CH222964A - Process for the preparation of 4-amino-benzenesulfonamido-benzene-4'-sulfonacetylamide. - Google Patents
Process for the preparation of 4-amino-benzenesulfonamido-benzene-4'-sulfonacetylamide.Info
- Publication number
- CH222964A CH222964A CH222964DA CH222964A CH 222964 A CH222964 A CH 222964A CH 222964D A CH222964D A CH 222964DA CH 222964 A CH222964 A CH 222964A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzene
- amino
- benzenesulfonamido
- sulfonacetylamide
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 239000012345 acetylating agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- YBUXKQSCKVQATK-UHFFFAOYSA-N 4-amino-n-phenylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1 YBUXKQSCKVQATK-UHFFFAOYSA-N 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- -1 diacetyl compound Chemical class 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4-Amino-benzolsulfonamido-benzol-4'-sulfonacetylamid. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 4-Aminobenzolsulfonamido-benzol-4'-sulfon- acetylamid, das dadurch gekennzeichnet ist, dass man ein BenzoIsulfonamido-benzol-4'- sulfonacetamid, das in 4-Stellung eine durch Hydrolyse in die Aminogruppe überführbare Gruppe enthält, mit einem hydrolysierenden Mittel behandelt.
Solehe in die Amino- gruppo überführbaren Gruppen sind z. B. die Acylamina-, Alkylamino-, Arylamino-, Aralkylamino- und die Azomethin-Gruppe, der Isoeyansäureesterrest (entstanden durch Ho.fmannschen Abbau aus Säureamiden),
der Alkylearbaminsäurerest (entstanden durch Curtius' Abbau aus Säureamiden) und dergl., insbesondere sind verwendbar die Acetyl- amino-, Carbalkoxyamino-Verbindungün.
Die neue Verbindung soll als Arznei mittel oder als Zwischenprodukt zur Herstel lung von Arzneimitteln oder andern technisch wertvollen Verbindungen dienen.
Mit Vorteil verwendet man das 4-Acetyl- amino - benzolsulf onamido - Benzol - 4'- sulfon- acetylamid, das durch Behandlung von 4 - Amino-benzolsulf onamido-benzol-4'-sulf on- amid mit einem acetylierenden Mittel erhal ten wurde. <I>Beispiel:</I> 32,7 g 4-Amino-benzol-sulfonamiclo-ben- zol-4'-sulfonamid werden mit 200 cm' Essig säureanhydrid zum Sieden erhitzt.
Nachdem vollständige Lösung eingetreten ist, wird während einer weiteren Stunde gekocht und die Diacetylverbindung durch Eingiessen in Eiswasser ausgeschieden. Der Niederschlag wird durch Auflösen in Natriumearbonat- lösung und Ausfällen des Filtrates mit Essig säure ausgeschieden und gereinigt. Nach Um- kristallisieren aus verdünntem Alkohol bildet das Produkt farblose Nadeln, die bei 178 C schmelzen.
Es wird anschliessend durch par tielle Verseifung mit n-Natronlauge in das entsprechende Aminoprodukt vom Smp. 20,9 übergeführt.
Process for the preparation of 4-amino-benzenesulfonamido-benzene-4'-sulfonacetylamide. The present patent is a process for the preparation of 4-aminobenzenesulfonamido-benzene-4'-sulfonacetylamide, which is characterized in that a BenzoIsulfonamido-benzene-4'-sulfonacetamide, which is in the 4-position by hydrolysis in the Amino group convertible group contains, treated with a hydrolyzing agent.
Sole marriage in the amino group convertible groups are z. B. the acylamino, alkylamino, arylamino, aralkylamino and the azomethine group, the isoeyanic acid ester residue (formed by Ho.fmann's degradation from acid amides),
the alkylearbamic acid residue (created by Curtius' degradation from acid amides) and the like, especially the acetylamino, carbalkoxyamino compounds can be used.
The new compound is intended to be used as a medicinal product or as an intermediate product for the production of medicinal products or other technically valuable compounds.
It is advantageous to use the 4-acetylamino-benzenesulfonamido-benzene-4'-sulfonacetylamide, which was obtained by treating 4-amino-benzenesulfonamido-benzene-4'-sulfonamide with an acetylating agent . <I> Example: </I> 32.7 g of 4-amino-benzene-sulfonamiclo-benzene-4'-sulfonamide are heated to the boil with 200 cm of acetic anhydride.
After complete solution has occurred, the mixture is boiled for a further hour and the diacetyl compound is eliminated by pouring it into ice water. The precipitate is separated out and purified by dissolving it in sodium carbonate solution and precipitating the filtrate with acetic acid. After recrystallization from dilute alcohol, the product forms colorless needles that melt at 178 ° C.
It is then converted into the corresponding amino product with a melting point of 20.9 by partial saponification with sodium hydroxide solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE222964X | 1938-02-02 | ||
| CH213045T | 1939-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH222964A true CH222964A (en) | 1942-08-15 |
Family
ID=25725338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH222964D CH222964A (en) | 1938-02-02 | 1939-01-19 | Process for the preparation of 4-amino-benzenesulfonamido-benzene-4'-sulfonacetylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH222964A (en) |
-
1939
- 1939-01-19 CH CH222964D patent/CH222964A/en unknown
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