CH240221A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents
Process for the preparation of a new benzenesulfonamide derivative.Info
- Publication number
- CH240221A CH240221A CH240221DA CH240221A CH 240221 A CH240221 A CH 240221A CH 240221D A CH240221D A CH 240221DA CH 240221 A CH240221 A CH 240221A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydroquinazoline
- preparation
- new
- benzenesulfonamido
- amino
- 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 3
- 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
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- IPDKSGJFMBIZJI-UHFFFAOYSA-N 4-amino-n-(5,6,7,8-tetrahydroquinazolin-2-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=C(CCCC2)C2=N1 IPDKSGJFMBIZJI-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MTGJFBFNVKFUHG-UHFFFAOYSA-N O=S(C1=CC=CC=C1)(NC1=NC(CCCC2)=C2C=N1)=O Chemical compound O=S(C1=CC=CC=C1)(NC1=NC(CCCC2)=C2C=N1)=O MTGJFBFNVKFUHG-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 p-amino-benzenesulfonamido Chemical group 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 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
- 125000001424 substituent group Chemical group 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
- AIOOBFYEASSZHV-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazolin-2-amine Chemical compound C1CCCC2=NC(N)=NC=C21 AIOOBFYEASSZHV-UHFFFAOYSA-N 0.000 description 1
- SMSHIXOEBWOYJS-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazoline Chemical class C1=NC=C2CCCCC2=N1 SMSHIXOEBWOYJS-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
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 238000010992 reflux Methods 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 Benzolsulfonamidderivates, das dadurch ge kennzeichnet ist, dass man ein 2-Benzo,1sul- fonamido-5;6,7,8-tetrahydrochinazo-Iin, das in p-Stellung einen durch Hydrolyse in die Aminobgruppe überführbaren Substituenten aufweist, mit einem hydrolysierenden Mittel behandelt.
Das so erhaltene 2-(p-Amino-benzolsul- fonamido)-5,6,7,8-tetrahydroehinazolin istein kristallines Pulver vom F.'23'9 . Die neue Verbindung soll als Arzneimittel sowie als Zwischenprodukt Verwendung finden.
Das 2-Benzolsulfonamido-5,6"7,8-tetra- hydrochina.zolin, das in p@Stellung zur Sul- fonamidgruppe einen durch Hydrolyse in die Aminogruppe überführbaren Substituenten enthält, kann auf verschiedene Art und Weise gewonnen werden.
Besonders geeignet ist die Umsetzung der entsprechenden reak tionsfähigen Benzolsulfonsäurederivate, ins besondere der Benzolsulfonsäurehalogenide rnit 5,6,7,8 -Tetrahydrochinazolinverbindun- gen, die in 2-Stellung eine Gruppe enthalten, die mit dem Benzolsulfonsäurederivat ein 2-Benzolsulfonamido- 5:
,6,7,8 -tetrahydrochin- azolin zu bilden vermag, wie mit 2-Amino- 5,6,7,8-tetrahydroohinazolin. Man kann auch entsprechende Sulfonamide der Formel R . SOZNHY, in der Y einen bei der nachfolgenden Reak tion sich abspaltenden Rest bedeutet, mit 2'-Halogen-5,6,7,8-tetrahydrochinazolinen um setzen. Auch können andere dem Fach mann geläufige Herstellungsmethoden be nutzt werden.
Beispiel 34,6 g 2 - (p - Acetylamino - benzolsulf on- amido) -<B>5"6"7,8</B> - tetrahydrochinazolin, das durch Kondensation von p-Acetylaminoben- zolsulfochlorid mit 2,-Amino-5,6,7,8-tetra- hydrochinazälin erhalten wurde, werden mit einer Lösung von 12g Natriumhydrogyd in <B>150</B> cm' Wasser zwei Stunden unter Rück fluss gekocht.
Die Lösung wird gegebenen falls unter Zusatz von. Tierkohle filtriert und mit konz. Salzsäure neutralisiert. Dabei fällt das 2 - (p- Amino-benzolsulfonamido) - 5,6,7,8 tetrahydrochinazolin als kristallines Pulver aus. Die Verbindung kann durch Umkristal lisation aus Eisessig gereinigt werden. Schmelzpunkt 239 .
