Phenylacetyl chloride → 2-Amino-4-{3-methoxy-4-[3-(2-phenylacetyl)thioureido]phenoxy}pyridine

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Reaction Steps

2-Phenylacetyl chloride (0.198 ml) was dissolved in acetonitrile (10 ml) under a nitrogen atmosphere, and then potassium thiocyanate (292 mg) was added at 60° C., followed by stirring at the same temperature for 3.5 hrs. The reaction mixture was cooled down to room temperature, and then 2-amino-4-(4-amino-3-methoxyphenoxy)pyridine (231.3 mg) was added thereto, followed by further stirring for 2 hrs. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1) to provide the titled compound (158 mg, 39%) as pale brown powder.

Provenance & Evidence