Triethylamine → HCID 178484369, compound

Participants

Reaction Steps

To a solution of 5-amino-3-(4-quinolylmethylen) -2-oxindole (431 mg, 1.5 mmol) in DMF (100 ml) containing triethylamine (202 mg, 2 mmol) was added 1-t-butoxycarbonyl-3,3-dimethylthiourea (409 mg, 2 mmol) and HgCl2 (543 mg, 2 mmol). The mixture was stirred at room temperature for 1 h and then filtered on a pad of celite. The residue was washed with ethyl acetate, the organic layer washed several times with water, dried and evaporated to dryness. The residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1. The above obtained BOC-derivative was taken up in trifluoroacetic acid (10 ml) and then stirred for 1 h at room temperature. Ethyl acetate was added, the organic layer washed with 1N sodium hydroxide and brine, dried and evaporated. The residue was chromatographed on a LoBar RP18 column with water as eluant to give pure title compound after freeze-drying. Yield 50% (268 mg).

Provenance & Evidence