NL8202994A - PROCESS FOR PREPARING A SULFONAMIDE GROUP CONTAINING PHENOXYBENZOIC ACID DERIVATIVES - Google Patents

PROCESS FOR PREPARING A SULFONAMIDE GROUP CONTAINING PHENOXYBENZOIC ACID DERIVATIVES Download PDF

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NL8202994A
NL8202994A NL8202994A NL8202994A NL8202994A NL 8202994 A NL8202994 A NL 8202994A NL 8202994 A NL8202994 A NL 8202994A NL 8202994 A NL8202994 A NL 8202994A NL 8202994 A NL8202994 A NL 8202994A
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group
formula
reaction
process according
alkyl
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NL8202994A
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Rhone Poulenc Agrochimie
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
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    • C07C311/52—Y being a hetero atom
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    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
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    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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    • C07C323/10—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 singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07C323/35—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
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Description

* -1- 9 ** -1- 9 *

Werkwijze voor het bereiden van een sulfon-amidegroep bevattende fenoxybenzoezuurderivaten.Process for preparing a sulfone amide group containing phenoxybenzoic acid derivatives.

De uitvinding heeft betrekking op een verbeterde werk- wijze voor het bereiden van een sulfonamidegroep bevattende fenoxybenzoezuurderivaten met herbicide eigenschappen.The invention relates to an improved method for preparing a sulfonamide group containing phenoxybenzoic acid derivatives with herbicidal properties.

In de Europese octrooiaanvragen 3.416 en 23.392 zijn 5 een sulfonamidegroep bevattende fenoxybenzoezuurderivaten en zouten daarvan met herbicide eigenschappen beschreven, Deze verbindingen hebben de formule 1 op het formuleblad waarin A waterstof, fluor, chloor, broom, jood, een nitrogroep, -N=NCFg, PO3H2 en de alkytesters met 1-4 koolstofatomen 10 daarvan, NE^, NHOH, N^» een carboxylgroep of een functioneel derivaat daarvan, een monoalkylamino- of dialkylaminogroep, 1 1 of een groep NH-CO-R voorstelt waarin R een alkyl-, alkoxy-, monoalkylamino- of dialkylaminogroep voorstelt, A verder een 2 alkylgroep, een trialkylammoniumgroep of een groep NHSO-R of 2 2 Z 15 NHCONHSC^R voorstelt waarin R een alkyl- of fenylgroep voorstelt, en A voorts alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonium, cyanosulfonyl, hydroxyl, alkanoyloxy, al dan niet alkoxycarbonyl gesubstitueerd alkoxy, SH, nitroso, -SCN, azide, CF0, -N=N-P-(OCEL)0 of acyl voorstelt, 3 I ό Δ 20 ? B waterstof, fluor, chloor, broom, jood, alkyl, alkoxy, alkylsulfinyl, alkylsulfonyl, CF^, NC^, CN, NI^, NHCOR waarin R^ boven aangegeven betekenis heeft, of CONH^, voorstelt, C waterstof, een halogeenatoom of een alkyl- of dialkyl-25 aminogroep voorstelt, D fluor, chloor, broom, jood, CF^, alkylthio, alkylsulfinyl, alkylsulfonyl, halogeenalkyl, sulfamoyl, formyl, 8202994 *» * -2- 4 alkylcarbonyl, CN of een dimethylaminogroep voorstelt, E waterstof, een halogeenalkyl-, alkoxy-, alkyl- sulfinyl- of alkylsulfonylgroep, CN, CF„, NH9, C0NH_ of 1.1 J z z NH-CO-R waarin R boven aangegeven betekenis heeft, voorstelt, 5 F een van de voor B aangegeven betekenissen heeft, enEuropean patent applications 3,416 and 23,392 disclose a sulfonamide group containing phenoxybenzoic acid derivatives and salts thereof with herbicidal properties. These compounds have the formula 1 on the formula sheet in which A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N = NCFg, PO3H2 and the alkytesters with 1 to 4 carbon atoms thereof, NE ^, NHOH, N ^ »a carboxyl group or a functional derivative thereof, a monoalkylamino or dialkylamino group, 1 L or a group NH-CO-R wherein R represents an alkyl , alkoxy, monoalkylamino or dialkylamino group, A further represents a 2 alkyl group, a trialkylammonium group or a group NHSO-R or 2 2 Z 15 NHCONHSC ^ R where R represents an alkyl or phenyl group, and A further represents alkylthio, alkylsulfinyl, alkylsulfonyl , dialkylsulfonium, cyanosulfonyl, hydroxyl, alkanoyloxy, whether or not alkoxycarbonyl substituted alkoxy, SH, nitroso, -SCN, azide, CF0, -N = NP- (OCEL) 0 or acyl, 3 I ό Δ 20? B hydrogen, fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylsulfinyl, alkylsulfonyl, CF ^, NC ^, CN, NI ^, NHCOR where R ^ has the meaning indicated above, or CONH ^, C represents hydrogen, a halogen atom or an alkyl or dialkyl-25 amino group, D represents fluorine, chlorine, bromine, iodine, C 25, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, sulfamoyl, formyl, 8202994 * -2-4 alkylcarbonyl, CN or a dimethylamino group E represents hydrogen, a haloalkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CN, CF 4, NH 9, CO 2 NH or 1.1 J 2 NH-CO-R where R has the meaning indicated above, 5 F represents one of the B has declared meanings, and

