4-(2-chloroethyl)thiomorpholine1,1-dioxide synthesis

Yield:55160-66-2 74%

Reaction Conditions:

with thionyl chloride;N,N-dimethyl-formamide in dichloromethane at 0 - 40;

Steps:

1.2 Synthesis of4-(2-chloroethyl)thiomorpholine 1,1-dioxide

To a stirred solution of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide (step 1, 2.5 g, 13.88 mmol, 1.0 eq) in DCM (25 ml) at 0 °C then added thionyl chloride (5.06 mL, 69.44 mmol, 5.0 eq) followed by DMF (Cat.). The reaction mixture was heated to 40 °C for overnight. After completion of the reaction (monitored by TLC), the solvent was evaporated in vacuo providing a crude residue was diluted with DCM and washed with saturated sodium bicarbonate solution. Organic layer was concentrated in vacuo to give crude residue which was purified by column chromatography by using 3% MeOH and DCM as an eluent to afford the desired compound (2.0 g, yield: 74.0%) as a white solid. 1H NMR (DMSO-d₆, 300 MHz): δ 3.70 (t, 2H), 3.08 (m, 4H), 3.01 (m, 4H) and 2.87 (t, 2H); Mass: [M+H]⁺198.10 (30%).

References:

WO2017/149518,2017,A1 Location in patent:Page/Page column 25