3-Thiomorpholinone

To a solution of 2-aminoehtane-1-thiol (4.5 g, 40 mmol, 1.0 equiv) and Ke (5. Og, 0.042 mol) was dissolved in a 1 :1 mixture of t-BuOH/Water (250ml_) and cooled to 0C. Potassium peroxymonosulfate (31.37g, 0.051 mol) was added and the resulting mixture was stirred at room temperature for 1 hour. The crude reaction mixture was partially concentrated, in order to remove t-BuOH. The resulting mixture was extracted with EtOAc (2 x 200ml_). The organic layer was concentrated in vacuum, giving 1.3g, 20.44% of l 6, 4-thiomorpholine-1 , 1 , 3-trione, which was used directly for subsequent steps. LCMS RT= 0.634min (Method B); ESI-MS m/z (150.05) 1H- NMR (400 MHz, DMSO-de) d ppm: 3.36-3.54 (m, 4H, NH-CH2-CH2-S02), 4.1 (s, 2H, CO- CH2-S02), 8.3 (s, 1 H, NH).e (5. Og, 0.042 mole) was dissolved in methanol (250ml) and stirred at room temperature. To this solution was added Montmorillonite K 10 (10g, 0.01 1 mole) followed by dropwise addition of a 30% solution of hydrogen peroxide (4.8ml_, 0.044 mole). The resulting mixture was stirred at room temperature for 2 days. The crude reaction mixture was filtered and filtrate concentrated. The resulting residue was purified by column chromatography using 0 to 8% methanol in chloroform as an eluent to generate 2.65g of ^4, 4-thiomorpholine-1 , 3-dione as a solid. 1H-NMR (400 MHz, DMSO- d6) d ppm: 2.52-3.0 (m, 2H, -CO-CH2-SO-), 3.35-3.44 (m, 2H, NH-CH2-CH2-SO), 3.65- (0407) 3.76 (m, 2H, NH-CH2-CH2-SO), 8.03 (s, 1 H, -NH)

Molecular Weight:117.17
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:117.02483502
Monoisotopic Mass:117.02483502
Topological Polar Surface Area:54.4
Heavy Atom Count:7
Complexity:83.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes