Sodium → HCID 67262655, compound

Participants

Reaction Steps

A 500-mL one-necked flask was equipped with a magnetic stir bar and a reflux condenser. 200 mL of methanol were added to the flask, sodium (3.0 g, 0.13 mole) was added to the methanol as small pieces (approximately 0.5 g). After the sodium dissolved, N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]-benzamide (19.0 g, 0.056 mole) was added to the flask and the reaction mixture was heated at reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and the methanol was evaporated using a rotary evaporator. The residue was treated with 200 mL of water and extracted with dichloromethane (3×100 mL). Combined organic extracts were dried over magnesium sulfate and the solvent was evaporated on a rotary evaporator. The red solid was recrystallized from methanol-water (7:3) to give slightly red crystals. The yield was 4.5 g (40% of theory). Mp=74-76° C.

Provenance & Evidence