Sulfuric Acid → 2-Chloro-N-[2-hydroxy-4,6-bis(trichlorovinyl)benzyl]acetamide

Participants

Reaction Steps

A mixture of 0.352 g (1.0 mmol) of the product of Step D and 0.123 g (1.0 mmol) of N-hydroxymethyl-2-chloroacetamide was added in portions to a vigorously stirred solution of 0.9 mL acetic acid and 0.1 mL (98%) sulfuric acid at 0-10° C. The reaction mixture was allowed to warm to room temperature, and stirring was maintained for a total of 4 days. The reaction mixture was poured into ice-water, neutralized with saturated aqueous NaHCO3 solution and extracted into CH2Cl2. The organic extracts were combined, washed with brine, dried Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 5-10% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Provenance & Evidence