Dichloromethane → HCID 19890949, compound

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Reaction Steps

To a solution of 3 g (0.0103 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) in 20 ml dichloromethane that has been cooled to -10° C. is added with stirring 1.32 g (0.0103 mol) chloromethylenedimethyliminium chloride, the mixture is then stirred at room temperature for 2 hours then a solution of 0.97 g (0.0103 mol) 3-aminopyridine and 2.32 g (0.023 mol) triethylamine in 20 ml dichloromethane are added dropwise with in 10 minutes and stirring is continued at room temperature for 14 hours, the reaction mixture is extracted with 50 ml water and the separated dichloromethane phase is dried and the solvent removed. The oily residue is treated with 50 ml 1 N HCl and filtered, it is then basified with NaOH (5%) and extracted twice with 50 ml portions of dichloromethane. The organic phase is dried over sodium sulfate and the solvent removed, the residue is dissolved in 40 ml 2-propanol and treated slowly with stirring with 15 ml 2-propanol/10% HCl when the hydrochloride crystallizes out. This is washed with 50 ml diethyl ether.

Provenance & Evidence