GB2103611A - Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group - Google Patents

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group Download PDF

Info

Publication number
GB2103611A
GB2103611A GB08221574A GB8221574A GB2103611A GB 2103611 A GB2103611 A GB 2103611A GB 08221574 A GB08221574 A GB 08221574A GB 8221574 A GB8221574 A GB 8221574A GB 2103611 A GB2103611 A GB 2103611A
Authority
GB
United Kingdom
Prior art keywords
process according
group
formula
alkyl
carbon atoms
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.)
Granted
Application number
GB08221574A
Other versions
GB2103611B (en
Inventor
El-Ahmadi I Heiba
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.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
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 Rhone Poulenc Agrochimie SA filed Critical Rhone Poulenc Agrochimie SA
Publication of GB2103611A publication Critical patent/GB2103611A/en
Application granted granted Critical
Publication of GB2103611B publication Critical patent/GB2103611B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C301/00—Esters of sulfurous acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • 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
    • C07C303/38—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • 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
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C07C323/10—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
    • 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
    • C07C323/23—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
    • C07C323/31—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
    • C07C323/33—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
    • 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
    • C07C323/36—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 the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • 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
    • C07C323/23—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
    • C07C323/39—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 at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • 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
    • C07C323/23—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
    • C07C323/39—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 at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • 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
    • C07C323/62—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • 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
    • C07C323/64—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
    • 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
    • C07C323/64—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/67—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • 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
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Abstract

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group, by reacting an appropriate phenoxy benzoic acid halide with a sulphonamide in the absence of an acid acceptor and with elimination of hydrohalic acid in the gaseous form.

Description

SPECIFICATION Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group The present invention relates to an improved process for the preparation of certain phenoxybenzoic acid derivatives containing a sulphonamide group, which have herbicidal properties.
Herbicidal derivatives of phenoxybenzoic acids containing a sulphonamide group are known from European Patent Applications 3,416 and 23,392.
These patent applications disclose products of the formula:
and their salts, in which formula: A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N=NCF3, PO3H2 or an alkyl ester thereof having 1 to 4 carbon atoms, NH2, NHOH, N;, a carboxy group or one of its functional derivatives, a monoalkylamino or dialkylamino group, a group NH-CO-R1, in which R1 is an alkyl, alkoxy, monoalkylamino or dialkylamino radical, an alkyl group, trialkylammonio, NHSO2R2, in which R2 is an alkyl or phenyl radical, NHCONHSO2R2, in which R2 is hereinbefore defined; alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylsulphonio, cyanosulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substituted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF3,
oracyl; B is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CF3, NO2, CN, NH2, NHCOR1, in which R1 is as hereinbefore defined, or CONH2; C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group; D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogenoalkyl, preferably CF3, sulphamoyl, formyl, alkylcarbonyl, CN or dimethylamino group;; E is hydrogen, fluorine, chlorine, bromine iodine, an alkyl, alkoxy alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, preferably CF3, NH2, CONH2 or NH-CO-R1, wherein R1 is as hereinbefore defined; F is as hereinbefore defined for B; and R is a group -CON(R4)SO2R3, in which: R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R3 is a phenyl, pyridyl orthienyl group optionally substituted by one or more halogen atoms, alkyl groups or nitro groups, an alkenyl or alkynyl radical having 2 to 4carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, preferably CF3, or by one or more of the following substituents: carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio, alkysulphinyl, alkylsulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 carbon atoms, alkylcarbonylamino having 2 to 5 carbon atoms, or cyano.
In the above definitions, where reference is made to alkyl radicals or radicals containing one or more alkyl groups, for example mono- and di-alkylamino, or alkoxy, the alkyl radial may be for example a lower alkyl radical having for example 1 to 6 carbon atoms.
In the known processes, the products of the formula (I) are prepared by reacting an intermediate acid halide of the formula:
wherein X is chlorine, bromine or iodine and A, B, C, D, E and F are as hereinbefore defined, with a sulphonamide of the formula R3So2NH2 (Ill) wherein R3 is as hereinbefore defined, at from 25 to 140"C, in the presence of an acid acceptor, in particular a tertiary amine, such as N,N-dimethylaniline or pyridine, an alkali metal carbonate, such as anhydrous potassium carbonate, or an alkali metal fluoride, such as caesium fluoride.
The compounds of formula (I) in which R4 is hydrogen can be alkylated in a known manner, e.g. by reaction with a diazoalkane having 1 to 4 carbon atoms, so as to give the corresponding products in which R4 is an alkyl group having 1 to 4 carbon atoms.
The compunds of formula I in which, for example, R4 is a hydrgoen atom are acids and form salts with bases: such compounds may be converted in known manner into their salts.
This process for the condensation of the products of formulae (II) and (III) has a number of disadvantages: the yields are mediocre (e.g. it is possible to calculate a yield of 27% for Example 14 of European Patent Application 23,392 and of 9.5% for Example 34). It is now considered that it is the presence of the acid acceptor which lowers the yield by promoting a diacylation reaction. Furthermore, the use of an acid acceptor makes the final products more difficult and more expensive to isolate and purify. An object of the invention is to overcome these disadvantages.
The process according to the invention comprises reacting an acid halide of formula II wherein X, A, B, C, D, E and F are as hereinbefore defined with a sulphonamide of formula (III), wherein R3 is as hereinbefore defined, in the absence of an acid acceptor and at a temperature at which the gaseous hydrogen halide (HCI, HBr or He) formed during the reaction is eliminated from the reaction medium, as it is formed, the reaction temperature being below the decomposition temperature of the product of formula (I) (i.e. the reaction is carried out at a temperature at which appreciable decomposition of the reaction product of the formula (i) does not occur) and optionally converting in known manner a compound thus obtained into a salt thereof or converting in known manner a compound thus obtained wherein R4 represents a hydrogen atom into a corresponding compound wherein R4 represents an alkyl group having 1 to 4 carbon atoms.
