Diethyl Ether → HCID 68183049, compound

Participants

Reaction Steps

6-chloro-2,3-dihydro-4H-thieno[3,2-e][1,2]thiazin-4-one 1,1-dioxide (0.820 g, 3.45 mmol) was dissolved in THF (31 mL) and 1 M of 4-Chlorophenylmagnesium bromide in ether (8.2 mL, 8.2 mmol) was added. The solution was stirred at room temperature overnight. At that time, TLC indicated good conversion. Reaction was quenched by addition of satd NaHCO3 (20 mL) and extracted with EA (3×50 mL). The combined organic extracts were washed with brine (20 mL), dried with MgSO4, filtered and evaporated. The residue was purified using column chromatography on silica gel (80 g Analogix column, gradient 10% EA in hexane to 40% EA in hexane over 20 minutes) to give the product (0.34 g, 26%). LCMS: (FA) ES-348, 350, 352. 1H NMR (400 MHz, d6-DMSO) δ: 8.41 (dd, J=8.75, 5.76 Hz, 1H), 7.49-7.42 (m, 2H), 7.33-7.25 (m, 2H), 6.74 (s, 1H), 6.57 (s, 1H), 3.70-3.60 (m, 2H).

Provenance & Evidence