Chloroacetonitrile → HCID 71059752, compound

Participants

Reaction Steps

Chloroacetonitrile (0.32 mL, 5.06 mmol) was added to a solution of 4,4-difluoropiperidinothiocarboxamide (839 mg, 4.66 mmol) prepared above in methanol (15 mL), followed by heating overnight under reflux. The reaction solution was concentrated, and the residue was dissolved in acetic acid (15 mL), followed by addition of commercially available ethyl 4-phenyl-2,4-dioxobutyrate (1.03 g, 4.68 mmol) and sodium acetate (573 mg, 6.99 mmol) thereto. The mixture was heated for 1.5 hr under reflux in an argon atmosphere. The reaction solution was concentrated, and the residue was put into a saturated aqueous solution of sodium hydrogen carbonate. The precipitated crystals were collected by filtration, washed with water, and dried to obtain 2-(4,4-difluoropiperidino)-5-phenyl-7-thiazolo[4,5-b]pyridinecarboxylic acid ethyl ester (1.63 g, 4.04 mmol) as a brown powder.

Provenance & Evidence