Thionyl Chloride → 4,4'-Dicyano-2,2'-bipyridine

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:15]=[C:14]([C:16](=O)[NH2:17])[CH:13]=[CH:12][N:11]=2)[CH:5]=1)(=O)[NH2:2].S(Cl)(Cl)=O>N1C=CC=CC=1.C(Cl)Cl>[C:16]([C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:6]2[CH:5]=[C:4]([C:1]#[N:2])[CH:9]=[CH:8][N:7]=2)[CH:15]=1)#[N:17]

Participants

Procedure

A suspension of 4.73 g (0.0195 mol) of 4,4'-dicarbamoyl-2,2'-bipyridine [J. Am. Chem. Soc. 80. 2745 (1958)] and 5.67 g (0.0476 mol) of thionyl chloride in 30 ml of pyridine is stirred for 16 hours at 100° . After cooling, the reaction mixture is diluted with 100 ml of methylene chloride, filtered and concentrated to dryness by evaporation. The residue is then chromatographed with methylene chloride over silica gel. In this manner, 4,4'-dicyano-2,2'-bipyridine is obtained in the form of white crystals having a melting point of 238°-240°.