DE847898C - Process for the production of Schiff bases from sulfanilic acid amides of the pyrimidine series - Google Patents
Process for the production of Schiff bases from sulfanilic acid amides of the pyrimidine seriesInfo
- Publication number
- DE847898C DE847898C DESCH1599D DESC001599D DE847898C DE 847898 C DE847898 C DE 847898C DE SCH1599 D DESCH1599 D DE SCH1599D DE SC001599 D DESC001599 D DE SC001599D DE 847898 C DE847898 C DE 847898C
- Authority
- DE
- Germany
- Prior art keywords
- production
- pyrimidine
- acid amides
- sulfanilic acid
- schiff bases
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Schiff'schen Basen aus Sulfanilsäureamiden der Pyrimidinreihe Fkkaltntlirh hat sich herausgestellt, daß c1ie Wirkstunkeit vorn liondensationsproduktcn von Stllfaiiilsättru;tmid und p-Arnittohenzolsulfonamidopyridin mit Aldehyden in Form von Schiff'schen Base?; in dun meisten Fällen gleich der der nicht substituierten Sulfanilsä ureamide ist (vgl. E. H. N o r t h e y , Chernical Reviews, Bd. 27 119401, S. 12,- und 128 sowie S. 1:15 und r69). Die Autoren führen dies darauf zurück, daß die erhaltenen Schiff'schen Basen nicht besonders stabil sind und daß ihre ebenfalls bekannten stabileren R,eduktiotispro>dukte sich leicht spalten.Process for the production of Schiff bases from sulfanilic acid amides The pyrimidine series has been found to be effective Liondensationsprodukte von Stllfaiiilsättru; tmid and p-Arnittohenzolsulfonamidopyridin with aldehydes in the form of Schiff's base ?; in most cases equal to that of the is unsubstituted sulfanilic acid amide (cf. E. H. N o r t h e y, Chernical Reviews, Vol. 27 119401, pp. 12, - and 128 as well as pp. 1:15 and r69). The authors lead this is due to the fact that the Schiff bases obtained are not particularly stable are and that their also known more stable R, eduktiotispro> products are easy columns.
Ülierrascliritderiveise "wurde nun gefunden, daß Verbindungen von Sulfanilsäul-caniiden, die in der Stilfevit2tniidgrttl>pe durch einett 1'yrimidinrest substituiert sind, mit Aldehyden eine besonders gute Wirksamkeit zeigen, die die der Ausgangsstoffe sogar noch übertrifft.Ülierrascliritderiveise "has now been found that compounds of Sulfanilsäul-caniiden, which in the Stilfevit2tniidgrttl> pe by a 1'yrimidine residue are substituted, with aldehydes show a particularly good effectiveness that the the starting materials even surpasses.
Als Ausgangsmaterialien kommen vor allem in Frage solche Pyrimidinverbindungen, in denen rlie Sulfonamidgruppe in 2-Stellung mit dem Pyrimidinrest verknüpft ist. Auch kann man Verbindungen, die im Pyrimidinrest Substituenten tragen, besonders solche, die durch einen Alkylrest, z. B. durch einen Methyl- oder Äthylrest, zweckmäßig in .f-Stellung substituiert sind, als Ausgangsmaterialien verwenden.The main starting materials are those pyrimidine compounds, in which the sulfonamide group is linked to the pyrimidine residue in the 2-position. Compounds which have substituents in the pyrimidine radical can also be used, in particular those replaced by an alkyl radical, e.g. B. by a methyl or ethyl radical, appropriate Substituted in the .f-position, use as starting materials.
Als Aldehyde kommen in Frage Aldehyde der aliphatischen, aromatisch-aliphatischen, aromatischen und heterocyclischen Reihe. Als besonders geeignet haben sich erwiesen Benzaldehyd, p-<>xy-und p-Alkoxybenzaldehyde, Zimaldchyd, Phthalaldehydsäure u. dgl.Suitable aldehydes are aldehydes of the aliphatic, aromatic-aliphatic, aromatic and heterocyclic series. As special suitable have been shown to be benzaldehyde, p - <> xy- and p-alkoxybenzaldehydes, zimaldehydes, Phthalaldehyde acid and the like
Die Herstellung der Schiff'sch.en Basen dieser Sulfonamidverbindungen erfolgt nach an sich bekannten Methoden. Am zweckmäßigsten hat sich das Verfahren erwiesen, bei dem man das p-Aminobenzolsulforiamidpyrimidin mit dem Aldehyd erhitzt.The manufacture of the Schiff's bases of these sulfonamide compounds takes place according to methods known per se. The procedure has proven to be most expedient proven by heating the p-aminobenzene sulforiamide pyrimidine with the aldehyde.
Man kann auch die Reaktionskomponenten in einem geeigneten Lösungsmittel, z. B. in Alkohol, stehenlassen, wobei die unlösliche Schiff'sche Base auskristallisiert.You can also use the reaction components in a suitable solvent, z. B. in alcohol, leave the insoluble Schiff base crystallized.
Die erfindungsgemäß erhaltenen Verbindungen haben bezüglich der Wirksamkeit gegenüber den zu ihrer Herstellung verwendeten sowie anderen Sulfaliamidverbindungen, welche alle verhältnismäßig schnell aus dem Organismus wieder ausgeschieden werden, den Vorteil einer protahierenden Wirkung, d. h. sie erzeugen einen möglichst hohen und für eine optimale Wirkung genügend langen Zeitraum hindurch dauernden Blutspiegel.The compounds obtained according to the invention have the effectiveness in terms of effectiveness compared to the sulfaliamide compounds used for their production and other sulfaliamide compounds, which are all excreted from the organism relatively quickly, the advantage of a protahing effect, d. H. they generate as high a level as possible and blood levels that are long enough for optimal effect.
Die erfindungsgemäße Reaktion sei in folgenden Beispielen näher erläutert: Beispiel 1 25g 2 - (p - Aminobetizolsulfonamido )- pyrimiditi werden mit 8o ccm Benzaldehyd auf dem Olbad 3 Stunden auf 13o' erhitzt, nach dem Erkalten wird abgesaugt und der Niederschlag zweimal mit Alkohol ausgekocht. Man erhält 17 g 2-(p-Benzalamiiiolmtizolsulfotiamido)-pyrimidin vom F.23ö'.The reaction according to the invention is explained in more detail in the following examples: Example 1 25 g of 2 - (p - aminobetizolsulfonamido) - pyrimiditi are mixed with 80 ccm Benzaldehyde heated to 130 'for 3 hours in the oil bath, after cooling it is suctioned off and the precipitate is boiled twice with alcohol. 17 g of 2- (p-Benzalamiiiolmtizolsulfotiamido) pyrimidine are obtained from F.23ö '.
Beispiele 25 g 2 - (p -Aminobenzolsulfoliamido) - pyrimiditi werden mit l oo g Salicylaldehyd 3 Stunden auf 130" erhitzt, nach dem Erkalten wird abgesaugt und der Niederschlag zweimal mit Alkohol ausgekocht. Man erhält in quantitativer Ausbeute (35g) 2-:;p-(.o'-oxybenzal] - aminoli:etizolsulfotiamido).- pyrimidin VO'nl F. 248°.Examples 25 g of 2 - (p -aminobenzenesulfoliamido) - pyrimiditi become Heated to 130 "with loo g of salicylaldehyde for 3 hours, after cooling it is suctioned off and the precipitate is boiled twice with alcohol. One gets in quantitative Yield (35g) 2 - :; p - (. O'-oxybenzal] - aminoli: etizolsulfotiamido) .- pyrimidine VO'nl F. 248 °.
Beispiel 3 259 2 - (p - Aminobetizolsulfonamido) - pyrimidin werden mit ioo g Furfurol 3 Stunden auf 130° erhitzt, die Lösung wird nach dem Erkalten mit Äther gefällt und die Fällung nach 2o Stunden abgesaugt. Die Ausbeute an 2-(p-Fitrfurylamitiobetizolsulfo,namido)-pyrimidiii ist fast quantitativ. F.235 (aus Alkohol) unter Zersetzung.Example 3 259 2 - (p - aminobetizolsulfonamido) - pyrimidine are heated to 130 ° with 100 g of furfural for 3 hours, the solution is precipitated with ether after cooling and the precipitate is filtered off with suction after 20 hours. The yield of 2- (p-Fitrfurylamitiobetizolsulfo, namido) -pyrimidiii is almost quantitative. F.235 (from alcohol) with decomposition.
Beispiel 4 25 g 2 - (p -Aminobetizolsulfotiamido) - pyrimidin werden mit toog Anisaldehyd 3 Stunden lang auf 120) ' erhitzt. Nach dem Erkalten saugt man die ausgeschiedene Substanz ab und kocht das entstandene 2 - (p - [p'- Methoxybenzal] - aminobenzolsulfonamido)-pyrimidin mit Alkohol aus. F. 243".Example 4 25 g of 2 - (p -aminobetizolsulfotiamido) - pyrimidine become with toog anisaldehyde heated to 120) for 3 hours. Sucks after cooling the excreted substance is removed and the resulting 2 - (p - [p'- methoxybenzal] - aminobenzenesulfonamido) pyrimidine with alcohol. F. 243 ".
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH1599D DE847898C (en) | 1942-05-16 | 1942-05-16 | Process for the production of Schiff bases from sulfanilic acid amides of the pyrimidine series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH1599D DE847898C (en) | 1942-05-16 | 1942-05-16 | Process for the production of Schiff bases from sulfanilic acid amides of the pyrimidine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE847898C true DE847898C (en) | 1952-08-28 |
Family
ID=7422921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH1599D Expired DE847898C (en) | 1942-05-16 | 1942-05-16 | Process for the production of Schiff bases from sulfanilic acid amides of the pyrimidine series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE847898C (en) |
-
1942
- 1942-05-16 DE DESCH1599D patent/DE847898C/en not_active Expired
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