Hexachloroethane → HCID 71226242, compound

Temperature

-78 °C

To a round bottom flask was added N-methyl-3-(oxazol-5-yl)benzamide (0.50 gm, 2.47 mmol) and THF (25 mL). The reaction was cooled to −78° C. and 1.6 M nBuLi (3.86 mL, 6.18 mmol) was added dropwise. The reaction turned orange-red in color. After 60 min, a solution of hexachloroethane (0.88 gm, 3.71 mmol) in THF (5 mL) was slowly added. The reaction was slowly warmed to rt over 30 min. After 2 h at rt the reaction was quenched by slow addition of sat. NH4Cl (10 mL). The mixture was concentrated to remove most of the THF. The mixture was then partitioned between EtOAc (40 mL) and water (20 mL). The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes to give the product, 3-(2-chlorooxazol-5-yl)-N-methylbenzamide, (123 mg, 0.52 mmol, 21% yield) as a light yellow solid. Anal. Calcd. for C11H9ClN2O2 m/z 236.0, found: 237.0 (M+H)+.

1. temperatureThe reaction was slowly warmed to rt over 30 min
2. customAfter 2 h at rt the reaction was quenched by slow addition of sat. NH4Cl (10 mL)
3. concentrationThe mixture was concentrated
4. customto remove most of the THF
5. customThe mixture was then partitioned between EtOAc (40 mL) and water (20 mL)
6. customThe organic phase was isolated
7. washwashed with saturated aqueous NaCl
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting residue was purified
12. washeluting with a gradient of 0-100% EtOAc/Hexanes

ORD record

ord-e4836859facf4fc7920f03f1f86479f1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2