A3 AA3 A.

R een groep -C0N(R jSCLRJ voorstelt waarin RH waterstof 1 3R represents a group -C0N (R jSCLRJ in which RH hydrogen 1 3

of een alkylgroep met 1 - 4 koolstofatomen voorstelt, en Ror represents an alkyl group of 1 to 4 carbon atoms, and R

een fenyl-, pyridyl- of thienylgroep eventueel gesubstitueerd door een of meer halogeenatomen, alkylgroepen of nitrogroepen, 10 een alkenyl- of alkynylgroep met 2-4 koolstofatomen, of een alkylgroep met 1 - 4 koolstofatomen eventueel gesubstitueerd door een of meer fluor-, chloor-, broom- en/of joodatomen, bij voorkeur CF^, of door een of meer van de volgende substitu-enten: carboxyl, alkoxycarbonyl met 2-5 koolstofatomen, 15 alkylcarbonyl met 2-5 koolstofatomen, monoalkylcarbamoyl of dialkylcarbamoyl met in de alkylgroepen 1 - 4 koolstofatomen, alkylthio, alkylsulfinyl, alkylsulfonyl, elk met 1 - 4 koolstofatomen, alkylcarbonyloxy met 2-5 koolstofatomen, alkyl-carbonylamino met 2-5 koolstofatomen of cyaan.a phenyl, pyridyl or thienyl group optionally substituted by one or more halogen, alkyl or nitro groups, an alkenyl or alkynyl group with 2 to 4 carbon atoms, or an alkyl group with 1 to 4 carbon atoms optionally substituted by one or more fluorine, chlorine -, bromine and / or iodine atoms, preferably CF ^, or by one or more of the following substituents: carboxyl, alkoxycarbonyl with 2-5 carbon atoms, alkylcarbonyl with 2-5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl with in the alkyl groups 1-4 carbon atoms, alkylthio, alkylsulfinyl, alkylsulfonyl, each having 1-4 carbon atoms, alkylcarbonyloxy having 2-5 carbon atoms, alkylcarbonylamino having 2-5 carbon atoms, or cyano.

20 Volgens de bekende werkwij zen kunnen de verbindingen met de formule 1 worden bereid door reaktie van een overeen-komstig zuurhalogenide met de formule 2 waarin X chloor, broom of jood voorstelt en A, B, C, D, E en F de boven aangegeven betekenis hebben, met een sulfonamide met de . 3 ...According to the known methods, the compounds of the formula I can be prepared by reacting a corresponding acid halide of the formula 2 wherein X represents chlorine, bromine or iodine and A, B, C, D, E and F the above indicated meaning, with a sulfonamide with the. 3 ...

25 formule 3 waarin R de boven aangegeven betekenis heeft, bij 25 - 140°C, in aanwezigheid van een zuuracceptor, in het bij-zonder een tertiair amine zoals Ν,Ν-dimethylaniline of pyridine, een alkalimetaalcarbonaat zoals watervrij kaliumcarbonaat, of een alkalimetaalfluoride zoals cesiumfluoride.Formula 3 wherein R has the meaning indicated above, at 25-140 ° C, in the presence of an acid acceptor, especially a tertiary amine such as Ν, Ν-dimethylaniline or pyridine, an alkali metal carbonate such as anhydrous potassium carbonate, or an alkali metal fluoride such as cesium fluoride.

