DE19605678A1 - Diacarbamoyl compounds - Google Patents

Diacarbamoyl compounds

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Publication number
DE19605678A1
DE19605678A1 DE1996105678 DE19605678A DE19605678A1 DE 19605678 A1 DE19605678 A1 DE 19605678A1 DE 1996105678 DE1996105678 DE 1996105678 DE 19605678 A DE19605678 A DE 19605678A DE 19605678 A1 DE19605678 A1 DE 19605678A1
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Germany
Prior art keywords
formula
compounds
alkyl
phenyl
bromine
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DE1996105678
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German (de)
Inventor
Claus Dr Marschner
Manfred Dr Patsch
Ulrike Dr Schloesser
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BASF SE
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BASF SE
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Priority to DE1996105678 priority Critical patent/DE19605678A1/en
Priority to AU18724/97A priority patent/AU1872497A/en
Priority to PCT/EP1997/000616 priority patent/WO1997030025A1/en
Priority to IDP970442A priority patent/ID15951A/en
Publication of DE19605678A1 publication Critical patent/DE19605678A1/en
Withdrawn legal-status Critical Current

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    • 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

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

Abstract

Dicarbamoyl compounds of general formula (I) wherein: m is 1 or 2, n is 0, 1 or 2, W if necessary C2 to C4 alkylene is substituted by C1 to C4 alkyl, chlorine, bromine or phenyl or phenylene optionally substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, chlorine, bromine, hydroxysulfonyl, nitro, amino, acetalamino, or carboxyl; X is C2-C8 alkylene interrupted one to three times, optionally substituted by ether oxygen, imino, phenylimino or C1 to C4 alkylamino or a residue of the formula (II); Z is a residue of formula (III) or (IV); R is hydrogen, C1 to C4 alkyl, phenyl, CH2CH2OH, CH2CH2OSO3H, CH2CH2SO3H or a residue of formula (V); L<1> and L<2> are independently C1 to C4 alkylenes; Y is vinyl or a residue of the formula C2H4Q where Q means hydroxy or a residue separable under alkalic reaction conditions; and Ar means phenyl or naphthyl and both residues can be substituted one to three times by C1-C6 alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine, nitro, amino, hydroxy, hydroxysulfonyl, carboxyl, C1 to C6 alkoxycarbonyl, acetylamino, a residue of formula (VI), (VII), SO2NH-X-S(O)n-Y or S(O)n-Y where R<1> and R<2> are independently hydrogen or C1 to C6 alkyl and n, X and Y have the given meaning. The invention also relates to the use of these compounds for the preparation of fiber reactive dyes.

Description

Die Erfindung betrifft Verbindungen der allgemeinen Formel IThe invention relates to compounds of general formula I.

in der
m 1 oder 2,
n 0, 1 oder 2,
W gegebenenfalls durch C₁- bis C₄-Alkyl, Chlor, Brom oder Phenyl substituiertes C₂- bis C₄-Alkylen, Cycloalkylen oder Alkenylen oder gegebenenfalls durch Methyl, Ethyl, Methoxy, Ethoxy, Hydroxy, Chlor, Brom, Hydroxysulfonyl, Nitro, Amino, Acetylamino oder Carboxyl substituiertes Phenyl,
X gegebenenfalls durch Ethersauerstoff, Imino, Phenyl­ imino oder C₁- bis C₄-Alkylimino ein- bis dreimal un­ terbrochenes C₂- bis C₈-Alkylen oder ein Rest der Formelin the
m 1 or 2,
n 0, 1 or 2,
W optionally substituted by C₁ to C₄ alkyl, chlorine, bromine or phenyl, C₂ to C₄ alkylene, cycloalkylene or alkenylene or optionally by methyl, ethyl, methoxy, ethoxy, hydroxy, chlorine, bromine, hydroxysulfonyl, nitro, amino, acetylamino or carboxyl substituted phenyl,
X optionally by ether oxygen, imino, phenyl imino or C₁ to C₄ alkylimino one to three times uninterrupted C₂ to C₈ alkylene or a radical of the formula

Z ein Rest der FormelnZ is a remainder of the formulas

R Wasserstoff, C₁- bis C₄-Alkyl, Phenyl, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂SO₃H oder ein Rest der FormelR is hydrogen, C₁ to C₄ alkyl, phenyl, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂SO₃H or a radical of the formula

