Benzyl mercaptan → 2-Benzylsulphanyl-5-chlorobenzamide

Benzyl mercaptan (0.61 mL, 5.20 mmol) was added dropwise over 10 min to a stirred suspension of sodium hydride (60% in oil, 230 mg, 5.75 mmol) in THF (10 mL) at ambient temperature under a nitrogen atmosphere. The white suspension was stirred for a further 1 h and then added dropwise to a stirred solution of 5-chloro-2-fluorobenzamide (900 mg, 5.20 mmol) in THF (10 mL), under nitrogen, over 10 min. The mixture was stirred at ambient temperature for 1 h, at 50° C. for 1 h and at reflux for 3 h and then quenched with water (200 mL). The product mixture was extracted with EtOAc (3×30 mL) and the combined extracts washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (3:2, v/v) as eluent to give the title compound as a white solid (523 mg, 36%).

1. stirringThe mixture was stirred at ambient temperature for 1 h, at 50° C. for 1 h
2. temperatureat reflux for 3 h
3. customquenched with water (200 mL)
4. extractionThe product mixture was extracted with EtOAc (3×30 mL)
5. washthe combined extracts washed with brine (50 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by chromatography on silica gel with EtOAc:heptane (3:2

ORD record

ord-6cbe3f07c3e24df78ac0e1d912c00f34

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868017B2