4 30 De verbindingen met de formule 1 waarin R een waterstof- atoom is, kunnen op bekende wijze worden gealkyleerd bijvoor-beeld door reaktie met een diazoalkaan met 1 - 4 koolstofatomen, onder vorming van een overeenkomstige verbinding 4 waarin R een alkylgroep met 1 - 4 koolstofatomen is.The compounds of formula I wherein R is a hydrogen atom can be alkylated in known manner, for example, by reaction with a diazoalkane of 1 to 4 carbon atoms to form a corresponding compound 4 wherein R is an alkyl group of 1 - 4 Is 4 carbon atoms.

35 Deze bekende werkwijzen voor de condensatie van een verbinding met de formule 2 met een verbinding met de formule 3 8202994 * ·«*.These known processes for the condensation of a compound of the formula II with a compound of the formula 38202994 * * «*.

-3- heeft verschillende nadelen. De opbrengsten zijn middelmatig (de opbrengsten in voorbeeld 14 en 34 van de Europese octrooiaan-vrage . 23.392 bijvoorbeeld kunnen worden berekend op respectie-velijk 27% en 9,5%).-3- has several drawbacks. The yields are mediocre (the yields in Examples 14 and 34 of European Patent Application. 23,392, for example, can be calculated at 27% and 9.5%, respectively).

5 Gevonden is, dat deze slechte opbrengsten kunnen worden toegeschreven aan de aanwezigheid van de zuuracceptor die bij deze bekende werkwijzen wordt toegepast. Aangenomen wordt, dat de zuuracceptor de diacyleringsreaktie bevordert.It has been found that these poor yields can be attributed to the presence of the acid acceptor used in these known processes. The acid acceptor is believed to promote the diacylation reaction.

De uitvinding heeft geleid tot een werkwijze voor het 10 bereiden van verbindingen met de formule 1 door reaktie van een overeenkomstig zuurhalogenide (bij voorkeur een chloride, bromide of jodide) met een sulfonamide met de formule 3 in afwezigheid van een zuuracceptor en bij een temperatuur waar-bij het gevormde waterstofhalogenide (HC1, HBr, HI) als damp 15 uit het reaktiemedium wordt verwijderd, maar zonder dat het reaktieprodukt met de formule 1 aanmerkelijk wordt ontleed.The invention has led to a process for preparing compounds of the formula 1 by reacting a corresponding acid halide (preferably a chloride, bromide or iodide) with a sulfonamide of the formula 3 in the absence of an acid acceptor and at a temperature where - the hydrogen halide (HCl, HBr, HI) formed is removed from the reaction medium as vapor 15, but without the reaction product of formula I being decomposed significantly.

Met de werkwijze volgens de uitvinding is het mogelijk om aanzienlijk hogere opbrengsten van sulfonamidederivaten van fenoxybenzoezuren te verkrijgen, bijvoorbeeld van tenminste 20 ongeveer 30% en meestal van tenminste ongeveer 50%.Bovendien heeft de werkwijze volgens de uitvinding het voordeel dat de reaktieprodukten makkelijker kunnen worden gelsoleerd en ge-zuiverd dan bij de bekende werkwijzen waarbij een zuuracceptor wordt gebruikt.With the process according to the invention it is possible to obtain considerably higher yields of sulfonamide derivatives of phenoxybenzoic acids, for example from at least about 30% and usually from at least about 50%. In addition, the process according to the invention has the advantage that the reaction products can be made easier isolated and purified then in the known methods using an acid acceptor.

25 Bij uitvoering van de werkwijze volgens de uitvinding wordt een zuurhalogenide met de formule 2 gebruikt waarinWhen carrying out the process according to the invention, an acid halide of the formula II is used in which

A bij voorkeur fluor, chloor, broom, jood of NO2 is, BA is preferably fluorine, chlorine, bromine, iodine or NO2, B

halogeen is, C, E en F elk waterstof zijn en D CF^ is.halogen, C, E and F are each hydrogen and D is CF ^.

Als sulfonamiden worden bij voorkeur verbindingen met de . 3 .As sulfonamides, compounds with the. 3.

30 formule 3 gebruikt waarin R een alkylgroep is, m het bij-zonder CH^ of CF^.30 uses formula 3 wherein R is an alkyl group, m especially CH 2 or CF 2.

