Dimethylcarbamoyl Chloride → HCID 11198140, compound

Participants

Reaction Steps

A solution of 3-[4-(4-fluorophenoxy)phenyl]-1H-pyrazole (467 mg, 1.84 mmol) in 7 mL of THF containing 0.3 mL (2.13 mmol) of triethylamine was treated with 0.3 mL (3.2 mmol) dimethylcarbamyl chloride added via syringe. No reaction was observed at room temperature. An additional 0.3 mL of dimethylcarbamyl chloride was added and the reaction was heated at reflux overnight. The reaction was then added to a saturated aqueous NaHCO3 solution and EtOAc. The aqueous layer was washed with EtOAc and the pooled organic layers were dried (Na2SO4), filtered and concentrated to dryness. Column chromatography (7/3 hexane/EtOAc) afforded 282 mg of the title compound as a yellow oil that solidified on standing, mp 59-63° C. 1H NMR (CDCl3): δ8.15 (d, 1H, J=2.7 Hz), 7.80 (d, 2H, J=8.4 Hz), 7.06-6.88 (m, 6H), 6.62 (d, 1H, J=2.7 Hz), 3.30 (br s, 6H).

Provenance & Evidence