By virtue of the process according to the invention, substantially higher yields of sulphonamide derivatives of phenoxybenzoic acids can be obtained, e.g. yields of at least about 30% and frequently of at least about 50%, and with a much simpler method of recovering and purifying the final product than the methods of the known processes.
It is preferred to use an acid halide (preferably the chloride) of formula (II) in which A is the group NO2 or a fluorine, chlorine, bromine or iodine atom, B is a halogen (preferably chlorine) atom, C, E and F are hydrogen and D is the group CF3. It is also preferred to use sulphonamides of formula (III) in which R3 is an alkyl group, especially CH3, or a group CF3.
The temperature at which the process of the invention can be carried out depends, in particular, on whether either the acid halide of the formula (II) or the sulphonamide of the formula (Ill) is in large excess, or on whether or not a solvent having catalytic properties is used.
The reaction may be carried out in the presence of an excess of acid halide of formula (II). If the acid halide (II) is in large excess, i.e. the molar ratio (11)1(111) is from about 1.5 to 5, as is preferred, the acid halide (II) can serve as a solvent for the reaction and the reaction temperature can be from 80 to 200"C, but it is then preferably from 90 to 160"C.
The unreacted acid halide (II) can be recovered from the reaction medium by washing with an inert solvent, such as a hydrocarbon, in particular pentane, hexane, heptane, cyclopentane, cyclohexane, cycloheptane, benzene, toluene or xylene, a halogenated hydrocarbon, in particular chlorobenzenes, CS2, tetrahydrofuran, dioxane and the like.
When an excess of sulphonamide is used, for example when the molar ratio of the compounds (III)/(II) is from 1.5 to 5, the reaction temperature is then generally from 90 to 200"C and preferably from 140 to 160"C. In any case, it must be at least sufficient to melt the reaction medium. The excess sulphonamide (III) can be recovered from the reaction medium by washing with water or another inert solvent for this reactant (III).
The reactants can also be dissolved in an inert solvent having a boiling point above the reaction temperature, e.g. a chlorinated or non-chlorinated liquid hydrocarbon, such as benzene, toluene, xylenes, mixtures of xylenes of cumene; the maximum reaction temperature is advantageously slightly below the boiling point of the solvent. Thus, in the case of cumene, which boils at about 153"C, the reaction is preferably carried out at from 130 to 150"C. The use of an inert solvent has the practical advantage of permitting better heat transfer in an industrial-scale process; it also makes it possible to avoid local overheating of the reaction medium.
According to another feature of the invention, a solvent is used which catalyses the reaction of the acid halide (Il) with the sulphonamide (Ill) to give the phenoxybenzoylsulphonamide (I). Dimethylformamide (DMF, which boils at about 154"C) and dimethylacetamide (DMAC, which boils at about 164"C) are particularly advantageous in this respect, and their use makes it possible to use relatively low temperatures, e.g. from 80 to 1 20C, preferably from 90 to 11 0C, or higher temperataures slightly below the boiling point of these solvents; the reaction rate is then more rapid. It is especially preferred to carry out the reaction at a temperature from 80"C to the boiling point of the solvent, preferably at a temperature above 90"C.
The following Examples illustrate the present invention.
Example 1 Methanesulphonamide (2 g; 0.021 mol) is mixed with 5-[2'-chloro-4'-(trifluoromethyl)-phenoxy]-2 nitrobenzoyl chloride (3.8 g; 0.01 mol). The mixture is heated for 20 minutes at 150"C. The hydrochloric acid is released from the reaction medium as it is formed. The medium is cooled to give a black oil, which is dissolved in aqueous sodium hydroxide solution; the solution is filtered and the filtrate is acidified with dilute HCI, which precipitates the product of the formula (IV). This gave, with a yield of 71%, a product (3.1 g) melting at 1 95-1970C and having an infra-red absorption band at 1,692 cm-1 (C=O group). This product has the formula:
Example 2 Example 1 is repeated, but 250 g of acid chloride and 130 g of methanesulphonamide are used. The reaction product is isolated directly after the mixture has cooled, by recrystallisation from isopropanol. This gives a yield of 64% (185 g) of the product of the formula (IV). The structure of this product is confirmed by infra-red (absorption band at 1,692 cm-1) and by nuclear magnetic resonance (singlet at 3.5 ppm; multiplet at 8.07 ppm).
When applying the process of this example of European Patent Application 23,392, using pyridine as an acid acceptor, the yield was only 25%.

