Chloroacetonitrile → HCID 14369600, compound

Participants

Reaction Steps

2.5 g (0.0326 mol) of chloroacetonitrile and 5.4 g (0.0326 mol) of triethyl phosphite are heated to 200° C. until the evolution of gas has ended. 30 ml of dimethylformamide and 1.8 g (0.034 mol) of sodium methylate are added to the cooled mixture and 3.0 g (0.0162 mol) of 3-(2-methylphenyl)-pyrrole-4-aldehyde in 5 ml of dimethylformamide are then added dropwise at 0° C. with stirring. After completion of the addition, the reaction mixture is stirred for 16 hours at room temperature and then added to water, the mixture is extracted with ethyl acetate, washed using water, dried over sodium sulphate and concentrated in vacuo, and the residue is purified by chromatography on silica gel (eluant ethyl acetate/cyclohexane 5 : 1). 0.5 g (15% of theory) of (Z)-β-[3-(2-methylphenyl)pyrrol -4-yl]-acrylonitrile of melting point 74° C.-75° C. and 1.2 g (36% of theory) of (E)-β-[3-(2-methylphenyl)pyrrol -4-yl]-acrylonitrile of melting point 152° C.-154° C. are obtained.

Provenance & Evidence