CH242487A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents
Process for the preparation of a new benzenesulfonamide derivative.Info
- Publication number
- CH242487A CH242487A CH242487DA CH242487A CH 242487 A CH242487 A CH 242487A CH 242487D A CH242487D A CH 242487DA CH 242487 A CH242487 A CH 242487A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- preparation
- benzenesulfonamido
- amino
- tetrahydroquinazoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 3
- UBPAMEHBOSJLJV-UHFFFAOYSA-N CC1=NC(NS(C(C=C2)=CC=C2N)(=O)=O)=NC2=C1CCCC2 Chemical compound CC1=NC(NS(C(C=C2)=CC=C2N)(=O)=O)=NC2=C1CCCC2 UBPAMEHBOSJLJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- TUYAPRVQZNITOO-UHFFFAOYSA-N CC1=NC(NS(C2=CC=CC=C2)(=O)=O)=NC2=C1CCCC2 Chemical compound CC1=NC(NS(C2=CC=CC=C2)(=O)=O)=NC2=C1CCCC2 TUYAPRVQZNITOO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 benzenesulfonic acid halides Chemical class 0.000 description 4
- SNRKDMNNDAVJSI-UHFFFAOYSA-N 4-methyl-5,6,7,8-tetrahydroquinazolin-2-amine Chemical compound C1CCCC2=C1N=C(N)N=C2C SNRKDMNNDAVJSI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- BEMZWSZJDPWKBU-UHFFFAOYSA-N 4-methyl-5,6,7,8-tetrahydroquinazoline Chemical class C1CCCC2=C1N=CN=C2C BEMZWSZJDPWKBU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- OGGCTXBAHQPJCB-UHFFFAOYSA-N O=S(=O)N=CC1=CC=CC=C1 Chemical class O=S(=O)N=CC1=CC=CC=C1 OGGCTXBAHQPJCB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Benzolsulfonamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Benzalsulfonamidderivates, das dadurch ge kennzeichnet ist, dass man ein 2-Benzol- sulfonamido - 4 - methyl - 5,6,7,8 - tetrahydro - chinazolin,
das in p-Stellung einen durch Hydrolysie in die Aminogruppe überführ baren Substituenten aufweist, mit einem hydrolysierenden Mittel behandelt.
Das so erhaltene 2 - (p - Amino - benzol- sulfonamido) -4 - methyl- 5,6,7,8 - tetrahydro- chinazolin ist ein kristallines Pulver vom F. 228 . Die neue Verbindung soll als Arznei mittel sowie als Zwischenprodukt Verwen dung finden.
Das 2-Benzolsulfonamido-4-methyl-5,6,7,8- tetrahydrochina.zolin, das in p-Stellung zur Sulfonamidgruppe einen durch Hydrolyse in die Aminogruppe überführbaren Substituen- ten enthält, kann auf verschiedene Art und Weise gewonnen werden.
Besonders geeignet ist die Umsetzung der entsprechenden reak tionsfähigen Benzolsulfonsäurederivate, ins- besondere der Benzolsulfonsäurehalogenide, mit 4-Methyl-5,6,7,8-tetrahydrochinazolin- verbindungen, die in 2-Stellung eine Gruppe enthalten, die mit dem Benzolsulfonsäure- derivat ein 2-Benzolsulfonamido-4-methyl- 5,6,7,8-tetrahydrochinazolin zu bilden ver mag, wie mit 2-Amino-4-methyl-5,6,7,
8- tetrahydrochinazolin. Man kann auch ent sprechende Sulfonamide der Formel R . SO,NHY, in der Y einen bei der nachfolgenden Reak- tion sich abspaltenden Rest bedeutet, mit 2 - Halogen - 4 - methyl-5,6,7,8-tetrahydrochin- azolinen umsetzen. Auch können andere dem Fachmann geläufige Herstellungsmethoden benutzt werden.
<I>Beispiel 1:</I> 36 g 2 - (p - Acetylamino - benzolsulfon- amido) - 4 - methyl - 5,6,7,8 - tetrahydrocbin - azolin, das durch Kondensation von p-Acetyl- amino-benzolsulfochlorid mit 2-Amino-4- methyl-5,6,7,8-tetrahydrochinazolin erhalten wurde, werden mit einer Lösung von 12 g Natriumhydrogyd in<B>150</B> cm' Wasser zwei Stundenunter RüAflul3, gekocht.
Die Lösung wird gegebenenfalls unter Zusatz von Tier kohle filtriert und mit konzentrierter Salz säure neutralisiert. Dabei fällt das 2-(p- Amino - benzolsulf onamido) -4-methyl-5, 6, 7, 8 tetrahydrochinazolin als kristallines Pulver aus. Die Verbindung kann durch Umkristal- lisation aus 65%iger Essigsäure gereinigt werden. Schmelzpunkt 228 .