De temperatuur waarbij de werkwijze volgens de uitvinding kan worden uitgevoerd, is in het bijzonder afhanke-lijk van de omstandigheid of het zuurhalogenide met de formule 35 2 of het sulfonamide met de formule 3 in grote overmaat wordt toegepast, of dat al of niet een oplosmiddel met katalytische 8202994 -4- eigenschappen wordt gebruikt.The temperature at which the process according to the invention can be carried out depends in particular on the fact whether the acid halide of the formula II 2 or the sulfonamide of the formula 3 is used in large excess or whether or not a solvent with catalytic 8202994-4 properties is used.

Wanneer het zuurhalogenide met de formule 2 in een grote overmaat wordt toegepast, bijvoorbeeld in een mol-verhouding met het sulfonamide met de formule 3 van ongeveer 5 1,5 tot 5, kan het zuurhalogenide als oplosmiddel voor de reaktie dienen en kan de reaktie bij een temperatuur van 80 - 200°C, bij voorkeur 90 - 160°C, worden uitgevoerd.When the acid halide of the formula II is used in a large excess, for example in a molar ratio with the sulfonamide of the formula 3 of about 1.5 to 5, the acid halide can serve as a solvent for the reaction and the reaction can a temperature of 80-200 ° C, preferably 90-160 ° C.

Niet-gereageerd zuurhalogenide met de formule 2 kan uit het reaktiemengsel worden teruggewonnen door was sen met een 10 inert oplosmiddel zoals een koolwaterstof, in het bijzonder pentaan, hexaan, heptaan, cyclopentaan, cyclohexaan, cyclo-heptaan, benzeen, tolueen of xyleen, een gehalogeneerde koolwaterstof, in het bijzonder chloorbenzenen, CS2, tetra-hydrofuran, of dioxan.Unreacted acid halide of the formula II can be recovered from the reaction mixture by washing with an inert solvent such as a hydrocarbon, in particular pentane, hexane, heptane, cyclopentane, cyclohexane, cyclo-heptane, benzene, toluene or xylene, a halogenated hydrocarbon, especially chlorobenzenes, CS2, tetrahydrofuran, or dioxane.

15 Wanneer het sulfonamide met de formule 3 in een overmaat wordt toegepast, bijvoorbeeld in een molverhouding ten opzichte van het zuurhalogenide met de formule 2 van 1,5 - 5, wordt de reaktie in het algemeen uitgevoerd bij 90 - 200°C en bij voorkeur bij 140 - 160°C. In elk geval moet de reaktietemperatuur 20 voldoende hoog zijn om het reaktiemengsel te doen smelten.When the sulfonamide of the formula III is used in excess, for example in a molar ratio to the acid halide of the formula II of 1.5-5, the reaction is generally carried out at 90-200 ° C and preferably at 140-160 ° C. In any case, the reaction temperature must be high enough to melt the reaction mixture.

Overmaat sulfonamide met de formule 3 kan uit het reaktiemengsel worden teruggewonnen door wassen met wafer of een ander oplosmiddel dat inert is voor het sulfonamide : · met de formule 3.Excess sulfonamide of the formula III can be recovered from the reaction mixture by washing with a wafer or other solvent inert to the sulfonamide: of the formula III.

25 De reaktanten kunnen 00k worden opgelost in een inert oplosmiddel met een kookpunt dat boven de reaktietemperatuur ligt, bijvoorbeeld een al dan niet gechloreerde vloeibare koolwaterstof zoals benzeen, tolueen, xylenen, mengsels van xylenen of cumeen. In dat geval is het voordelig wanneer de 30 maximum reaktietemperatuur even onder het kookpunt van het oplosmiddel ligt. Bij gebruik van cumeen (kookpunt ongeveer 153°C) bijvoorbeeld, wordt de reaktie bij voorkeur uitgevoerd tussen 130 en 150°C. Het gebruik van een inert oplosmiddel heeft het voordeel van een betere warmteoverdracht bij uit-35 voering op technische schaal. Bovendien kan er plaatselijke 8202994 -5- λ: ·£·The reactants can also be dissolved in an inert solvent with a boiling point above the reaction temperature, for example a chlorinated or non-chlorinated liquid hydrocarbon such as benzene, toluene, xylenes, mixtures of xylenes or cumene. In that case it is advantageous if the maximum reaction temperature is just below the boiling point of the solvent. For example, using cumene (boiling point about 153 ° C), the reaction is preferably conducted between 130 and 150 ° C. The use of an inert solvent has the advantage of better heat transfer on a technical scale. In addition, local 8202994 -5- λ: · £ ·

<S<S

oververhitting van het reaktiemengsel mee worden vermeden.overheating of the reaction mixture should also be avoided.