X-S(O)nYXS (O) n Y

L¹ und L² unabhängig voneinander C₁- bis C₄-Alkylen,
Y CH=CH₂, CH₂CH₂OH oder ein Rest der Formel C₂H₄Q, wobei Q für Hydroxy oder einen unter alkalischen Reaktions­ bedingungen abspaltbaren Rest steht,
Ar gegebenenfalls unabhängig voneinander ein- bis dreifach durch C₁- bis C₆-Alkyl, C₁- bis C₆-Alkoxy, Fluor, Chlor, Brom, Nitro, Amino, Hydroxy, Hydroxysulfonyl, Carboxyl, C₁- bis C₆-Alkoxycarbonyl, Acetylamino,L¹ and L² independently of one another C₁- to C₄ alkylene,
Y CH = CH₂, CH₂CH₂OH or a radical of the formula C₂H₄Q, where Q is hydroxyl or a radical which can be split off under alkaline reaction conditions,
Ar optionally independently from one to three times by C₁ to C₆ alkyl, C₁ to C₆ alkoxy, fluorine, chlorine, bromine, nitro, amino, hydroxy, hydroxysulfonyl, carboxyl, C₁ to C₆ alkoxycarbonyl, acetylamino,

oder einen Rest der Formelor a residue of the formula

SO₂NH-X-S(O)n-Y oder S(O)n-YSO₂NH-XS (O) n -Y or S (O) n -Y

substituiertes Phenyl oder Naphthyl sind, wobei R¹ und R² unabhängig voneinander für Wasserstoff oder C₁- bis C₆-Alkyl stehen und n, X und Y die angegebene Bedeutung haben.
m ist vorzugsweise 1 und n insbesondere 2.are substituted phenyl or naphthyl, where R¹ and R² independently represent hydrogen or C₁- to C--alkyl and n, X and Y have the meaning given.
m is preferably 1 and n is in particular 2.

Einzelne Reste W sind z. B.:Individual W are z. B .:

Weiterhin sind C₆H₃CH₃, C₆H₃Cl, C₆H₃Br, C₆H₂(CH₃)₂, C₆H₃NO₂, C₆H₃COOH und C₆H₃SO₃H zu nennen.Furthermore, C₆H₃CH₃, C₆H₃Cl, C₆H₃Br, C₆H₂ (CH₃) ₂, C₆H₃NO₂, C₆H₃COOH and to call C₆H₃SO₃H.

X ist insbesondere gegebenenfalls durch O, NH, NC₆H₅ oder N(C₁- bis C₄-Alkyl) unterbrochenes C₂- bis C₈-Alkylen.X is in particular optionally by O, NH, NC₆H₅ or N (C₁ to C₄ alkyl) interrupted C₂ to C₈ alkylene.

Einzelne Reste X sind beispielsweise CH₂CH₂, CH₂CH₂CH₂, CH₂CH₂OCH₂CH₂, CH₂CH₂NHCH₂CH₂,Individual radicals X are, for example, CH₂CH₂, CH₂CH₂CH₂, CH₂CH₂OCH₂CH₂, CH₂CH₂NHCH₂CH₂,

CH₂CH₂OCH₂CH₂OCH₂CH₂, CH₂CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₂, CH₂CH₂NHCH₂CH₂NHCH₂CH₂, C₄H₈ oderCH₂CH₂OCH₂CH₂OCH₂CH₂, CH₂CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₂, CH₂CH₂NHCH₂CH₂NHCH₂CH₂, C₄H₈ or

wobei die drei ersten Reste besonders bevorzugt sind.the first three radicals being particularly preferred.

Für R sind Methyl, Phenyl oder der Rest der Formel X-S(O)nY und insbesondere Wasserstoff bevorzugt.For R, methyl, phenyl or the rest of the formula XS (O) n Y and in particular hydrogen are preferred.

Unter alkalischen Reaktionsbedingungen abspaltbare Reste Q sind z. B.: OSO₃H, Cl, Br, OPO₃H, SO₂B oder OCOB, wobei B z. B. C₁- bis C₄-Alkyl oder Phenyl ist.Residues Q which can be split off under alkaline reaction conditions are e.g. Example: OSO₃H, Cl, Br, OPO₃H, SO₂B or OCOB, where B z. B. C₁ to C₄-alkyl or phenyl.

Y ist vorzugsweise CH=CH₂, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂Cl oder CH₂CH₂OCOCH₃.Y is preferably CH = CH₂, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂Cl or CH₂CH₂OCOCH₃.

