Thioacetamide → 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-bromo-4-(bromoacetyl)-2H-chromen-2-one (1.45 g, 4.19 mmol) in N,N-dimethylformamide (12.5 mL), thioacetamide (346 mg, 4.6 mmol) was added. The reaction was then stirred overnight at 100° C. After cooling, the reaction mixture was dissolved with a 4:1 mixture of CH2Cl2/hexanes. The mixture obtained was washed (3×) with water and the organic layer was concentrated under reduced pressure. The solid obtained was swished in a 4:1 mixture of hexanes/EtOAc. The solid obtained was collected by filtration and used as such for the next step. 1H NMR (400 MHz, acetone-d6): 8.32 (d, 1H), 8.14 (s, 1H), 7.66 (s, 1H), 7.54 (d, 1H), 6.73 (s, 1H), 2.74 (s, 3H).

Provenance & Evidence