Dichlone → HCID 67331251, compound

Participants

Reaction Conditions

Reaction Steps

A well-stirred suspension of 4-Amino-N-o-tolyl-benzenesulfonamide 12a (47 mg, 179 mmol) and 2,3-dichloro-1,4-naphthquinone (41 mg, 179 mmol) in 10.0 mL of 95% EtOH/5% water solution mixture was refluxed at 115° C. for three days. The orange precipitate obtained was filtered and washed with hot ethanol (5×5 mL), dried under reduced pressure to afford the title compound (23 mg, 28%). Mp=265-266° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.55 (br s, 1H), 9.45 (br s, 1H), 8.04 (d, J=7.2 Hz, 2H), 7.89-7.80 (m, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.17-7.07 (m, 5H), 6.98-6.96 (m, 1H), 1.97 (s, 3H); ESI-LRMS m/z 453.0 (M+35Cl+H)+, 455.0 (M+37Cl+H)+; ESI-HRMS m/z calculated for C23H8ClN2O4S (M+H)+ 453.0670, found 453.0665.

Provenance & Evidence