<I>Beispiel 2:</I> 39 g 2-(p-Carbäthogyamino-benzolsulfon- amido) - 4 - methyl - 5,6,7,8 - tetrahydrochin - azolin, das durch Kondensation von p-Carb- äthogyamino-benzolsulfochlorid mit 2-Amino- 4-methyl-5,6,7,8-tetrahydrochinazolin erhal ten wurde,
werden wie im Beispiel 1 mit einer wässrigen Lösung von 12 g Natrium- hydrogyd in 150 cm' Wasser unter Kochen verseift. Nach der Neutralisation mit Salz säure wird das gebildete 2-(p-Amino-benzol- sulfonamido) - 4 - methyl - 5,6,7,8 - tetrahydro- chinazolin isoliert und gegebenenfalls durch s Umkristallisieren gereinigt. Schmelzpunkt 228 .
Die Hydrolyse kann auch mit andern alkalischen Mitteln, beispielsweise Erdalkali hydroayden, wie Calciumhydrogyd, oder mit sauren Mitteln, z. B. Salzsäure, in Gegenwart von Wasser oder organischen Lösungsmitteln, wie Alkohol, durchgeführt werden.
Das gebildete p-Amino-benzolsulfonamid- derivat lässt sich ferner in Form seiner Salze, z. B. des Natriums oder des Calciums, isolieren.
Process for the preparation of a new benzenesulfonamide derivative. The subject of the present patent is a process for the preparation of a new benzalsulfonamide derivative, which is characterized in that a 2-benzene sulfonamido - 4 - methyl - 5,6,7,8 - tetrahydro - quinazoline,
which has a substituent which can be converted into the amino group by hydrolysis in the p-position, treated with a hydrolyzing agent.
The 2 - (p - amino - benzenesulfonamido) -4 - methyl - 5,6,7,8 - tetrahydroquinazoline obtained in this way is a crystalline powder with a melting point of 228. The new compound is to be used as a medicinal product and as an intermediate product.
The 2-benzenesulfonamido-4-methyl-5,6,7,8-tetrahydroquina.zoline, which contains a substituent which can be converted into the amino group by hydrolysis in the p-position to the sulfonamide group, can be obtained in various ways.
The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with 4-methyl-5,6,7,8-tetrahydroquinazoline compounds which contain a group in the 2-position which is associated with the benzenesulfonic acid derivative is particularly suitable 2-benzenesulfonamido-4-methyl-5,6,7,8-tetrahydroquinazoline is able to form, as with 2-amino-4-methyl-5,6,7,
8-tetrahydroquinazoline. You can also ent speaking sulfonamides of the formula R. SO, NHY, in which Y denotes a radical which is split off in the subsequent reaction, react with 2 - halogen - 4 - methyl-5,6,7,8-tetrahydroquinazolines. Other production methods familiar to the person skilled in the art can also be used.
<I> Example 1: </I> 36 g of 2 - (p - acetylamino - benzenesulfonamido) - 4 - methyl - 5,6,7,8 - tetrahydrocbin - azoline, which is produced by condensation of p-acetylamino- benzene sulfochloride was obtained with 2-amino-4-methyl-5,6,7,8-tetrahydroquinazoline, are boiled with a solution of 12 g of sodium hydrogen in <B> 150 </B> cm 'of water for two hours under RüAflul3.
The solution is filtered with the addition of animal charcoal and neutralized with concentrated hydrochloric acid. The 2- (p-amino-benzenesulfonamido) -4-methyl-5, 6, 7, 8 tetrahydroquinazoline precipitates out as a crystalline powder. The compound can be purified by recrystallization from 65% acetic acid. Melting point 228.
<I> Example 2: </I> 39 g of 2- (p-carbethogyamino-benzenesulfonamido) - 4 - methyl - 5,6,7,8 - tetrahydroquin - azoline, which is produced by condensation of p-carb - ethogyamino- benzenesulfochloride with 2-amino-4-methyl-5,6,7,8-tetrahydroquinazoline was obtained,
are saponified as in Example 1 with an aqueous solution of 12 g of sodium hydroxide in 150 cm 'of water while boiling. After neutralization with hydrochloric acid, the 2- (p-amino-benzenesulfonamido) -4-methyl-5,6,7,8-tetrahydroquinazoline formed is isolated and, if necessary, purified by recrystallization. Melting point 228.
The hydrolysis can also hydroayden with other alkaline agents, such as alkaline earth metal, such as calcium hydrogen, or with acidic agents, e.g. B. hydrochloric acid, in the presence of water or organic solvents such as alcohol.
The p-amino-benzenesulfonamide derivative formed 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 |
|---|---|---|---|
| DE242487X | 1939-05-23 | ||
| CH240221T | 1945-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242487A true CH242487A (en) | 1946-05-15 |
Family
ID=25728485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242487D CH242487A (en) | 1939-05-23 | 1941-05-23 | Process for the preparation of a new benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH242487A (en) |
-
1941
- 1941-05-23 CH CH242487D patent/CH242487A/en unknown
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