Benzaldehyde → HCID 15700638, compound

Participants

Reaction Steps

Preparation of the starting material a solution of 15.0 g (67 mmol) of 3-amino-2-phenyl-benzo(b)thiophene and 7.8 g (74 mmol) of benzaldehyde freshly distilled in 50 milliliters of benzene is refluxed for 10 hours with a water trap. After cooling, it is diluted with benzene, the excess benzaldehyde is eliminated by stirring with a solution of sodium bisulphite, the organic phase is dried over Na2SO4 and evaporated: 3-benzylidenamino-2-phenyl-benzo(b)thiophene in the form of a crude oily product which crystallises when it is triturated with methanol: 19.0 g (91% of theory) of yellow crystals, mp 92°-93° C. (ethanol). 9.6 g (31 mmol) of this Schiff base and 12 g (0.32 mol) of NaBH4 in 300 milliliters of absolute ethanol are refluxed with stirring for 25 hours. The cooled reaction mixture is diluted in water and extracted with ether. By evaporating the organic phase dried over K2CO3, the 3-benzylamino-2-phenyl-benzo(b)thiophene is obtained in the form of a crude oily product which crystallises when it is triturated with methanol. 9.0 g (92% of theory), colourless crystals, mp 52°-53° C. (methanol).

Provenance & Evidence