alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile → alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

Participants

Reaction Steps

A mixture of 6.12 g of α-(5-iodopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.22 g of potassium phthalimide and 50 mL of N,N-dimethylformamide is heated on a steam bath for 2 hours. The reaction solution is concentrated in vacuo and the residue is distributed between diethyl etherwater, with agitation. The organic layer is washed with 1N sodium hydroxide, followed by aqueous potassium bicarbonate. The solution is dried (sodium sulfate), and the volatiles removee in vacuo. Chromatography on silica gel, with gradient elution progressing from hexane to chloroform to methyl alcohol, affords 4.77 g of the desired product as a fluorescent oil. MS(FAB): m/z 515(M+H), 391(M-TolSH). Calcd for C30H30N2O4S 3/8H2O: C=69.11, H=5.95, N=5.37, S=6.14 Found C=69.34, H=5.78, N=5.23, S=5.79

Provenance & Evidence