Claims (23)

1. A process for the preparation of a phenoxybenzoic acid derivative containing a sulphonamide group, of the formula:
and its salts, in which formula: A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N=NCF3, PO3H2 or an alkyl ester thereof having 1 to 4 carbon atoms, NH2, NHOH, N+2, a carboxy group or one of its functional derivatives, a monoalkylamino or dialkylamino group, a group NH-CO-R1, in which R1 is an alkyl, alkoxy, monoalkylamino or dialkylamino radical, an alkyl group, trialkylammonio, NHSO2R2, in which R2 is an alkyl or phenyl radical, NHCONHSO2R2, in which R2 is as hereinbefore defined, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylsulphonio, cyanosulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substituted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF3,
or acyl;; B is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group CF3, NO2, CN, NH2, NHCOR', in which R1 is as hereinbefore defined, or CONH2; C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group; D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogenoalkyl, sulphamoyl, formyl, alkylcarbonyl, CN or dimethylamino group; E is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, NH2, CON H2 or NH-CO-R1, wherein R1 is as hereinbefore defined; F is as hereinbefore defined for B; and R is a group -CON(R4)SO2R3, in which: R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R3 is a phenyl, pyridyl orthienyl group optionally substituted by one or more halogen atoms, alkyl groups or nitro groups, an alkenyl or alkynyl radical having 2 to 4 carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, or by one or more of the following substituents: carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio, alkylsulphinyl, alkysulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 carbon atoms, alkylcarbonylamino having 2 to 5 carbon atoms, or cyano, which process comprises reacting an acid halide of the formula:
wherein X is a chlorine, bromine, or iodine atom and A, B, C, D, E and F are as hereinbefore defined, with a sulphonamide of the formula:: R3So2NH2 (Ill) wherein R3 is as hereinbefore defined in the absence of an acid acceptor and at a temperature at which the gaseous hydrogen halide formed during the reaction is eliminated from the reaction medium as it is formed, the reaction temperature being below the decomposition temperature of the product of formula (I) and optionally converting in known manner a compound thus obtained into a salt thereof or converting in known manner a compound thus obtained wherein R4 represents a hydrogen atom into a corresponding compound wherein R4 represents an alkyl group having 1 to 4 carbon atoms.
2. A process according to claim 1, wherein the reaction is carried out in the presence of an excess of acid halide of formula (II).
3. A process according to claim 2, wherein the molar ratio of acid halide of formula (II) to sulphonamide of formula (III) is from 1.5 to 5.
4. A process according to claim 2 or 3, wherein the reaction temperature is from 80 to 200"C.
5. A process according to claim 4 in which the temperature is from 90 to 160 C.
6. A process according to claim 1, wherein the reaction is carried out in the presence of an excess of sulphonamide.
7. A process according to claim 6, wherein the molar ratio of sulphonamide of formula (Ill) to acid halide of formula (II) is from 1.5 to 5.
8. A process according to claim 6 or 7, wherein the reaction temperature is from 90 to 200"C.
9. A process according to claim 7 in which the temperature is from 140 to 160"C.
10. A process according to any one of claims 1 to 9, wherein the reaction is carried out in the presence of a solvent having a boiling point above the reaction temperature.
11. A process according to claim 10, wherein the solvent is a chlorinated or non-chlorinated liquid hydrocarbon.
12. A process according to claim 11, wherein the solvent is cumene and wherein the reaction tem peratu re is from 130 to 15CC.
13. A process according to any one of claims 1 to 10, wherein the reaction is carried out in a solvent which catalyses the reaction of the acid halide of formula II and the sulphonamide of formula Ill.
14. A process according to claim 13, wherein the solvent is dimethylformamide or dimethylacetamide and the reaction temperature is from 80"C to the boiling point of the solvent.
15. A process according to claim 14, wherein the temperature is above 90"C.
16. A process according to any one of the preceding claims wherein, in formulae (II) and (III), B is halogen, X is chlorine, A is the group NO2 or a fluorine, chlorine, bromine or iodine atom, C, E and F are hydrogen and D is CF3.
17. A process according to any one of the preceding claims wherein, the formulae (I) and (II), B and X are chlorine, A is chlorine or NO2, C, E and F are hydrogen and D is CF3.
18. A process according to any one of the preceding claims wherein in the sulphonamide of formula Ill R3 is an alkyl or CF3 group.
19. A process according to claim 18 wherein R3 is methyl.
20. A process according to any one of the preceding claims wherein
is reacted with CH3-SO2-NH2.
21. A process according to claim 1 substantially as herein before described in Example 1 or 2.
22. A phenoxybenzoic acid derivative of formula (i) or a salt thereof, when prepared by a process according to any one of claims 1 to 21.
23. A phenoxybenzoic acid derivative according to claim 22 of the formula
GB08221574A 1981-07-27 1982-07-26 Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group Expired GB2103611B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US28693881A 1981-07-27 1981-07-27

Publications (2)

Publication Number Publication Date
GB2103611A true GB2103611A (en) 1983-02-23
GB2103611B GB2103611B (en) 1985-04-03

Family

ID=23100791

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08221574A Expired GB2103611B (en) 1981-07-27 1982-07-26 Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group

Country Status (23)

Country Link
JP (1) JPS5826860A (en)
KR (1) KR880002591B1 (en)
AT (1) AT385985B (en)
BE (1) BE893940A (en)
BR (1) BR8204357A (en)
CA (1) CA1194472A (en)
CH (1) CH652384A5 (en)
DD (1) DD203716A5 (en)
DE (1) DE3227847A1 (en)
DK (1) DK333282A (en)
ES (1) ES8306108A1 (en)
FR (1) FR2510105A1 (en)
GB (1) GB2103611B (en)
HU (1) HU191186B (en)
IE (1) IE53978B1 (en)
IL (1) IL66197A (en)
IT (1) IT1198399B (en)
LU (1) LU84295A1 (en)
NL (1) NL8202994A (en)
PL (1) PL136683B1 (en)
PT (1) PT75322B (en)
RO (1) RO85388B (en)
SU (1) SU1215620A3 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4845285A (en) * 1986-11-25 1989-07-04 Imperial Chemical Industries Plc Chemical process
US11834714B2 (en) 2021-12-20 2023-12-05 Enumerix, Inc. Detection and digital quantitation of multiple targets

