GB656472A - Manufacture of new imidazolines - Google Patents

Manufacture of new imidazolines

Info

Publication number
GB656472A
GB656472A GB2851/48A GB285148A GB656472A GB 656472 A GB656472 A GB 656472A GB 2851/48 A GB2851/48 A GB 2851/48A GB 285148 A GB285148 A GB 285148A GB 656472 A GB656472 A GB 656472A
Authority
GB
United Kingdom
Prior art keywords
phenyl
methyl
hydroxyl group
radicals
substituted
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
GB2851/48A
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 GB656472A publication Critical patent/GB656472A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2-(N : N-Diphenylaminomethyl)-imidazolines, or salts thereof, which compounds are substituted in meta- and/or para-position only of one or both the phenyl radicals at least one of said substituents being an unsubstituted or etherified nuclear hydroxyl group, are prepared by heating a 2-oxymethyl-imidazoline ester of a hydrohalic acid or an alkyl or aryl sulphonic acid or a salt of such ester with a diphenylamine which is substituted in meta- and/or para-position only of one or both of the phenyl radicals, at least one of the substituents being an unsubstituted, etherified or esterified hydroxyl group or with an N-metal derivative of a diphenylamine which is substituted as specified except by a free hydroxyl group. The further substituents may be alkyl radicals, e.g. methyl, ethyl or propyl radicals. The imidazoline residue may also contain substituents, e.g. alkyl radicals such as methyl, ethyl or propyl radicals. The hydroxy groups may be etherified with an aliphatic alcohol, e.g. methyl or ethyl alcohol. In the case of an esterified hydroxyl group hydrolysis to the free hydroxyl group takes place during the process. The imidazolines are also prepared by heating an N : N-diphenylamino-acetic acid which is substituted in meta- and/or para-position only of one or both of the phenyl radicals at least one of the substituents being an unsubstituted, etherified or esterified nuclear hydroxyl group, or an imido-ether, imido-halide, thioamide, thioimido-ether, amide, ester, halide, amidine or nitrile of such acid, with an alkylene diamine in which the amino groups are bound to vicinal carbon atoms and are unsubstituted, or a salt thereof, or with ethylene urea. The alkylene diamines may be substituted on the carbon atoms, e.g. by an alkyl group such as a methyl or ethyl group. The acid derivatives of the diphenylamino acetic acid may be formed during the course of the reaction, e.g. by using a nitrile in the presence of hydrogen sulphide while the hydrogen sulphide may be formed from a compound forming hydrogen sulphide. The alkylene diamine may be a 1 : 2-diamine acylated with an N : N-diphenylamino-acetic acid specified above and the desired imidazoline is obtained by splitting out water. Salts of the desired imidazolines may be converted in the free bases, or the desired imidazolines may be converted into salts. A number of detailed examples are given. Specifications 528,915 and 529,054 are referred to. N-(p-Methoxy-phenyl)-N-phenylaminoacetonitrile is obtained by the condensation of p-methoxy-diphenylamine with formaldehyde and hydrocyanic acid in glacial acetic acid. It can be converted into the corresponding imido ether by treatment with an alcohol and a hydrohalic acid in an inert diluent. N-(p-Methoxy-phenyl)-N-phenylamino-acetamidine is prepared by reacting the imido ether referred to in the previous paragraph with ammonia. N-(p-Methyl-phenyl)-m-acetoxyphenylamine is prepared by reacting the sodium salt of N-(p-methyl-phenyl)-m-oxyphenylamine and acetyl chloride. N-(p-Methyl-phenyl)-N-(m-acetoxy-phenyl)-amino-acetonitrile is prepared by reacting N-(p-methyl-phenyl)-m-acetoxyphenylamine with paraformaldehyde and potassium cyanide. N-(p-Methyl-phenyl)-N-(m-oxyphenyl)-amino-acetonitrile is prepared by the mild alkaline hydrolysis of the corresponding aminoacetonitrile having a m-acetoxyphenyl radical. The Specification as open to inspection under Sect. 91 refers to the above process wherein the diphenylamine or the N : N-diphenyl-amino-alkane carboxylic or derivative contains at least one substituted or unsubstituted hydroxyl group in any position of the phenyl radicals. This subject-matter does not appear in the Specification as accepted.
GB2851/48A 1947-01-31 1948-01-30 Manufacture of new imidazolines Expired GB656472A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH656472X 1947-01-31

Publications (1)

Publication Number Publication Date
GB656472A true GB656472A (en) 1951-08-22

Family

ID=4526534

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2851/48A Expired GB656472A (en) 1947-01-31 1948-01-30 Manufacture of new imidazolines

Country Status (1)

Country Link
GB (1) GB656472A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0598962A1 (en) * 1991-05-23 1994-06-01 Neurosearch A/S Imidazole derivatives as calcium channel blockers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0598962A1 (en) * 1991-05-23 1994-06-01 Neurosearch A/S Imidazole derivatives as calcium channel blockers

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