tert-butyl 1,1-dioxo-1,2,6-thiadiazinane-2-carboxylate

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

Procedure: To a solution of tert-butyl N-(3-chloropropyl)sulfamoylcarbamate (2 g, 7.333 mmol) in DMSO (10 mL), was added K2CO3 (5.068 g, 36.665 mmol) at room temperature. The reaction mixture was agitated for 4 hr and extracted using ethyl acetate and NH4Cl solution. The organic layer was dried over MgSO4. The residue was purified by silica gel column chromatography to give tert-butyl 1,2,6-thiadiazinan-2-carboxylate 1,1-dioxide (689 mg, 2.92 mmol, 40%, white solid). 1H NMR (300 MHz, CDCl3): δ 4.47 (br, 1H), 3.95-3.91 (m, 2H), 3.55-3.49 (m, 2H), 1.89-1.82 (m, 2H), 1.54 (m, 9H). extracted The organic layer was dried over MgSO4 The residue was purified by silica gel column chromatography