Volgens een andere uitvoeringsvorm van de werkwijze volgens de uitvinding wordt een oplosmiddel gebruikt dat de reaktie van het zuurhalogenide met de formule 2 met het . 5 sulfonamide met de formule 3 tot het fenoxybenzoylsulfonamide met de formule 1 katalyseert. Bijzonder geschikt zijn dimethylformamide ( kookpunt ongeveer 154°C) en dimethy1-aceetamide (kookpunt ongeveer 164°C) waarmee betrekkelijk lage reaktietemperaturen kunnen worden toegepast, bijvoor-10 beeld van 80 - 120°C en bij voorkeur van 90 - 110°C, of hogere temperaturen even beneden het kookpunt van deze oplosmiddelen.According to another embodiment of the process according to the invention, a solvent is used which reacts the acid halide of the formula II with the. 5 catalyses sulfonamide of the formula 3 until the phenoxybenzoyl sulfonamide of the formula 1. Particularly suitable are dimethylformamide (boiling point about 154 ° C) and dimethyl acetamide (boiling point about 164 ° C) with which relatively low reaction temperatures can be used, for example from 80 to 120 ° C and preferably from 90 to 110 ° C, or higher temperatures just below the boiling point of these solvents.

De reaktie verloopt dan sneller.The reaction then proceeds faster.

Voorbeeld IExample I

Methaansulfonamide (2g, 0,021 mol) wordt gemengd met 15 5-Cl' -chloor-41 - (tr if luormethyl) -f enoxy^^-nitrobenzoyl- chloride (3,8g, 0,01 mol). Het mengsel wordt 20 minuten ver- warmd bij 150°C. Tijdens de reaktie wordt gevormd waterstof- chloride afgevoerd. Na afkoelen wordt het reaktieprodukt, een zwarte olie, opgelost in een waterige natriumhydroxyde- 20 oplossing. De oplossing wordt gefiltreerd en het filtraat wordt aangezuurd met verdund zoutzuur onder precipitatie van een verbinding met de formule 4 in een opbrengst van 71% (3,1g) en met een smeltpunt van 195 - 197°C. I.R. absorptie _ 1 bij 1692 cm (C = 0 groep).Methanesulfonamide (2g, 0.021 mol) is mixed with 15 5-Cl'-chloro-41 - (trofluoromethyl) phenoxy nitrobenzoyl chloride (3.8g, 0.01 mol). The mixture is heated at 150 ° C for 20 minutes. Hydrogen chloride formed is removed during the reaction. After cooling, the reaction product, a black oil, is dissolved in an aqueous sodium hydroxide solution. The solution is filtered and the filtrate is acidified with dilute hydrochloric acid to precipitate a compound of the formula 4 in a yield of 71% (3.1g) and mp 195-197 ° C. I.R. absorbance _ 1 at 1692 cm (C = 0 group).

25 Voorbeeld IIExample II

Voorbeeld I wordt herhaald maar met 250g zuurchloride en 130g methaansulfonamide. Het reaktieprodukt wordt meteen na afkoelen van het reaktiemengsel gelsoleerd, door omkristalli- seren in isopropanol.De opbrengst waarin de verbinding met 30 de formule 4 wordt verkregen, bedraagt 64% (185g). I.R. ab- . ..-1 sorptie bij 1692 cm . NMR: singlet bij 3,5 ppm, multiplet bij 8,07 ppm.Example I is repeated but with 250g of acid chloride and 130g of methanesulfonamide. The reaction product is isolated immediately after cooling the reaction mixture by recrystallization in isopropanol. The yield in which the compound of the formula IV is obtained is 64% (185g). I.R. ab-. ..- 1 sorption at 1692 cm. NMR: singlet at 3.5 ppm, multiplet at 8.07 ppm.

VergelijkingsvoorbeeldComparative example

Voorbeeld II wordt herhaald maar met pyridine als zuur-35 acceptor. De opbrengst bedraagt slechts 25%.Example II is repeated but with pyridine as an acid acceptor. The yield is only 25%.

