CH239702A - Process for the preparation of a sulfonamide. - Google Patents
Process for the preparation of a sulfonamide.Info
- Publication number
- CH239702A CH239702A CH239702DA CH239702A CH 239702 A CH239702 A CH 239702A CH 239702D A CH239702D A CH 239702DA CH 239702 A CH239702 A CH 239702A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- sulfonamide
- preparation
- benzene
- dimethyl
- Prior art date
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)
- Cephalosporin Compounds (AREA)
Description
Verfahren zur Darstellung eines Sulfonamides.
EMI0001.0002
Das <SEP> in <SEP> der <SEP> Medizin <SEP> als <SEP> antibakterielles
<tb> Mittel <SEP> bekannt <SEP> gewordene <SEP> 2-(p-Aminobenz:ol sulfon3#lamino) <SEP> - <SEP> 4,6 <SEP> - <SEP> dimethyl <SEP> - <SEP> pyrimidin <SEP> üt
<tb> infolge <SEP> seiner <SEP> igeringen <SEP> Löslichkeit <SEP> zu <SEP> intra venäsen <SEP> Injektionen <SEP> wenig <SEP> geeignet. <SEP> Man <SEP> ist
<tb> daheTdazu <SEP> übergegangen, <SEP> an <SEP> seiner <SEP> Stehle
<tb> .die <SEP> in <SEP> Wasser <SEP> viel <SEP> ileichter <SEP> und <SEP> mit <SEP> neutraler
<tb> Reaktion <SEP> löslichen <SEP> Alkalisalze <SEP> des <SEP> <B>2-(p-N</B>4<B>_</B>
<tb> Succinyl-amino#b:
enzol-su <SEP> #lfonylamino)-4,6-di methyl-pyrimidins <SEP> zu <SEP> verwenden. <SEP> Das <SEP> .diesen
<tb> Seilzen <SEP> zu <SEP> runde <SEP> liegende <SEP> Sulfonamid <SEP> ist
<tb> bisher <SEP> @durch <SEP> Befiand@lung <SEP> von <SEP> 2-(p-Amino benzoT@-ssulfanyJamino@) <SEP> -4,6 <SEP> - <SEP> dim@ethyl-pyrimi Jin <SEP> mit <SEP> Bernste:insäureauhydrid <SEP> gewonnen
<tb> worden.
<tb>
Gegenstand <SEP> der <SEP> vorliegenden <SEP> Erfindung
<tb> ist <SEP> ein <SEP> in <SEP> seiner <SEP> Art <SEP> neues <SEP> Verfahren <SEP> zur <SEP> Dar stellung <SEP> des <SEP> 2-(p-N4-Suecinyl-aminobenzol sulf <SEP> onylamino <SEP> )-4, <SEP> 6-dimethyl-py <SEP> rimidins, <SEP> wei ehes <SEP> dadurch <SEP> gekennzeichnet <SEP> ist, <SEP> @dass <SEP> man <SEP> p Succinylamino-benzol-sulfornylguanidin <SEP> mit
<tb> A.eetylaceto:n <SEP> kondensiert. <SEP> Die <SEP> I#ondensation
<tb> kann. <SEP> durch <SEP> Erhitzen, <SEP> einer <SEP> innigen <SEP> Mischung ,der beiden. Ausgangsstoffe auf eine Tempe ratur von wenigstens 120' C durchgeführt werden.
<I>Aas f</I> ührwngsbeispiel: Ein inniges Gemisch von 31,5 g p-Succinyl- amino - Benzol - sulfonylbo^uanidin und 35 g Acetylacetan wird im Druckgefäss unter Rüh ren 3 @Stunden auf 140 bis<B>160'</B> C erhitzt. Damauf wird das überschüssige Acetylaeeton abdestilliert und der Rückstand aus 6 n.
Essig säure umkristallisiert. Ausbeute: 35 g oder 92,69o' d. Th. Das so .erhaltene 2-(p-N4- Succinylamino,-benzol-sulf onylamino) - 4, 6- di- methyl-pyrimidin zeigt, in Übereinstimmung ,mit dem Schrifttum, einen Schmelzpunkt (u. Zers.) von 226 C.
Process for the preparation of a sulfonamide.
EMI0001.0002
The <SEP> in <SEP> of <SEP> medicine <SEP> as <SEP> antibacterial
<tb> Medium <SEP> known <SEP> <SEP> 2- (p-aminobenz: ol sulfon3 # lamino) <SEP> - <SEP> 4,6 <SEP> - <SEP> dimethyl <SEP> - < SEP> pyrimidine <SEP> üt
<tb> due to <SEP> its <SEP> low <SEP> solubility <SEP> for <SEP> intravenous <SEP> injections <SEP> not very suitable <SEP>. <SEP> Man <SEP> is
<tb> daheT to <SEP> passed over, <SEP> to <SEP> his <SEP> steals
<tb> .the <SEP> in <SEP> water <SEP> much <SEP> ole easier <SEP> and <SEP> with <SEP> more neutral
<tb> Reaction <SEP> soluble <SEP> alkali salts <SEP> of <SEP> <B> 2- (p-N </B> 4 <B> _ </B>
<tb> succinyl-amino # b:
Use enzol-su <SEP> #lfonylamino) -4,6-dimethyl-pyrimidins <SEP> for <SEP>. <SEP> The <SEP> .this
<tb> Seilzen <SEP> to <SEP> round <SEP> lying <SEP> sulfonamide <SEP> is
<tb> so far <SEP> @by <SEP> Befiand @ lung <SEP> from <SEP> 2- (p-Amino benzoT @ -ssulfanyJamino @) <SEP> -4,6 <SEP> - <SEP> dim @ ethyl-pyrimi Jin <SEP> with <SEP> amber: obtained insäureauhydrid <SEP>
<tb> been.
<tb>
Subject <SEP> of the <SEP> present <SEP> invention
<tb> is <SEP> a <SEP> in <SEP> of its <SEP> type <SEP> new <SEP> method <SEP> for <SEP> display <SEP> of <SEP> 2- (p-N4 -Suecinyl-aminobenzol sulf <SEP> onylamino <SEP>) -4, <SEP> 6-dimethyl-py <SEP> rimidins, <SEP> because <SEP> is marked with <SEP>, <SEP> @that <SEP> one <SEP> p succinylamino-benzene-sulfornylguanidine <SEP> with
<tb> A.eetylaceto: n <SEP> condensed. <SEP> The <SEP> I # ondensation
<tb> can. <SEP> by <SEP> heating, <SEP> a <SEP> intimate <SEP> mixture of the two. Starting materials are carried out to a temperature of at least 120 ° C.
<I> Aas f </I> ührwngsbeispiel: An intimate mixture of 31.5 g of p-succinylamino - benzene - sulfonylbo ^ uanidine and 35 g of acetylacetane is stirred in a pressure vessel for 3 hours to 140 to 160 '</B> C heated. Then the excess Acetylaeeton is distilled off and the residue from 6 n.
Acetic acid recrystallized. Yield: 35 g or 92.69o 'd. The 2- (p-N4-succinylamino, -benzene-sulfonylamino) -4, 6- dimethyl-pyrimidine obtained in this way shows, in accordance with the literature, a melting point (and decomposition) of 226 C.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH226118T | 1943-08-20 | ||
CH239702T | 1943-08-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH239702A true CH239702A (en) | 1945-10-31 |
Family
ID=25726970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH239702D CH239702A (en) | 1943-08-20 | 1943-08-20 | Process for the preparation of a sulfonamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH239702A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2466456A1 (en) * | 1979-09-27 | 1981-04-10 | Niviere Pierre | Soluble antibacterial sulphonamide derivs. - prepd. from a sulphonamide, an aldehyde and a di:carboxylic acid mono:amide |
-
1943
- 1943-08-20 CH CH239702D patent/CH239702A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2466456A1 (en) * | 1979-09-27 | 1981-04-10 | Niviere Pierre | Soluble antibacterial sulphonamide derivs. - prepd. from a sulphonamide, an aldehyde and a di:carboxylic acid mono:amide |
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