Chlorosuccinimide → HCID 10214919, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared by reacting 1-(Acetyloxy)-6H-dibenzo[c,h]chromen-8-yl acetate(360 mg, 1.03 mmol) with NCS (210 mg, 1.57 mmol) and anhydrous DMF (20 ml) according to method B for 2.0 h at room temperature, followed by heating to 100° C. for 1 h. The reaction was concentrated under reduced pressureAnd the solids were dissolved in MeOH (30 ml). NH3 was bubbled in for 0.5 h while acetate removal was monitored by LC-MS. The reaction was concentrated to a dark sludge, dissolved in EtOAc and passed through a silica plug to produce 200 mg (65%) foam. An analytical sample was produced by silica chromatography (1:1 EtOAc:hexanes). mp ˜185° C. dec.; 1H NMR (400 MHz, DMSO-d6) δ 5.23 (2H, s), 6.72 (1H, d, J=2.3 Hz), 6.81 (1H, dd, J=8.6 Hz, 2.6 Hz), 6.92 (1H, dd, J=7.5 Hz, 1.0 Hz), 7.33 (1H, appt), 7.62 (1H, dd, J=8.5 Hz, 1.0 Hz), 7.69 (1H, d, J=8.6 Hz), 7.79 (1H, s), 9.78 (1H, s), 10.11 (1H, s); MS m/z297/399 (Cl pattern) (M−H+).

Provenance & Evidence