82029948202994

Claims (17)

1. Werkwi j ze voor het bereiden van een sulfonamide-groep bevattend fenoxybenzoezuurderivaat met de formule 1 en de zouten daarvan, waarin 5. waterstof, fluor, chloor, broom, jood, een nitro- groep, -N=NCF3, en alkylesters met 1 - 4 koolstof- atomen daarvan, N^, NHOH, N* , een carboxylgroep of een functioneel derivaat daarvan, een monoalkylamino of dialky1- 1 . 1 aminogroep of een groep NH-CO-R voorstelt waarin R een 10 alkyl, alkoxy, monoalkylamino of dialkylaminogroep voorstelt, A verder een alkylgroep, trialkylammoniumgroep of een groep 2 2 2 NHSO2R of NHCONHSOgR voorstelt waarin R een alkyl of fenyl-groep voorstelt, en A voorts alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonium, eyaansulfonyl, hydroxyl, 15 alkanoyloxy, al dan niet alkoxycarbonyl gesubstitueerd alkoxy, SH, nitroso, -SCN, azide, CF^, -N=N-P-(OCH^^ of acyl voorstelt, 4/ 0 B waterstof, fluor, chloor, broom, jood, een alkyl, alkoxy, alkylsulfinyl of alkylsulfonylgroep, CF„, NCL, CN, 20 1.1 . L NH^, NHCOR waarin R boven aangegeven betekenis heeft, of CONH2 voorstelt, C waterstof, een halogeenatoom of een alkyl of dialkyl-aminogroep voorstelt, D fluor, chloor, broom, jood of een CF«, alkylthio, 25 ^ alkylsulfinyl, alkylsulfonyl, halogeenalkyl, sulfamoyl, formyl, alkylcarbonyl, CN of dimethylaminogroep voorstelt, E waterstof, een halogeenalkyl, alkoxy, alkylsulfinyl of alkylsulfonylgroep, CN, CF3, NH2, C0NH2 of NH-CO-R1 waarin R1 boven aangegeven betekenis heeft, voorstelt, 30 F een van de voor B aangegeven betekenissen heeft, en / 4% 3 . 4 R een groep -C0N(R )S0„R voorstelt waarin R waterstof 8202994 3 of een alkylgroep met 1 - 4 koolstofatomen voorstelt en R een fenyl, pyridyl of thienylgroep eventueel gesubstitueerd door een of meer halogeenatomen, alkylgroepen of nitrogroepen, een 35 alkenyl of alkynylgroep met 2-4 koolstofatomen, of een alkyl- -7- groep met 1 - 4 koolstofatomen eventueel gesubstitueerd door een of meer fluor, chloor, broom of joodatomen, bij voorkeur CF^, of door een of meer carboxyl, alkoxycarbonyl met 2-5 koolstofatomen, alkylcarbonyl met 2-5 koolstofatomen, 5 monoalkylcarbamoyl of dialkylcarbamoyl met in de alkylgroepen 1 - 4 koolstofatomen, alkylthio, alkylsulfinyl, alkylsulfonyl, elk met 1-4 koolstofatomen, alkoxycarbonyloxy met 2-5 koolstofatomen, alkylcarbonylamino met 2-5 koolstofatomen of cyaangroepen, voorstelt, door reaktie van een zuurhalogenide met 10 de formule 2 waarin X een chloor, broom of joodatoom voorstelt en A, B, C, E en F boven aangegeven betekenis hebben, met een sulfonamide met de formule 3 waarin R boven aangegeven betekenis heeft, met het kenmerk, dat de reaktie wordt uitge-voerd bij afwezigheid .van een zuuracceptor en bij een tempera-15 tuur waarbij gevormd waterstofhalogenide als damp uit het reaktiemengsel wordt verwijderd maar beneden een temperatuur waarbij de gevormde verbinding met de formule 1 al te zeer wordt ontleed.1. Process for preparing a sulfonamide group containing phenoxybenzoic acid derivative of the formula 1 and its salts, wherein 5. hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N = NCF3, and alkyl esters with 1-4 carbon atoms thereof, N4, NHOH, N *, a carboxyl group or a functional derivative thereof, a monoalkylamino or dialky1-1. 