Sodium hydride → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

A mixture of thiomorpholine 1,1-dioxide (270 mg, 2.0 mmol) in DMF (10 ml) was prepared at room temperature and sodium hydride (60 wt % in oil, 96 mg, 2.40 mmol) added in one portion and the mixture stirred at room temperature for 1 h. 1-Bromo-4-(bromomethyl)benzene was then added in one portion and the mixture stirred overnight for 17.5 h under argon. The mixture was then quenched with saturated aqueous ammonium chloride solution (10 ml) and diluted with ethyl acetate (30 ml). The mixture was partitioned and the aqueous layer removed. The organic layers were then washed with 5% aqueous lithium chloride solution (2×10 ml), brine (10 ml), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was then purified by column (0-5% methanol/dichloromethane) to afford 4-(4-bromobenzyl)thiomorpholine 1,1-dioxide as a colourless solid (283 mg, 0.93 mmol, 47%).

1. customwas prepared at room temperature
2. stirringthe mixture stirred overnight for 17.5 h under argon
3. customThe mixture was then quenched with saturated aqueous ammonium chloride solution (10 ml)
4. additiondiluted with ethyl acetate (30 ml)
5. customThe mixture was partitioned
6. customthe aqueous layer removed
7. washThe organic layers were then washed with 5% aqueous lithium chloride solution (2×10 ml), brine (10 ml)
8. dry with materialdried over magnesium sulphate
9. customthe solvent removed under reduced pressure
10. customThe crude product was then purified by column (0-5% methanol/dichloromethane)

ORD record

ord-efa2b41976074a86b1a0be61b672fb9d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115088B2