Hexachloroethane → HCID 71226242, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence