Hydrochloric Acid → HCID 66826400, compound

Participants

Reaction Steps

A mixture of 2-phenyl-1-(thiophen-3-yl)ethanone (Intermediate 39) (100 mg, 0.49 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (95 mg, 0.45 mmol), urea (81 mg, 1.35 mmol), and concentrated HCl solution (0.04 mL, 0.45 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was diluted with water, and extracted with EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, evaporated in vacuo, and purified by preparative HPLC to give Compound 79 (45 mg, yield 23%). 1H NMR (DMSO-d6 300 MHz): δ 10.19 (s, 1H), 8.50 (s, 1H), 7.43-7.40 (m, 2H), 7.30-7.24 (m, 2H), 7.04-7.00 (m, 4H), 6.83-6.80 (m, 2H), 6.52 (s, J=5.1 Hz, 1H), 5.07 (d, J=2.4 Hz, 1H), 3.97-3.88 (m, 2H), 1.22 (t, J=6.9 Hz, 3H); MS (ESI): m/z 438.0 [M+1]+.

Provenance & Evidence