Thionyl Chloride → 4,4'-DICYANO-2,2'-BIPYRIDINE

HRID 973548Notes

Reaction equation

HRID 973548 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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 15687180HCID 15687180, compound

Product 1

HCID 104429584,4'-DICYANO-2,2'-BIPYRIDINE

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

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°.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. concentrationconcentrated to dryness by evaporation
  4. customThe residue is then chromatographed with methylene chloride over silica gel

Sources & evidence

ORD record
ord-a7d3f212fd7c4b859b63fe3a616e3c3b
Source dataset
uspto-grants-1991_11
Patent number
US05064832

Reaction notes

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