GB608295A - Manufacture of imidazolines - Google Patents

Manufacture of imidazolines

Info

Publication number
GB608295A
GB608295A GB16196/46A GB1619646A GB608295A GB 608295 A GB608295 A GB 608295A GB 16196/46 A GB16196/46 A GB 16196/46A GB 1619646 A GB1619646 A GB 1619646A GB 608295 A GB608295 A GB 608295A
Authority
GB
United Kingdom
Prior art keywords
sulphide
nitrile
naphthyl
methyl
imidazoline
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
GB16196/46A
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 GB608295A publication Critical patent/GB608295A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic 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
    • C07D233/20—Heterocyclic 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
    • C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic 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
    • C07D233/06—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic 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
    • C07D233/20—Heterocyclic 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
    • C07D233/22—Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Imidazolines are prepared by reacting a nitrile with an aliphatic diamine in which the two amino groups are attached to vicinal carbon atoms, in the presence of hydrogen sulphide or a substance capable of yielding hydrogen sulphide during the reaction, e.g. carbon disulphide, phosphorus pentasulphide, on alkali metal sulphide, an ammonium sulphide, iron sulphide or aluminium sulphide. The reaction may be effected in the presence of a smaller quantity of hydrogen sulphide than which corresponds to equimolecular proportions of the nitrile and hydrogen sulphide. The nitrile employed may be an aliphatic, alicyclic, aromatic, araliphatic or heterocyclic nitrile which may carry substituents such as halogen atoms, substituted or unsubstituted hydroxyl or amino groups. The reaction is advantageously carried out in an organic solvent, e.g. ethanol, xylene or toluene, at a raised temperature and in a closed vessel, and a mineral acid such as a hydrogen halide, sulphuric or phosphoric acid may be added. In examples, the preparation of the following compounds is described: 2-benzyl-imidazoline, 2-[naphthyl-(11)-methyl]-, 2-[41-methoxy - naphthyl - (11) - methyl]-, 2 - (31 : 41 : 51 - trimethoxybenzyl-, 2-(21-methoxy-naphthyl-(11)- and 2-(N - phenyl - aminomethyl) - imidazoline hydrochlorides, and 2-phenyl-, 2-n-pentyl-, 2-cyclohexylmethyl-, 2 - [b - phenylethyl]-, 2 - [pyridyl - (31)- and 2-[quinolyl-(81)-methyl]-imidazolines. The samples furnished under Sect. 2 (5) comprise 2-benzyl- and 2-(N-diphenyl-aminomethyl)-imidazoline.
GB16196/46A 1945-06-06 1946-05-28 Manufacture of imidazolines Expired GB608295A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH608295X 1945-06-06

Publications (1)

Publication Number Publication Date
GB608295A true GB608295A (en) 1948-09-13

Family

ID=4523216

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16196/46A Expired GB608295A (en) 1945-06-06 1946-05-28 Manufacture of imidazolines

Country Status (1)

Country Link
GB (1) GB608295A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2751393A (en) * 1953-05-13 1956-06-19 Imidazoline derivatives of aryl indoles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2751393A (en) * 1953-05-13 1956-06-19 Imidazoline derivatives of aryl indoles

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