Als Substituenten für Ar sind insbesondere Fluor, Chlor, Brom, Methyl, Hydroxy, Methoxy, Ethoxy, Hydroxysulfonyl, Carboxyl, Carbamoyl, Sulfamoyl, Nitro, Amino, Acetylamino oder Reste der FormelnAr, in particular fluorine, chlorine, bromine, Methyl, hydroxy, methoxy, ethoxy, hydroxysulfonyl, carboxyl, Carbamoyl, sulfamoyl, nitro, amino, acetylamino or residues of Formulas

SO₂NHX-S(O)nY oder S(O)nYSO₂NHX-S (O) n Y or S (O) n Y

zu nennen, wobei n, X und Y die angegebene Bedeutung haben und Verbindungen mit 1 oder 2 Substituenten bei Phenyl und bis zu drei Substituenten bei Naphthyl für Ar bevorzugt sind.to name, where n, X and Y have the meaning given and Compounds with 1 or 2 substituents on phenyl and up to three naphthyl substituents for Ar are preferred.

Die Verbindungen der Formel I eignen sich in Abhängigkeit von der Konstitution z. B. als Diazokomponenten (Ar durch NH₂ substi­ tuiert), als Kupplungskomponenten (Kupplungsstelle im Ar-Rest) oder als Reaktivanker, beispielsweise durch Verknüpfung einer Aminogruppe im Ar-Rest mit Cyanurchlorid.The compounds of formula I are suitable depending on the Constitution z. B. as diazo components (Ar by NH₂ substi tuiert), as coupling components (coupling point in the Ar rest) or as a reactive anchor, for example by linking one Amine group in the Ar residue with cyanuric chloride.

Zur Herstellung der Verbindungen der Formel I kann man z. B. Verbindungen der FormelTo prepare the compounds of formula I, z. B. Compounds of the formula

mit Verbindungen der Formelwith compounds of the formula

HZ-X-S(O)n-YHZ-XS (O) n -Y

umsetzen, m, n, W, Ar, Z, X und Y haben dabei die angegebenen Be­ deutungen.implement, m, n, W, Ar, Z, X and Y have the specified Be interpretations.

Einzelheiten der Umsetzungen können den Beispielen entnommen wor­ den, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.Details of the implementations can be found in the examples those in which there are details of parts and percentages, if not otherwise noted, refer to the weight.

Beispiel 1example 1

Eine Mischung aus 220 g des Bernsteinsäureimids der FormelA mixture of 220 g of the succinimide of the formula

und 133 g 2-Aminoethyl-2′-hydroxyethylsulfid wurde 3 Stunden auf 60-65°C erhitzt. Nach vollständigem Umsatz (DC-Kontrolle) wurde abgekühlt und die Produktsuspension mit 0,5 l Ethanol verdünnt.and 133 g of 2-aminoethyl-2'-hydroxyethyl sulfide was on for 3 hours Heated 60-65 ° C. After complete conversion (TLC control) cooled and the product suspension diluted with 0.5 l of ethanol.

Der Niederschlag wurde abgesaugt und getrocknet. Man isolierte 298 g der Verbindung der FormelThe precipitate was filtered off and dried. You isolated 298 g of the compound of the formula

¹H-NMR [D₆-DMSO]: δ = 2.3-2,7 (M, 8H), 3.2 (M, 2H), 35 (M, 2H), 4.7 (brS, OH), 7.6 (M, Aromaten-H), 7.9 (M, Aromaten-H), 8.1 (M, Aromaten-H), 8.7 (S, NH), 10.5 (S, NH) ppm.1 H-NMR [D₆-DMSO]: δ = 2.3-2.7 (M, 8H), 3.2 (M, 2H), 35 (M, 2H), 4.7 (brS, OH), 7.6 (M, aromatics-H), 7.9 (M, Aromatic H), 8.1 (M, Aromatic H), 8.7 (S, NH), 10.5 (S, NH) ppm.

