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ES8609301A1 - PROCEDURE FOR THE OBTAINING OF 3-METHYL-7-FLUOR-5-NITRO- BENZOTIOFEN - Google Patents

PROCEDURE FOR THE OBTAINING OF 3-METHYL-7-FLUOR-5-NITRO- BENZOTIOFEN

Info

Publication number
ES8609301A1
ES8609301A1 ES540669A ES540669A ES8609301A1 ES 8609301 A1 ES8609301 A1 ES 8609301A1 ES 540669 A ES540669 A ES 540669A ES 540669 A ES540669 A ES 540669A ES 8609301 A1 ES8609301 A1 ES 8609301A1
Authority
ES
Spain
Prior art keywords
acid
followed
fluor
methyl
procedure
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
Application number
ES540669A
Other languages
Spanish (es)
Other versions
ES540669A0 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Troponwerke GmbH
Original Assignee
Troponwerke 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 Troponwerke GmbH filed Critical Troponwerke GmbH
Publication of ES8609301A1 publication Critical patent/ES8609301A1/en
Publication of ES540669A0 publication Critical patent/ES540669A0/en
Expired 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
    • 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
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PROCEDIMIENTO PARA LA OBTENCION DE 3-METIL-7-FLUOR-5-NITROBENZOTIOFENO. COMPRENDE LA TRANSFORMACION DE LA 2-FLUORANILINA EN 7-FLUORISATINA POR TRATAMIENTO CON TRICLOROACETALDEHIDO E HIDROXIANILINA EN MEDIO SULFURICO MEDIANTE TECNICAS CONVENCIONALES; SEGUIDA DE LA NITRACION DE LA 7-FLUORISATINA Y OXIDACION DEL PRODUCTO FORMADO; DIAZOTACION DEL DERIVADO ANTRANILICO OBTENIDO, REACCION CON ACIDO CLORHIDRICO EN PRESENCIA DE CLORURO CUPROSO Y A CONTINUACION CON CLORURO DE TIONILO; TRATAMIENTO DEL CLORURO DE ACIDO CON ETOXIMAGNESIOMALONATO DE DIETILO, SEGUIDA DE LA REACCION CON ACIDO PROPIONICO EN PRESENCIA DE ACIDO SULFURICO, TRANSFORMACION DE LA ACETOFENONA FORMADA CON ACIDO MERCAPTOACETICO, Y FINALMENTE, CICLACION DEL PRODUCTO OBTENIDO. ESTE COMPUESTO TIENE APLICACIONES FARMACOLOGICAS POR SU ACCION SOBRE EL SISTEMA NERVIOSO CENTRAL.PROCEDURE FOR OBTAINING 3-METHYL-7-FLUOR-5-NITROBENZOTHIOPHENE. IT INCLUDES THE TRANSFORMATION OF 2-FLUORANILINE IN 7-FLUORISATIN BY TREATMENT WITH TRICHLOROACETALDEHIDO AND HYDROXIANILINE IN SULFURIC MEDIUM BY MEANS OF CONVENTIONAL TECHNIQUES; FOLLOWED BY THE NITRATION OF 7-FLUORISATIN AND OXIDATION OF THE FORMED PRODUCT; DIAZOTATION OF THE ANTRANILIC DERIVATIVE OBTAINED, REACTION WITH HYDROCHLORIC ACID IN THE PRESENCE OF CUPROSE CHLORIDE AND FOLLOWED WITH THIONYL CHLORIDE; TREATMENT OF ACID CHLORIDE WITH DIETHYL ETHOXYMAGNESIOMALONATE, FOLLOWED BY REACTION WITH PROPIONIC ACID IN THE PRESENCE OF SULFURIC ACID, TRANSFORMATION OF ACETOPHENONE FORMED WITH MERCAPTOACETIC ACID, AND FINALLY, CYCLING OF THE PRODUCT. THIS COMPOUND HAS PHARMACOLOGICAL APPLICATIONS DUE TO ITS ACTION ON THE CENTRAL NERVOUS SYSTEM.

ES540669A 1984-02-27 1985-02-25 PROCEDURE FOR THE OBTAINING OF 3-METHYL-7-FLUOR-5-NITRO- BENZOTIOFEN Expired ES8609301A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19843406997 DE3406997A1 (en) 1984-02-27 1984-02-27 Process for the preparation of 3-methyl-7-fluoro-5-nitro- benzothiophene

Publications (2)

Publication Number Publication Date
ES8609301A1 true ES8609301A1 (en) 1986-08-01
ES540669A0 ES540669A0 (en) 1986-08-01

Family

ID=6228903

Family Applications (1)

Application Number Title Priority Date Filing Date
ES540669A Expired ES8609301A1 (en) 1984-02-27 1985-02-25 PROCEDURE FOR THE OBTAINING OF 3-METHYL-7-FLUOR-5-NITRO- BENZOTIOFEN

Country Status (9)

Country Link
KR (1) KR850006398A (en)
CA (1) CA1249284A (en)
DE (1) DE3406997A1 (en)
DK (1) DK87285A (en)
ES (1) ES8609301A1 (en)
FI (1) FI850758A7 (en)
GR (1) GR850475B (en)
NO (1) NO850561L (en)
PT (1) PT80006B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE920483A1 (en) * 1991-02-14 1992-08-12 Brocades Pharma Bv Use of tetra:hydro-thieno-pyrido-indole derivatives for the¹preparation of a medicine for the treatment of skin¹disorders

Also Published As

Publication number Publication date
DK87285D0 (en) 1985-02-26
FI850758L (en) 1985-08-28
DK87285A (en) 1985-08-28
PT80006A (en) 1985-03-01
DE3406997A1 (en) 1985-08-29
FI850758A0 (en) 1985-02-25
PT80006B (en) 1986-11-12
CA1249284A (en) 1989-01-24
GR850475B (en) 1985-06-25
KR850006398A (en) 1985-10-05
NO850561L (en) 1985-08-28
ES540669A0 (en) 1986-08-01
FI850758A7 (en) 1985-08-28

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