Sulfuric Acid → HCID 22921548, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 4.3 grams (0.010 mole) of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl) benzimidazol-1-yl]propan-1-ol in 120 mL of acetone was stirred, and 16 mL chromic acid (prepared by dissolving about five grams of chromium trioxide in 12 mL of water, then adding five mL of concentrated sulfuric acid), was added dropwise during a one hour period. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for about 18 hours. The reaction was quenched with about three mL of 1-methylethanol, and the mixture was made basic with an aqueous solution saturated with sodium bicarbonate. The mixture was filtered to remove chromium salts, and the filtrate was extracted with ethyl acetate. The combined extracts were then washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 3.0 grams of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanoic acid. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence