GB669402A - Improvements relating to the preparation of benziminazoles and benzoxazoles - Google Patents

Improvements relating to the preparation of benziminazoles and benzoxazoles

Info

Publication number
GB669402A
GB669402A GB247849A GB247849A GB669402A GB 669402 A GB669402 A GB 669402A GB 247849 A GB247849 A GB 247849A GB 247849 A GB247849 A GB 247849A GB 669402 A GB669402 A GB 669402A
Authority
GB
United Kingdom
Prior art keywords
benzoxazole
benziminazole
nitrophenyl
benziminazoles
benzoxazoles
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
GB247849A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB247849A priority Critical patent/GB669402A/en
Publication of GB669402A publication Critical patent/GB669402A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Benziminazoles and benzoxazoles are prepared from ring systems containing two adjacent amino groups or an amino group adjacent to a hydroxyl group such as o-phenylenediamines and o-amino-phenols by the oxidation of a mixture of the diamine and an aldehyde or the aminophenol and an aldehyde or of the schiffs base derived from the above reactants characterized by the use of lead tetra-acetate as the oxidizing agent. The reaction may be conducted in glacial acetic acid or benzene. The examples show the following oxidations: (1) N - (m - nitrobenzal) - o - phenylene diamine to 2-(m-nitro-phenyl)-benziminazole; (2) N - (p - nitrobenzal) - o - phenylenediamine to 2 - (p - nitrophenyl) - benziminazole; (3) N-(p - cyanobenzal) - o - phenylenediamine to 2-(p - cyanophenyl) - benziminazole; (4) 2 - p-nitrobenzalaminophenol to 2-(p-nitrophenyl)-benzoxazole; (5) p-nitrobenzaldehyde and o-aminophenol in solution together to 2-(p-nitrophenyl-benzoxazole; (6) 2-cinnamylideneaminophenol to 2 - styryl - benzoxazole; (7) methyl-2 - (p - acetylaminobenzalamino) - phenol - 4-carboxylic ester to 2-(p-acetylaminophenyl)-benzoxazole-5-carboxylic ester; (8) 2-(p-chlorobenzalamino) - phenol to 2 - (p - chlorophenyl)-benzoxazole.
GB247849A 1949-01-28 1949-01-28 Improvements relating to the preparation of benziminazoles and benzoxazoles Expired GB669402A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB247849A GB669402A (en) 1949-01-28 1949-01-28 Improvements relating to the preparation of benziminazoles and benzoxazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB247849A GB669402A (en) 1949-01-28 1949-01-28 Improvements relating to the preparation of benziminazoles and benzoxazoles

Publications (1)

Publication Number Publication Date
GB669402A true GB669402A (en) 1952-04-02

Family

ID=9740260

Family Applications (1)

Application Number Title Priority Date Filing Date
GB247849A Expired GB669402A (en) 1949-01-28 1949-01-28 Improvements relating to the preparation of benziminazoles and benzoxazoles

Country Status (1)

Country Link
GB (1) GB669402A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2780633A (en) * 1957-02-05 Method of making benzoxazole
US3262929A (en) * 1961-09-12 1966-07-26 Mitsui Kagaku Kogyo Kabushiki 2-styrylbenzoxazole compounds
US3341529A (en) * 1964-09-10 1967-09-12 American Cyanamid Co Method for preparing 2-styrylnaphthoxazole compounds
US3347694A (en) * 1961-09-12 1967-10-17 Mitsui Kagaku Kogyo Kabushiki Method for optical brightening of polymeric substrates utilizing 2-styryloxazole compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2780633A (en) * 1957-02-05 Method of making benzoxazole
US3262929A (en) * 1961-09-12 1966-07-26 Mitsui Kagaku Kogyo Kabushiki 2-styrylbenzoxazole compounds
US3347694A (en) * 1961-09-12 1967-10-17 Mitsui Kagaku Kogyo Kabushiki Method for optical brightening of polymeric substrates utilizing 2-styryloxazole compounds
US3341529A (en) * 1964-09-10 1967-09-12 American Cyanamid Co Method for preparing 2-styrylnaphthoxazole compounds

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