GB1387652A - Process for preparing furan carboxamides - Google Patents

Process for preparing furan carboxamides

Info

Publication number
GB1387652A
GB1387652A GB2184572A GB2184572A GB1387652A GB 1387652 A GB1387652 A GB 1387652A GB 2184572 A GB2184572 A GB 2184572A GB 2184572 A GB2184572 A GB 2184572A GB 1387652 A GB1387652 A GB 1387652A
Authority
GB
United Kingdom
Prior art keywords
formula
acid
salt
compounds
alkyl
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.)
Expired
Application number
GB2184572A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB2184572A priority Critical patent/GB1387652A/en
Priority to CA169,078A priority patent/CA1023756A/en
Priority to IT2374173A priority patent/IT987147B/en
Priority to DE19732323197 priority patent/DE2323197C2/en
Priority to JP48050411A priority patent/JPS5848559B2/en
Priority to CH651673A priority patent/CH586691A5/xx
Priority to NL7306383A priority patent/NL179535C/en
Priority to FR7316452A priority patent/FR2183909B1/fr
Publication of GB1387652A publication Critical patent/GB1387652A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D307/56—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 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • A01N43/08—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 oxygen as the ring hetero atom

Abstract

1387652 2,5-Dimethylfuran-3-carboxamide derivatives SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ BV 8 May 1973 [10 May 1972] 21845/72 Heading C2C Furan carboxamide derivatives of Formula I wherin R represents an optionally substituted alkyl, cycloalkyl, aryl, aralkyl or heterocyclic group (e.g. pyridyl) are prepared by (a) cyclizing a compound of Formula II wherein R<SP>1</SP> represents a C 1-6 alkyl group, in the presence of a solid heterogeneous acid catalyst (e.g. an acid clay or an ion-exchange resin) and preferably in an aromatic hydrocarbon solvent (e.g. benzene, toluene) and (b) converting the furan carboxylic ester product of (a) to the carboxamide. Step (b) is preferably effected by reaction with a strong base (e.g. NaH) and an amine of formula, RNH 2 , generally in a polar aprotic solvent (e.g. DMSO), or by hydrolysis of the ester product of step (a) to the corresponding acid, formation of the amine salt of this acid and dehydration of the salt in the presence of an acid catalyst. Starting material of Formula II is prepared by reacting the salt of an acetoacetic acid ester with chloro- or bromoacetone in the presence of an alkali metal iodide. The sodium salt of methyl acetoacetate is formed by reacting methyl acetate with sodium and absorbing the methanol by-product on molecular sieve of pore size 4-5Š. The compounds of Formula I in which R is an alkyl group are novel compounds, are claimed per se and possess fungicidal properties. Examples describe the preparation of compounds of Formula I wherein R is C 1-12 alkyl, phenyl or cyclohexyl.
GB2184572A 1972-05-10 1972-05-10 Process for preparing furan carboxamides Expired GB1387652A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB2184572A GB1387652A (en) 1972-05-10 1972-05-10 Process for preparing furan carboxamides
CA169,078A CA1023756A (en) 1972-05-10 1973-04-18 Process for preparing fungicidal compounds
IT2374173A IT987147B (en) 1972-05-10 1973-05-04 PROCESS FOR THE PREPARATION OF FUNGHICIDE COMPOUNDS
DE19732323197 DE2323197C2 (en) 1972-05-10 1973-05-08 Process for the preparation of 2,5-dimethyl-3-furancarboxamides, certain of these 2,5-dimethyl-3-furancarboxamides as such and fungicidal agents containing the latter
JP48050411A JPS5848559B2 (en) 1972-05-10 1973-05-08 Satsukin Seika Gobutsu no Seizou Hohou
CH651673A CH586691A5 (en) 1972-05-10 1973-05-08
NL7306383A NL179535C (en) 1972-05-10 1973-05-08 PROCESS FOR THE PREPARATION OF FUNGICIDE PREPARATIONS BASED ON FURANCARBOXAMIDE DERIVATIVES, THE FORMED FUNGICIDE PREPARATION, AND METHOD FOR PREPARING THESE FURANCARBOXAMIDE DERIVATIVES
FR7316452A FR2183909B1 (en) 1972-05-10 1973-05-08

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2184572A GB1387652A (en) 1972-05-10 1972-05-10 Process for preparing furan carboxamides

Publications (1)

Publication Number Publication Date
GB1387652A true GB1387652A (en) 1975-03-19

Family

ID=10169783

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2184572A Expired GB1387652A (en) 1972-05-10 1972-05-10 Process for preparing furan carboxamides

Country Status (8)

Country Link
JP (1) JPS5848559B2 (en)
CA (1) CA1023756A (en)
CH (1) CH586691A5 (en)
DE (1) DE2323197C2 (en)
FR (1) FR2183909B1 (en)
GB (1) GB1387652A (en)
IT (1) IT987147B (en)
NL (1) NL179535C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006149A1 (en) * 1978-06-14 1980-01-09 BASF Aktiengesellschaft Process for the preparation of alkyl esters of 2,5-dimethylfuran-3-carboxylic acid
EP1772449A1 (en) * 2005-10-05 2007-04-11 Bayer CropScience S.A. New N-alkyl-heterocyclyl carboxamide derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2614285C3 (en) * 1976-04-02 1979-06-13 Bayerische Motoren Werke Ag, 8000 Muenchen Independent suspension of a steered wheel of a motor vehicle
JPS6374706A (en) * 1986-09-18 1988-04-05 Honda Motor Co Ltd Double wishbone type rear suspension

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1768686B1 (en) * 1968-06-19 1971-05-27 Basf Ag Furan-3-carboxylic acid anilides and their use as a fungicide
US3959481A (en) * 1969-02-13 1976-05-25 Uniroyal Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives
CA932334A (en) * 1969-02-13 1973-08-21 Kulka Marshall Furan-3-carboxamide derivatives and method of preparing same
DE2019535B2 (en) * 1970-04-23 1973-04-05 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen 2,5-DIMETHYLFURAN-3-CARBONIC ACID CYCLOALKYLAMIDE AND FUNGICIDES CONTAINING THESE COMPOUNDS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006149A1 (en) * 1978-06-14 1980-01-09 BASF Aktiengesellschaft Process for the preparation of alkyl esters of 2,5-dimethylfuran-3-carboxylic acid
EP1772449A1 (en) * 2005-10-05 2007-04-11 Bayer CropScience S.A. New N-alkyl-heterocyclyl carboxamide derivatives
WO2007039615A1 (en) * 2005-10-05 2007-04-12 Bayer Cropscience Sa New n-alkyl-heterocyclyl carboxamide derivatives
US8148538B2 (en) 2005-10-05 2012-04-03 Bayer Cropscience Ag N-alkyl-heterocyclyl carboxamide derivatives

Also Published As

Publication number Publication date
NL7306383A (en) 1973-11-13
CH586691A5 (en) 1977-04-15
FR2183909B1 (en) 1976-06-11
IT987147B (en) 1975-02-20
JPS4947364A (en) 1974-05-08
FR2183909A1 (en) 1973-12-21
DE2323197A1 (en) 1973-11-22
NL179535B (en) 1986-05-01
NL179535C (en) 1986-10-01
JPS5848559B2 (en) 1983-10-28
DE2323197C2 (en) 1984-02-02
CA1023756A (en) 1978-01-03

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Legal Events

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

Effective date: 19920508