Beispiel <I>2:</I> 37,6 g 2- (p-Carbäthoxyamino-benzolsul- fonamido)-5,6,7,8-tetrahydrochinazolin, das durch Kondensation von p-Carbäthoxya.mino- benzolsulfochlorid mit 2-Amino-5,6,7,8-tetra- hydrochinazolin erhalten wurde, werden wie im Beispiel 1 mit einer wässerigen Lösung von 12 g Natriumhydroxyd in 150 cm' Was ser unter Kochen verseift.
Nach der Neutra lisation mit Salzsäure wird das gebildete 2 - (p -A@minobenzolsulfonamido)-5,6,7,8-tetra- hydrochinazolin isoliert und gegebenenfalls durch Umkristallisieren gereinigt. Schmelz punkt 239 .
Die Hydrolyse kann auch mit andern alkalischen Mitteln, beispielsweise Erdalkali- hydroxyden, wie Calciumhydroxyd, oder mit sauren :Mitteln, z. B. Salzsäure in Gegenwart von Wasser oder organischen Lösungsmitteln, \vie Alkohol, durchgeführt werden.
Das gebildete p-Aminobenzolsulfonamid- derivat lässt sich ferner in Form seiner Salze, z. B. des Natriums oder des Calciums, i6o- lieren.
Process for the preparation of a new benzenesulfonamide derivative. The present patent relates to a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that a 2-benzo, 1sulfonamido-5; 6,7,8-tetrahydroquinazo-Iin, which is in the p-position by hydrolysis Has in the amino group convertible substituents, treated with a hydrolyzing agent.
The 2- (p-amino-benzenesulfonamido) -5,6,7,8-tetrahydroehinazoline obtained in this way is a crystalline powder with a melting point of 23.9. The new compound is to be used as a drug and as an intermediate product.
The 2-benzenesulfonamido-5,6 "7,8-tetrahydrochina.zoline, which contains a substituent which can be converted into the amino group by hydrolysis in the p @ position relative 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 5,6,7,8-tetrahydroquinazoline compounds which contain a group in the 2-position which, with the benzenesulfonic acid derivative, form a 2-benzenesulfonamido-5:
, 6,7,8-tetrahydroquinazoline is able to form, as with 2-amino-5,6,7,8-tetrahydroohinazoline. Corresponding sulfonamides of the formula R can also be used. SOZNHY, in which Y denotes a radical which is split off in the subsequent reaction, with 2'-halogen-5,6,7,8-tetrahydroquinazolines. Other manufacturing methods familiar to the expert can also be used.
Example 34.6 g of 2 - (p - acetylamino - benzenesulfonamido) - <B> 5 "6" 7,8 </B> - tetrahydroquinazoline, which is obtained by condensation of p-acetylaminobenzenesulfochloride with 2, -amino- 5,6,7,8-tetrahydroquinazälin is boiled under reflux for two hours with a solution of 12 g sodium hydrogen in 150 cm water.
The solution is if necessary with the addition of. Animal charcoal filtered and with conc. Hydrochloric acid neutralized. The 2 - (p-amino-benzenesulfonamido) -5,6,7,8 tetrahydroquinazoline precipitates out as a crystalline powder. The compound can be purified by recrystallization from glacial acetic acid. Melting point 239.
Example <I> 2: </I> 37.6 g of 2- (p-carbethoxyamino-benzenesulfonamido) -5,6,7,8-tetrahydroquinazoline, which is obtained by condensation of p-carbethoxy.mino-benzenesulfonyl chloride with 2- Amino-5,6,7,8-tetrahydroquinazoline was obtained as in Example 1 with an aqueous solution of 12 g of sodium hydroxide in 150 cm 'of water saponified with boiling.
After neutralization with hydrochloric acid, the 2 - (p -A @ minobenzenesulfonamido) -5,6,7,8-tetrahydroquinazoline formed is isolated and, if necessary, purified by recrystallization. Melting point 239.
The hydrolysis can also be carried out with other alkaline agents, for example alkaline earth metal hydroxides such as calcium hydroxide, or with acidic agents, e.g. B. hydrochloric acid in the presence of water or organic solvents, such as alcohol, can be carried out.
The p-aminobenzenesulfonamide derivative formed can also be used in the form of its salts, e.g. B. sodium or calcium, olate.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE240221X | 1939-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240221A true CH240221A (en) | 1945-12-15 |
Family
ID=5905029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240221D CH240221A (en) | 1939-05-23 | 1941-05-23 | Process for the preparation of a new benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240221A (en) |
-
1941
- 1941-05-23 CH CH240221D patent/CH240221A/en unknown
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