1 represents an amino group or a group NH-CO-R wherein R represents an alkyl, alkoxy, monoalkylamino or dialkylamino group, A further represents an alkyl group, trialkylammonium group or a group 2 2 2 NHSO2R or NHCONHSOgR wherein R represents an alkyl or phenyl group, and A further represents alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonium, eyanesulfonyl, hydroxyl, alkanoyloxy, whether or not alkoxycarbonyl substituted alkoxy, SH, nitroso, -SCN, azide, CF ^, -N = NP- (OCH ^ ^ or acyl, 4/0 B hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CF 1, NCL, CN, 1.1 L NH 2, NHCOR wherein R has the meaning indicated above, or CONH 2, C hydrogen represents a halogen atom or an alkyl or dialkyl amino group, D represents fluorine, chlorine, bromine, iodine or a CF 1, alkylthio, alkyl sulfulfyl, alkyl sulfonyl, haloalkyl, sulfamoyl, formyl, alkyl carbonyl, CN or dimethylamino group, E represents hydrogen, a haloalkyl, alkoxy, a 1kylsulfinyl or alkylsulfonyl group, CN, CF 3, NH 2, CO 3 NH 2 or NH-CO-R 1 wherein R 1 has the meanings indicated above, 30 F has one of the meanings indicated for B, and / 4% 3. 4 R represents a group -CON (R) S0 „R wherein R represents hydrogen 8202994 3 or an alkyl group having 1 to 4 carbon atoms and R represents a phenyl, pyridyl or thienyl group optionally substituted by one or more halogen, alkyl or nitro groups, an alkenyl or alkynyl group with 2-4 carbon atoms, or an alkyl -7 group with 1 - 4 carbon atoms optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, preferably CF ^, or by one or more carboxyl, alkoxycarbonyl with 2 -5 carbon atoms, alkylcarbonyl of 2-5 carbon atoms, 5 monoalkylcarbamoyl or dialkylcarbamoyl of in the alkyl groups 1 to 4 carbon atoms, alkylthio, alkylsulfinyl, alkylsulfonyl, each of 1-4 carbon atoms, alkoxycarbonyloxy of 2-5 carbon atoms, alkylcarbonylamino of 2-5 carbon atoms or cyano groups, by reacting an acid halide of formula 2 wherein X represents a chlorine, bromine or iodine atom and A, B, C, E and F have the meanings indicated above, with a sulfonamide of formula III wherein R has the meaning indicated above, characterized in that the reaction is carried out in the absence of an acid acceptor and at a temperature in which hydrogen halide formed is removed from the reaction mixture as vapor but below a temperature wherein the formed compound of formula 1 is decomposed too much. 2. Werkwijze volgens conclusie 1, met het kenmerk dat, 20 de reaktie wordt uitgevoerd bij aanwezigheid van een over- maat zuurhalogenide met de formule 2,2. Process according to claim 1, characterized in that the reaction is carried out in the presence of an excess of acid halide of the formula 2, 3. Werkwijze volgens conclusie 2, met het kenmerk dat, het zuurhalogenide met de formule 2 wordt toegepast in een molverhouding ten opzichte van het sulfonamide met de formule 25. van 1,5 tot 5.Process according to claim 2, characterized in that the acid halide of the formula II is used in a molar ratio to the sulfonamide of the formula 25. from 1.5 to 5. 4. Werkwijze volgens conclusie 2 of 3, met het kenmerk dat, de reaktie wordt uitgevoerd bij een temperatuur van 80 - 200°C en bij voorkeur van 90 - 160°C.Process according to claim 2 or 3, characterized in that the reaction is carried out at a temperature of 80 - 200 ° C and preferably of 90 - 160 ° C. 5. Werkwijze volgens conclusie 1, met het kenmerk dat, 30 de reaktie wordt uitgevoerd bij aanwezigheid van een over- maat sulfonamide.5. Process according to claim 1, characterized in that the reaction is carried out in the presence of an excess of sulfonamide. 6. Werkwijze volgens conclusie 5, met het kenmerk dat, het sulfonamide met de formule 3 wordt toegepast in een molverhouding ten opzichte van het zuurhalogenide met de formule 35. van 1,5 tot 5. 8202994 (: -8- * τ·Process according to claim 5, characterized in that the sulfonamide of the formula III is used in a molar ratio to the acid halide of the formula 35. from 1.5 to 5. 8202994 (: -8- * τ · 7. Werkwijze volgens conclusie 5 of 6, met het kenmerk dat, de reaktie wordt uitgevoerd bij een temperatuur van 90 - 200°C en bij voorkeur van 140 - 160°C.Process according to claim 5 or 6, characterized in that the reaction is carried out at a temperature of 90-200 ° C and preferably 140-160 ° C. 8. Werkwijze volgens conclusies 1-7, met het kenmerk 5 dat, de reaktie wordt uitgevoerd in een oplosmiddel met een kookpunt hoger dan de reaktietemperatuur.8. Process according to claims 1-7, characterized in that the reaction is carried out in a solvent with a boiling point higher than the reaction temperature. 