CH264452A - Process for the preparation of an acylated p-amino-benzenesulfonamide. - Google Patents
Process for the preparation of an acylated p-amino-benzenesulfonamide.Info
- Publication number
- CH264452A CH264452A CH264452DA CH264452A CH 264452 A CH264452 A CH 264452A CH 264452D A CH264452D A CH 264452DA CH 264452 A CH264452 A CH 264452A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- benzenesulfonamide
- acylated
- preparation
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 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
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines acylierten p-Amino-benzolsulfonamids. CTegenstand vorliegenden Patentes ist. ein Verfahren zur Herstellung eines acylierten p-Amino-benzolsulfonamids. Das Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0007
mit einer Verbindung der Formel
EMI0001.0008
umsetzt, worin X und F zwei bei der Reak tion mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sieh abspal tende Reste bedeuten.
Die entstandene neue Verbindung, das p-Amino - benzolsulfon - N,- (a-- isopropoxy-pro- pionyl)-amid, bildet farblose Kristalle vom Schmelzpunkt 150 . Sie lässt sich mit anorga nischen oder organischen Basen in Salze über führen. Sie soll therapeutische Verwendung finden.
<I>Beispiel:</I> 67,4 Teile N,- (a-Brom-propionyl)-p-nitro- benzolsulfonamid (dargestellt aus a-Brom- propionylehlorid und p-Nitro-benzolsulfon- amid) werden in 600 Teilen Alkohol gelöst und mit Raney-Nickel und Platin-Kohle als Katalysator kalt bei Atmosphärendruck hy driert.
Nach Abfiltrieren des Katalysators wird der Alkohol abdestilliert. Der Rückstand ist N,-(a-Brom-propionyl)-sulfanilamid. 30,7 Teile. N,- (a-Brom-propionyl)-sulfanil- amid werden in eine Lösung von 10 Teilen Natrium in 150 Teilen Isopropylalkohol ein getragen. Die klare Lösung wird 15 Minuten zum Sieden erhitzt.
Nach Abkühlen wird vom ausgeschiedenen Natriumbromid abgesaugt, der Alkohol abdestilliert und der Rückstand mit Salzsäure kongoneutral gestellt, wobei das p-Amino-benzolsulfon-N,-(a-isopropoxi-- propionyl)-amid ausfällt. Es bildet, nach Um kristallisieren aus Alkohol, farblose Kristalle -vom Smp. 150 .
Statt des N,-(a-Brom-propionyl)-p-a.mino- benzolsulfonamids kann man auch die äqui valente --Henge der entsprechenden a-Chlor- oder a-Jodverbindung oder des N,- [a-(p- Tosy 1- oxy) -propionyl] -p-amino -benzolsulfon- amids verwenden.
An Stelle des Natriumisopropylats können auch andere Metallverbindungen des Iso- propylalkohols verwendet werden.
Der als Lösungsmittel verwendete Isopro- pylalkohol kann ganz oder teilweise durch ein inertes Lösungsmittel, wie Benzol, Toluol, Äther, ersetzt werden.
Process for the preparation of an acylated p-amino-benzenesulfonamide. C is the subject of this patent. a process for the preparation of an acylated p-amino-benzenesulfonamide. The process is characterized in that a compound of the formula
EMI0001.0007
with a compound of the formula
EMI0001.0008
converts, wherein X and F are two in the reac tion with the exception of an oxygen atom contained in one of them see splitting radicals.
The resulting new compound, p-amino-benzenesulfone-N, - (a-isopropoxy-propionyl) -amide, forms colorless crystals with a melting point of 150. It can be converted into salts with inorganic or organic bases. It should find therapeutic use.
<I> Example: </I> 67.4 parts of N, - (a-bromo-propionyl) -p-nitro-benzenesulfonamide (prepared from a-bromopropionyl chloride and p-nitro-benzenesulfonamide) are in 600 parts Dissolved alcohol and hydrated with Raney nickel and platinum carbon as a catalyst cold at atmospheric pressure.
After filtering off the catalyst, the alcohol is distilled off. The residue is N, - (a-bromo-propionyl) -sulfanilamide. 30.7 parts. N, - (a-Bromo-propionyl) -sulfanil- amide are carried into a solution of 10 parts of sodium in 150 parts of isopropyl alcohol. The clear solution is heated to boiling for 15 minutes.
After cooling, the precipitated sodium bromide is filtered off with suction, the alcohol is distilled off and the residue is rendered Congo-neutral with hydrochloric acid, the p-amino-benzenesulfone-N, - (a-isopropoxy-propionyl) -amide precipitating out. After recrystallizing from alcohol, it forms colorless crystals with a melting point of 150.
Instead of the N, - (a-bromo-propionyl) -pa.mino-benzenesulfonamide, the equivalent amount of the corresponding a-chlorine or a-iodine compound or the N, - [a- (p-tosy 1 - Use oxy) -propionyl] -p-amino -benzenesulfonamide.
Instead of sodium isopropylate, other metal compounds of isopropyl alcohol can also be used.
The isopropyl alcohol used as solvent can be completely or partially replaced by an inert solvent, such as benzene, toluene, ether.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH264452T | 1943-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264452A true CH264452A (en) | 1949-10-15 |
Family
ID=4475299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264452D CH264452A (en) | 1943-11-05 | 1943-11-05 | Process for the preparation of an acylated p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264452A (en) |
-
1943
- 1943-11-05 CH CH264452D patent/CH264452A/en unknown
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