Amino-functionalized ionic liquid as a nucleophilic scavenger in solution phase combinatorial synthesis.
A new functionalized ionic liquid, 1-aminoethyl-3-methylimidazolium hexafluorophosphate was synthesized from 1-methylimidazole and 2-bromoethylamine hydrobromide. This ionic liquid was found to be an efficient scavenger for removing excess electrophiles, such as benzoyl chloride, p-toluenesulfochloride, phenyl isothiocyanate, and p-chlorophenyl isocyanate, in a solution-phase parallel synthesis. The resulting ionic liquid derivatives can be separated directly from the reaction mixture. Desired products were obtained with high purity. Only 1.5-2.0 equiv of this scavenger was needed with a sequestration time of less than 35 min. In addition, the used ionic liquid can be regenerated and recycled several times without significant loss of activity.
Song
Gonghua
G
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology, Shanghai 200237, China. ghsong@ecust.edu.cn
Cai
Yueqin
Y
Peng
Yanqing
Y
D000588:Amines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D012996:Solutions / Q000737:chemistry
C507932:1-aminoethyl-3-methylimidazolium hexafluorophosphate; D000588:Amines; D006845:Hydrocarbons, Fluorinated; D007093:Imidazoles; D012996:Solutions