Beispiel 2Example 2

Eine Mischung aus 220 g des Bernsteinsäureimids der FormelA mixture of 220 g of the succinimide of the formula

und 133 g 2-Aminoethyl-2′-hydroxyethylsulfid wurde 3 Stunden auf 60-65°C erhitzt. Nach dem Abkühlen gab man 250 ml Wasser zu und stellte den pH-Wert mit konz. Salzsäure auf 5,0. Nach Zugabe von 1 g Wolframsäure wurden dann bei 65 bis 80°C 248 g 30 gew.-%iges wäßriges Wasserstoffperoxid innerhalb einer Stunde zugetropft. Nach dem Abkühlen wurde der Niederschlag abgesaugt und getrock­ net. Man isolierte 325 g der Verbindung der Formeland 133 g of 2-aminoethyl-2'-hydroxyethyl sulfide was on for 3 hours Heated 60-65 ° C. After cooling, 250 ml of water were added and adjusted the pH with conc. Hydrochloric acid to 5.0. After adding 1 g of tungstic acid then became 248 g of 30% by weight at 65 to 80 ° C aqueous hydrogen peroxide added dropwise within an hour. After cooling, the precipitate was filtered off and dried net. 325 g of the compound of the formula were isolated

¹H-NMR [D⁶-DMSO]: δ= 2.5 (M, 3H), 2.6 (M, 2H), 3.2 (M, 4H), 3.5 (M, 1H), 3.8 (M, 2H), 5.1 (brS, OH), 7.6 (M, 1H, Aromaten-H), 7.9 (M, 2H, Aroma­ ten-H), 8.2 (M, 1H, Aromaten-H) 8.7 (brS,NH), 10.5 (brS, NH) ppm.1 H-NMR [D⁶-DMSO]: δ = 2.5 (M, 3H), 2.6 (M, 2H), 3.2 (M, 4H), 3.5 (M, 1H), 3.8 (M, 2H), 5.1 (brS, OH), 7.6 (M, 1H, aromatics-H), 7.9 (M, 2H, flavor ten-H), 8.2 (M, 1H, aromatics-H) 8.7 (brS, NH), 10.5 (brS, NH) ppm.

Beispiel 3Example 3

250 g des Produkts aus Beispiel 2 wurden in 1,5 Litern Äthanol/ THF-Gemisch (2/1) gelöst und in Gegenwart von 5 g eines Raney- Nickel-Katalysators bei 25-30°C unter Schütteln mit Wasserstoff begast. Nach beendeter Wasserstoffaufnahme wurde vom Katalysator abfiltriert und das Filtrat unter vermindertem Druck eingeengt. Man isolierte nach der Trocknung 228 g der Verbindung der Formel250 g of the product from Example 2 were dissolved in 1.5 liters of ethanol / THF mixture (2/1) dissolved and in the presence of 5 g of a Raney Nickel catalyst at 25-30 ° C with shaking with hydrogen fumigated. After the hydrogen uptake was complete, the catalyst filtered off and the filtrate was concentrated under reduced pressure. After drying, 228 g of the compound of the formula were isolated

Gehaltsbestimmung durch Diazotierung: 94%
¹H-NMR [D⁶-DMSO] δ= 2.4 (M, 2H), 2.5 (M, 2H), 3.2 (M, 4H), 3.4 (M, 2H), 3.8 (M, 2H), 5.0 (brS, NH₂), 5.1 (T, OH), 6.2 (M, 1H, Aromaten-H) 6.6 (M, 1H, Aromaten-H), 6.8 (M, 2H, Aromaten-H), 8.1 (brS, NH) 9.6 (brS, NH) ppm.Diazotization content determination: 94%
1 H-NMR [D⁶-DMSO] δ = 2.4 (M, 2H), 2.5 (M, 2H), 3.2 (M, 4H), 3.4 (M, 2H), 3.8 (M, 2H), 5.0 (brS, NH₂ ), 5.1 (T, OH), 6.2 (M, 1H, aromatics-H) 6.6 (M, 1H, aromatics-H), 6.8 (M, 2H, aromatics-H), 8.1 (brS, NH) 9.6 (brS , NH) ppm.

Beispiel 4Example 4

33 g der gemäß Beispiel 3 erhaltenen Verbindung wurden unter Eis­ kühlung bei 35-40°C in 98 g Monohydrat eingetragen und ungefähr 12 Stunden bei Raumtemperatur gerührt.33 g of the compound obtained according to Example 3 were under ice cooling at 35-40 ° C in 98 g monohydrate and approx Stirred for 12 hours at room temperature.

Nach vollständigem Umsatz (DC-Kontrolle) wurde die Mischung auf 300 g Eis gegossen, und anschließend durch Einstreuen von kalzi­ nierter Soda unter Rühren und Kühlung auf pH-Wert 5 eingestellt.After complete conversion (TLC control), the mixture was opened Poured 300 g of ice, and then sprinkled with kalzi nated soda adjusted to pH 5 with stirring and cooling.