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003416B1 (en) * 1978-01-19 1981-08-26 Imperial Chemical Industries Plc Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them
EP0023392B1 (en) * 1979-07-18 1984-06-06 Imperial Chemical Industries Plc Diphenyl ether compounds, and herbicidal compositions and processes utilising them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4845285A (en) * 1986-11-25 1989-07-04 Imperial Chemical Industries Plc Chemical process
US11834714B2 (en) 2021-12-20 2023-12-05 Enumerix, Inc. Detection and digital quantitation of multiple targets

Also Published As

Publication number Publication date
IL66197A (en) 1985-11-29
GB2103611B (en) 1985-04-03
CA1194472A (en) 1985-10-01
IT8222545A0 (en) 1982-07-23
IT8222545A1 (en) 1984-01-23
FR2510105B1 (en) 1984-09-07
NL8202994A (en) 1983-02-16
IL66197A0 (en) 1982-11-30
ES514352A0 (en) 1983-05-01
FR2510105A1 (en) 1983-01-28
SU1215620A3 (en) 1986-02-28
PL136683B1 (en) 1986-03-31
CH652384A5 (en) 1985-11-15
DK333282A (en) 1983-01-28
PT75322A (en) 1982-08-01
PT75322B (en) 1985-11-29
IT1198399B (en) 1988-12-21
PL237639A1 (en) 1983-05-23
HU191186B (en) 1987-01-28
RO85388B (en) 1984-11-30
AT385985B (en) 1988-06-10
KR840000466A (en) 1984-02-22
BE893940A (en) 1983-01-26
JPH0149262B2 (en) 1989-10-24
KR880002591B1 (en) 1988-12-03
ES8306108A1 (en) 1983-05-01
BR8204357A (en) 1983-07-19
LU84295A1 (en) 1984-03-22
ATA290082A (en) 1987-11-15
IE53978B1 (en) 1989-05-10
DE3227847A1 (en) 1983-02-10
JPS5826860A (en) 1983-02-17
IE821786L (en) 1983-01-27
RO85388A (en) 1984-11-25
DD203716A5 (en) 1983-11-02

Similar Documents

Publication Publication Date Title
JPS5934702B2 (en) Method for producing α・α-dimethylbenzyl isocyanate or its nuclear substituted product
GB2103611A (en) Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group
GR3017517T3 (en) Process for preparing aromatic nitriles.
US5310738A (en) Process for producing a hexahydropyridazine-1,2-dicarboxy derivative
EP0646566B1 (en) Process for the preparation of acid chloride compounds
EP0110559A1 (en) Process for the preparation of 4-chloro-2-nitrobenzonitrile
CA2175420C (en) Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes
US4959487A (en) Process for producing aromatic nitrile
US4731479A (en) N-sulfamyl-3-halopropionamidines
JP3784865B2 (en) Method for producing 4,4'-bis (chloromethyl) biphenyl
US4461918A (en) Process for producing pentachloronitrobenzene from hexachlorobenzene
US5908955A (en) Process for producing alkyl 3-amino-4-substituted benzoates
US4562260A (en) Preparation of 1,3,4-thiadiazole-5-sulfonamides
CA1215706A (en) Process for the preparation of aryloxybenzoic acids containing a sulphonamide group
KR910003635B1 (en) Process for the preparation of 2-(2-naphthyloxy)propion anilide derivatives
US4612395A (en) Process for the production of N-(2-methyl-4-chlorophenyl)-formamidine derivatives
JPS61151165A (en) Production of polythiobisphenol
CA1215357A (en) Process for the preparation of aryloxybenzoic acids containing a sulphonamide group
JP4183781B2 (en) Method for producing S, S- (6-methylquinoxaline-2,3-diyl) dithiocarbonate
JPH01117853A (en) N-phenyl-2,2,6,6-tetrahalocyclohexanimine
JPH01117849A (en) Production of 2,6-dihaloaniline derivative
JPH0273044A (en) Difluoroanthranilic acid and preparation thereof
JP3653779B2 (en) Process for producing 1,2,3-trichloro-4,6-dinitrobenzene
KR840001563B1 (en) Process for preparing 1-carbymayl-3-(3,5-dichlorophenyl)-hydantoins
GB2140417A (en) A process for the preparation of N-aryloxybenzoyl sulphonamides

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee