ZA794144B - Process for the preparation of n-substituted alpha -halogeno acetanilides - Google Patents

Process for the preparation of n-substituted alpha -halogeno acetanilides

Info

Publication number
ZA794144B
ZA794144B ZA00794144A ZA794144A ZA794144B ZA 794144 B ZA794144 B ZA 794144B ZA 00794144 A ZA00794144 A ZA 00794144A ZA 794144 A ZA794144 A ZA 794144A ZA 794144 B ZA794144 B ZA 794144B
Authority
ZA
South Africa
Prior art keywords
carbon atoms
alkyl
halogen
phenyl
see diagramm
Prior art date
Application number
ZA00794144A
Inventor
J Stetter
T Schmidt
R Thomas
Original Assignee
Bayer Ag
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 Bayer Ag filed Critical Bayer Ag
Publication of ZA794144B publication Critical patent/ZA794144B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1. Process for the preparation of N-substituted alpha-halogenoacetanilides of the formula see diagramm : EP0008057,P17,F1 in which R represents pyrazol-1-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,3,4-triazol-1-yl, 1,2,3,4-tétrazol-1-yl or pyrrol-1-yl, it being possible for each of these radicals to be substituted by halogen and/or alkyl with 1 to 4 carbon atoms and R also represents the grouping see diagramm : EP0008057,P17,F2 in which A represents oxygen, sulphur or see diagramm : EP0008057,P17,F3 wherein R**2 represents hydrogen, alkyl with 1 to 4 carbon atoms or phenyl, and B represents hydrogen, alkyl with 1 to 4 carbon atoms, halogenoalkyl with up to 3 carbon atoms and up to 5 identical or different halogen atoms, halogen, phenyl, benzyl or the groupings -OR**3, -SR**3 or -NR**2R**3, wherein R**2 has the meanings given above and R**3 represents hydrogen or alkyl with 1 to 4 carbon atoms, and R furthermore represents furyl, thiophenyl, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part or phenyl, phenoxy or phenylcarbonyl, it being possible for each of the three last-mentioned radicals to be substituted by halogen and/or alkyl with 1 to 4 carbon atoms, R**1 represents hydrogen, alkyl with 1 to 4 carbon atoms or phenyl, X**1 represents alkyl with 1 to 4 carbon atoms, X**2 represents hydrogen or alkyl with 1 to 4 carbon atoms and Hal represents chlorine or bromine, characterized in that halogenoacetanilides of the formula see diagramm : EP0008057,P18,F4 in which X**1, X**2 and Hal have the meaning indicated above, are reacted with compounds of the formula see diagramm : EP0008057,P18,F5 in which R and R**1 have the meaning indicated above and Y represents chlorine, bromine, iodine, alkylsulphonyl with 1 to 4 carbon atoms or phenylsulphonyl optionally substituted by halogen or alkyl with 1 to 4 carbon atoms, in the presence of an alkali metal hydroxide or an alkali metal carbonate as acid binder and optionally in the presence of an organic solvent, at temperatures between -20 degrees C and +100 degrees C, it being possible optionally to react the compounds of the formula (XIII) in the form of acide addition salts.
ZA00794144A 1978-08-10 1979-08-09 Process for the preparation of n-substituted alpha -halogeno acetanilides ZA794144B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19782835157 DE2835157A1 (en) 1978-08-10 1978-08-10 METHOD FOR PRODUCING N-SUBSTITUTED ALPHA -HALOGENACETANILIDES

Publications (1)

Publication Number Publication Date
ZA794144B true ZA794144B (en) 1980-09-24

Family

ID=6046745

Family Applications (1)

Application Number Title Priority Date Filing Date
ZA00794144A ZA794144B (en) 1978-08-10 1979-08-09 Process for the preparation of n-substituted alpha -halogeno acetanilides

Country Status (11)

Country Link
EP (1) EP0008057B1 (en)
JP (1) JPS5524194A (en)
AT (1) ATE1009T1 (en)
BR (1) BR7905112A (en)
CA (1) CA1116607A (en)
CS (1) CS214801B2 (en)
DE (2) DE2835157A1 (en)
DK (1) DK333479A (en)
ES (1) ES483280A1 (en)
IL (1) IL57998A (en)
ZA (1) ZA794144B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4258196A (en) * 1978-04-17 1981-03-24 Monsanto Company Process for the production of tertiary 2-haloacetamides
EP0029011A1 (en) * 1979-11-13 1981-05-20 Ciba-Geigy Ag N-(Azolyl-1-eth-1'-yl)-halogenacetanilides, their preparation and their use as herbicides
DE3011084A1 (en) * 1980-03-22 1981-10-01 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING SUBSTITUTED N-AZOLYLMETHYL HALOGEN ACETANILIDES
US4260782A (en) * 1980-06-09 1981-04-07 Ciba-Geigy Corporation Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines
US4266071A (en) * 1980-06-09 1981-05-05 Ciba-Geigy Corporation Process for the preparation of N-(1-alkoxycarbonylethyl)-2,6-dialkylanilines
DE3120990A1 (en) * 1981-05-26 1982-12-23 Bayer Ag, 5090 Leverkusen N- (1-ALKENYL) -CHLOROACETIC ACID ANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS
HU190681B (en) * 1982-01-15 1986-10-28 Eszakmagyar Vegyimuevek Process for production of n-alcoxi-alkyl-2,6-dialkylchlor-acetanilids
JPS604181A (en) * 1983-06-22 1985-01-10 Tokuyama Soda Co Ltd N-substituted-chloroacetanilide
DE3572809D1 (en) * 1984-05-23 1989-10-12 Ciba Geigy Ag MICROBICIDAL 1-FLUORO-1-AZOLYL-2,2-DIARYLETHANE DERIVATIVES
FI102748B (en) * 1992-06-19 1999-02-15 Daiichi Seiyaku Co Process for the preparation of N- (2,6-dialkyl) -2- (2-oxo-1-pyrrolidinyl) acetamide derivatives
TW201033163A (en) * 2008-10-20 2010-09-16 Sumitomo Chemical Co Method for manufacturing oxadiazolinone compound and intermediate thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1019752A (en) * 1973-02-12 1977-10-25 Sidney B. Richter Heterocyclic anilids
US3901917A (en) * 1974-11-04 1975-08-26 Velsicol Chemical Corp N-thienylalkylacetanilides
DE2648008C3 (en) * 1976-10-23 1980-09-04 Basf Ag, 6700 Ludwigshafen Acetanilide
DE2704281A1 (en) * 1977-02-02 1978-08-03 Bayer Ag Herbicidal N-heterocyclyl-methyl-halo-acetanilide derivs. - prepd. from a N-halomethyl-chloro:acetanilide and a heterocycle

Also Published As

Publication number Publication date
BR7905112A (en) 1980-05-06
IL57998A0 (en) 1979-12-30
EP0008057A1 (en) 1980-02-20
DK333479A (en) 1980-02-11
JPS5524194A (en) 1980-02-21
DE2962806D1 (en) 1982-07-01
CS214801B2 (en) 1982-06-25
ATE1009T1 (en) 1982-05-15
DE2835157A1 (en) 1980-02-21
EP0008057B1 (en) 1982-05-12
IL57998A (en) 1982-08-31
ES483280A1 (en) 1980-04-16
CA1116607A (en) 1982-01-19

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