Water → HCID 43299165, compound

Sodium hydride [0.153 g (50% in mineral oil), 3.2 mmol] was added to a solution of 4-aminothiophenol (0.20 g, 1.6 mmol) in 5 ml anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature under nitrogen for 15 min, then 4-trifluoromethylbenzyl chloride (0.236 ml, 1.6 mmol) was added. The reaction mixture was stirred overnight at room temperature under nitrogen. Water (50 ml) was then added and the resulting mixture was extracted with 2×50 ml ethyl acetate. The combined ethyl acetate extracts were washed sequentially with 60 ml saturated aqueous sodium bicarbonate solution, 60 ml water and 60 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was purified by flash column chromatography (silica gel, 15 g), eluting with 85:15 hexane/ethyl acetate to yield the title compound as an off-white solid (0.318 g, 70% yield). MS: 284.1 (M+1)

1. stirringThe reaction mixture was stirred overnight at room temperature under nitrogen
2. extractionthe resulting mixture was extracted with 2×50 ml ethyl acetate
3. washThe combined ethyl acetate extracts were washed sequentially with 60 ml saturated aqueous sodium bicarbonate solution, 60 ml water and 60 ml brine
4. dry with materialdried (anhydrous sodium sulfate)
5. concentrationconcentrated under reduced pressure
6. customThe solid residue was purified by flash column chromatography (silica gel, 15 g)
7. washeluting with 85:15 hexane/ethyl acetate

ORD record

ord-b27ab58e9ae04d068c054ed678f1a628

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262318B2