Man erhält eine elektrolythaltige Lösung der Verbindung der FormelAn electrolyte-containing solution of the compound of the formula is obtained

die ohne weitere Reinigung zu Folgeumsetzungen, insbesondere Farbstoffsynthesen, verwendet werden kann.which follow up without further purification, in particular Dye syntheses can be used.

Beispiel 5Example 5

33 g des in Beispiel 3 erhaltenen Anilins wurden unter Eiskühlung bei 35-40°C in 98 g Oleum (24%ig) eingetragen und ungefähr 6 Stunden bei 55°C gerührt.33 g of the aniline obtained in Example 3 were cooled with ice at 35-40 ° C in 98 g of oleum (24%) and approx Stirred at 55 ° C for 6 hours.

Nach vollständigem Umsatz (DC-Kontrolle) wurde die Mischung auf 300 g Eis gegossen und anschließend durch Einstreuen kalzinierter Soda unter Rühren und Kühlung auf pH-Wert 5 gebracht.After complete conversion (TLC control), the mixture was opened 300 g of ice poured and then calcined by sprinkling Bring the soda to pH 5 with stirring and cooling.

Durch Abkühlen auf 0-5°C unter Rühren fiel Natriumsulfat aus, das nach ungefähr einer Stunde durch Absaugen entfernt wurde.Sodium sulfate precipitated out by cooling to 0-5 ° C. with stirring, which was removed by suction after about an hour.

Man erhält dann eine elektrolythaltige Lösung der Verbindung der FormelAn electrolyte-containing solution of the compound is then obtained formula

die ohne weitere Reinigung zu Folgeumsetzungen, insbesondere Farbstoffsynthesen verwendet werden kann.which follow up without further purification, in particular Dye syntheses can be used.

Claims (9)

