Sodium Azide → HCID 86723302, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of NaN3 (6.2 g, 95 mmol) in water (100 mL) and acetone (100 mL) was added a solution of (E)-3-(2-(2-chloro-6-fluorophenyl)thiazol-4-yl)acryloyl chloride (5.7 g, 19 mmol) in dioxane (100 mL) dropwise over 15 minutes. After addition, the resulting mixture was stirred for another 1 hour at 0° C. The reaction was quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organic extract was washed brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography, eluting with EtOAc/petroleum ether (1:8) to give the desired product as a yellow solid (5.3 g, 90% yield). LCMS (ESI) m/z: 309.0 [M+H+].

Provenance & Evidence