Ethylenediamine → N,N'-Bis(salicylidene)ethylenediamine

HRID 429001Notes

Reaction equation

HRID 429001 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10]([NH2:13])[CH2:11][NH2:12]>C(O)C>[CH:1](=[N:12][CH2:11][CH2:10][N:13]=[CH:1][C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 6998Salicylaldehyde

Product 1

HCID 26518N,N'-Bis(salicylidene)ethylenediamineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were combined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° C.). 1H NMR (DMSO-d6) δ8.57 (s 2H, HC═N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ166.94 (2C, CO), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2).

Workup

  1. customA yellow crystalline material immediately formed
  2. filtrationThe solution was filtered
  3. washthe crystals were washed with cold ethanol
  4. filtrationThe resulting crystals were collected by vacuum filtration
  5. washwashed with water
  6. customThe collected solids were dried in vacuo

Sources & evidence

ORD record
ord-c21c1a5c28984876a1d4d3159e5549db
Source dataset
uspto-grants-2001_11
Patent number
US06315978B1

Reaction notes

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