CH242520A - Process for the preparation of an acylated sulfonamide. - Google Patents
Process for the preparation of an acylated sulfonamide.Info
- Publication number
- CH242520A CH242520A CH242520DA CH242520A CH 242520 A CH242520 A CH 242520A CH 242520D A CH242520D A CH 242520DA CH 242520 A CH242520 A CH 242520A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dimethyl
- sulfonamide
- benzene
- preparation
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 150000003456 sulfonamides Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- -1 4-aminobenzenesulfonyl Chemical group 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- FDDDEECHVMSUSB-IDEBNGHGSA-N 4-aminobenzenesulfonamide Chemical class N[13C]1=[13CH][13CH]=[13C](S(N)(=O)=O)[13CH]=[13CH]1 FDDDEECHVMSUSB-IDEBNGHGSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- CWWYEELVMRNKHZ-UHFFFAOYSA-N 2,3-dimethylbut-2-enamide Chemical compound CC(C)=C(C)C(N)=O CWWYEELVMRNKHZ-UHFFFAOYSA-N 0.000 claims 1
- BMNDNPMJFWNHCX-UHFFFAOYSA-N 2-(2-iminoethoxy)ethanimine Chemical compound N=CCOCC=N BMNDNPMJFWNHCX-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N trimethyl acrylic acid Chemical compound CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines acylierten Sulfonamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines acylierten Sulfonamides. Das Verfahren ist dadurch gekennzeichnet, dass man ein substituiertes 4-Amino-benzolsulfonamid der Formel
EMI0001.0006
in der R einen durch hydrolysierende Mittel abspaltbaren Rest bedeutet, durch Verseifung in 4-Amino-benzol-N,-(.a,ss-dimethyl-cro- tonoyl)=sulfonamid überführt.
Die neue Verbindung bildet farblose Kri stalle vom Schmelzpunkt 160-162 . Sie soll als Arzneimittel Verwendung finden.
<I>Beispiel 1:</I> 10 Teile N-(4-Amino-benzolsulfonyl)-a,ss- dimethyl - crotonsäureamidin vom Schmelz punkt 168-169 und der Formel
EMI0001.0021
werden mit 200 Teilen 3,5 % iger Salzsäure 20 Stunden auf 90-100 erhitzt. Nach dem Erkalten wird sodaalkalisch gestellt, filtriert und mit Essigsäure angesäuert. Man erhält das 4-Amino-benzol-N,-(a,ss-dimethyl-cro- tonoyl)-sulfonamid. Aus Alkohol umkristal lisiert bildet es farblose Kristalle vom Schmelzpunkt 160-162 .
<I>Beispiel 2:</I> 10 Teile N-(4-Amino-benzolsulfonyl)-a,ss- dimethyl - crotonsäure - iminoäthyläther vom Schmelzpunkt 150-151 und der Formel
EMI0001.0033
werden mit 200 Teilen 3,5 joiger Salzsäure 4 Stunden auf 90-100 erhitzt. Nach dem Erkalten wird sodaalkalisch gestellt, filtriert und mit Essigsäure angesäuert.
Man erhält das 4-Amino-benzol-N,.-(a,ss-dimethyl-cro- tonoyl)-sulfonamid. Aus Alkohol umkristal lisiert bildet es farblose Kristalle vom Schmelzpunkt 160-162 .
Process for the preparation of an acylated sulfonamide. The present patent relates to a process for the preparation of an acylated sulfonamide. The process is characterized in that a substituted 4-amino-benzenesulfonamide of the formula
EMI0001.0006
in which R denotes a radical that can be split off by hydrolyzing agents, converted by saponification into 4-amino-benzene-N, - (. a, ss-dimethyl-cotonoyl) = sulfonamide.
The new compound forms colorless crystals with a melting point of 160-162. It should be used as a medicine.
<I> Example 1: </I> 10 parts of N- (4-amino-benzenesulfonyl) -a, ss- dimethyl-crotonic acid amidine with a melting point of 168-169 and the formula
EMI0001.0021
are heated to 90-100 for 20 hours with 200 parts of 3.5% hydrochloric acid. After cooling, it is made alkaline with soda, filtered and acidified with acetic acid. The 4-amino-benzene-N, - (α, ß-dimethyl-cotonoyl) -sulfonamide is obtained. Recrystallized from alcohol, it forms colorless crystals with a melting point of 160-162.
<I> Example 2: </I> 10 parts of N- (4-amino-benzenesulfonyl) -a, ss- dimethyl-crotonic acid-iminoethyl ether with a melting point of 150-151 and the formula
EMI0001.0033
are heated to 90-100 for 4 hours with 200 parts of 3.5 hydrochloric acid. After cooling, it is made alkaline with soda, filtered and acidified with acetic acid.
The 4-amino-benzene-N, .- (a, ss-dimethyl-cotonoyl) -sulfonamide is obtained. Recrystallized from alcohol, it forms colorless crystals with a melting point of 160-162.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242520T | 1943-05-21 | ||
| CH239850T | 1944-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242520A true CH242520A (en) | 1946-05-15 |
Family
ID=25728449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242520D CH242520A (en) | 1943-05-21 | 1943-05-21 | Process for the preparation of an acylated sulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH242520A (en) |
-
1943
- 1943-05-21 CH CH242520D patent/CH242520A/en unknown
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