2-Acetamidothiazole → HCID 45121693, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(thiazol-2-yl)acetamide (150 g, 1056 mmol, Combi-Blocks, San Diego, Calif.) in acetonitrile (3 L) was added 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) (486 g, 1373 mmol, Air Products, Allentown, Pa.) and the mixture was heated at 80° C. for 4 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and water (2 L) was added. The mixture was extracted with ethyl acetate (2×1.5 L). The combined organic extract was washed with saturated aqueous NaHCO3 (1.5 L) and 2N HCl (1 L). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude N-(5-fluorothiazol-2-yl)acetamide (70.0 g, crude) which was used for next reaction without any purification. m/z (ESI) 161.0 (M+H)+

Provenance & Evidence