EP1899312A2 - Amelioration de la synthese du 1-halomethyl-2-phenyl-1-phenyloxyrane substitue - Google Patents

Amelioration de la synthese du 1-halomethyl-2-phenyl-1-phenyloxyrane substitue

Info

Publication number
EP1899312A2
EP1899312A2 EP06745168A EP06745168A EP1899312A2 EP 1899312 A2 EP1899312 A2 EP 1899312A2 EP 06745168 A EP06745168 A EP 06745168A EP 06745168 A EP06745168 A EP 06745168A EP 1899312 A2 EP1899312 A2 EP 1899312A2
Authority
EP
European Patent Office
Prior art keywords
phenyl
oxirane
halomethyl
chlorophenyl
propene
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.)
Withdrawn
Application number
EP06745168A
Other languages
German (de)
English (en)
Inventor
David Leonov
David Ovadia
Raya Sturkovich
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.)
Adama Makhteshim Ltd
Original Assignee
Makhteshim Chemical Works Ltd
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 Makhteshim Chemical Works Ltd filed Critical Makhteshim Chemical Works Ltd
Publication of EP1899312A2 publication Critical patent/EP1899312A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C07D301/16—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof formed in situ, e.g. from carboxylic acids and hydrogen peroxide
    • C07D301/18—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof formed in situ, e.g. from carboxylic acids and hydrogen peroxide from polybasic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Definitions

  • the present invention is from the field of chemical synthesis, particularly the field of the synthesis of substituted methyl oxirane compounds, e.g. cis- l-(chloromethyl)-2-(2- chlorophenyl)- 1 -(4-fluorophenyl) oxirane.
  • the present invention provides a process for the preparation of l-halomethyl-2-phenyl-l- phenyl oxirane, wherein the phenyl substituents may be mono-, di- or poly- halo substituted, wherein 3-halo-2-phenyl- 1-phenyl propene is reacted with an anhydride and hydrogen peroxide in a solvent selected from among alkyl esters, followed by subsequent extraction and separation of the organic phase and isolation of the oxirane.
  • l-halomethyl-2-phenyl-l -phenyl oxirane wherein the phenyl substituents may be mono-, di- or poly- halo substituted, is prepared by reacting 3-halo-2-phenyl- 1 -phenyl propene with an anhydride and hydrogen peroxide in a solvent selected from among alkyl esters, followed by subsequent extraction and separation of the organic phase and isolation of the oxirane.
  • suitable anydrides include acetic anhydride and maleic anhydride.
  • Suitable solvents are alkyl acetates, preferably butyl acetate and ethyl acetate.
  • the reaction time is between 2 and 25 hours and the reaction temperature is from 5°C and 70 0 C.
  • the isolation and purification of the oxirane is carried out subsequent to the reaction and includes extraction and crystallization in single, multiple or repeated stages.
  • cis-l-(chloromethyl)-2-(2-chlorophenyl)-l-(4-fluorophenyl) oxirane is prepared wherein Z-3-chloro-2-(4-fluorophenyl)-l-(2-chlorophenyl) propene is reacted with maleic anhydride and hydrogen peroxide wherein the solvent is selected from among butyl acetate and ethyl acetate.
  • the reaction time is between 2 to 25 hours, preferably 8 to 13 hours, and the reaction temperature is from 15°C to 7O 0 C, preferably 25 0 C to 5O 0 C.
  • the organic phase of the reaction is extracted with water to remove all the water miscible reagents and the remaining organic phase is then subject to purification of the oxirane derivative therefrom.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)

Abstract

La présente invention concerne une amélioration du procédé d'élaboration du 1-halométhyl-2-phényl-1-phényloxyrane substitué. Les substituants phényle peuvent être mono-, di- ou poly-halo-substitués. En l'occurrence, on prend le 3-halo-2-phényl-1-phénylpropène et on le fait réagir avec un anhydride et du peroxyde d'hydrogène dans un solvant choisi dans les esters alkyliques, puis on procède à l'extraction et séparation de la phase organique puis à l'isolation de l'oxyrane. Les améliorations apportées concernent essentiellement le rendement, la procédure d'isolation et la sécurité. L'isolation et purification de l'oxyrane se font après la réaction, avec une extraction et cristallisation en une ou plusieurs opérations éventuellement répétées.
EP06745168A 2005-06-27 2006-06-22 Amelioration de la synthese du 1-halomethyl-2-phenyl-1-phenyloxyrane substitue Withdrawn EP1899312A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL16942005 2005-06-27
PCT/IL2006/000729 WO2007000759A2 (fr) 2005-06-27 2006-06-22 Amelioration de la synthese du 1-halomethyl-2-phenyl-1-phenyloxyrane substitue

Publications (1)

Publication Number Publication Date
EP1899312A2 true EP1899312A2 (fr) 2008-03-19

Family

ID=37547032

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06745168A Withdrawn EP1899312A2 (fr) 2005-06-27 2006-06-22 Amelioration de la synthese du 1-halomethyl-2-phenyl-1-phenyloxyrane substitue

Country Status (5)

Country Link
EP (1) EP1899312A2 (fr)
KR (1) KR20080024207A (fr)
CN (1) CN101208322A (fr)
BR (1) BRPI0613843A2 (fr)
WO (1) WO2007000759A2 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3218129A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, ihre herstellung und verwendung als arzneimittel

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3218130A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide
US5268517A (en) * 1989-07-14 1993-12-07 Basf Aktiengesellschaft Stereoselective preparation of Z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes, and novel intermediates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3218129A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, ihre herstellung und verwendung als arzneimittel

Also Published As

Publication number Publication date
WO2007000759A2 (fr) 2007-01-04
CN101208322A (zh) 2008-06-25
WO2007000759A3 (fr) 2007-04-05
BRPI0613843A2 (pt) 2011-02-15
KR20080024207A (ko) 2008-03-17

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