Preparation and utility of trihaloethyl imidates: useful reagents for the synthesis of amidines.
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.
Caron
Stéphane
S
Chemical R&D, Pfizer Global R&D, MS-8118D/4002, Eastern Point Road, Groton, Connecticut 06340, USA. stephane.caron@pfizer.com
Wei
Lulin
L
Douville
Jasmin
J
Ghosh
Arun
A
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
D000578:Amidines; D006846:Hydrocarbons, Halogenated; D007096:Imidoesters; D007202:Indicators and Reagents