Sodium hydride → HCID 21928110, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the above 2-mercapto-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridine-3-carbonitrile (12.5 g, 63.0 mmol) in DMF (300 mL), cooled to 0° C., was added sodium hydride (2.60 g, 65.0 mmol) as a 60% dispersion in mineral oil. The mixture was stirred at 0° C. for 30 min then 2-bromoacetamide (8.80 g, 63.8 mmol) was added as a solid in one portion. The mixture was allowed to slowly warm to room temperature and stirred for 15 h. The mixture poured into ice—H2O and stirred until all of the ice had melted, during which time a solid precipitated from solution. The mixture was acidified with 2N HCl then cooled to 0° C. and the solid collected by filtration. The material was washed with Et2O followed by hexanes to provide 11.2 g (69.9%) of 2-(3-cyano-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridin-2-ylsulfanyl)-acetamide as a tan solid.

Provenance & Evidence