Ethylenediamine → HCID 178515944, compound

HRID 1470062Notes

Reaction equation

HRID 1470062 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH:5](=O)[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8]>C(O)C>[CH:11]1[CH:10]=[CH:9][C:7](=[O:8])/[C:6](=[CH:5]\[NH:3][CH2:2][CH2:1][NH:4]/[CH:5]=[C:6]2\[C:7]([CH:9]=[CH:10][CH:11]=[CH:12]\2)=[O:8])/[CH:12]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 6998Salicylaldehyde

Product 1

HCID 178515944HCID 178515944, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethylenediamine (50 mmol, 3.3 mL) was added via a syringe to a stirred solution of salicylaldehyde (100 mmol, 10.5 mL) in ethanol (100 mL). A yellow precipitate formed immediately. The reaction mixture was refluxed for 3 hours and the solvent was then removed in vacuo to leave a yellow crystalline solid which was washed with diethyl ether (ca. 100 mL) to give salen ligand (C0) (12.0 g, 90%). Mp. 126-130° C. 1H NMR 3.96 (4H, s, CH2CH2), 6.87 (2H, t J=8.4 Hz, 2×HAr), 6.97 (2H, t J=8.7 Hz, 2×HAr), 7.2-7.3 (4H, m, 4×HAr), 8.38 (2H, s, 2×CH═N), 13.23 (2H, s, 2×OH).

Workup

  1. customA yellow precipitate formed immediately
  2. temperatureThe reaction mixture was refluxed for 3 hours
  3. customthe solvent was then removed in vacuo
  4. customto leave a yellow crystalline solid which
  5. washwas washed with diethyl ether (ca. 100 mL)

Sources & evidence

ORD record
ord-bed2df12790e45768dae0b43f99824d6
Source dataset
uspto-grants-2015_04
Patent number
US09006425B2

Reaction notes

Loading…