Related Experiment Video
Updated: Nov 4, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
α-[Amino(4-aminophenyl)thio]methylene-2-(trifluoromethyl)benzeneacetonitrile; Configurational equilibria in solution
Charles J McElhinny1, Anita H Lewin1, Larry Brieaddy1
1Research Triangle Institute, P.O. Box 12194, Research Triangle Park, NC 27709, United States.
Abstract:
Inconsistent results have been reported for the effects of the mitogen-activating extracellular kinase (MEK) inhibitor α-[amino(4-aminophenyl)thio]methylene-2-(trifluoromethyl)benzeneacetonitrile (SL 327) on ethanol-induced conditioned place preference (EtOH-CPP). Since such inconsistencies may be due to the configurational composition of administered SL 327, the interconvertibility of the geometric isomers of this class of compounds has been investigated. This study provides conditions for determination of configurational composition of this class of compounds by HPLC and by 1H NMR and reports details of configurational equilibria as a function of medium and time in solution along with solubility data for SL 327 in aqueous DMSO. The results suggest that the apparently inconsistent results reported for CPP-EtOH may be due to the administration of suspension vs. solutions, as well as to different configurational compositions of SL 327.
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
NMR Spectroscopy of Benzene Derivatives
Structure of Amines
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Nucleophilic Aromatic Substitution: Elimination–Addition
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