9. Werkwijze volgens conclusie 8, met het kenmerk dat, de reaktie wordt uitgevoerd in een koolwaterstof als oplosmiddel .Process according to claim 8, characterized in that the reaction is carried out in a hydrocarbon as a solvent. 10. Werkwijze volgens conclusie 9, met het kenmerk dat, de reaktie wordt uitgevoerd in cumeen als oplosmiddel en bij een temperatuur van 130 - 150°C.Process according to claim 9, characterized in that the reaction is carried out in cumene as a solvent and at a temperature of 130-150 ° C. 11. Werkwijze volgens conclusies 1-8, met het kenmerk dat, de reaktie wordt uitgevoerd in een oploaniddel dat 15 de reaktie van het zuurhalogenide met de formule 2 en het sulfonamide met de formule 3 katalyseert.11. Process according to claims 1-8, characterized in that the reaction is carried out in a solubilizing agent which catalyzes the reaction of the acid halide of the formula 2 and the sulfonamide of the formula 3. 12. Werkwijze volgens conclusie 11, met het kenmerk dat, de reaktie wordt uitgevoerd in dimethylformamide of dimethylaceetamide als oplosmiddel en bij een temperatuur 20 tussen 80°C en het kookpunt van het oplosmiddel.12. Process according to claim 11, characterized in that the reaction is carried out in dimethylformamide or dimethylacetamide as a solvent and at a temperature between 80 ° C and the boiling point of the solvent. 13. Werkwijze volgens conclusie 12, met het kenmerk dat, de reaktie wordt uitgevoerd bij een temperatuur boven 90°C.Process according to claim 12, characterized in that the reaction is carried out at a temperature above 90 ° C. 14. Werkwijze volgens conclusies 1-13, met het kenmerk dat, de reaktie wordt uitgevoerd met een zuurhalogenide met 25 de formule 2 waarin B en X een chlooratoom, A een chlooratoom of NO2, C, E en F een waterstofatoom en D een groep CF^ voor-stellen, onder vorming van een overeenkomstige verbinding met de formule 1.14. Process according to claims 1-13, characterized in that the reaction is carried out with an acid halide of the formula 2 in which B and X a chlorine atom, A a chlorine atom or NO2, C, E and F a hydrogen atom and D a group CF5 to form a corresponding compound of the formula I. 15. Werkwijze volgens conclusie 6 of 7, met het kenmerk 30 dat, de reaktie wordt uitgevoerd met een sulfonamide met . 3 de formule 3 waarin R een alkylgroep of een groep CF^ en bij voorkeur een methylgroep voorstelt,onder vorming van een overeenkomstige verbinding met de formule 1.15. Process according to claim 6 or 7, characterized in that the reaction is carried out with a sulfonamide with. 3 is the formula 3 wherein R represents an alkyl group or a group of CF 4 and preferably a methyl group, to form a corresponding compound of the formula 1. 16. Werkwijze volgens conclusies 1-15, met het kenmerk 35 dat, een verbinding met de formule 5 tot reaktie wordt ge- bracht met een sulfonamide CH2-SO2-NH2. 8202994 c -4- W4 -9-16. Process according to claims 1-15, characterized in that a compound of the formula 5 is reacted with a sulfonamide CH2-SO2-NH2. 8202994 c -4- W4 -9- 17. Werkwijzen alsmede daarbij toegepaste, verkrijg-bare en verkregen verbindingen zoals beschreven in de beschrijving en voorbeelden. 820299417. Methods and compounds used, available and obtained as described in the description and examples. 8202994
NL8202994A 1981-07-27 1982-07-26 PROCESS FOR PREPARING A SULFONAMIDE GROUP CONTAINING PHENOXYBENZOIC ACID DERIVATIVES NL8202994A (en)

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