Sodium Carbonate → 5-(4-Fluoro-phenyl)-thiomorpholine-3-thione

A mixture of phosphorus pentasulfide (5.12 g, 11.5 mmol) and sodium carbonate (1.22 g, 11.5 mmol) in THF (30 mL) was stirred at room temperature. A solution of 5-(4-fluoro-phenyl)-thiomorpholin-3-one (2.0 g, 9.5 mmol) in THF (25 mL) was slowly added, and the mixture was stirred at room temperature for 90 minutes. The mixture was diluted with 10% aqueous Na3PO4 solution (40 mL), and stirred at room temperature for five minutes. The mixture was extracted with a 1:4 mixture of ethyl acetate and diethyl ether, and the organic phase was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Elution of the residue through silica (15-20% ethyl acetate/hexanes) gave 1.36 g of 5-(4-fluoro-phenyl)-thiomorpholine-3-thione, MP=107-108° C.

1. stirringthe mixture was stirred at room temperature for 90 minutes
2. stirringstirred at room temperature for five minutes
3. extractionThe mixture was extracted with a 1:4 mixture of ethyl acetate and diethyl ether
4. customthe organic phase was separated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. washElution of the residue through silica (15-20% ethyl acetate/hexanes)

ORD record

ord-16ce7495b3464151b09de987fcc0ca7e

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871760B2