GB1028152A - Manufacture of nitrofuran derivatives - Google Patents

Manufacture of nitrofuran derivatives

Info

Publication number
GB1028152A
GB1028152A GB4914462A GB4914462A GB1028152A GB 1028152 A GB1028152 A GB 1028152A GB 4914462 A GB4914462 A GB 4914462A GB 4914462 A GB4914462 A GB 4914462A GB 1028152 A GB1028152 A GB 1028152A
Authority
GB
United Kingdom
Prior art keywords
nitro
furyl
thiadiazole
formula
imidate
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
GB4914462A
Inventor
Justus Kenneth Landquist
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 GB4914462A priority Critical patent/GB1028152A/en
Publication of GB1028152A publication Critical patent/GB1028152A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/73—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by amino or imino, or substituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises 2-dimethylamino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole, 2-methylamino - 5 - [2 - (5 - nitro - 2 - furyl)vinyl]-1,3,4 - thiadiazole, 2 - methoxy - 5 - (5 - nitro-2 - furyl) - 1,3,4 - thiadiazole, 2 - methoxy - 5-[2 - (5 - nitro - 2 - furyl)vinyl] - 1,3,4 - thiadiazole and 2 - dimethylamino - 5 - [2 - (5-nitro - 2 - furyl)vinyl] - 1,3,4 - thiadiazole, and a process for the preparation of compounds of the formula: <FORM:1028152/C2/1> wherein R represents an alkoxy radical, or a radical of the formula -NR1R2 wherein R1 and R2, which may be the same or different, represent hydrogen atoms or alkyl, aryl, aralkyl or heterocyclic radicals, comprising ring closure of an N-amino imidate derivative of the formula: <FORM:1028152/C2/2> wherein R3 represents a C1- 4 alkyl radical, in the presence of an acid catalyst. The N-amino imidate derivative starting material may be generated in situ by reaction of a thiocarbonyl derivative of the formula H2N.NH.CS.R with an acid-addition salt, e.g. the hydrochloride, of an imidate of the formula: <FORM:1028152/C2/3> In many instances of this generation in situ, sufficient acid is liberated by hydrolysis or decomposition of the imidate salt, or of the ammonium salt produced from it during the reaction, to catalyse the ring closure of the N-amino imidate derivative so formed. In such cases no additional acid catalyst is required and the desired 1,3,4-thiadiazole may be isolated directly from the reaction mixture. Ethyl 5 - nitro - 2 - furimidate hydrochloride is prepared by saturating a cooled mixture of 5-nitro-2-furonitrile, ethanol and chloroform with dry hydrogen chloride. Ethyl 2-(5-nitro-2-furyl)acrylylimidate hydrochloride is similarly prepared using 2-(5-nitro-2-furyl) acrylonitrile in place of 5-nitro-2-furonitrile. Reference has been directed by the Comptroller to Specification 966,832.
GB4914462A 1962-12-31 1962-12-31 Manufacture of nitrofuran derivatives Expired GB1028152A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4914462A GB1028152A (en) 1962-12-31 1962-12-31 Manufacture of nitrofuran derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4914462A GB1028152A (en) 1962-12-31 1962-12-31 Manufacture of nitrofuran derivatives

Publications (1)

Publication Number Publication Date
GB1028152A true GB1028152A (en) 1966-05-04

Family

ID=10451325

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4914462A Expired GB1028152A (en) 1962-12-31 1962-12-31 Manufacture of nitrofuran derivatives

Country Status (1)

Country Link
GB (1) GB1028152A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5116530A (en) * 1988-10-17 1992-05-26 Canon Kabushiki Kaisha Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5116530A (en) * 1988-10-17 1992-05-26 Canon Kabushiki Kaisha Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same

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