Potassium Carbonate → 4-[[(Diphenylmethylene)amino]methyl]benzonitrile

HRID 1584096Notes

Reaction equation

HRID 1584096 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)#[N:22]>C(#N)C>[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:20]=[C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:25][CH:24]=1)#[N:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 136809Benzophenone imine

Product 1

HCID 184240674-[[(Diphenylmethylene)amino]methyl]benzonitrileYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

270 g (2.0 mol) of anhydrous K2CO3 were added to a solution of 150 g (0.8 mol) of 97% pure benzophenone imine and 144.8 g (0.74 mol) of p-cyanobenzyl bromide in 450 ml of acetonitrile, and the mixture was left to stir at room temperature for 6 h. The inorganic salts were filtered off with suction and then most of the solvent was removed by distillation, 300 ml of water were added to the residue, and the mixture was extracted several times with ethyl acetate. The organic phase was washed 2× with water, dried over Na2SO4 and evaporated to dryness. Digestion with ether resulted in 180 g of white crystals, melting point 101-102° C.

Workup

  1. waitthe mixture was left
  2. filtrationThe inorganic salts were filtered off with suction
  3. custommost of the solvent was removed by distillation, 300 ml of water
  4. additionwere added to the residue
  5. extractionthe mixture was extracted several times with ethyl acetate
  6. washThe organic phase was washed 2× with water
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-6e4329a533274bb8ac71dfdc95e019c9
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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