CH250001A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents
Process for the preparation of a benzenesulfonamide derivative.Info
- Publication number
- CH250001A CH250001A CH250001DA CH250001A CH 250001 A CH250001 A CH 250001A CH 250001D A CH250001D A CH 250001DA CH 250001 A CH250001 A CH 250001A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- preparation
- benzenesulfonamido
- benzenesulfonamide derivative
- phtalazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WTHAUEICOFPESL-UHFFFAOYSA-N 4-amino-n-(4-methylphthalazin-1-yl)benzenesulfonamide Chemical compound C12=CC=CC=C2C(C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 WTHAUEICOFPESL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- -1 p-nitro-benzenesulfonamido Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- AQHQGNYQXCIWDG-UHFFFAOYSA-N 4-methylphthalazin-1-amine Chemical compound C1=CC=C2C(C)=NN=C(N)C2=C1 AQHQGNYQXCIWDG-UHFFFAOYSA-N 0.000 description 1
- YBZDHMOYLCOTAW-UHFFFAOYSA-N CC(C1=CC=CC=C11)=NN=C1NS(C1=CC=CC=C1)(=O)=O Chemical compound CC(C1=CC=CC=C11)=NN=C1NS(C1=CC=CC=C1)(=O)=O YBZDHMOYLCOTAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- KKHJTSPUUIRIOP-UHFFFAOYSA-J tetrachlorostannane;hydrate Chemical compound O.Cl[Sn](Cl)(Cl)Cl KKHJTSPUUIRIOP-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines Benzolsulfonamidderivates. Gegenstand des, vorliegenden Patentes ist ein Verfahren zur Herstellung des im schweiz. Patent Nr.242491 beschriebenen Benzolsulfonamidderivates, das dadurch ge kennzeichnet ist, daB man ein 1-Benzols ulfon- amido-4-methyl-phtalazin,
das im Benzolring in p-Stellung zur Sulfonamidgruppe einen durch Reduktion in die Aminogruppe über führbaren Substituenten aufweist, mit einem reduzierenden Mittel behandelt.
Das 1 - Benzolsulfonamido - 4 - methyl- phtalazin, das im Benzolring in p-Stellung zur Sulfonamidgruppe einen durch Reduk tion in die Aminogruppe überführbaren Substituenten enthält, kann auf verschiedene Art und Weise gewonnen werden.
Besonders geeignet ist die Umsetzung der entsprechen den reaktionsfähigen Benzolsulfonsäure- derivate, insbesondere der Benzoleulfonsäure- lialogerride, mit 4-Methyl-phtalazinverbirr- dungen, die in 1-Stellung eine Gruppe ent- balten, die mit dem Benzolsulfonsäurederivat ein l.-Benzolsulfonamido-4-methyl-phtalazin nr bilden vermag,
insbesondere mit1-Amino-4- methyl-phtalazin. Man l.:ann aberauch entspre chende Sulfonamide der Formel RSO.@NHY, in der Y einen bei der Reaktion sich abspal tenden Rest bedeutet, mit 1-Halogen-4- methyl-phtala.zinen umsetzen oder andere dem Fachmann geläufige Herstellungsmetho den benutzen.
<I>Beispiel 1:</I> 28,4 g 1-(p-Nitro-benzolsulfonamido)-4- methyl-phta.lazin, das durch Kondensation von p-Nitro-benzolsulfochlorid mit 1-Amino- 4-methyl-phtalazin erhalten wurde,
werden in der 50fachen Menge absolutem Alkohol gelöst und mit 10 Gewichtsprozenten eines Nickel-Katalysators im Rührautoklaven mit Wasserstoff unter einem Überdruck von 50 Atm bis zur Beendigung der Wasserstoff aufnahme bei 100-120 behandelt-.
Nach dem Erkalten wird vom Katalysator abfil- triert und die alkoholische. Lösung einge,- dampft. Dabei fällt das gebildete 1- (p Amino- benzolsulfonamido)-4-methyl-phtalazin kri- stallin an. Die Verbindung kann zur Reini gung aus verdünntem Alkohol, gegebenen falls unter Zusatz von Tierkohle, umkristal lisiert werden. Schmelzpunkt 261 .
<I>Beispiel 2:</I> 28,4 g 1-(p-Nitro-benzolsulfonamido)-4- methyl-phta.lazin werden mittels 67,7 g Zinn- chlorür (Hydrat) und der doppelten Ge wichtsmenge konzentrierter Salzsäure redu ziert. Das gebildete 1-(p-Amino-benzolsulfon- amido)-4-methyl-phtalazin wird isoliert und gegebenenfalls umkristallisiert. Schmelz punkt 261 .
Das entstandene p-Amino-benzolsulfon- amidderivat lässt sich auch in Form seiner Salze, z. B. des Natriums oder des Kalziums, isolieren.
Process for the preparation of a benzenesulfonamide derivative. The subject of the present patent is a process for the production of the in Switzerland. Patent No. 242491 described benzenesulfonamide derivative, which is characterized in that a 1-benzenesulfonamido-4-methyl-phthalazine,
which has a substituent which can be converted into the amino group by reduction in the p-position to the sulfonamide group in the benzene ring, treated with a reducing agent.
The 1-benzenesulfonamido-4-methyl-phtalazine, which in the benzene ring in the p-position to the sulfonamide group contains a substituent which can be converted into the amino group by reduction, can be obtained in various ways.
The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid lialogerride, with 4-methyl-phtalazine compounds which contain a group in the 1-position which, together with the benzenesulfonic acid derivative, forms an 1.-benzenesulfonamido-4 -methyl-phtalazin nr can form,
especially with 1-amino-4-methyl-phthalazine. One l.:ann but also corresponding sulfonamides of the formula RSO. @ NHY, in which Y denotes a radical which splits off in the reaction, with 1-halo-4-methyl-phtala.zinen or use other manufacturing methods familiar to those skilled in the art .
<I> Example 1: </I> 28.4 g of 1- (p-nitro-benzenesulfonamido) -4- methyl-phtalazin, which is obtained by condensation of p-nitro-benzenesulfochloride with 1-amino-4-methyl- phtalazine was received,
are dissolved in 50 times the amount of absolute alcohol and treated with 10 percent by weight of a nickel catalyst in a stirred autoclave with hydrogen under an overpressure of 50 atm until the end of the hydrogen absorption at 100-120.
After cooling, the catalyst is filtered off and the alcoholic. Solution concentrated - evaporated. The 1- (p-aminobenzenesulfonamido) -4-methyl-phthalazine that is formed is crystalline. The compound can be recrystallized for cleaning from dilute alcohol, if necessary with the addition of animal charcoal. Melting point 261.
<I> Example 2: </I> 28.4 g of 1- (p-nitro-benzenesulfonamido) -4-methyl-phtalazine are converted into concentrated hydrochloric acid using 67.7 g of tin chloride (hydrate) and twice the amount by weight reduced. The 1- (p-amino-benzenesulfonamido) -4-methyl-phthalazine formed is isolated and, if necessary, recrystallized. Melting point 261.
The resulting p-amino-benzenesulfonamide derivative can also be used in the form of its salts, e.g. B. of sodium or calcium, isolate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE250001X | 1939-05-23 | ||
| CH244345T | 1941-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH250001A true CH250001A (en) | 1947-07-31 |
Family
ID=25728929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH250001D CH250001A (en) | 1939-05-23 | 1941-05-23 | Process for the preparation of a benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH250001A (en) |
-
1941
- 1941-05-23 CH CH250001D patent/CH250001A/en unknown
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