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WO1997030025A1 - Composes de dicarbamoyle - Google Patents

Composes de dicarbamoyle Download PDF

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Publication number
WO1997030025A1
WO1997030025A1 PCT/EP1997/000616 EP9700616W WO9730025A1 WO 1997030025 A1 WO1997030025 A1 WO 1997030025A1 EP 9700616 W EP9700616 W EP 9700616W WO 9730025 A1 WO9730025 A1 WO 9730025A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
alkyl
phenyl
radical
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.)
Ceased
Application number
PCT/EP1997/000616
Other languages
German (de)
English (en)
Inventor
Claus Marschner
Manfred Patsch
Ulrike Schlösser
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to AU18724/97A priority Critical patent/AU1872497A/en
Publication of WO1997030025A1 publication Critical patent/WO1997030025A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
    • C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group

Definitions

  • the invention relates to compounds of general formula I.
  • n 0, 1 or 2
  • W is optionally substituted by Ci to C4 alkyl, chlorine, bromine or phenyl substituted C 2 - to C 4 -alkylene, Cs-C 7 -cycloalkyl alkenylene or C 2 -C 4 alkenylene or optionally substituted by methyl, ethyl, methoxy , Ethoxy, hydroxy, chlorine, bromine, hydroxysulfonyl, nitro, amino, acetylamino or carboxyl-substituted phenylene,
  • C 2 is optionally substituted by ether oxygen, imino, imino or C Phenyl ⁇ -C 4 -alkylimino - ß alkylene or a radical of the For ⁇ to C mel
  • L 1 and L 2 independently of one another C -.- to C 4 -alkylene
  • Y is vinyl or a radical of the formula C 2 H 4 Q, where Q is
  • Ar phenyl or naphthyl where both radicals are mono- to triple by Cx to C 6 alkyl, C x to C 6 alkoxy, fluorine, chlorine, bromine, nitro, amino, hydroxy, hydroxysulfonyl, carboxyl, Ci to C 6 -alkoxycarbonyl, acetylamino, a radical of the formula
  • R 1 and R 2 are independently hydrogen or
  • Ci to C 6 alkyl and n, X and Y have the meaning given, mean
  • the object of the present invention was to provide new dicarbamoyl compounds.
  • the new compounds should be easily accessible and advantageously be suitable as intermediates for dyes.
  • the bridge member X is in particular optionally C 2 to C 8 alkylene interrupted simply by oxygen, imino, phenylimino or (C (-C 4 ) -alkylimino.
  • radicals X are, for example, CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NHCH 2 CH 2 ,
  • the first three radicals being particularly preferred.
  • the rest Q stands for hydroxy or for a group which can be split off under alkaline reaction conditions.
  • groups are, for example, chlorine, bromine, C 1 -C 4 -alkylsulfonyl, phenylsulfonyl, OSO 3 H, SS0 3 H, OP (0) (OH) 2 , C 1 -C 4 -alkylsulfonyloxy, phenylsulfonyloxy, C ⁇ -C 4 -alka- noyloxy, -CC 4 -dialkylamino or a radical of the formula
  • L 1 , L 2 and L 3 independently of one another each have the meaning of C ⁇ -C 4 alkyl or benzyl and An each have the meaning of one equivalent of an anion.
  • Anions which may be used here are, for example, fluoride, chloride, bromide, iodide, mono-, di- or trichloroacetate, methanesulfonate, benzenesulfonate or 2- or 4-methylbenzenesulfonate.
  • the substituents for Ar are in particular fluorine, chlorine, bromine, methyl, hydroxy, methoxy, ethoxy, hydroxysulfonyl, carboxyl, carbamoyl, sulfamoyl, nitro, amino, acetylamino or radicals of the formulas
  • the compounds of the formula I are suitable, for example, as diazo components (Ar substituted by NH 2 ) or as coupling components (coupling point in the Ar radical) and are valuable intermediates for the preparation of reactive dyes.
  • Example 3 20 33 g of the aniline obtained in Example 3 were introduced into 98 g of oleum (24% strength) with ice cooling at 35-40 ° C. and stirred at 55 ° C. for about 6 hours.

Landscapes

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

Abstract

L'invention concerne des composés de dicarbamoyle de formule générale (I), dans laquelle: m vaut 1 ou 2; n vaut 0, 1 ou 2; W est alkylène C2-C4 éventuellement substitué par alkyle C1-C4, chlore, brome ou phényle, cyclo-alcénylène C5-C7 ou alcénylène C2-C4 ou phénylène éventuellement substitué par méthyle, éthyle, méthoxy, éthoxy, hydroxy, chlore, brome, hydroxysulfonyle, nitro, amino, acétylamino ou carboxyle; X est alkylène C2-C8 interrompu 1 à 3 fois, éventuellement substitué par étheroxygène, imino, phénylimino ou alkylimino C1-C4, ou un résidu de formule (II); Z est un résidu de formule (III) ou (IV); R est hydrogène, alkyle C1-C4, phényle, CH2CH2OH, CH2CH2OSO3H, CH2CH2SO3H ou un résidu de formule (V); L1 et L2 sont indépendamment C¿1?-C4 alkylène; Y est vinyle ou un résidu de formule C2H4Q, où Q est hydroxy ou un résidu pouvant être séparé dans des conditions alcalines de réaction; et Ar est phényle ou naphtyle, les deux résidus peuvent être substitués une à trois fois par alkyle C1-C6, alcoxy C1-C6, fluor, chlore, brome, nitro, amino, hydroxy, hydroxysulfonyle, carboxyle, alcoxycarbonyle C1-C6, acétylamino, un résidu de formule (VI), (VII), SO2NH-X-S(O)n-Y ou S(O)n-Y, où R?1 et R2¿ sont indépendamment hydrogène ou alkyle C¿1?-C6, et n, X et Y ont la signification donnée. L'invention concerne également l'utilisation de ces composés pour la production de colorants réactifs.
PCT/EP1997/000616 1996-02-15 1997-02-11 Composes de dicarbamoyle Ceased WO1997030025A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18724/97A AU1872497A (en) 1996-02-15 1997-02-11 Dicarbamoyl compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19605678.0 1996-02-15
DE1996105678 DE19605678A1 (de) 1996-02-15 1996-02-15 Diacarbamoylverbindungen

Publications (1)

Publication Number Publication Date
WO1997030025A1 true WO1997030025A1 (fr) 1997-08-21

Family

ID=7785525

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/000616 Ceased WO1997030025A1 (fr) 1996-02-15 1997-02-11 Composes de dicarbamoyle

Country Status (4)

Country Link
AU (1) AU1872497A (fr)
DE (1) DE19605678A1 (fr)
ID (1) ID15951A (fr)
WO (1) WO1997030025A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174909A1 (fr) * 1984-08-30 1986-03-19 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation
EP0414637A1 (fr) * 1989-08-23 1991-02-27 Ciba-Geigy Ag Procédé de préparation d'amines aromatiques
EP0552605A1 (fr) * 1992-01-23 1993-07-28 BASF Aktiengesellschaft Diamides mélangées de l'acide oxalique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174909A1 (fr) * 1984-08-30 1986-03-19 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation
EP0414637A1 (fr) * 1989-08-23 1991-02-27 Ciba-Geigy Ag Procédé de préparation d'amines aromatiques
EP0552605A1 (fr) * 1992-01-23 1993-07-28 BASF Aktiengesellschaft Diamides mélangées de l'acide oxalique

Also Published As

Publication number Publication date
DE19605678A1 (de) 1997-08-21
AU1872497A (en) 1997-09-02
ID15951A (id) 1997-08-21

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