title: Preparation and utility of trihaloethyl imidates: useful reagents for the synthesis of amidines.
abstract: 2,2,2-Trifluoro- and trichloroethyl imidates, which are easily prepared by reaction of a nitrile and a trihaloethanol in the presence of HCl, have proven to be excellent reagents for the preparation of amidines under mild reaction conditions. Depending on the nature of the amine nucleophile, the imidates can react either as the free-base or the hydrochloride salt in a telescoped process. In several cases, the p-bromobenzoate salt of the desired product was directly isolated from the reaction mixture.
authors.affiliation: Chemical R&D, Pfizer Global R&D, MS-8118D/4002, Eastern Point Road, Groton, Connecticut 06340, USA. stephane.caron@pfizer.com
authors.forename: Stéphane
authors.initials: S
authors.lastname: Caron
authors.forename: Lulin
authors.initials: L
authors.lastname: Wei
authors.forename: Jasmin
authors.initials: J
authors.lastname: Douville
authors.forename: Arun
authors.initials: A
authors.lastname: Ghosh
mesh_terms: D000578:Amidines / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D007096:Imidoesters / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000578:Amidines; D006846:Hydrocarbons, Halogenated; D007096:Imidoesters; D007202:Indicators and Reagents