CH239157A - Process for the production of a new benzene sulfonamide derivative. - Google Patents
Process for the production of a new benzene sulfonamide derivative.Info
- Publication number
- CH239157A CH239157A CH239157DA CH239157A CH 239157 A CH239157 A CH 239157A CH 239157D A CH239157D A CH 239157DA CH 239157 A CH239157 A CH 239157A
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyl
- pyrimidine
- amino
- production
- benzenesulfonamido
- Prior art date
Links
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 p-Amino-benzenesulfonamido Chemical group 0.000 claims description 7
- 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
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YKVWHWNSINXNPF-UHFFFAOYSA-N 5-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)C1=CN=C(N)N=C1 YKVWHWNSINXNPF-UHFFFAOYSA-N 0.000 description 3
- WXHHXHGQHMHCSM-UHFFFAOYSA-N CC(C)C1=CN=C(NS(C2=CC=CC=C2)(=O)=O)N=C1 Chemical compound CC(C)C1=CN=C(NS(C2=CC=CC=C2)(=O)=O)N=C1 WXHHXHGQHMHCSM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- WOLROTLRGIGKBA-UHFFFAOYSA-N 4-amino-N-(5-propan-2-ylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(C(C)C)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 WOLROTLRGIGKBA-UHFFFAOYSA-N 0.000 description 1
- BAUXVVCVEDWRGY-UHFFFAOYSA-N 5-propan-2-ylpyrimidine Chemical class CC(C)C1=CN=CN=C1 BAUXVVCVEDWRGY-UHFFFAOYSA-N 0.000 description 1
- BAYLKQTUHWVOCQ-UHFFFAOYSA-N CC(C)C(C(Cl)=N1)=CNC1(N)Cl Chemical compound CC(C)C(C(Cl)=N1)=CNC1(N)Cl BAYLKQTUHWVOCQ-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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 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
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Benzol-sulfonamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Benzolsulfonamidderivates, das dadurch ge kennzeichnet ist, dass man ein 2-Benzolsul- fonamido - 5 - isopropyl - pyrimidin, das in p-Stellung einen durch Hydrolyse in die Aminogruppe überführbaren Substituenten aufweist, mit einem hydrolysierenden Mittel behandelt.
Das so erhaltene 2-(p-Amino-benzolsul- fonamido)-5-isopropyl-pyrimidin schmilzt bei 202 . Die neue Verbindung soll als Arznei mittel sowie als Zwischenprodukt Verwen dung finden.
Das 2 - Benzolsulfonamido - 5 - isopropyl- pyrimidin, das in p-Stellung zur Sulfon- amidgruppe 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, mit 5-Isopropyl-pyrimidinverbindungen, die in 2-Stellung eine Gruppe enthalten, die mit dem Benzolsulfonsäurederivat ein 2-Benzol- sulfonamido-5-isopropyl-pyrimidin zu bilden vermag,
wie mit 2-Anino-5-isopropyl-pyri- midin. Man kann auch entsprechende Sulfon amide der Formel R S02 NH Y, in der Y einen bei der nachfolgenden Reaktion sich abspaltenden Rest bedeutet, mit 2-Halogen- 5-isopropyl-pyrimidinen umsetzen. Auch können andere dem Fachmann geläufige Herstellungsmethoden benutzt werden.
<I>Beispiel 1:</I> 26,4 g p-Carbäthögyamino-benzolsulfo- chlorid werden mit 13,7 g 2-Amino-5-iso- propyl-pyrimidin (F. 74 ; hergestellt über das Monoisopropylmalonylguanidin durch Umsetzung von Isopropylmalonester mit Guanidin, Überführung in das 2-Amino-5- isopropyl-2,4-dichlorpyrimidin vom F.
179 mittels Phosphorogychlorid und Behandlung der Dichlorverbindung mit Zinkstaub) und 30 cm' Pyridin eine Stunde auf dem Wasser bad erhitzt. Nach Zusatz von Wasser scheidet sich ein nach kurzer Zeit fest. erdendes 01 ab.
Die Verseifung der Carbäthoxyverbin- dung (F. 191-192 ) mit 2n-Natronlauge durch einstündiges Erwärmen auf 80-90 liefert das 2-(p-Amino-benzolsulfona.mido)- 5-isopropyl-pyrimidin, das bei 202 (aus ver dünntem Alkohol) schmilzt. Die Ausbeute beträgt<B>70%</B> der Theorie.
Das gebildete p-Aminobenzolsulfonamid- derivat lässt sich auch in Form seiner Salze. z. B. des Natriums oder des Calciums. isolieren.
Beispiel <I>2:</I> 137 g 2 - Amino - 5 - isopropyl - pyrimidin werden in 250 cm'' trockenem Py ridin mit 240 g p - Acetylamino - benzolsulfochlorid unter Rühren versetzt, wobei die Temperatur nicht über 55 steigen soll. Man erwärmt noch 2 Stunden auf 55 und versetzt mit Wasser.
