DE190291C - - Google Patents

Info

Publication number
DE190291C
DE190291C DENDAT190291D DE190291DA DE190291C DE 190291 C DE190291 C DE 190291C DE NDAT190291 D DENDAT190291 D DE NDAT190291D DE 190291D A DE190291D A DE 190291DA DE 190291 C DE190291 C DE 190291C
Authority
DE
Germany
Prior art keywords
acid
thionaphthene
oxy
alkalis
cooh
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.)
Active
Application number
DENDAT190291D
Other languages
German (de)
Publication of DE190291C publication Critical patent/DE190291C/de
Active legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2

Landscapes

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

Description

KAISERLICHESIMPERIAL

PATENTAMT.PATENT OFFICE.

PATENTSCHRIFTPATENT LETTERING

- M 190291 — KLASSE 12 o. GRUPPE- M 190291 - CLASS 12 or GROUP

Zusatz zum Patente 184496 vom 11. März 1906.Addendum to patent 184496 of March 11, 1906.

Patentiert im Deutschen Reiche vom 29. März 1906 ab. Längste Dauer: 10. März 1921.Patented in the German Empire on March 29, 1906. Longest duration: March 10, 1921.

Die Patente 184496 und 190674 betreffen die Überführung der ο - Aminophenylthioglykolsäure in Thionaphthenderivate. Sie werden in der Weise erhalten, daß man die 5 o-Aminophenylthioglykolsäure in die o-Cyanphenylthioglykolsäure überführt und diese mit Alkalien verseift, "wobei die 3-Amino(i)thionaphthen-2-carbonsäure entsteht, welche durch weitere Einwirkung wässeriger Alkalien, besser durch Säuren in der Wärme unter Abspaltung von Ammoniak und Kohlensäure in die 3 - Oxy (1) thionaphthen - 2 - carbonsäure bzw. das 3 - Oxy (1) thionaphthen übergeht. Der chemische Vorgang läßt sich vermutlich durch folgende Formelbilder wiedergeben: Patents 184496 and 190674 relate to the conversion of ο - aminophenylthioglycolic acid into thionaphthene derivatives. she are obtained in such a way that the 5 o-aminophenylthioglycolic acid is converted into o-cyanophenylthioglycolic acid transferred and this saponified with alkalis, "whereby the 3-amino (i) thionaphthen-2-carboxylic acid arises, which by further action of aqueous alkalis, better by acids in the heat with separation from ammonia and carbonic acid to 3 - oxy (1) thionaphthen - 2 - carboxylic acid or the 3 - oxy (1) thionaphthene passes over. The chemical process can presumably represented by the following formula images:

NH0 NH 0

CNCN

^S-CH2- COOH^ S-CH 2 - COOH

CO-NHCO-NH

CZJT2 · COOH CZJT 2 • COOH

(intermediär)(intermediate)

4545

C-COOHC-COOH

NHNH

OHOH

C HC H

CH.CH.

5555

Im weiteren Verfolge der Erfindung wurde gefunden, daß die Überführung des Nitrils die 3-Amino(1)thionaphthen - 2 - carbon-In the further pursuit of the invention it was found that the conversion of the nitrile the 3-amino (1) thionaphthene - 2 - carbon-

säure auch durch die Einwirkung von Säuren ausgeführt werden kann. Zu diesem Zweck ist es nur erforderlich, das nach dem Verfahren des Hauptpatentes erhaltene Nitril der Phenylthioglykolsäure (o-Cyanphenylthioglykolsäure) in etwa die zehnfache Menge Schwefelsäure von 6o° Be. einzutragen, und die so erhaltene Lösung längere Zeit, z. B. 60 Stunden, sich selbst zu überlassen. Nachacid can also be carried out by the action of acids. To this end it is only necessary to use the nitrile obtained by the process of the main patent of phenylthioglycolic acid (o-cyanophenylthioglycolic acid) about ten times the amount of sulfuric acid of 60 ° Be. to be entered, and the solution thus obtained for a long time, e.g. B. 60 hours left to your own devices. To

dieser Zeit wird die Reaktionsmasse mit Wasser verdünnt und durch Einleiten eines Dampfstromes das entstandene 3-Oxy(i)thionapbth'en abdestilliert.this time, the reaction mass is diluted with water and by introducing a Steam stream, the 3-oxy (i) thionapbth'en formed is distilled off.

Ein gleiches Resultat erreicht man, wenn riian die Schwefelsäure durch konzentrierte Salzsäure ersetzt. Wie in den meisten Fällen bewirkt auch hier die Salzsäure die Verseifung des Nitrils.The same result is obtained when the sulfuric acid is concentrated by means of it Hydrochloric acid replaced. As in most cases, the hydrochloric acid also causes the saponification of nitrile.

Claims (1)

Patent-Anspruch:Patent claim: Abänderung des durch Patent 184496 geschützten Verfahrens zur Darstellung von Thionaphthenderivaten, darin bestehend, daß man zwecks Darstellung des 3-Oxy(i)thionaphthens die o-Cyanphenyl· thioglykolsäure anstatt mit Alkalien hier mit Säuren behandelt.Modification of patent 184496 Protected process for the preparation of thionaphthene derivatives, consisting of that for the purpose of preparing 3-oxy (i) thionaphthene the o-cyanophenyl thioglycolic acid treated here with acids instead of alkalis.
DENDAT190291D Active DE190291C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE190291T

Publications (1)

Publication Number Publication Date
DE190291C true DE190291C (en)

Family

ID=33035716

Family Applications (4)

Application Number Title Priority Date Filing Date
DENDAT190291D Active DE190291C (en)
DENDAT190674D Active DE190674C (en)
DE1906184496D Expired - Lifetime DE184496C (en) 1906-03-10 1906-03-10
DE1906202696D Expired - Lifetime DE202696C (en) 1906-06-02 1906-06-02

Family Applications After (3)

Application Number Title Priority Date Filing Date
DENDAT190674D Active DE190674C (en)
DE1906184496D Expired - Lifetime DE184496C (en) 1906-03-10 1906-03-10
DE1906202696D Expired - Lifetime DE202696C (en) 1906-06-02 1906-06-02

Country Status (1)

Country Link
DE (4) DE184496C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7674822B2 (en) 2004-11-24 2010-03-09 Wyeth PTP1b inhibitors

Also Published As

Publication number Publication date
DE202696C (en)
DE190674C (en)
DE184496C (en)

Similar Documents

Publication Publication Date Title
DE1493576A1 (en) Process for the production of amino alcohols, their acid addition salts and quaternary ammonium compounds
DE190291C (en)
DE691944C (en) solutions in organic solvents
DE1270024B (en) Process for the reductive dimerization of acrylonitrile to adipic dinitrile
DE1248642B (en) Process for the production of acrylonitrile by reacting propylene with oxygen and ammonia
DE157909C (en)
DE293905C (en)
DE130963C (en)
DE195656C (en)
AT162952B (en) Process for the revitalization of used gas cleaning mass
DE624695C (en) Process for the production of potassium tetraoxalate
DE568670C (en) Process for the preparation of phenylcarboxamide-o-thioglycolic acids
DE85230C (en)
DE223306C (en)
DE185962C (en)
DE305449C (en)
DE175589C (en)
DE496980C (en) Process for the preparation of amines
DE161515C (en)
DE444014C (en) Process for the preparation of thiuram disulfides
DE181992C (en)
DE851494C (en) Process for the production of unsaturated nitriles
DE241425C (en)
DE386396C (en) Process for developing hydrocyanic acid from cyanides
DE283548C (en)