist ein in Wasser lösliches farbloses Pulver: Es soll therapeutische Anwendung finden.
<I>Beispiel:</I> Zu einer konzentrierten wässerigen Lö sung von 12,5g Natriumcyanid werden un ter guter Kühlung 25 g 30%ige Formal dehydlösung zugetropft, dann 50 g 4-Amino- benzolsulfonsäuedimethylamid vom Schmelz punkt<B>168'</B> und 250 cm' Alkohol zugegeben und einige Stunden im Wasserbad gekocht, wobei man Ammoniakentwicklung beobach tet.
Dann wird der Alkohol abdestilliert. Das im Rückstand enthaltene 4-sulfonsäuredime- thylamid - phenylaminoessigsaure Natrium wird zur weiteren Reinigung noch zweck mässig in Wasser aufgenommen, die Lösung mit Tierkohle filtriert und das Filtrat mit Salzsäure angesäuert.
Die ausgefällte 4- Sulfonsäuredimethylamid- phenylaminoessig- säure (aus Methylalkohol umkristallisiert farblose Kristalle vom Schmelzpunkt 1.87 ) wird durch die äquivalente Menge Natron lauge in das N atriumsalz zurückverwandelt.
Process for the preparation of an aminobenzenesulfonic acid amide derivative. Patent No. 197718 states that N-alkylsulfonic acid, N-alkylsulfinic acid, and N'-alkylcarboxylic acid compounds of aminobenzenesulfonic acid amides;
which contain either a sulfonic acid amide group in the p position to the amino group or several sulfonic acid amide groups in the ring, represent therapeutically valuable products which are effective against bacterial infection.
The subject of the present patent is a process for the decoration of an aminobenzenesulfonic acid amide derivative, which is characterized in that 4-aminobenzenesulfonic acid dimethylamide is converted to sodium 4-sulfonic acid dimethyl amide - phenylaminoacetic acid by heating with an aqueous solution of sodium cyanide and formaldehyde. The reaction mixture is expediently also added alcohol as a solvent.
The sodium salt obtained in this way is a colorless powder that is soluble in water: it is said to be of therapeutic use.
<I> Example: </I> To a concentrated aqueous solution of 12.5 g of sodium cyanide, 25 g of 30% formaldehyde solution are added dropwise under good cooling, then 50 g of 4-aminobenzenesulfonic acid dimethylamide with a melting point of <B> 168 ' </B> and 250 cm 'of alcohol were added and the mixture was boiled in a water bath for a few hours, during which ammonia development was observed.
Then the alcohol is distilled off. The 4-sulfonic acid dimethylamide-phenylaminoacetic acid sodium contained in the residue is conveniently taken up in water for further purification, the solution is filtered with animal charcoal and the filtrate is acidified with hydrochloric acid.
The precipitated 4-sulfonic acid dimethylamidephenylaminoacetic acid (colorless crystals with a melting point of 1.87 recrystallized from methyl alcohol) is converted back into the sodium salt by the equivalent amount of sodium hydroxide solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE203065X | 1936-02-06 | ||
| CH197718T | 1937-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203065A true CH203065A (en) | 1939-02-15 |
Family
ID=25723041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203065D CH203065A (en) | 1936-02-06 | 1937-01-13 | Process for the preparation of an aminobenzenesulfonic acid amide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203065A (en) |
-
1937
- 1937-01-13 CH CH203065D patent/CH203065A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH203065A (en) | Process for the preparation of an aminobenzenesulfonic acid amide derivative. | |
| DE503031C (en) | Process for the preparation of the N-oxyethyl derivatives of core substitution products of -amino-1-oxybenzene | |
| DE199148C (en) | ||
| AT126160B (en) | Process for the preparation of aminoketo alcohols. | |
| AT146504B (en) | Process for the preparation of amides of pyrazine monocarboxylic acid. | |
| DE414261C (en) | Process for the preparation of ar-tetrahydro-ª ‰ -naphthol derivatives | |
| CH213388A (en) | Process for producing a thiazolium compound. | |
| DE488682C (en) | Process for the preparation of the N-oxyaethyl derivatives of 2-amino-1-oxybenzene | |
| CH220971A (en) | Process for the preparation of a condensation product. | |
| AT200154B (en) | Process for the production of citrulline | |
| CH220970A (en) | Process for the preparation of a condensation product. | |
| CH213384A (en) | Process for producing a thiazolium compound. | |
| CH206118A (en) | Process for the preparation of a thiazolium compound. | |
| CH314215A (en) | Process for the preparation of a quaternary ammonium salt | |
| CH204380A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH213387A (en) | Process for producing a thiazolium compound. | |
| CH276621A (en) | Process for the preparation of p-amino-salicylic acid-n-butylmide. | |
| CH193771A (en) | Process for the preparation of phenyl-amino-acetic acid-4-sulfonic acid-diamide. | |
| CH127782A (en) | Process for the preparation of p-oxymethylaminoacetophenone. | |
| CH200907A (en) | Process for the preparation of a nitrogen-containing aromatic aldehyde. | |
| CH213385A (en) | Process for producing a thiazolium compound. | |
| CH186667A (en) | Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate. | |
| CH242291A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH234253A (en) | Process for the preparation of a sulfonamide compound. | |
| CH120257A (en) | Process for the preparation of a new oxynaphthalene carboxylic acid. |