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

HRID 1282276Notes

Reaction equation

HRID 1282276 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. After the organic salts had been removed by filtration with suction, the solvent was substantially removed by distillation, and the residue was mixed with 300 ml of water and 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. customAfter the organic salts had been removed by filtration with suction
  3. customthe solvent was substantially removed by distillation
  4. additionthe residue was mixed with 300 ml of water
  5. extractionextracted 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-8babfd14ba3240f7aaa911efaae5627b
Source dataset
uspto-grants-2002_09
Patent number
US06455671B1

Reaction notes

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