2-Naphthalenethiol → HCID 18668987, compound

Participants

Reaction Conditions

Reaction Steps

A 2.5 mol/L sodium hydroxide aqueous solution (2.1 mL, 5.2 mmol) and tetrabutylammonium bromide (0.020 g, 0.061 mmol) were added to 2-naphthalenethiol (0.20 g, 1.2 mmol), followed by stirring at 25° C. for 15 minutes. A toluene (2.1 mL) solution of 2-fluoro-5-nitrobenzaldehyde (0.21 g, 1.2 mmol) was added to the reaction liquid, followed by stirring at 110° C. for 3.5 hours. The conventional post-reaction treatment was performed to give 2-[(2-formyl-4-nitrophenyl)thio]naphthalene. 2-[(2-Formyl-4-nitrophenyl)thio]naphthalene (0.30 g, 0.98 mmol) was dissolved in toluene (15 mL), and 2,4-thiazolidinedione (0.46 g, 3.9 mmol), piperidine (0.039 mL, 0.39 mmol), acetic acid (0.022 mL, 0.039 mmol) and molecular sieves 4A (1.5 g) were added thereto, followed by stirring at 110° C. for 2.5 hours. After the conventional post-reaction treatment, the product was triturated with ethanol to give Compound 171 (0.13 g, yield 33%).

Provenance & Evidence