Acetic Acid → HCID 15461585, compound

Participants

Reaction Steps

To a suspension of 5.0 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 130 mL of water, 8.4 g (35 mmol) of nonahydrated sodium sulfide are added. The reaction mixture is heated to reflux for 20 min, then 50 mL of an aqueous solution containing 1.0 g of sodium sulfate are added. The color of the medium changes completely to blue. 2.60 mL (24 mmol) of 4-fluorobenzaldehyde and 6.36 mL of glacial acetic acid are added successively. After 1 h of reflux, the greenish precipitate obtained is filtered, dried, and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 60/40). The yellow crystals formed after evaporation of the solvent are washed successively with the isopropanol and ether, then uncolored and recrystallized in dichloromethane to produce 2.0 g of 4,9-dihydro-4,9-dioxo-2-(4-fluorophenyl)naphtho[2,3-d]thiazole in the form of yellow crystals.

Provenance & Evidence