GB243766A - Process for the manufacture of benzimidazoles - Google Patents

Process for the manufacture of benzimidazoles

Info

Publication number
GB243766A
GB243766A GB30276/25A GB3027625A GB243766A GB 243766 A GB243766 A GB 243766A GB 30276/25 A GB30276/25 A GB 30276/25A GB 3027625 A GB3027625 A GB 3027625A GB 243766 A GB243766 A GB 243766A
Authority
GB
United Kingdom
Prior art keywords
phenylenediamine
ethoxy
heating
benzimidazole
benzimidazoles
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
GB30276/25A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB243766A publication Critical patent/GB243766A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms

Abstract

2-Alkyl- or aryl-oxyalkyl-benzimidazoles are obtained by the interaction of an o-phenylenediamine with an alkyl- or aryl-ether acid in the manner known for the production of benzimidazole derivatives. The products have antipyretic properties. The following compounds are produced according to examples:- (1) 2-ethoxymethyl-benzimidazole by heating o-phenylenediamine with ethoxyacetic anhydride at 120 DEG C., separating the diacyl compound, and heating it dry at 180 DEG C.; (2) 5-ethoxy-2-ethoxymethylbenzimidazole hydrochloride by heating 4-ethoxy-1 : 2-phenylenediamine with ethoxyacetic anhydride at 150 DEG C. and passing gaseous hydrochloric acid into an ethereal solution of the product; (3) 2-phenoxymethyl-benzimidazole and 5-ethoxy-2-phenoxymethylbenzimidazole from o-phenylenediamine or ethoxy-o-phenylenediamine and phenoxyacetic acid. The Specification as open to inspection under Sect. 91 (3) (a) comprises also the production of the new benzimidazoles by reduction of the corresponding o-nitroacylaminobenzenes so as to effect simultaneous reduction and ring closure. 2-Methoxymethylbenzimidazole and 2-propyloxymethylbenzimidazole are also mentioned. This subject-matter does not appear in the Specification as accepted.
GB30276/25A 1924-12-01 1925-12-01 Process for the manufacture of benzimidazoles Expired GB243766A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE243766X 1924-12-01

Publications (1)

Publication Number Publication Date
GB243766A true GB243766A (en) 1926-07-29

Family

ID=5922476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30276/25A Expired GB243766A (en) 1924-12-01 1925-12-01 Process for the manufacture of benzimidazoles

Country Status (1)

Country Link
GB (1) GB243766A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3147274A (en) * 1962-05-24 1964-09-01 Dow Chemical Co Anisic acid derivatives of benzimidazoles
US3182070A (en) * 1962-05-24 1965-05-04 Dow Chemical Co Benzimidazole compounds
US3256288A (en) * 1962-05-24 1966-06-14 Dow Chemical Co 1-substituted aminoalkyl-2-aryloxymethylbenzimidazole compounds
US4323688A (en) * 1977-08-01 1982-04-06 Ciba-Geigy Corporation Benzimidazole-2-carboxylic acid and derivatives thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3147274A (en) * 1962-05-24 1964-09-01 Dow Chemical Co Anisic acid derivatives of benzimidazoles
US3182070A (en) * 1962-05-24 1965-05-04 Dow Chemical Co Benzimidazole compounds
US3256288A (en) * 1962-05-24 1966-06-14 Dow Chemical Co 1-substituted aminoalkyl-2-aryloxymethylbenzimidazole compounds
US4323688A (en) * 1977-08-01 1982-04-06 Ciba-Geigy Corporation Benzimidazole-2-carboxylic acid and derivatives thereof

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