2-Phenyl-1,2,6-thiadiazinane 1,1-dioxide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-phenyl-1,2,6-thiadiazinan 1,1-dioxide (400 mg, 1.89 mmol) in DMSO (15 mL), were added K2CO3 (522.4 mg, 3.78 mmol) and ethyl bromoacetate (379.1 mg, 2.27 mmol). The reaction mixture was agitated for 4 hr and extracted with ethyl acetate and brine. The organic layer was dried over MgSO4 and the residue was purified by silica gel column chromatography to yield ethyl 2-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetate (468 mg, 1.56 mmol, 83%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.45-7.34 (m, 3H), 7.30-7.25 (m, 1H), 4.28-4.20 (q, J=7.1 Hz, 2H), 4.03 (s, 2H), 3.82-3.73 (m, 4H), 1.99-1.91 (m, 2H), 1.30 (t, J=7.1 Hz, 3H). extracted with ethyl acetate and brine The organic layer was dried over MgSO4 the residue was purified by silica gel column chromatography