1. Dicarbamoylverbindungen der allgemeinen Formel I in der
m 1 oder 2,
n 0,1 oder 2,
W gegebenenfalls durch C₁- bis C₄-Alkyl, Chlor, Brom oder Phenyl substituiertes C₂- bis C₄-Alkylen, Cycloalkylen oder Alkenylen oder gegebenenfalls durch Methyl, Ethyl, Methoxy, Ethoxy, Hydroxy, Chlor, Brom, Hydroxysulfonyl, Nitro, Amino, Acetylamino oder Carboxyl substituiertes Phenyl,
X gegebenenfalls durch Ethersauerstoff, Imino, Phe­ nylimino oder C₁- bis C₄-Alkylimino ein- bis drei­ mal unterbrochenes C₂- bis C₈-Alkylen oder ein Rest der Formel Z ein Rest der Formeln R Wasserstoff, C₁- bis C₄-Alkyl, Phenyl, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂SO₃H oder ein Rest der FormelX-S(O)nYL¹ und L² unabhängig voneinander C₁- bis C₄-Alkylen,
Y CH=CH₂, CH₂CH₂OH oder ein Rest der Formel C₂H₄Q, wobei Q für Hydroxy oder einen unter alkalischen Reaktionsbedingungen abspaltbaren Rest steht,
und
Ar gegebenenfalls unabhängig voneinander ein- bis dreifach durch C₁- bis C₆-Alkyl, C₁- bis C₆-Alkoxy, Fluor, Chlor, Brom, Nitro, Amino, Hydroxy, Hydroxysulfonyl, Carboxyl, C₁- bis C₆-Alkoxy­ carbonyl, Acetylamino, oder einen Rest der FormelSO₂NH-X-S(O)n-Y oder S(O)n-Ysubstituiertes Phenyl oder Naphthyl sind, wobei R¹ und R² unabhängig voneinander für Wasserstoff oder C₁- bis C₆-Alkyl stehen und n, X und Y die angegebene Bedeutung haben.1. Dicarbamoyl compounds of the general formula I in the
m 1 or 2,
n 0.1 or 2,
W optionally substituted by C₁ to C₄ alkyl, chlorine, bromine or phenyl, C₂ to C₄ alkylene, cycloalkylene or alkenylene or optionally by methyl, ethyl, methoxy, ethoxy, hydroxy, chlorine, bromine, hydroxysulfonyl, nitro, amino, acetylamino or carboxyl substituted phenyl,
X optionally by ether oxygen, imino, phenylimino or C₁- to C₄-alkylimino one to three times interrupted C₂- to C₈-alkylene or a radical of the formula Z is a remainder of the formulas R is hydrogen, C₁ to C₄ alkyl, phenyl, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂SO₃H or a radical of the formula X-S (O) n YL¹ and L² independently of one another C₁ to C- alkylene,
Y CH = CH₂, CH₂CH₂OH or a radical of the formula C₂H₄Q, where Q is hydroxyl or a radical which can be split off under alkaline reaction conditions,
and
Ar optionally independently from one to three times by C₁- to C Alkyl-alkyl, C₁- to C₆-alkoxy, fluorine, chlorine, bromine, nitro, amino, hydroxyl, hydroxysulfonyl, carboxyl, C₁- to C₆-alkoxy carbonyl, acetylamino, or a radical of the formula SO₂NH-XS (O) n -Y or S (O) n -Ysubstituted phenyl or naphthyl, where R¹ and R² independently of one another are hydrogen or C₁- to C₆-alkyl and n, X and Y are the indicated Have meaning. 2. Verbindungen der Formel gemäß Anspruch 1, wobei m 1 ist.2. Compounds of the formula according to claim 1, wherein m is 1. 3. Verbindungen der Formel gemäß Anspruch 1, wobei n 2 ist.3. Compounds of the formula according to claim 1, wherein n is 2. 4. Verbindungen der Formel gemäß Anspruch 1, wobei ist.4. Compounds of the formula according to claim 1, wherein is. 5. Verbindungen der Formel gemäß Anspruch 1, wobei
X gegebenenfalls durch O, NH oder NR⁴ unterbrochenes C₂- bis C₈-Alkylen mit R⁴ C₁- bis C₄-Alkyl oder Phenyl ist.5. Compounds of the formula according to claim 1, wherein
X is optionally interrupted by O, NH or NR⁴ C₂ to C₈ alkylene with R⁴ C₁ to C₄ alkyl or phenyl. 6. Verbindungen der Formel gemäß Anspruch 1, wobei
R Wasserstoff, Methyl, Phenyl oder ein Rest der Formel X-S(O)nY ist und n, X und Y die angegebene Bedeutung ha­ ben.6. Compounds of the formula according to claim 1, wherein
R is hydrogen, methyl, phenyl or a radical of the formula XS (O) n Y and n, X and Y have the meaning given. 7. Verbindungen der Formel gemäß Anspruch 1, wobei
Y CH=CH₂, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂Cl oder CH₂CH₂OCOCH₃ ist.7. Compounds of the formula according to claim 1, wherein
Y is CH = CH₂, CH₂CH₂OH, CH₂CH₂OSO₃H, CH₂CH₂Cl or CH₂CH₂OCOCH₃. 8. Verbindungen der Formel gemäß Anspruch 1, wobei
Ar gegebenenfalls ein- bis dreifach durch Fluor, Chlor, Brom, Methyl, Hydroxy, Methoxy, Ethoxy, Hydroxysulfonyl, Carboxyl, Carbamoyl, Sulfamoyl, Nitro, Amino, Acetylamino oder einen Rest der Formel SO₂NH-X-S(O)nY oder S(O)n-Y substituiertes Phenyl oder Naphthyl sind, wobei n, X und Y die angegebene Bedeutung haben.8. Compounds of the formula according to claim 1, wherein
Ar optionally one to three times by fluorine, chlorine, bromine, methyl, hydroxy, methoxy, ethoxy, hydroxysulfonyl, carboxyl, carbamoyl, sulfamoyl, nitro, amino, acetylamino or a radical of the formula SO₂NH-XS (O) n Y or S ( O) n -Y are substituted phenyl or naphthyl, where n, X and Y have the meaning given. 9. Verwendung der Verbindungen gemäß Anspruch 1 zur Herstellung von faserreaktiven Farbstoffen.9. Use of the compounds according to claim 1 for the preparation of fiber-reactive dyes.
DE1996105678 1996-02-15 1996-02-15 Diacarbamoyl compounds Withdrawn DE19605678A1 (en)

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DE1996105678 DE19605678A1 (en) 1996-02-15 1996-02-15 Diacarbamoyl compounds
AU18724/97A AU1872497A (en) 1996-02-15 1997-02-11 Dicarbamoyl compounds
PCT/EP1997/000616 WO1997030025A1 (en) 1996-02-15 1997-02-11 Dicarbamoyl compounds
IDP970442A ID15951A (en) 1996-02-15 1997-02-17 COMPOUNDS IN CARBAMOIL

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