Sodium Hydroxide → HCID 42630234, compound

Participants

Reaction Steps

To a suspension of 0.128 g sodium cyanate in 3.0 ml acetonitrile was added 0.11 ml pyridine and 0.19 ml m-toluenesulfonyl chloride and the mixture was sonicated in a ultrasound bath at ca 40° C. for 1.5 h. HPLC showed disappearance of 3-Chloro-benzenesulfonyl chloride. The resulting suspension was added with stirring to a solution of 0.169 g 2-amino-6-chloropyridine in 1.0 ml of acetonitrile and the mixture was stirred at room temperature for 2 h. The reaction mixture was partioned between 0.1N sodium hydroxide and ethyl acetate (pH 10). The phases were separated and the aqueous phase was washed twice with ethyl acetate. The aqueous phase was acidified by addition of 25% hydrochloric acid and extracted with ethyl acetate, the organic phase was evaporated under reduced pressure. The residue was purified by silica column chromatography and crystallisation to yield 0.0995 g of a off-white solid. MS (ISN) M−H+=324.4

Provenance & Evidence