GB641605A - Manufacture of an imidazoline - Google Patents

Manufacture of an imidazoline

Info

Publication number
GB641605A
GB641605A GB18493/47A GB1849347A GB641605A GB 641605 A GB641605 A GB 641605A GB 18493/47 A GB18493/47 A GB 18493/47A GB 1849347 A GB1849347 A GB 1849347A GB 641605 A GB641605 A GB 641605A
Authority
GB
United Kingdom
Prior art keywords
imidazoline
ethylene diamine
prepared
treating
sodium
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
GB18493/47A
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 GB641605A publication Critical patent/GB641605A/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
    • C07D233/04Heterocyclic 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

Landscapes

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

Abstract

2-(Benzhydryloxymethyl)-imidazoline is prepared by (1) treating a reactive ester, such as the halide, of 2-(hydroxymethyl)-imidazoline, e.g. 2-(chloromethyl)-imidazoline with a metal alcoholate of the constitution <FORM:0641605/IV (b)/1> where M is an alkali or an alkaline-earth metal, (2) treating a reactive ester, e.g. chloride, bromide or sulphonate of benzhydrol with a 2-(hydroxy methyl)-imidazoline or an alkali metal compound thereof, or (3) by reacting benzhydryloxy acetic acid or a reactive derivative thereof, such as an iminoether, iminohalide, thioamide, thioiminoether, amide, ester, halide or amidine or reactants which give rise to these in the course of the reaction (e.g. instead of a thioamide the corresponding nitrile may be used in the presence of hydrogen sulphide or agents yielding hydrogen sulphide such as carbon disulphide, phosphorus pentasulphide, an alkali metal sulphide, an ammonium sulphide, iron sulphide or aluminium sulphide with an aliphatic 1 : 2-diamine. Suitable 1 : 2-diamines are ethylene diamine, N-methyl-ethylene diamine, N-ethyl-ethylene diamine, N-propyl-ethylene diamine, 1-methyl-ethylene diamine, 1 : 2-dimethyl-ethylene diamine and 1-phenyl-ethylene diamine. The reactions may be carried out in the presence or absence of a solvent or condensing agent. In examples: (1) sodium benzhydrolate and 2-(chloromethyl)-imidazoline are refluxed in dioxane and the resulting 2-(benzhydryl-oxymethyl) imidazoline isolated as the picrate. (2) 2-(Hydroxymethyl)-imidazoline is refluxed with diphenyl methyl bromide and the desired compound again isolated as the picrate. (3) Benzhydrol is converted to sodium benzhydrolate which is reacted first with ethyl bromacetate and then with strong ammonia to give benzhydryloxyacetamide, which is then converted to benzhydryloxy-acetothioamide and treated with ethylene diamine to give the required product. (4) Benzhydryloxyacetamide is dehydrated with phosphorus pentoxide in the presence of triethylamine to benzhydryloxyacetanitrile which is then reacted with ethylene diamine. (5) Benzhydryloxyacetonitrile is treated with hydrochloric acid to form benzhydryloxyacetimidoether which is then refluxed with an ethanolic solution of ethylene diamine. Benzyloxyacetonitrile is prepared by reacting chloracetonitrile and benzyl alcohol in the presence of an acid binding agent such as sodium. b -Benxyloxypropionitrile is prepared by reacting benzyl alcohol with acrylonitrile in the presence of a catalytic quantity of sodium. Benhydryloxyacetonitrile is prepared by treating benzhydryloxyacetamide with phosphorus pentoxide in the presence of triethylamine or N-methyl-piperidine. Benzyloxy-acetimido-ethyl ether hydrochloride is prepared by treating benzyloxyacetonitrile with ethanol and hydrogen chloride in chloroform. b -Benzyloxy-propionimido-ethyl ether hydrochloride is prepared by treating b -benzyloxy-propionitrile with ethanol and hydrogen chloride. b -Benzyloxy-propionamidine hydrochloride is prepared by treating b -benzyloxy-propionimido ethyl ether hydrochloride with alcoholic ammonia. Ethyl benzhydryloxyacetate is prepared by reacting sodium benzhydrolate with ethyl bromacetate. Benzhydryloxyacetamide is prepared by treating ethyl benzhydryloxyacetate with concentrated aqueous ammonia. Benzhydryloxyacetothioamide is prepared by reacting benzhydryloxyacetamide with phosphorus pentasulphide and potassium sulphide in xylene or by treating benzhydryloxyacetonitrile with ammonia in ethanol saturated with hydrogen sulphide. The Specification as open to inspection under Sect. 91 includes also the preparation of 2-(aralkoxy-alkyl)-imidazolines in general and the following additional examples are included: (1) Sodium benzylate and 2-(chloromethyl) imidazoline are reacted to form 2-(benzyloxymethyl)-imidazoline. (2) Benzyloxyacetonitrile is treated with dry HCl and the product refluxed with ethylene diamine to form the same compound as in the previous example. (3) b -Benzyl-oxypropionitrile is treated with dry HCl and the product refluxed with ethylene diamine to form benzyloxyethyl imidazoline. (4) Phenyl-benzyl carbinol is converted into its sodium alcoholate and refluxed with 2-(chloromethyl) imidazoline. Additional carboxylic acids mentioned are benzyloxy-acetic acid, b -benzyloxypropionic acid and a : b -diphenyl-ethoxy-acetic acid. This subject-matter does not appear in the Specification as accepted.
GB18493/47A 1946-07-13 1947-07-11 Manufacture of an imidazoline Expired GB641605A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US641605XA 1946-07-13 1946-07-13

Publications (1)

Publication Number Publication Date
GB641605A true GB641605A (en) 1950-08-16

Family

ID=22053963

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18493/47A Expired GB641605A (en) 1946-07-13 1947-07-11 Manufacture of an imidazoline

Country Status (1)

Country Link
GB (1) GB641605A (en)

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