Ethyl Bromide → HCID 20041061, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methylthiazole (4.95 g) in ether (5 ml) was added to ethylmagnesium bromide prepared under nitrogen from magnesium turnings (1.2 g) and ethyl bromide (5.5 g) in ether (40 ml). A yellow precipitate was formed which dissolved when the ether was replaced by tetrahydrofuran (70 ml). 1-(4-Chlorophenyl)cyclobutanecarbonitrile (6.0 g) was added and the solvent replaced by toluene and the mixture heated at 90° C. for two hours. Water and 2N sodium hydroxide solution were added and the reaction mixture extracted with ether. The extract was dried and the solvents removed by evaporation. The residue was dissolved in ether and hydrogen chloride gas was passed into the solution to give a pale yellow solid which is believed to be [1-(4-chlorophenyl)cyclobutyl](4-methylthiazol2-yl)methanimine hydrochloride. This salt was heated at 95° C. for two hours with a solution of sodium borohydride (2 g) in diethyleneglycoldimethylether (100 ml). Water and 2N sodium hydroxide solution were added and the reaction mixture extracted with ether. The extract was dried and the solvents removed by evaporation. The residue was dissolved in ether and hydrogen chloride gas was passed into the solution to give a yellow solid. This solid was converted into the free base which was purified by column chromatography on a florisil column eluted with a mixture of ether and cyclohexane to give [1-(4-chlorophenyl)cyclobutyl](4-methylthiazol-2-yl)methylamine which was converted into a hydrochloride salt [m.p. 230°-232° C. (dec)]containing 1.5 moles of hydrochloride by dissolving the free base in ether and passing hydrogen chloride gas through the solution.

Provenance & Evidence