Sodium Sulfide → HCID 58710059, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(2-methoxy-5-nitrophenyl)thiazole (156 mg, 0.660 mmol) and anhydrous sodium sulfide (309 mg, 3.96 mmol) in N-methylpyrrolidinone (2 mL) was heated at 160° C. for 2 h. After cooling to rt, the solvent was removed in vacuo, and the residue was partitioned between water (5 mL) and dichloromethane (20 mL). The organic phase was separated, dried over MgSO4, and purified by silica gel chromatography (3% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz): δ=7.18 (d, J=9.2 Hz, 1H), 8.08 (dd, J=1.6, 9.2 Hz, 1H), 8.45 (s, 1H), 8.52 (d, J=2.4 Hz, 1H), 8.86 (s, 1H), 11.95 (s, br, 1H). MS (ES+): m/z 223.14 [MH+]. HPLC: tR=2.68 min (ZQ2000, polar—5 min).

Provenance & Evidence