CH236170A - Process for the preparation of 4-amino-benzenesulfone-4'-isopropylmercapto-benzamide. - Google Patents

Process for the preparation of 4-amino-benzenesulfone-4'-isopropylmercapto-benzamide.

Info

Publication number
CH236170A
CH236170A CH236170DA CH236170A CH 236170 A CH236170 A CH 236170A CH 236170D A CH236170D A CH 236170DA CH 236170 A CH236170 A CH 236170A
Authority
CH
Switzerland
Prior art keywords
benzamide
amino
isopropylmercapto
benzenesulfone
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH236170A publication Critical patent/CH236170A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides

Landscapes

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

Description

  

  Verfahren zur Herstellung von     4-Amino-benzolsulfon-4'-isopropylmereapto-benzamid.       Gegenstand des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Herstellung von       4-Amino-benzolsulfon-4'-isopropylmercapto-          benzamid,    welches dadurch gekennzeichnet  ist, dass man ein     4-Isopropylmercapto-benzovl-          halogenid    auf     p-Carbomethoxy-amino-benzol-          sulfonamid    einwirken lässt und die     Carbo-          methoxy-aminogruppe    anschliessend verseift.  



  Die neue Verbindung bildet farblose Kri  stalle vom Schmelzpunkt 215  und soll thera  peutische Verwendung finden.  



       Beispiel:     23 Teile     p-Carbomethoxyamino-benzolsul-          fonamid    werden unter Rühren in 100 Teilen  absolutem     Pyridin    bei     70-80     gelöst und bei  dieser Temperatur langsam 21,5 Teile     4-Iso-          propylmercapto-benzoesäurechlorid    eingetra  gen (Darstellung der Säure nach Am.     Chem.          Soo.    62, Seite 220 [1940], Säure     Kpo,;    180 .  F. 147-149 ; daraus mit     Thionylchlorid    das.

         4-Isopropylmercapto-benzoesäurechlorid,        Kp"-,          135-140 ).    Das Reaktionsgemisch wird eine    halbe Stunde auf 95  gehalten und hierauf  mit verdünnter Salzsäure angesäuert.  



  Das erhaltene     Kondensationsprodukt    wird  zur Abspaltung der     Carbomethoxygruppe    mit  überschüssiger Natronlauge kurze Zeit ge  kocht und das freie Amin mit 80 %     iger    Essig  säure ausgefällt.  



  Aus Alkohol umkristallisiert schmilzt das  4 -     Amino    -     benzolsulf        on-4'-        isopropylmercapto-          benzarnid    bei 215 .



  Process for the preparation of 4-amino-benzenesulfone-4'-isopropylmereapto-benzamide. The subject of the present additional patent is a process for the production of 4-aminobenzenesulfone-4'-isopropylmercaptobenzamide, which is characterized in that a 4-isopropylmercaptobenzene halide is acted on p-carbomethoxy-aminobenzenesulfonamide leaves and the carbonomethoxy-amino group is then saponified.



  The new compound forms colorless crystals with a melting point of 215 and is intended to find therapeutic use.



       Example: 23 parts of p-carbomethoxyamino-benzenesulfonamide are dissolved with stirring in 100 parts of absolute pyridine at 70-80 and 21.5 parts of 4-isopropylmercaptobenzoic acid chloride are slowly introduced at this temperature (the acid is represented by Am. Chem . Soo. 62, page 220 [1940], acid Kpo,; 180. F. 147-149; from it with thionyl chloride das.

         4-Isopropylmercaptobenzoic acid chloride, bp "-, 135-140). The reaction mixture is kept at 95 for half an hour and then acidified with dilute hydrochloric acid.



  The condensation product obtained is boiled for a short time with excess sodium hydroxide solution to split off the carbomethoxy group and the free amine is precipitated with 80% acetic acid.



  Recrystallized from alcohol, 4-amino-benzenesulfone-4'-isopropyl mercaptobenzarnide melts at 215.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 4-Amino- benzolsulfon - 4'- isopropylmercapto-benzamid, dadurch gekennzeichnet, dass man ein 4-Iso- propylmer capto-benzoylhalogenid auf p-Carbo- methoxy - aminobenzolsulfonamid einwirken lässt und die Carbomethoxyaminogruppe an schliessend verseift. Die neue Verbindung bildet farblose Kri stalle vom Schmelzpunkt 215 und soll thera peutische Verwendung finden. PATENT CLAIM: A process for the production of 4-aminobenzenesulfone-4'-isopropylmercapto-benzamide, characterized in that a 4-isopropylmer capto-benzoyl halide is allowed to act on p-carbomethoxy-aminobenzenesulfonamide and the carbomethoxyamino group is then saponified. The new compound forms colorless crystals with a melting point of 215 and is intended to find therapeutic use.
CH236170D 1941-10-24 1941-10-24 Process for the preparation of 4-amino-benzenesulfone-4'-isopropylmercapto-benzamide. CH236170A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH236170T 1941-10-24
CH222076T 1943-05-06

Publications (1)

Publication Number Publication Date
CH236170A true CH236170A (en) 1945-01-15

Family

ID=25726588

Family Applications (1)

Application Number Title Priority Date Filing Date
CH236170D CH236170A (en) 1941-10-24 1941-10-24 Process for the preparation of 4-amino-benzenesulfone-4'-isopropylmercapto-benzamide.

Country Status (1)

Country Link
CH (1) CH236170A (en)

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