Benzophenone imine → [(Diphenylmethylene)amino]acetonitrile

HRID 1696057Notes

Reaction equation

HRID 1696057 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][CH2:17][C:18]#N>ClCCl>[C:1](=[N:14][CH2:18][C:17]#[N:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 612957[(Diphenylmethylene)amino]acetonitrileYield 157.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzophenone imine (25 g, 0.138 mol, Aldrich) and aminoacetonitrile hydrochloride (25 g, 0.270 mol, Lancaster) in dichloromethane (1000 mL) was stirred in a 2 L Erlenmeyer flask under nitrogen at room temperature for 5 days. The reaction mixture was filtered to remove the precipitated ammonium chloride and the filtrate was evaporated to dryness in vacuo. The resulting residue was dissolved in ether (400 mL) washed with water (200 mL) and brine. After drying over magnesium sulfate the solution was evaporated to give (benzhydrylideneamino)-acetonitrile (47.89 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the precipitated ammonium chloride
  3. customthe filtrate was evaporated to dryness in vacuo
  4. dissolutionThe resulting residue was dissolved in ether (400 mL)
  5. washwashed with water (200 mL) and brine
  6. dry with materialAfter drying over magnesium sulfate the solution
  7. customwas evaporated

Sources & evidence

ORD record
ord-bd51acdbeac44452869e16294e4c6e41
Source dataset
uspto-grants-2012_04
Patent number
US08163735B2

Reaction notes

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