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GB1377248A - Furan derivatives - Google Patents

Furan derivatives

Info

Publication number
GB1377248A
GB1377248A GB1908872A GB1908872A GB1377248A GB 1377248 A GB1377248 A GB 1377248A GB 1908872 A GB1908872 A GB 1908872A GB 1908872 A GB1908872 A GB 1908872A GB 1377248 A GB1377248 A GB 1377248A
Authority
GB
United Kingdom
Prior art keywords
hydrogen atom
prepared
general formula
chlorophenylfuran
dimethyl
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
GB1908872A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1908872A priority Critical patent/GB1377248A/en
Priority to ZA732239A priority patent/ZA732239B/en
Priority to IL41978A priority patent/IL41978A0/en
Priority to DE2319091A priority patent/DE2319091A1/en
Priority to NL7305354A priority patent/NL7305354A/xx
Priority to BE130184A priority patent/BE798421A/en
Priority to CH565173A priority patent/CH564004A5/xx
Priority to ZM66/73*UA priority patent/ZM6673A1/en
Priority to CH1089374A priority patent/CH566331A5/en
Priority to FR7314771A priority patent/FR2183001B1/fr
Priority to JP48047198A priority patent/JPS4947363A/ja
Priority to AR247707A priority patent/AR195223A1/en
Priority to ES414054A priority patent/ES414054A1/en
Priority to DD170430A priority patent/DD106168A6/xx
Priority to AR249863A priority patent/AR195753A1/en
Publication of GB1377248A publication Critical patent/GB1377248A/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
    • C07D307/38—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
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1377248 α - (5 - Phenylfur - 2 - yl) alkanoic acid derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 19 March 1973 [25 April 1972 16 June 1972] 19088/72 and 28296/72 Heading C2C [Also in Division A5] Novel α - (5 - phenylfur - 2 - yl) alkanoic acid derivatives of the general formula wherein Y is a p-chloro- or p-bromo-phenyl group, R<SP>1</SP> is a hydrogen atom or C 1-5 alkyl group and R<SP>2</SP> is a methyl or ethyl group, and when R<SP>1</SP> is a hydrogen atom, pharmaceutically acceptable salts thereof are prepared (a) when R<SP>1</SP> is a hydrogen atom, by reacting a malonic acid ester derivative of the general formula wherein R<SP>3</SP> is an alkyl, benzyl or phenyl group, with a strong inorganic base in the presence of water at an elevated temperature, acidifying the reaction mixture, isolating the crude product and heating it at 120-150‹ C. until effervescence ceases; (b) when R<SP>1</SP> is a hydrogen atom, by hydrolysing a compound of the general formula wherein Cy is an alkoxycarbonyl, phenylalkoxycarbonyl, phenoxycarbonyl, cyano, carbamoyl or thiocarbamoyl group; (c) when R<SP>1</SP> is a C 1-5 alkyl group, by esterifying the corresponding compound in which R<SP>1</SP> is a hydrogen atom or an acid halide or anhydride thereof; and (d) by α- methylating or -ethylating an acetic acid derivative of the general formula Dimethyl α - (5 - p - bromophenylfur - 2 - yl)- α - methylmalonate and dimethyl α - (5 - pchlorophenylfur - 2 - yl) - α - ethylmalonate are prepared by a process analogous or similar to that employed in Example 7 of Specification 1,226,981. Dimethyl α - (5 - p - bromophenylfur- 2-yl) malonate is prepared by a process analogous to that employed in Example 6 of the said Specification. 2 - α - Cyanoethyl - 5 - p - chlorophenylfuran is prepared by reacting 2-formyl-5-p-chlorophenylfuran with a Grignard reagent prepared from methyl iodide and hydrolysing the obtained complex, and treating the resulting 2-(ahydroxyethyl) - 5 - p - chlorophenylfuran with thionyl chloride, followed by sodium cyanide.
GB1908872A 1972-04-25 1972-04-25 Furan derivatives Expired GB1377248A (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
GB1908872A GB1377248A (en) 1972-04-25 1972-04-25 Furan derivatives
ZA732239A ZA732239B (en) 1972-04-25 1973-04-02 Furan derivatives
IL41978A IL41978A0 (en) 1972-04-25 1973-04-08 Furan derivatives
DE2319091A DE2319091A1 (en) 1972-04-25 1973-04-16 FURANDERIVATE
NL7305354A NL7305354A (en) 1972-04-25 1973-04-17
BE130184A BE798421A (en) 1972-04-25 1973-04-18 FURANNE DERIVATIVES
CH565173A CH564004A5 (en) 1972-04-25 1973-04-19
ZM66/73*UA ZM6673A1 (en) 1972-04-25 1973-04-19 Furan derivatives
CH1089374A CH566331A5 (en) 1972-04-25 1973-04-19 Alpha-(5-p-halophenylfur-2-yl) propionic acid derivs - - anti-inflammatories, analgesics and anti-pyretics
FR7314771A FR2183001B1 (en) 1972-04-25 1973-04-24
JP48047198A JPS4947363A (en) 1972-04-25 1973-04-25
AR247707A AR195223A1 (en) 1972-04-25 1973-04-25 PROCEDURE FOR THE MANUFACTURE OF FURAN DERIVATIVES
ES414054A ES414054A1 (en) 1972-04-25 1973-04-25 Furan derivatives
DD170430A DD106168A6 (en) 1972-04-25 1973-04-25
AR249863A AR195753A1 (en) 1972-04-25 1973-08-30 PROCEDURE FOR THE MANUFACTURE OF FURAN DERIVATIVES

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1908872A GB1377248A (en) 1972-04-25 1972-04-25 Furan derivatives
GB2829672 1972-06-16

Publications (1)

Publication Number Publication Date
GB1377248A true GB1377248A (en) 1974-12-11

Family

ID=26253837

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1908872A Expired GB1377248A (en) 1972-04-25 1972-04-25 Furan derivatives

Country Status (11)

Country Link
JP (1) JPS4947363A (en)
AR (1) AR195223A1 (en)
CH (1) CH564004A5 (en)
DD (1) DD106168A6 (en)
DE (1) DE2319091A1 (en)
ES (1) ES414054A1 (en)
FR (1) FR2183001B1 (en)
GB (1) GB1377248A (en)
IL (1) IL41978A0 (en)
NL (1) NL7305354A (en)
ZM (1) ZM6673A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5413877A (en) * 1977-07-04 1979-02-01 Japanese National Railways<Jnr> Fixed pressure air rescervoir automatic decompression process in automatic air brake system using 3-pressure control valve

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE33054B1 (en) * 1968-04-16 1974-03-06 Ici Ltd Heterocyclic compounds

Also Published As

Publication number Publication date
DD106168A6 (en) 1974-06-12
DE2319091A1 (en) 1973-11-15
NL7305354A (en) 1973-10-29
IL41978A0 (en) 1973-06-29
ES414054A1 (en) 1976-05-16
ZM6673A1 (en) 1974-01-21
FR2183001A1 (en) 1973-12-14
FR2183001B1 (en) 1977-01-28
CH564004A5 (en) 1975-07-15
JPS4947363A (en) 1974-05-08
AR195223A1 (en) 1973-09-19

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees