CH239689A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents
Process for the preparation of a new benzenesulfonamide derivative.Info
- Publication number
- CH239689A CH239689A CH239689DA CH239689A CH 239689 A CH239689 A CH 239689A CH 239689D A CH239689D A CH 239689DA CH 239689 A CH239689 A CH 239689A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimidine
- ethyl
- preparation
- amino
- benzenesulfonamido
- Prior art date
Links
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XVYRUUWBRCOGRJ-UHFFFAOYSA-N 4-amino-n-(5-ethylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(CC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 XVYRUUWBRCOGRJ-UHFFFAOYSA-N 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
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 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 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- -1 benzenesulfonic acid halides Chemical class 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YCHYGGNTIXJETG-UHFFFAOYSA-N 5-ethylpyrimidin-2-amine Chemical compound CCC1=CN=C(N)N=C1 YCHYGGNTIXJETG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NYLDSZZVGMBEKZ-UHFFFAOYSA-N n-(5-ethylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(CC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 NYLDSZZVGMBEKZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- MJTSPTRANGPNRJ-UHFFFAOYSA-N 5-ethylpyrimidine Chemical class CCC1=CN=CN=C1 MJTSPTRANGPNRJ-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 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
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000725 suspension Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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 Benzolsulfonamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Benzolsulfonamidderivates, das dadurch ge kennzeichnet ist, dass man ein 2-Benzolsulfon- amido-5-äthyl-pyrimidin, das in p-Stellung einen durch Reduktion in die Aminogruppe überführbaren Substituenten aufweist, mit einem reduzierenden Mittel behandelt.
Das so erhaltene 2-(p-Amino-benzolsulfon- amido)-5-äthyl-pyrimidin schmilzt bei 214 bis 215 . Die neue Verbindung soll als Arz neimittel sowie als Zwischenprodukt Verwen- dung finden.
Das 2-Benzolsulfonamido-5-äthyl-pyrimi- din, das in p-Stellung zur Sulfonamidgruppe einen durch Reduktion in die Aminogruppe überführbaren Substituenten enthält, kann auf verschiedene Art und Weise gewonnen werden.
Besonders geeignet ist die Um setzung der entsprechenden reaktionsfähigen Benzolsulfonsäurederivate, insbesondere der Benzolsulfonsäurehalogenide mit 5-Äthyl- pyrimidinverbindungen, die in 2-Stellung eine Gruppe enthalten, die mit dem Benzol- sulfonsäurederivat ein 2-Benzolsulfonamiclo- 5-äthyl-pyrimidin zu bilden vermag, insbe sondere mit 2-Amino-5-äthyl-pyrimidin. Man kann auch entsprechende Sulfonamide der Formel RSOzNHY,
in der Y einen bei der nachfolgenden Reaktion sich abspaltenden Rest bedeutet, mit 2-Halogen-5-äthyl-pyrimi- din umsetzen oder andere, dem Fachmann geläufige Herstellungsmethoden benutzen.
Beispiel <I>Z:</I> In eine Suspension von 12,3 g 2-Amino- 5-äthyl-pyrimidin (F. 143 ; hergestellt über das Monoäthylmalonylguanidin aus Mono äthylmalonester und Guanidin, Überführung in die Dichlorverbindung vom F. 193 mittels Phosphorogychlorid und Behandlung dersel ben mit Zinkstaub in kochendem Wasser) in 45 cm' trockenem Pyridin werden 22,2 g p-Nitro-benzolsulfochlorid eingetragen.
Nach einstündigem Erwärmen der Mischung auf dem Dampfbad wird die Nitroverbindung mit Wasser ausgefällt und aus Alkohol um kristallisiert. Die Reduktion zur Amino- verbindung erfolgt mittels Salzsäure und Zinnchlorür. Nach dem Umkristallisieren des Rohproduktes aus verdünntem Alkohol schmilzt das so erhaltene 2-(p-Amino-benzol- sulfonamido)-5-äthyl-pyrimidin bei 214 bis 215 .
Das gebildete p-Amino-benzolsulfonamid- derivat lässt sich auch in Form seiner Salze, z. B. des Natriums oder des Calciums, isolieren..
<I>Beispiel 2:</I> 123 g 2-Amino-5-äthyl-pyrimidin werden in 250 cm' trockenem Pyridin bei 45-55 mit 222 g p-Nitro-benzolsulfochlorid unter Rühren versetzt. 'Man erwärmt die Mischung noch 1 Stunde auf 55-60 und versetzt mit verdünnter Salzsäure. Das abgeschiedene 2-(p-Nitro - benzolsulfonamido) - 5- äthy l-pyri- midin- kann durch Lesen in --In-Sodaliisung. Filtrieren und Fällen mit Salzsäure gereinigt. werden.
In die kochende Reduktionsmischung von 20 g Eisenpulver, 10 cm' 2n-Salzsäure und 3.50 cm' 50 % gem Alkohol trägt man nach und nach 30,8 g 2-(p-Nitro-benzolsulfon- amido)-5-äthy 1-pyrimidin ein.
Nach 4stündi- gem Kochen am Rückf luss wird der Alkohol abdestilliert. Nun gibt man 100 cm' 2n-Na- tronlauge zu, erwärmt zum Sieden, nutscht ab und fällt aus dem Filtrat mit verdünnter Essigsäure das 2-(p-Amino-benzolsulfon- amido)-5-äthyl-pyrimidin kristallin aus. Zur Reinigung kristallisiert man unter Be nutzung von Tierkohle aus verdünntem Al kohol um. F. 214-215 .
Die Reduktion kann auch mit Ferro- hydroxyd in Gegenwart von Natrium- oder Calciumhydroxy d und Wasser durchgeführt werden, wobei sich die Natrium- bezw. Ca.lciumverbindung des Benzolsulfonamids bildet.
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-benzenesulfonamido-5-ethyl-pyrimidine, which has a substituent in the p-position which can be converted into the amino group by reduction, with treated with a reducing agent.
The 2- (p-amino-benzenesulfonamido) -5-ethyl-pyrimidine thus obtained melts at 214 to 215. The new compound is to be used as a medicinal product and as an intermediate product.
The 2-benzenesulfonamido-5-ethyl-pyrimidine, which contains a substituent which can be converted into the amino group by reduction in the p-position to the sulfonamide group, can be obtained in various ways.
The implementation of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides with 5-ethyl-pyrimidine compounds, which contain a group in the 2-position which is able to form a 2-benzenesulfonamiclo-5-ethyl-pyrimidine with the benzenesulfonic acid derivative, is particularly suitable, in particular with 2-amino-5-ethyl-pyrimidine. You can also use corresponding sulfonamides of the formula RSOzNHY,
in which Y denotes a radical which is split off in the subsequent reaction, react with 2-halo-5-ethyl-pyrimidine or use other production methods familiar to the person skilled in the art.
Example <I> Z: </I> In a suspension of 12.3 g of 2-amino-5-ethyl-pyrimidine (F. 143; prepared via monoethylmalonylguanidine from monoethylmalonic ester and guanidine, conversion into the dichloro compound of F. 193 by means of phosphorogychloride and treatment of the same ben with zinc dust in boiling water) in 45 cm 'of dry pyridine, 22.2 g of p-nitro-benzenesulfochloride are entered.
After heating the mixture on the steam bath for one hour, the nitro compound is precipitated with water and recrystallized from alcohol. The reduction to the amino compound takes place using hydrochloric acid and tin chloride. After the crude product has been recrystallized from dilute alcohol, the 2- (p-amino-benzenesulfonamido) -5-ethyl-pyrimidine thus obtained melts at 214-215.
The p-amino-benzenesulfonamide derivative formed can also be used in the form of its salts, e.g. B. of sodium or calcium, isolate ..
Example 2: 123 g of 2-amino-5-ethyl-pyrimidine are mixed with 222 g of p-nitrobenzenesulfochloride in 250 cm 'of dry pyridine at 45-55 while stirring. The mixture is warmed to 55-60 for a further hour and diluted hydrochloric acid is added. The separated 2- (p-nitro-benzenesulfonamido) -5-ethy-l-pyrimidine- can be read in -In-Sodaliization Filter and precipitate purified with hydrochloric acid. will.
30.8 g of 2- (p-nitro-benzenesulfonamido) -5-ethy-1-pyrimidine are gradually added to the boiling reduction mixture of 20 g of iron powder, 10 cm 2N hydrochloric acid and 3.50 cm 50% alcohol one.
After refluxing for 4 hours, the alcohol is distilled off. 100 cm 2N sodium hydroxide solution is then added, heated to boiling, suction filtered and 2- (p-amino-benzenesulfonamido) -5-ethyl-pyrimidine precipitates in crystalline form from the filtrate with dilute acetic acid. For cleaning, it is recrystallized from dilute alcohol using animal charcoal. F. 214-215.
The reduction can also be carried out with ferrous hydroxide in the presence of sodium or calcium hydroxide and water, the sodium or. Forms calcium compound of benzene sulfonamide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE239689X | 1939-11-23 | ||
| DE239685X | 1939-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239689A true CH239689A (en) | 1945-10-31 |
Family
ID=32963249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239689D CH239689A (en) | 1939-11-23 | 1940-11-22 | Process for the preparation of a new benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239689A (en) |
-
1940
- 1940-11-22 CH CH239689D patent/CH239689A/en unknown
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