GB916560A - Process for the manufacture of substituted nitrophenyl-1,3,4-oxdiazoles - Google Patents

Process for the manufacture of substituted nitrophenyl-1,3,4-oxdiazoles

Info

Publication number
GB916560A
GB916560A GB4485160A GB4485160A GB916560A GB 916560 A GB916560 A GB 916560A GB 4485160 A GB4485160 A GB 4485160A GB 4485160 A GB4485160 A GB 4485160A GB 916560 A GB916560 A GB 916560A
Authority
GB
United Kingdom
Prior art keywords
nitrophenyl
chlorophenyl
oxdiazole
chloro
amino
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
GB4485160A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB916560A publication Critical patent/GB916560A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Abstract

Polyvinyl chloride is pigmented by substituted nitrophenyl-1:3:4-oxdiazoles prepared by reacting with an aromatic amine a 1:3:4-oxdiazole containing at least one 4-halogeno-3-nitrophenyl substituent. The nitrohalogen compound may have the formula (I) wherein R1 is a divalent organic radical, R2 an organic substituent and m and n each=1 or 2. In examples, starting materials <FORM:0916560/IV(a)/1> , (1) of formula (I) in which (a) n=1 and R2=methyl, phenyl, 4-chlorophenyl or 4-chloro-3-nitrophenyl or (b) m=1, n=2 and R2=4-chloro-3-nitrophenyl. (2) bis-(3:5-dinitro-4-chlorophenyl)oxdiazole, (3) bis-(2:4-dichloro-3-nitrophenyl)oxdiazole and (4) 3:5-dinitro-4-chlorophenyl-41-chlorophenyloxdiazole are reacted with materials selected from aniline, o- and ptoluidines, oanisidine, 1-amino-2-methyl-5-chlorobenzene, 1-amino-2:5-dimethylbenzene, p-phenylenediamine and its monoacetyl derivative, N-methylaniline, 1-amino-2:5-dimethoxy 4-benzoylaminobenzene, 1-aminonaphthalene, 1:4-diamino-2-chloro (or methyl)-5-methylbenzene, benzidine and its 3:31-dimethyl or -dimethoxy derivatives, and the products used to colour polyvinyl chloride. In one of the examples, the use of dioctyl phthalate is also specified.ALSO:Substituted nitrophenyl-1:3:4-oxdiazoles are prepared by reacting with a basic compound a 1:3:4-oxdiazole containing at least one 4-halogeno-nitrophenyl substituent. The nitrohalogen compound may have the formula (I) wherein R1 is a divalent organic radical, R2 an organic substituent and m and n each = 1 or 2. In examples, starting materials <FORM:0916560/IV (b)/1> (1) of formula (I) in which (a) n = 1 and R2 = methyl, phenyl, 4-chlorophenyl or 4-chloro-3-nitropheny or (b) m = 1, n = 2 and and R2 = 4-chloro-3-nitrophenyl, (2) bis-(3:5-dinitro-4-chlorophenyl)oxdiazole, (3) bis-(2:4-dichloro-3-nitrophenyl)oxdiazole and (4) 3:5-dinitro-4-chlorophenyl-41-chlorophenyloxdiazole are reacted with materials selected from NaOH/methanol, sodium methoxide, ethoxide and isopropoxide, ammonia, ethylamine, morpholine, aniline, o- and p-toluidines, o-anisidine, 1-amino-2-methyl-5-chlorobenzene, 1-amino-2:5-dimethylbenzene, p-phenylenediamine and its monoacetyl derivative, N-methylaniline, 1 - amino - 2:5 - dimethoxy-4-benzoylaminobenzene, 1-aminonaphthalene, 1:4-diamino - 2 - chloro-(or methyl)-5-methylbenzene, benzidine and its 3:31-dimethyl or -dimethoxy derivatives. Other basic reactants mentioned include NaOH and KOH. The starting materials are prepared by dehydration of the appropriate diacylhydrazides or the corresponding carboxylic acid/hydrazine salts or mixtures. Specific nitrohalogen compounds for which preparative details are given are those of formula (I) wherein n = 1 and R2 = methyl and 4-chloro-3-nitrophenyl, and compound 1(b), above. The substituted nitrophenyloxdiazoles prepared according to the invention may be converted by reduction to the corresponding aminophenyloxdiazoles; 4 - chlorophenyl-41-methoxy-31-aminophenyloxdiazole is specifically mentioned.ALSO:Pigments are constituted by substituted 4-animo- 3-nitrophenyl- 1:3:4-oxdiazoles, prepared by reacting with an aromatic amine a 1:3:4-oxdiazole containing at least one 4-rohalogeno-3-nitrophenyl substituent. The nitrohalogen compound may have the formula (1) wherein R1 is a divalent organic radical, R2 an organic substituent and m and n each = 1 or 2. In examples, starting materials <FORM:0916560/IV (b)/1> (1) of formula (I) in which (a) n = 1 and R2 = methyl, phenyl, 4-chlorophenyl or 4-chloro-3-nitrophenyl or (b) m = 1, n = 2 and R2 = 4-chloro-3-nitrophenyl, (2) bis-(3 : 5-dinitro-4-chlorophenyl)oxdiazole, (3) bis-(2 : 4-dichloro-3-nitrophenyl)oxdiazole and (4) 3 : 5-dinitro- 4-chlorophenyl- 41-chlorophenyloxdiazole are reacted with materials selected from aniline, o- and p-toluidines, p o-anisidine, 1-amino-2- methyl-5-chlorobenzene, 1-amino-2 : 5-dimethylbenzene, p-phenylenediamine and its monoacetyl derivative, N-methylaniline, 1-amino- 2 : 5- dimethoxy 4-benzoylaminobenzene, 1-aminonaphthalene, 1 : 4- diamino-2-chloro-(or methyl)-5-methylbenzene, benzidine and its 3 : 31-dimethyl or -dimethoxy derivatives. The substituted nitrophenyloxdiazoles, including those made by replacing the aromatic amine reactant by, e.g. sodium alkoxide, ammonia, ethylamine or morpholine NaOH or KOH may be converted by reduction to the corresponding aminophenyloxdiazoles; 4-chlorophenyl- 41-methoxy- 31-aminophenyl oxdiazole is specifically mentioned. Such amino-compounds may be converted to azo dyestuffs.
GB4485160A 1959-12-30 1960-12-30 Process for the manufacture of substituted nitrophenyl-1,3,4-oxdiazoles Expired GB916560A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH8248659A CH392520A (en) 1959-12-30 1959-12-30 Process for the preparation of 3'-nitro-4'-hydroxyphenyl-1,3,4-oxdiazoles etherified in the 4'-position

