CH112331A - Process for the preparation of a new arsic acid. - Google Patents

Process for the preparation of a new arsic acid.

Info

Publication number
CH112331A
CH112331A CH112331DA CH112331A CH 112331 A CH112331 A CH 112331A CH 112331D A CH112331D A CH 112331DA CH 112331 A CH112331 A CH 112331A
Authority
CH
Switzerland
Prior art keywords
sep
new
preparation
acid
arsic
Prior art date
Application number
Other languages
German (de)
Inventor
Leopold Cassella Co Ge Haftung
Original Assignee
Cassella Leopold & Co Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cassella Leopold & Co Gmbh filed Critical Cassella Leopold & Co Gmbh
Publication of CH112331A publication Critical patent/CH112331A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/66—Arsenic compounds
    • C07F9/70—Organo-arsenic compounds
    • C07F9/74—Aromatic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung einer neuen     Arsinsäure.       Während     o-Aminophenol    unter Einwir  kung von     Benzoylchlorid    nach     Schotten-          Baumann    das     Aminophenolbenzoat    und Benz  amidophenolbenzoat bildet  
EMI0001.0007     
  
    C"H.,NH. <SEP> (CO <SEP> Cf;

  H,) <SEP> 0 <SEP> . <SEP> (CO <SEP> C,H_),
<tb>  (1) <SEP> (2)       liefern die     Arsinsäuren    der     Orthoamino-          phenole        überraschenderweise    in glatter Re  aktion ausschliesslich die     Monobenzoylamino-          verbindungen.    Diese neuen     Substanzen    be  sitzen bei relativer     Ungiftigkeit    wertvolle  therapeutische und     prophylaktisehe    Wirkung  gegenüber     Trypanosomen    und     Spirochäten-          krankheiten;

      sie können     peroral    und     paren-          teral    verabreicht werden.  



  Gegenstand der Erfindung ist ein Ver  fahren zur Herstellung von 3-Benzoylamino-         4-oxybenzol-l-arsinsäure,    gemäss welchem  man     3-Amino-4-oxybenzol-l-arsinsäure    mit       Benzoylchlorid    behandelt.  



  <I>Beispiel:</I>  4,7 kg     3-Amino-4-oxybenzol-l-arsinsäure     werden gelöst- in 40 Liter normaler und  2 Liter     zehnfachnormaler    Natronlauge; die  Lösung wird mit 3 kg     Benzoylchlorid    unter  gutem     Umschütteln    kurze Zeit auf dem Was  serbad erwärmt.  



  Man versetzt dann mit 35 Liter normaler  Salzsäure und kühlt ab; die neue Verbin  dung fällt aus, 'man filtriert und wäscht sie  mit Wasser. Sie kann aus normaler Na  triumazetatlösung umkristallisiert werden.  Die Analyse ergab  
EMI0001.0030     
  
    C: <SEP> ber. <SEP> 46,29 <SEP> %, <SEP> H: <SEP> ber. <SEP> 3,56 <SEP> %, <SEP> As: <SEP> ber. <SEP> 22,25 <SEP> %,
<tb>  C: <SEP> gef. <SEP> 45,76 <SEP> %, <SEP> H: <SEP> gef. <SEP> 4,07 <SEP> %, <SEP> As: <SEP> gef. <SEP> 21,90 <SEP> %.       Die     Substanz    ist nicht     diazotierbar.    Sie  löst sich in Wasser, Alkohol und Salzsäure    schwer, in Äther gar     nicht,    dagegen in     Alka-          lien    leicht.



  Process for the preparation of a new arsic acid. While o-aminophenol under the action of benzoyl chloride according to Schotten-Baumann forms the aminophenol benzoate and benz amidophenol benzoate
EMI0001.0007
  
    C "H., NH. <SEP> (CO <SEP> Cf;

  H,) <SEP> 0 <SEP>. <SEP> (CO <SEP> C, H_),
<tb> (1) <SEP> (2) surprisingly, the arsinic acids of the orthoaminophenols deliver exclusively the monobenzoylamino compounds in a smooth reaction. These new substances have a valuable therapeutic and prophylactic effect against trypanosomes and spirochete diseases while being relatively non-toxic;

      they can be administered orally and parenterally.



  The invention relates to a method for the preparation of 3-benzoylamino-4-oxybenzene-1-arsic acid, according to which 3-amino-4-oxybenzene-1-arsic acid is treated with benzoyl chloride.



  <I> Example: </I> 4.7 kg of 3-amino-4-oxybenzene-l-arsic acid are dissolved in 40 liters of normal and 2 liters of tenfold sodium hydroxide solution; the solution is heated with 3 kg of benzoyl chloride while shaking well for a short time on the water bath.



  35 liters of normal hydrochloric acid are then added and the mixture is cooled; the new compound precipitates, it is filtered and washed with water. It can be recrystallized from normal sodium acetate solution. The analysis showed
EMI0001.0030
  
    C: <SEP> ber. <SEP> 46.29 <SEP>%, <SEP> H: <SEP> ber. <SEP> 3.56 <SEP>%, <SEP> As: <SEP> ber. < SEP> 22.25 <SEP>%,
<tb> C: <SEP> found. <SEP> 45.76 <SEP>%, <SEP> H: <SEP> found. <SEP> 4.07 <SEP>%, <SEP> As: <SEP> found. <SEP> 21.90 <SEP>%. The substance cannot be diazotized. It dissolves with difficulty in water, alcohol and hydrochloric acid, not at all in ether, but easily in alkali.

