CH242515A - Process for the preparation of an acylated sulfonamide. - Google Patents
Process for the preparation of an acylated sulfonamide.Info
- Publication number
- CH242515A CH242515A CH242515DA CH242515A CH 242515 A CH242515 A CH 242515A CH 242515D A CH242515D A CH 242515DA CH 242515 A CH242515 A CH 242515A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonamide
- dimethyl
- nitro
- benzoyl
- benzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940124530 sulfonamide Drugs 0.000 title description 4
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- -1 4-nitrobenzene - N - (3 ', 4'-dimethyl - benzoyl) - sulfonamide Chemical compound 0.000 claims description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-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
- 239000013078 crystal Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 3
- 230000007017 scission Effects 0.000 claims 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines aeylierten Sulfonamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung des bekannten 4 - Nitro - benzol - N - (3',4'-dimethyl-benzoyl)- sulfonamids. Das Verfahren ist dadurch ge kennzeichnet, daB man ein substituiertes 4-Nitro-benzolsulfonamid der Formel.
EMI0001.0009
in der R einen durch hydrolysierende Mittel abspaltbaren 1@est bedeutet, durch Verseifüng in 4-Nitro-benzol-N-(3',4'-diMethyl-lrenzoyl)- sulfonämid überführt.
Die Verbindung bildet farblose Kristalle vom Schmelzpunkt 192 . Sie soll als Arznei mittel Verwendung finden.
<I>Beispiel 1:</I> 10 Teile N-(4'-Nitro-benzolsuHonyl)-3,4- dimethyl-benzamidin vom Schmelzpunkt 193 und der Formel
EMI0001.0023
werden mit 100 Teilen konzentrierter Salz säure unter Rühren 2 Stunden auf -90-100 erhitzt. Nach dem Abkühlen verdünnt man mit-Wasser, nutscht ab und löst den Rück stand- in Sodalösung.
Man filtriert mit Tierkohle und stellt das Filtrat lackmussauer. Durch Absaugen und Umkristallisieren aus Alkohol erhält man in annähernd quantitativer Ausbeute das 4-Ni tro-benzol-N-(3',4'fdimethyl-benzoyl)-sulfon- amid
EMI0001.0038
<I>Beispiel 2:
</I> 20 Teile N-(4'-Nitro-benzolsulfonyl)-N'- phenyl-3,4-dimethyl-benzamidin (F. 200 , Zersetzung) von der Formel
EMI0002.0003
werden in einer Mischung von 100 Teilen Eisessig und 100 Teilen 15 %iger Salzsäure 2 Stunden zum Sieden erhitzt. Nach dem Erkalten wird- in Wasser gegossen und, wie in Beispiel 1 angegeben, aufgearbeitet.
In vorzüglicher Ausbeute erhält man das 4-Ni tro-benzol-N-(3',4'-dimethyl-benzoyl)-sulfon- amid vom F. 192 .
<I>" Beispiel 3:</I> 10 Teile N-(4'-Nitro-benzoIsulfonyl)-3,4- dimethyl-benziminoäthyläther (F. 320 , Zer setzung) von der Formel
EMI0002.0018
werden mit der zehnfachen Menge konzen trierter Salzsäure unter Rühren 3 Stariden auf . 90-100 erhitzt. Durch Aufarbeiten nach Beispiel 1 erhält man fast quantitativ das 4 - Nitro - benzol - N - (3',4'- dimethyl - benzoyl)-sulfonamid vom Schmelzpunkt 192 .
Process for the preparation of an alkylated sulfonamide. The present patent relates to a process for the preparation of the known 4 - nitro - benzene - N - (3 ', 4'-dimethyl-benzoyl) - sulfonamide. The process is characterized in that a substituted 4-nitrobenzenesulfonamide of the formula
EMI0001.0009
in which R denotes a 1 @ est which can be split off by hydrolyzing agents, converted by saponification into 4-nitro-benzene-N- (3 ', 4'-dimethyl-lrenzoyl) -sulfonamide.
The compound forms colorless crystals with a melting point of 192. It should be used as a medicinal product.
<I> Example 1: </I> 10 parts of N- (4'-nitro-benzenesuHonyl) -3,4-dimethyl-benzamidine with a melting point of 193 and the formula
EMI0001.0023
are heated with 100 parts of concentrated hydrochloric acid with stirring to -90-100 for 2 hours. After cooling, it is diluted with water, suction filtered and the residue is dissolved in soda solution.
It is filtered with animal charcoal and the filtrate is put into lackmussauer. By filtering off with suction and recrystallizing from alcohol, 4-nitro-benzene-N- (3 ', 4'fdimethyl-benzoyl) -sulfonamide is obtained in an approximately quantitative yield
EMI0001.0038
<I> Example 2:
</I> 20 parts of N- (4'-nitro-benzenesulfonyl) -N'-phenyl-3,4-dimethyl-benzamidine (M.p. 200, decomposition) of the formula
EMI0002.0003
are heated to boiling for 2 hours in a mixture of 100 parts of glacial acetic acid and 100 parts of 15% hydrochloric acid. After cooling, it is poured into water and, as indicated in Example 1, worked up.
The 4-nitro-benzene-N- (3 ', 4'-dimethyl-benzoyl) -sulphonamide with a melting point of 192 is obtained in excellent yield.
<I> "Example 3: </I> 10 parts of N- (4'-nitro-benzo-sulfonyl) -3,4-dimethyl-benziminoethyl ether (F. 320, decomposition) of the formula
EMI0002.0018
are with ten times the amount of concentrated hydrochloric acid with stirring on 3 Stariden. 90-100 heated. By working up according to Example 1, 4 - nitro - benzene - N - (3 ', 4'-dimethyl - benzoyl) sulfonamide with a melting point of 192 is obtained almost quantitatively.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242515T | 1943-05-21 | ||
| CH239850T | 1944-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242515A true CH242515A (en) | 1946-05-15 |
Family
ID=25728444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242515D CH242515A (en) | 1943-05-21 | 1943-05-21 | Process for the preparation of an acylated sulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH242515A (en) |
-
1943
- 1943-05-21 CH CH242515D patent/CH242515A/en unknown
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