Thionyl Chloride → HCID 60069839, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (1.04 mL) was added to a solution of (2E)-3-(5-bromothien-2-yl) acrylic acid (1.04 g, 4.46 mmol) in chloroform (20 mL) and the mixture was refluxed for 2 h at 75° C. and than used in the next step. The above solution was added drop wise to a stirred suspension of sodium azide (0.58 g, 8.93 mmol), dioxane (3 mL) and water (3 mL) in an ice bath. After 10 min a precipitate appeared which was filtered off and washed with water. The residue was dissolved in dichloromethane, dried with MgSO4, filtered and the solvent was removed to afford: 0.96 g (83.4%). 1H NMR (270 MHz CH3OH-d4) δ ppm 6.20 (d, J=15.57 Hz, 1H) 7.15-7.25 (m, 2H) 7.80 (d, J=15.57 Hz, 1H); MS 258.1 (M−H)+; Purity (HPLC) 65%.

Provenance & Evidence