Publications (1)

Publication Number Publication Date
GB916560A true GB916560A (en) 1963-01-23

Family

ID=4539820

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4485160A Expired GB916560A (en) 1959-12-30 1960-12-30 Process for the manufacture of substituted nitrophenyl-1,3,4-oxdiazoles

Country Status (2)

Country Link
CH (1) CH392520A (en)
GB (1) GB916560A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2659709A1 (en) * 1976-12-31 1978-07-13 Hoechst Ag 1,3,4-OXADIAZOLE, METHOD FOR THEIR MANUFACTURING AND USE

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY151199A (en) 2001-11-02 2014-04-30 Rigel Pharmaceuticals Inc Substituted diphenyl heterocycles useful for treating hcv infection
WO2004099164A1 (en) 2003-05-02 2004-11-18 Rigel Pharmaceuticals, Inc. Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating hcv infection
US7326790B2 (en) 2003-05-02 2008-02-05 Rigel Pharmaceuticals, Inc. Diphenylisoxazole compounds and hydro isomers thereof
US7220745B2 (en) * 2003-05-15 2007-05-22 Rigel Pharmaceuticals Heterocyclic compounds useful to treat HCV
WO2005049065A2 (en) 2003-11-19 2005-06-02 Rigel Pharmaceuticals, Inc. Synergistic combinations of dihaloacetamide with interferon or ribavirin for treatment hcv infections
US7514434B2 (en) 2004-02-23 2009-04-07 Rigel Pharmaceuticals, Inc. Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof
CN101203498A (en) 2005-05-02 2008-06-18 里格尔药品股份有限公司 Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2659709A1 (en) * 1976-12-31 1978-07-13 Hoechst Ag 1,3,4-OXADIAZOLE, METHOD FOR THEIR MANUFACTURING AND USE

Also Published As

Publication number Publication date
CH392520A (en) 1965-05-31

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