2-Mercaptobenzoic Acid → HCID 19887629, compound

Participants

Reaction Steps

A mixture of N-[1-(3-phenylthioindol-1-yl)prop-2-yl]-N-hydroxy urea from Example 3 (100 mg, 0.34 mmol), thiosalicylic acid (208 mg, 1.4 mmol) and trifluoroacetic acid (3 mL) was stirred at r.t. for one hour. The reaction mixture was then poured onto an aqueous saturated NaHCO3 solution and extracted with EtOAc. The combined organic phase was then washed with 1N NaOH, brine, dried and evaporated to dryness. Separation of two products by flash chromatography using 90% EtOAc in hexanes gave the N-[2-(indol-1-yl)eth-1-yl]-N-hydroxy urea, m.p.: 150°-152° C., and the N-[2-(2-phenylthioindole-1-yl)eth-1-yl]-N-hydroxy urea, m.p.: 57°-60° C.

Provenance & Evidence