Claims (1)

EMI0002.0001 <B>PATENTANSPRUCH</B> <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> von <SEP> 3-Ben zot-lamino-4-oxybenzol-l-arsins < iure, <SEP> dadureh <tb> 1ekennzeiehnet, <SEP> dass <SEP> man <SEP> 3-Aniino-4-oxy benzol-l-arsinsäure <SEP> mit <SEP> Benzoylchlorid <SEP> be handelt. <SEP> Die <SEP> Substanz <SEP> ist. <SEP> nicht <SEP> diazotierbar. EMI0002.0002 Sie <SEP> löst <SEP> sich <SEP> in <SEP> Wasser, <SEP> Alkohol <SEP> und <SEP> Salz siiure <SEP> schwer, <SEP> in <SEP> Ällier <SEP> (Iar <SEP> nicht:, <SEP> dagegen <SEP> in <tb> Alkalien <SEP> leicht. EMI0002.0001 <B> PATENT CLAIM </B> <tb> Method <SEP> for <SEP> representation <SEP> of <SEP> 3-Ben zot-lamino-4-oxybenzol-l-arsine <iure, <SEP> dadureh <tb> 1 designates <SEP> that <SEP> is treated <SEP> 3-aniino-4-oxy benzene-l-arsic acid <SEP> with <SEP> benzoyl chloride <SEP>. <SEP> The <SEP> substance <SEP> is. <SEP> not <SEP> diazotizable. EMI0002.0002 It <SEP> dissolves <SEP> <SEP> in <SEP> water, <SEP> alcohol <SEP> and <SEP> salt acid <SEP> difficult, <SEP> in <SEP> allier <SEP> (Iar < SEP> not :, <SEP> against <SEP> in <tb> alkalis <SEP> light.
CH112331D 1924-05-07 1924-05-07 Process for the preparation of a new arsic acid. CH112331A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH112331T 1924-05-07
CH111665T 1924-05-07

Publications (1)

Publication Number Publication Date
CH112331A true CH112331A (en) 1925-10-16

Family

ID=25707908

Family Applications (2)

Application Number Title Priority Date Filing Date
CH112331D CH112331A (en) 1924-05-07 1924-05-07 Process for the preparation of a new arsic acid.
CH111665D CH111665A (en) 1924-05-07 1924-05-07 Process for the preparation of a new arsic acid.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH111665D CH111665A (en) 1924-05-07 1924-05-07 Process for the preparation of a new arsic acid.

Country Status (1)

Country Link
CH (2) CH112331A (en)

Also Published As

Publication number Publication date
CH111665A (en) 1925-09-01

Similar Documents

Publication Publication Date Title
CH112331A (en) Process for the preparation of a new arsic acid.
AT166702B (en) Process for the preparation of new halogenated pyrimidyl mercaptocarboxylic acids and their derivatives
DE845347C (en) Process for the preparation of pyridine-mercury compounds
CH236178A (en) Process for the preparation of p-aminobenzenesulfonyl-butylthiourea.
CH232273A (en) Process for the production of a cyclopentano-dimethyl-polyhydro-phenanthrene-carboxylic acid.
DE560218C (en) Process for the preparation of arsenic compounds
CH236176A (en) Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea.
DE810027C (en) Process for the production of a novel Abkoemmlings des ‡ -Phenylaethylalkohols
CH207204A (en) Process for the preparation of the dioctodecyl ether of triethanolamine.
CH236175A (en) Process for the preparation of p-aminobenzenesulfonyl-methyl-thiourea.
CH287867A (en) Process for the preparation of 5-oxy-benz (cd) indoline.
CH252959A (en) Process for the preparation of a new benzenesulfonylguanidine.
CH215336A (en) Process for the preparation of an aminoarylsulfoxide.
CH123280A (en) Process for the production of a new organic mercury compound.
CH143292A (en) Process for the preparation of a cyclammonium compound.
CH236177A (en) Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea.
CH204437A (en) Process for the production of a new azo dye.
CH213144A (en) Process for the preparation of a benzenesulfonic acid derivative.
CH201509A (en) Process for the preparation of a quaternary aminobenzylacylamine.
CH194876A (en) Process for the preparation of 2 (3 &#39;, 5&#39;-Diiodo-2&#39;-B-oxethyl-4&#39;-oxypheny) - 6-iodoquinoline-4-carboxylic acid.
CH177265A (en) Process for the production of a new intermediate product.
CH164196A (en) Process for the preparation of 4,4&#39;-dioxyazobenzene-3,3&#39;-dicarboxylic acid.
CH236179A (en) Process for the preparation of p-aminobenzenesulfonyl-isoamylthiourea.
CH158386A (en) Process for the preparation of the acetic acid ester of 2-glycolylaminobenzene-1-arsic acid.
CH265119A (en) Method for producing a local anesthetic.