Dimethylformamide → p,p'-Dicyanobenzophenone

HRID 1768633Notes

Reaction equation

HRID 1768633 reaction equation
[C:1]([Cu])#[N:2].Br[C:5]1[CH:19]=[CH:18][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[CH3:20][N:21](C=O)C>C(OCC)(=O)C>[C:20]([C:5]1[CH:19]=[CH:18][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:1]#[N:2])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)#[N:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 728684,4'-DibromobenzophenoneHCID 178418546HCID 178418546, compound

Product 1

HCID 10657191p,p'-Dicyanobenzophenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.13 g of CuCN are added to a solution of 5.1 g of 4,4'-dibromobenzophenone in 90 ml of DMF, and the mixture is stirred under reflux for 13 hours. After cooling, the reaction mixture is diluted with ethyl acetate, washed twice with 50% aqueous ethylcnediamine solution, twice with water and then three times with brine, dried and concentrated. Column chromatography (SiO2, toluene to toluene/ethyl acetate 95:5) yields the crystalline title compound; TLC (toluene/ethyl acetate 9:1): Rf =0.34; IR (CH2Cl2): 2220, 1670, 1605, 1405 cm-1.

Workup

  1. temperatureunder reflux for 13 hours
  2. temperatureAfter cooling
  3. washwashed twice with 50% aqueous ethylcnediamine solution, twice with water
  4. dry with materialthree times with brine, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-432625baae5f4716ab07f3dbf07f949c
Source dataset
uspto-grants-1995_01
Patent number
US05378721

Reaction notes

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