4,5-Dihydro-2-thiazolamine → 3-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimine

Participants

Reaction Conditions

Reaction Steps

A mixture of 511 mg (5 mmol) of 2-amino-2-thiazoline and 1.03 g (5 mmol) of 5-bromomethyl-2-chloropyridine in 50 ml of acetonitrile was heated for 6 hours at 90° C. under refluxing. Then, the reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The resulting residue was mixed with dichloromethane and saturated sodium hydrogen-carbonate aqueous solution, and the organic layer was separated. The water layer was extracted with dichloromethane, and combined organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; hexane:ethyl acetate=2:1) to give 623 mg (yield; 54.7%) of 3-(6-chloro-3-pyridyl)methyl-2-iminothiazolidine as yellow oil and 173 mg (yield; 7.4%) of 3-(6-chloro-3-pyridyl)methyl-2-[(6-chloro-3-pyridyl)methyl]iminothiazolidine as yellow oil.

Provenance & Evidence