Water → HCID 59463447, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Thioxo-7-oxa-1-thia-3,4-diaza-s-indacen-3-yl)-butyric acid (0.2 mmol) was dissolved in dry acetonitrile (2 ml) under nitrogen atmosphere, and the solution was cooled to −10° C. Nitrosyltetrafluoroborate (NOBF4, 0.24 mmol) mixed in dry acetonitrile (1 ml) was added thereto, and the mixture turned red immediately. The resulting mixture was stirred for one hour at −10° C., and a mixture of nitrobenzene (0.4 mmol) and a solution of CuCl2 dihydrate (15 mmol) in acetonitrile (1 ml) was added dropwise. The reaction mixture was allowed to warm-up to 0° C., and TLC analysis using a 1:1 hexane:ethyl acetate mixture as eluent indicated complete conversion after 0.5-1.0 hours. Thereafter ethyl acetate and water were added, the organic and aqueous layers were separated, the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the crude product 4-[6-(4-nitro-phenyl)-2-thioxo-7-oxa-1-thia-3,4-diaza-s-indacen-3-yl]-butyric acid which was further purified by column chromatography using fine silica and a 4:1 hexane:ethyl acetate mixture as eluent.

Provenance & Evidence