Das ausgeschiedene 2-(p-Acety 1 amino -benzolsulfonamido) - 5 -isopropy 1-pyri- midin wird zur Reinigung in 2n-Sodalösung von 60 gelöst, filtriert und mit Salzsäure gefällt.
33,4 g 2-(p-Acetylamino-benzolsulfon- amido) - 5 -isopropyl - py rimidin werden in 100 cm' 2,5n-Natronlauge gelöst und 1 Stunde ani Riickfluss erwärmt.
Durch Neu tralisieren mit Säure erhält man das 2-(p- Amino-1>eiizolsulfonamido) -5-isopropyl-pyri- midin. Es wird durch Lösen in Alkali und Fällen mit Säure und durch L'mkrista.llisie- ren ans verdünntem Alkohol gereinigt. F.20? .
Die H- ydrolyse kann man auch mit an- dern alka,lisclien Mitteln, beispielsweise Erd- all@alihydroxyden, wie Calciumhydroxyd, oder mit sauren Mitteln, z. B.
Salzsäure, in Gegenwart von Nasser oder organischen 1.ii- sung.mitteln, wie Alkohol, durchführen.
Process for the production of a new benzene sulfonamide derivative. The subject of the present patent is a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that a 2-benzenesulfonamido - 5 - isopropyl - pyrimidine which has a substituent which can be converted into the amino group by hydrolysis in the p-position is used treated with a hydrolyzing agent.
The 2- (p-amino-benzenesulfonamido) -5-isopropyl-pyrimidine thus obtained melts at 202. The new compound is to be used as a medicinal product and as an intermediate product.
The 2-benzenesulfonamido-5-isopropylpyrimidine, 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 5-isopropyl-pyrimidine compounds which contain a group in the 2-position which, with the benzenesulfonic acid derivative, gives rise to a 2-benzenesulfonamido-5-isopropyl-pyrimidine, is particularly suitable able to form
as with 2-amino-5-isopropyl-pyrimidine. Corresponding sulfonamides of the formula R SO2 NH Y, in which Y is a radical which is split off in the subsequent reaction, can also be reacted with 2-halo-5-isopropyl-pyrimidines. Other production methods familiar to the person skilled in the art can also be used.
<I> Example 1: </I> 26.4 g of p-Carbäthögyamino-benzenesulfochloride are with 13.7 g of 2-amino-5-isopropyl-pyrimidine (F. 74; prepared via the monoisopropylmalonylguanidine by reacting Isopropyl malonic ester with guanidine, conversion into the 2-amino-5-isopropyl-2,4-dichloropyrimidine from F.
179 using phosphorogychloride and treatment of the dichloro compound with zinc dust) and 30 cm 'pyridine heated for one hour on the water bath. After adding water, it separates after a short time. grounding 01.
The saponification of the carbethoxy compound (F. 191-192) with 2N sodium hydroxide solution by heating to 80-90 for one hour yields 2- (p-amino-benzenesulfona.mido) -5-isopropyl-pyrimidine, which at 202 (from ver thin alcohol) melts. The yield is <B> 70% </B> of theory.
The p-aminobenzenesulfonamide derivative formed can also be in the form of its salts. z. B. of sodium or calcium. isolate.
Example <I> 2: </I> 137 g of 2 - amino - 5 - isopropyl - pyrimidine are mixed in 250 cm ″ of dry pyridine with 240 g of p - acetylamino - benzenesulfochloride while stirring, the temperature not exceeding 55. The mixture is heated to 55 for a further 2 hours, and water is added.
The separated 2- (p-acetyl amino-benzenesulfonamido) -5-isopropy-1-pyrimidine is dissolved in 2N soda solution of 60 for purification, filtered and precipitated with hydrochloric acid.
33.4 g of 2- (p-acetylamino-benzenesulfonamido) -5-isopropyl-pyrimidine are dissolved in 100 cm '2.5N sodium hydroxide solution and refluxed for 1 hour.
Neutralizing with acid gives 2- (p-amino-1> eiizolsulfonamido) -5-isopropyl-pyrimidine. It is cleaned by dissolving it in alkali and precipitating it with acid and by leaching it with diluted alcohol. Q.20? .
The hydrolysis can also be carried out with other alkali, liscic agents, for example Erdall® alihydroxides, such as calcium hydroxide, or with acidic agents, e.g. B.
Carry out hydrochloric acid in the presence of water or organic solvents such as alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE239153X | 1939-11-23 | ||
| DE239157X | 1939-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239157A true CH239157A (en) | 1945-09-15 |
Family
ID=32963238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239157D CH239157A (en) | 1939-11-23 | 1940-11-22 | Process for the production of a new benzene sulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239157A (en) |
-
1940
- 1940-11-22 CH CH239157D patent/CH239157A/en unknown
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